annapolis cruising yachts

Darling Charters Annapolis

Welcome aboard darling, a classic lobster yacht built on martha’s vineyard.

Perfect for those early risers, or for when you have an action packed day and want to fit it all in.

Harbor Cruise

This cruise will make you feel like a local and discover all that Annapolis has to offer from the water.

Sit back and enjoy this cruise around the harbor, and watch as Annapolis lights up with the setting sun.

Special Event

We are pleased to speak with you to design a unique day on the water.  We think we are the ultimate way to arrive at your special event or wedding , spectator boat for a regatta, or celebrate that special occasion with your friends, family or clients. Contact us to find out how we can bring that added classic elegance to your next event.

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What to bring, what to wear , refreshments, cancellation policy, departure & arrival, terms and conditions, the fine print, testimonials.

“The prettiest boat in Annapolis"

"Wonderful captain, conversation, sights, boat & charcuterie board! ‍ I would do it again!

“ l loved being out on the water on a beautiful August afternoon. It was the perfect way to entertain three of my close friends. We enjoyed Champagne, sunshine and a guided tour of Annapolis area creeks and the Chesapeake Bay. We all agreed that our time on the picnic boat was greatly enhanced because of our captain Alexandra"

About the Boat

Darling is a 1973 Wasque 32 (pronounced “Way-squee”) named after Wasque point on Martha’s Vineyard.  She is a much loved classic and one of only 50 built by Martha’s Vineyard Boatworks.     Based on the lobster boat hulls of Maine, she was designed to be a fishing boat for the often challenging waters around the Vineyard and Buzzards Bay. As result she is a seaworthy vessel, cruising smoothly on the near full length keel. Darling had a major refit in the early 2000s that included the hard top and a new engine, and has continued to be upgraded to keep her in great shape. She is a very sea worthy design and also provides a wonderful open cockpit - the perfect setting for your next cruise.

Founded by two lifelong sailors, we wanted to share our love of the water with you and provide the ultimate way to experience Annapolis! ‍ When we found Darling it was love at first sight - book your cruise today to find out why!

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312 Third St

Annapolis, MD 21403

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Christian B.

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Atlantic Cruising Yachts is a Jeaneau and Fountaine Pajot Yachting Dealership in Annapolis, MD. Featuring Boat as a Business as a method of Yacht ownership through tax advantages. …

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Waypoints BVI Shitshow! On a teacher salary, we booked a sailing catamaran in July 2021 for April 2022....this was a bucket list trip that was totally mismanaged by your company. Four days before our cruise, Susan Restauri called to inform me that our saling catamaran (2021 US Flamingo) was no longer available for our family of 6 to celebrate a special family event. The "booking error" per Kirsti Palmer, cost our family an additional $8,410 in fees. Afterwords Waypoints dumped us to VCY in exchange for a 7 year old boat which was unacceptable due to mechanical problems. After that their response was they would just give us a full refund. REALLY! After prepaying and after our family had already arrived in the islands! Then we were transferred to a motor cat with MarineMax. The compromise was only a 5 day charter vs 7 days! Kirstie Palmer, President of Waypoints, responded to my post on a FB group (BVI Charter Chat) that had a "booking error". Chris, please review the 73 responses to our post on BVI Charter Chat...it is evident that Waypoints has some MAJOR issues! Imagine our surprise and amazement when we saw our 2021 US Flamingo docked at Nanny Cay with new potential Waypoint owners sitting on board! That shoud have been us, since we had booked in July 2021. Chris Bent, we are entitled to a full refund including the additional cost that we unexpectedly incurred after booking on July of 2021! If were available we would give 0 stars to Waypoints and 5 to Marine Max! Just thought you should be aware of our experience. Thank you in advance for your help.

My experience so far has been nothing but courteous and professional. Chris Bent and his entire staff has been able to answer all my questions and address all my concerns to date. Its been a pleasure doing business with you all. www.svSeaOdyssey.com

in their defense... they do follow up immediately and they do show you how set up their entire boat ownership program. It is not a simple and easy to understand program but I had experience through my job so at least the number make sense. You do need to ask questions because it is actually quite complicated. The program would work well for someone in the higher tax bracket, and still has some disposible income. At the end, it is about owning a new sailboat, they are not cheap, and they are not for the everyone..

Don't waste your time going to this boat dealer. My husband and I went there after the fall sailboat show back in 2015 to attend one of their boat business yacht ownership seminars and we never received any follow-up paperwork on the program like the owner had mentioned he'd do the following day. Guess we didn't look wealthy enough for him or asked too many questions about what appeared to be a very dodgy tax savings boat ownership scheme! Either way we were not impressed! Go elsewhere if looking for a boat ownership program. There are plenty that will offer good and friendly service no matter who you are!

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Picture Perfect Sailing

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Sail in Annapolis, Book a Sailing Cruise Today

Enjoy quality time with family and friends sailing out of Annapolis. You'll fall in love with the Chesapeake Bay. Your sailing charter awaits. 

CHOOSE YOUR SAILING ADVENTURE

Sailing options.

With Picture Perfect Sailing, the options are virtually endless!

Your skipper will take you for a day sail in Annapolis for a few hours towards St Thomas Point Lighthouse or the Chesapeake Bay Bridge, or perhaps around Annapolis harbor. For a longer sailing charter, choose our all-day sailing experience or overnight. You'll find yourself sailing to Baltimore or Saint Michaels. Book a sailing cruise now, make the memories of a lifetime with your family and friends!

Day Sail: come sailing for a few hours

Duration: 3 hours (leaves and returns to Annapolis)

Starting at $650 for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.

Sunset Sails: come sailing as the sun goes down

Duration: 2.5 hours (leaves and returns to Annapolis)

Starting at $650 weekdays for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.

All Day of Sailing: come sailing on the Chesapeake Bay all day!

Duration: 6 hours (leaves and returns to Annapolis)

Starting at $1,550 weekdays for 2 guests. Your sailing charter includes: skipper, crew member, snacks, lunch & beverages. Please check rates and book a sailing cruise by clicking the button below.

Overnight Sailing: experience sailing and sleeping aboard!

Choose one or two overnights: (leaves and returns to Annapolis)

Single (one) overnight: typically departs at 10am, one overnight in Baltimore or St Michaels, with disembarkation at 5pm the next day. Variations upon request. Starting at $2,450 weekdays for 2 guests. Your sailing charter includes: skipper, hostess, lunches x 2, snacks, breakfast x 1 & beverages. 

Double (two) overnights: typically departs at 9am,  one overnight in Baltimore or St Michaels, second overnight at the dock back in Annapolis and disembarkation at 9am the next morning. Starting at $3,900 for 2 guests.  Your sailing charter includes: skipper, hostess, snacks, breakfast, lunch x 2 & beverages.

The prices displayed in the booking schedule include yacht fuel, dock fees, water, propane for cooking, yacht insurance, cabin linens & bath towels. 

What’s not included: water activities off the boat (due to insurance limitations) such as swimming, paddle boarding or dinghy use; dinners (plan dinners on shore); crew gratuity.

How to book a sailing cruise with an overnight? Contact us for availability and custom pricing.

*Rates vary by season. Holiday rates upon request. Special pricing for Navy families, veterans, and first responders.  Contact Picture Perfect Sailing for more information and to book a sailing cruise today!

The Sailboat

You'll sail aboard a Beneteau Oceanis 45, with extensive cockpit protected by canvas and well-appointed to accommodate up to 3 couple for overnight sailing in maximum comfort; a head (bathroom) with shower, a full galley (kitchen) and comfortable salon. Arguably the nicest charter boat to sail in Annapolis. Let the sailing adventures begin, book a sailing cruise now.

With Picture Perfect Sailing, your designated skipper (and mate, depending on your sailing option!) will lead the sailing charter: maneuver the boat, guide your visit of the Annapolis area on the water, and ensure the fun & safety of all! 

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Sailing Charters in Annapolis, MD

Classic Sail Charters offers Chesapeake Bay sailing adventures on our thoroughly refined sailing yacht, the Licentia. It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world.

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1 - 6 people | 3-hour (am/pm) - 2.5-hour (sunset) sailing yacht cruise | 25% deposit, minimum age: 7 years., gratuity not included in pricing.

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Sunset Sail - Licentia

Come join us for an unforgettable cruise on one of our world-class sailing yachts and enjoy the beautiful sunsets in Chesapeake bay!

• Hour Glass 3 Hours

Morning Sail - Licentia

Classic Sail Charters offers Chesapeake Bay sailing adventures on a thoroughly refined sailing yacht Licentia, a 2008 Catalina 42 MKII.

Afternoon Sail - Licentia

Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful!

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• Hour Glass 8 Hours

Full Day Sail - Licentia

Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful, fed by countless navigable rivers and home to an abundance of wildlife.

Chesapeake Bay - Annapolis

Looking for a unique sailing experience on the Chesapeake Bay? Our charters are the perfect way to explore the Bay and its navigable rivers. As the largest estuary in the world, the Chesapeake Bay is a natural beauty filled with an abundance of wildlife. Create your own sailing adventure on the Chesapeake Bay as we work with you to define your perfect excursion and then you may leave the rest to us!

Annapolis, located less than an hour from Washington, D.C., is noted not only as the location of the US Naval Academy but as America’s ‘Sailing Capital.’ It is home to a rich history that includes the oldest working state capitol building in the U.S., noted as the location where General Washington resigned his commission, as well as dozens of first-class bed and breakfasts, hotels, and fantastic restaurants. As a sailing venue, it is second to none.

Annapolis Cruises

Annapolis is a beautiful historic seaport that’s great to explore by water.

Whether it’s a narrated sightseeing cruise or a day trip to St. Michaels, get out on the water with Watermark for an unforgettable journey. Our boats have a full bar service with light snacks available for purchase and restrooms on board. Most of our vessels are handicapped accessible and climate controlled.

Come on down and find us at Annapolis City Dock, 1 Dock Street and look for the red umbrella!

Annapolis Harbor & USNA

Hear the history of the U.S. Naval Academy, Annapolis’ role as a historic seaport, the region’s waterways, and catch a glimpse of the Bay Bridge.

Spa Creek Cruise

Step aboard our cozy launch for an intimate cruise up Spa Creek into the residential area of Old Annapolis, Eastport, and the banks of the U.S. Naval Academy.

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Day on the Bay to St. Michaels

Cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore.  Enjoy fresh seafood, boutique shopping, and historic sites all within walking distance.

Scenic Severn River Cruise

A spectacular 6-mile cruise on the beautiful Scenic Severn River and historic Annapolis Harbor; includes the banks of the United States Naval Academy

Chesapeake Bay Bridge Cruise

Cruise through Annapolis’ historic harbor, by the United States Naval Academy, and under the twin spans of the famous Chesapeake Bay Bridge.

Thomas Point Lighthouse Cruise

View this National historic landmark as you cruise the Chesapeake Bay on a narrated cruise.  Not just for lighthouse enthusiast; everyone loves it!

Annapolis Sunset Cruise

Enjoy a fun music playlist, the sun setting, and a cool beverage from our River Run Bar as you relax on this 60-minute cruise through the Annapolis Harbor.

Water Taxi Service

Hop on a taxi to visit your favorite restaurant or to get downtown from Eastport.  Taxi’s operate in the Annapolis Harbor, including Spa Creek and Back Creek

Special or Seasonal Cruises

From live music cruises to New Year’s Eve, Watermark offers a variety of special and seasonal cruises throughout the year.  Click below to learn more.

Baltimore Cruises

From live music cruises to New Year’s Eve, Watermark offers a variety of special and seasonl cruises throughout the year.  Click below to learn more.

Sailing Season is Here. Join Us for a Sail!

The Woodwind Family

The owners of Woodwind , Captain Ken and Ellen Kaye, were public school teachers, who decided to retire while still young (after teaching for 25 years).

They dreamed of someday owning a schooner to introduce people to sailing. After their daughter, Jennifer, returned from a semester at sea aboard a 125′ schooner, the family pursued their dream in earnest. They had their handsome vessel custom designed and built based on their knowledge gained from more than 20 years of sailing. They fell in love with Annapolis and moved here after spending all their lives in Connecticut.

Jennifer became a Captain in 1996 and joined them full time. A second, identical “ Woodwind “- named “ Woodwind II ” was the latest addition to the family in 1998.

The extended “family” of crew members are chosen for their sailing knowledge, friendliness and enthusiasm. These are the qualities that make your on board experience a special one.

History of the Two, Identical 74-foot Schooners

Schooner woodwind was contracted to be designed.

Schooner  Woodwind  was contracted to be designed by John Scarano for Ken and Ellen Kaye, from Wallingford, CT. The schooner was specifically designed to provide a fun sailing experience for guests.

The schooner was finished!

The schooner was finished at the Scarano Boat Builder’s Yard in Albany, NY. Her hull was made of Port Orford Cedar ribs and then strip planked with the same material, her decks Douglas Fir, and a thin sheathing of fiberglass on the outside of the hull.

Woodwind’s first voyage!

Woodwind’s  first voyage! She was sailed down the Hudson River, up the Delaware Bay, through the C & D Canal, and down the Chesapeake Bay to Annapolis.

Certification of Inspection

The U.S. Coast Guard gave  Woodwind  the Certification of Inspection for 49 passengers, and our kick off sail was on July 3. Schooner Woodwind was now sailing the Bay four times a day with as many as 48 passengers. The dream became a reality.

Our First TRIFECTA RACE WIN

The Great Chesapeake Bay Schooner Race

1995: The first time we won the TRIFECTA of the Great Chesapeake Bay Schooner Race! TRIFECTA means First over the Finish Line, First in Corrected Time in our Class AND First Overall! This was the first of 8 Trifecta wins of the race (as of 2022). This one was extra special because it was our first big win and we only had the boat for 2 seasons.  We had a fine crew of guests and our professional crew. We had a finish time of 23 hours, 3 minutes, 59 seconds. 

The Dream Became a Reality

Woodwind  was very busy with many private charters and public cruises. We realized, in order to keep up with the demand for both private charters and public cruises, a second, identical Woodwind would be needed. The same boat builder was called to construct the new one.

A Second Identical Boat Was Commissioned

After the first successful Schooner Woodwind, the owners needed another Schooner for increased demand.

“Woodwind II“ was Completed

“ Woodwind   II ” was completed and sailed down to Annapolis the same way Woodwind was delivered. After three short weeks, we were up and running with both schooners.

May & June

“The Wedding Crashers“

“ Woodwind   II ” was selected to be the sailing yacht of Christopher Walken’s character in the movie, “The Wedding Crashers”. The filming took place in Oxford, Cambridge, St. Michael’s and on the Choptank and Miles Rivers. New Line Cinemas booked the boat for 9 days to film the scenes for the movie starring Vince Vaughn, Owen Wilson, Rachel McAdams, Jane Seymour, and Christopher Walken. The name of the boat was kept the same for the movie

Celebrated 25 Years

WON THE TRIFECTA of the Schooner Race

1st in class, 1st over the finish line and 1st overall

The year we won the TRIFECTA of the Great Chesapeake Bay Schooner Race with the biggest lead!

TRIFECTA means First over the Finish Line , First in Corrected Time in our Class, AND First Overall ! On corrected time (applying a handicap) the difference was 5 hrs: 39 min: 28 seconds. It may have been our largest win over our competitors, and we have been doing the race since 1993!

The crew consisted of Captain Mickey Lawlor, Captain Jen Kaye, Captain Ken Kaye, Rai Muhlbauer, Delaney Vorwick, Chris Garau, Courtney Boucher, and Dallas Elms. Guest Crew of Gene McCollum, Brett Harrison, Chris Lundberg, and Susan Brannigan worked hard for this amazing victory. 

Celebrated 30 Years

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Cruise in the most beautiful waters of the world with Waypoints ® Yacht Charters.

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Ranging from bareboat to all-inclusive, our charter specialists will work with you to find the best charter type.

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Our large fleet of award-winning luxury monohulls and catamarans are fully equipped to exceed your expectations.

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Our charter specialists know the best sailing and cruising waters, local life, bars, and other hidden gems unique to their destination — creating the most memorable experiences on the water. Speak with a charter specialist directly for assistance in crafting the perfect charter vacation.

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“There is a 100% chance that I would recommend Waypoints to my friends and family. The Waypoints team was so friendly during the entire process. They truly made the experience even more enjoyable.” Chelsea M., NCA Inc.

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• Since our establishment in 1953 by Lawrence Hartge in Annapolis, MD, we have been proudly serving boating enthusiasts on the stunning Chesapeake Bay with exceptional service and unparalleled expertise.
• Lawrence Hartge, a visionary and passionate boater, laid the foundation of our company with a simple yet powerful mission: to offer a full-service boat buying experience that surpasses expectations.
• His dedication to the craft and his love for the Chesapeake Bay set the tone for our company's values, which we continue to uphold to this day.
• Over the years, we have become synonymous with excellence in the Mid-Atlantic region.
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The National Sailing Hall of Fame announces Class of 2024 inductees

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The Sailing Museum and National Sailing Hall of Fame has revealed the names of 12 individuals who will be inducted into its fellowship of hall of famers this year.

This diverse list includes Jan C. O’Malley , a three-time US Sailing Yachtswoman of the Year, two-time Adams Cup winner, and the first ever winner of the IYRU Women’s World Sailing Championship; Peter Melvin , a multiple-class world and national champion, as well as an innovative yacht designer; and Charles Ulmer , a national champion and race winner throughout the 1970s and 80s and proponent of the sport of sailing through the many organizations through which he has been affiliated.

The National Sailing Hall of Fame induction committee met numerous times since nominations were gathered, eventually whittling down the original list to a slate of individuals to be inducted this year. While their biographies differ, they are all accomplished and dedicated to the sport and its community. Ten fall into its modern category, while another two represent historic classification.

Honored for technical accomplishment and contribution are brothers Eric Hall and Ben Hall , the late Gary Mull, one of the most prolific and successful U.S. sailboat designers working in the latter half of the 20th century, and the late Carl Alberg , whose 56 designs resulted in more than 10,000 boats. 

Others to be inducted in the modern classification in the sailing category are Kevin Burnham, an Olympic and Goodwill Games medalist in sailing; Conn Findlay , a consummate crew member for America’s Cup competitor Courageous and Maxi Ocean Racer  Windward Passage, and one of the few competitors to medal in two distinct sports (Rowing and Sailing); and Richard Tillman , the 1965 Sailor of the Year who held National, North American and World titles in the Snipe, Finn, Laser, Sunfish and Windsurfing classes. Franklin Wood , who founded the Annapolis Sailing School and established the Annapolis Sailboat Show, rounds out the modern classification in the contributor category.

Allegra Mertz , one of the two women to be inducted with O’Malley, was elected through the historic classification, along with Alberg.

“The Class of 2024 has left an indelible mark on sailing. Their achievements inspire us to explore, innovate and honor the sport. From Olympic champions to boat designers, they remind us that sailing is more than a pastime; it’s a legacy of courage and possibility,” co-chair Gary Jobson notes. “Trailblazers like Allegra Mertz, whose skill, determination and love of racing continues to inspire fellow sailors and set a high standard for excellence. Innovators such as Ben and Eric Hall, whose cutting-edge materials and championship-winning rigs have pushed innovation. These inductees are a formidable group. We look forward to celebrating their accomplishments on October 5 at the 2024 Hall of Fame Induction ceremony, hosted by the Chicago Yacht Club.”

“What an honor to welcome these remarkable individuals into The Sailing Museum and National Sailing Hall of Fame,” says Executive Director Ashley Householder.  “We take seriously the responsibility of preserving the legacy of our inductees for the countless ways in which each has contributed to the sport of sailing. Please join us as we embark on telling their exceptional stories.”

Each year, the induction committee of the National Sailing Hall of Fame reviews nominations and compiles a slate of those to be inducted into its hallowed fellowship of extraordinary achievement and service. Inductions have been taking place since 2011, when the Hall was in Annapolis. The Sailing Museum and National Sailing Hall of Fame has since moved to Newport, the sailing capital of the country. The number of legends in the Hall will be 135 total with this year’s class.

This year, the Induction will be held at the Chicago Yacht Club Oct. 4-5 . Tickets will be available soon on the Hall of Fame website at https://thesailingmuseum.org .

More information on the inductees will be available on the Hall of Fame website, as well as on its social media sites leading up to induction.

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Passing Thru Travel

15 Best Sailing Destinations: A Guide To Sailing Schools for Beginners

Posted: March 8, 2024 | Last updated: March 8, 2024

Embarking on the journey of learning to sail opens up a world of nautical adventure and discovery. This guide is tailored for those beginning their sailing voyage, highlighting the world’s top destinations renowned for their sailing schools and beginner-friendly waters. From New England’s breezy coasts to the Mediterranean’s serene waters, each destination offers a unique setting for learning the art of sailing. Whether you seek comprehensive courses or a casual introduction to sailing, these locales provide the perfect starting point for your nautical adventures.

1. Annapolis, Maryland, USA

Annapolis is known as America’s Sailing Capital and offers an ideal environment for novice sailors. The Chesapeake Bay’s calm waters and steady winds create perfect conditions for learning. Sailing schools in Annapolis provide a range of courses, from basic skills to advanced navigation. The city’s rich maritime history and vibrant sailing community enhance the learning experience.

Insider’s Tip: Enroll in a course that includes navigation of the Chesapeake Bay to gain practical experience.

When to Travel: Spring to early fall for ideal sailing conditions.

How to Get There: Fly into Baltimore-Washington International Airport and drive to Annapolis.

2. Auckland, New Zealand

Auckland, known as the “City of Sails,” is a premier destination for learning to sail. Its numerous harbors and islands provide diverse sailing experiences. Sailing schools in Auckland cater to all levels, offering courses in a city surrounded by stunning natural beauty.

Insider’s Tip: Choose a school that offers trips to nearby islands for a varied sailing experience.

When to Travel: October to April for warm weather and favorable sailing conditions.

How to Get There: Fly directly into Auckland International Airport.

3. Corfu, Greece

The island of Corfu in the Ionian Sea is a picturesque locale for sailing beginners. Its clear, calm waters and gentle winds make it an ideal place to learn. Sailing schools in Corfu often combine lessons with exploration of the island’s stunning coastlines and beaches.

Insider’s Tip: Opt for a sailing course that includes island-hopping around the Ionian Islands.

When to Travel: Late spring to early autumn for the best sailing weather.

How to Get There: Fly to Corfu International Airport or take a ferry from mainland Greece.

4. The Whitsundays, Australia

The Whitsundays, a collection of islands off Queensland’s coast, offer a tropical paradise for sailing novices. The Great Barrier Reef provides sheltered waters, ideal for learning. Sailing courses here often include snorkeling and exploration of the reef.

Insider’s Tip: Choose a sailing school that offers an introduction to sailing in the Great Barrier Reef for a unique experience.

When to Travel: May to September for cooler temperatures and optimal sailing conditions.

How to Get There: Fly to Hamilton Island and take a ferry or boat to your chosen island.

5. Cowes, Isle of Wight, UK

Cowes is a historic sailing town famous for the annual Cowes Week regatta. The Solent’s challenging waters provide an excellent training ground for beginners. Sailing schools in Cowes offer courses catering to all skill levels, set against British maritime heritage.

Insider’s Tip: Attend during Cowes Week for a thrilling introduction to the sailing community.

When to Travel: Summer for the best weather and to experience sailing events.

How to Get There: Take a ferry from Southampton or Portsmouth to the Isle of Wight.

6. Newport, Rhode Island, USA

Newport is a renowned sailing destination with a storied yachting history. Narragansett Bay’s varied conditions are perfect for beginners. Sailing schools in Newport, set in a picturesque New England town, offer a mix of practical training and theoretical knowledge.

Insider’s Tip: Participate in local regattas organized by sailing schools for hands-on experience.

When to Travel: Late spring to early fall for ideal sailing conditions.

How to Get There: Fly to T.F. Green Airport in Providence and drive to Newport.

7. San Diego, California, USA

San Diego’s consistent weather and diverse sailing areas make it an excellent place for beginners. San Diego Bay and the Pacific Ocean offer different sailing experiences. The city’s sailing schools provide a range of courses in these spectacular settings.

Insider’s Tip: Take advantage of San Diego’s ideal weather for year-round sailing activities.

When to Travel: Year-round, with the most stable conditions from spring to fall.

How to Get There: Fly directly into San Diego International Airport.

8. Split, Croatia

The historic city of Split on the Dalmatian coast offers idyllic conditions for learning to sail. The Adriatic Sea’s calm waters and the region’s many islands create a perfect sailing playground. Sailing schools in Split combine instruction with the exploration of Croatia’s stunning coastline.

Insider’s Tip: Include island visits to experience Croatia’s diverse maritime landscapes in your sailing course.

When to Travel: May to September for calm seas and pleasant weather.

How to Get There: Fly to Split Airport or travel by ferry from other parts of Croatia.

9. Tortola, British Virgin Islands

Tortola, part of the British Virgin Islands, is a Caribbean gem for beginner sailors. Its protected waters and steady trade winds offer ideal sailing conditions. Sailing schools on Tortola provide comprehensive beginner courses in this tropical paradise.

Insider’s Tip: Combine sailing lessons with snorkeling and beach visits for a complete Caribbean experience.

When to Travel: December to April for the best sailing weather.

How to Get There: Fly to Terrance B. Lettsome International Airport on Beef Island, which is connected to Tortola by a bridge.

10. The Florida Keys, USA

The Florida Keys offer a unique sailing experience with their shallow waters and coral reefs. The Keys’ relaxed atmosphere is perfect for beginners. Sailing schools here focus on practical skills in a laid-back environment.

Insider’s Tip: Extend your sailing trip to include a visit to Key West for its vibrant maritime culture.

When to Travel: November to May for the best weather and sailing conditions.

How to Get There: Fly to Miami International Airport and drive to the Keys or fly directly to Key West International Airport.

11. Antigua, Caribbean

Antigua is renowned for its 365 beaches and excellent sailing conditions. The island’s consistent winds and clear waters are ideal for beginners. Sailing schools in Antigua offer courses that let you explore the Caribbean Sea’s beauty.

Insider’s Tip: Time your visit to Antigua Sailing Week to witness world-class racing.

When to Travel: December to April for optimal sailing conditions.

How to Get There: Fly directly to V.C. Bird International Airport in Antigua.

12. Vancouver, Canada

Vancouver’s scenic coastline and diverse marine environments make it a fantastic location for learning to sail. The city’s sailing schools provide courses in the sheltered waters of English Bay and the Strait of Georgia.

Insider’s Tip: Take a sailing trip around the Gulf Islands for an unforgettable experience.

When to Travel: May to September is the most favorable weather.

How to Get There: Fly directly to Vancouver International Airport.

13. Saint Tropez, France

Saint Tropez, a glamorous destination on the French Riviera, offers a sophisticated setting for sailing beginners. The Mediterranean Sea’s mild conditions are perfect for learning. Sailing schools in Saint Tropez combine luxury with practical sailing instruction.

Insider’s Tip: Experience the glitz of Saint Tropez by visiting its famous beaches and restaurants.

When to Travel: Late spring to early autumn for ideal sailing weather.

How to Get There: Fly to Nice Côte d’Azur Airport and drive to Saint Tropez.

With its stunning barrier reef and numerous cayes, Belize is an extraordinary destination for beginner sailors. The Caribbean Sea’s warm waters and gentle winds create a relaxed environment for learning. Sailing schools in Belize often include reef exploration in their courses.

Insider’s Tip: Combine your sailing lessons with scuba diving or snorkeling to explore Belize’s rich marine life.

When to Travel: November to April for the best sailing and weather conditions.

How to Get There: Fly into Philip S. W. Goldson International Airport in Belize City.

15. Lake Garda, Italy

Lake Garda, Italy’s largest lake, offers a picturesque setting for learning to sail. Surrounded by mountains, the lake’s winds are predictable, making it an ideal place for beginners. Sailing schools around Lake Garda provide courses against stunning Italian scenery.

Insider’s Tip: Explore the charming towns around Lake Garda for a complete Italian experience.

When to Travel: April to October for the best wind conditions.

How to Get There: Fly to Verona Airport and drive to Lake Garda.

The Bottom Line

As you venture into the sailing realm, choosing where to begin this journey is crucial. Selecting a location and sailing school involves more than just finding picturesque waters; it’s about matching your learning ambitions with the right environment and expertise. Whether it’s the steady winds of the British Virgin Islands for a gentle start or the challenging conditions of the San Francisco Bay for a more rigorous approach, your decision should reflect your personal objectives and comfort level.

Consider practical aspects such as the climate, types of boats used for instruction, and the overall sailing culture of the area. Sailing is as much about understanding weather patterns and local maritime conditions as it is about handling the boat. It’s a skill that goes beyond the technicalities, encompassing a deep respect for the sea and its ever-changing nature.

Embark on this journey with a mindset geared towards learning and adapting. Sailing is a skill that offers a unique blend of adventure, tranquility, and a profound connection with nature. Each destination provides its own set of challenges and rewards, making your learning experience distinct. Your ideal starting point in sailing is out there, offering the thrill of navigating the waters and a pathway to new experiences and discoveries.

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The post 15 Best Sailing Destinations: A Guide To Sailing Schools for Beginners republished on Passing Thru with permission from The Green Voyage .

Featured Image Credit: Shutterstock / Ilija Ascic.

For transparency, this content was partly developed with AI assistance and carefully curated by an experienced editor to be informative and ensure accuracy.

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Published on June 17th, 2024 | by Editor

Class of 2024 Hall of Fame Inductees

Published on June 17th, 2024 by Editor -->

The National Sailing Hall of Fame has confirmed 12 individuals comprising its 14th class of inductees .

The recognition includes Jan C. O’Malley, a three-time US Sailing Yachtswoman of the Year, two-time Adams Cup winner, and the first ever winner of the IYRU Women’s World Sailing Championship; Peter Melvin, a multiple-class world and national champion, as well as an innovative yacht designer; and Charles Ulmer, a national champion and race winner throughout the 1970s and 80s and proponent of the sport of sailing through the many organizations through which he has been affiliated.

The National Sailing Hall of Fame induction committee reviews all nominations and reduces the original list to a slate of individuals to be inducted each year. Ten fall into its modern category, while two represent historic classification.

Honored for technical accomplishment and contribution are brothers Eric Hall and Ben Hall, the late Gary Mull, one of the most prolific and successful U.S. sailboat designers working in the latter half of the 20th century, and the late Carl Alberg, whose 56 designs resulted in more than 10,000 boats.

Others to be inducted in the modern classification in the sailing category are Kevin Burnham, an Olympic and Goodwill Games medalist in sailing; Conn Findlay, a consummate crew member for America’s Cup competitor Courageous and Maxi Ocean Racer Windward Passage, and one of the few competitors to medal in two distinct sports (Rowing and Sailing); and Richard Tillman, the 1965 Sailor of the Year who held National, North American and World titles in the Snipe, Finn, Laser, Sunfish and Windsurfing classes. Franklin Wood, who founded the Annapolis Sailing School and established the Annapolis Sailboat Show, rounds out the modern classification in the contributor category.

Allegra Mertz, one of the two women to be inducted with O’Malley, was elected through the historic classification, along with Alberg.

“The Class of 2024 has left an indelible mark on sailing,” observed co-chair Gary Jobson. “Their achievements inspire us to explore, innovate and honor the sport. From Olympic champions to boat designers, they remind us that sailing is more than a pastime; it’s a legacy of courage and possibility. Trailblazers like Allegra Mertz, whose skill, determination and love of racing continues to inspire fellow sailors and set a high standard for excellence. Innovators such as Ben and Eric Hall, whose cutting-edge materials and championship-winning rigs have pushed innovation. These inductees are a formidable group. We look forward to celebrating their accomplishments on October 5 at the 2024 Hall of Fame Induction ceremony, hosted by the Chicago Yacht Club.”

Each year, the induction committee of the National Sailing Hall of Fame reviews nominations and compiles a slate of those to be inducted into its hallowed fellowship of extraordinary achievement and service. Inductions have been taking place since 2011, when the Hall was in Annapolis. The Sailing Museum and National Sailing Hall of Fame has since moved to Newport, the sailing capital of the country. The number of legends in the Hall will be 135 total with this year’s class.

The 2024 Induction will be held October 4-5 at the Chicago Yacht Club in Chicago, IL.

Top, left to right: Carl A. Alberg, Kevin Burnham, Conn Findlay, Eric Hall, Ben Hall, Pete Melvin. Bottom, left to right: Allegra Knapp Brickell “Leggie” Mertz, Gary W. Mull, Jan O’Malley, Richard “Dick” Tillman, Charles “Butch” Ulmer, Franklin J. “Jerry” Wood

Tags: US National Sailing Hall of Fame

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The National Sailing Hall of Fame Announces 12 New Class of 2024 Inductees

The Sailing Museum and National Sailing Hall of Fame has revealed the names of 12 individuals who will be inducted into its fellowship of hall of famers this year.

This diverse list includes Jan C. O’Malley , a three-time US Sailing Yachtswoman of the Year, two-time Adams Cup winner, and the first ever winner of the IYRU Women’s World Sailing Championship; Peter Melvin , a multiple-class world and national champion, as well as an innovative yacht designer; and Charles Ulmer , a national champion and race winner throughout the 1970s and 80s and proponent of the sport of sailing through the many organizations through which he has been affiliated.

The National Sailing Hall of Fame induction committee met numerous times since nominations were gathered, eventually whittling down the original list to a slate of individuals to be inducted this year. While their biographies differ, they are all accomplished and dedicated to the sport and its community. Ten fall into its modern category, while another two represent historic classification.

Honored for technical accomplishment and contribution are brothers Eric Hall and Ben Hall , the late Gary Mull , one of the most prolific and successful U.S. sailboat designers working in the latter half of the 20th century, and the late Carl Alberg , whose 56 designs resulted in more than 10,000 boats.

Others to be inducted in the modern classification in the sailing category are Kevin Burnham , an Olympic and Goodwill Games medalist in sailing; Conn Findlay , a consummate crew member for America’s Cup competitor Courageous and Maxi Ocean Racer Windward Passage , and one of the few competitors to medal in two distinct sports (Rowing and Sailing); and Richard Tillman , the 1965 Sailor of the Year who held National, North American and World titles in the Snipe, Finn, Laser, Sunfish and Windsurfing classes. Franklin Wood , who founded the Annapolis Sailing School and established the Annapolis Sailboat Show, rounds out the modern classification in the contributor category.

Allegra Mertz , one of the two women to be inducted with O’Malley, was elected through the historic classification, along with Alberg.

“The Class of 2024 has left an indelible mark on sailing. Their achievements inspire us to explore, innovate and honor the sport. From Olympic champions to boat designers, they remind us that sailing is more than a pastime; it’s a legacy of courage and possibility,” co-chair Gary Jobson notes. “Trailblazers like Allegra Mertz, whose skill, determination and love of racing continues to inspire fellow sailors and set a high standard for excellence. Innovators such as Ben and Eric Hall, whose cutting-edge materials and championship-winning rigs have pushed innovation. These inductees are a formidable group. We look forward to celebrating their accomplishments on October 5 at the 2024 Hall of Fame Induction ceremony, hosted by the Chicago Yacht Club.”

“What an honor to welcome these remarkable individuals into The Sailing Museum and National Sailing Hall of Fame,” says Executive Director Ashley Householder. “We take seriously the responsibility of preserving the legacy of our inductees for the countless ways in which each has contributed to the sport of sailing. Please join us as we embark on telling their exceptional stories.”

Each year, the induction committee of the National Sailing Hall of Fame reviews nominations and compiles a slate of those to be inducted into its hallowed fellowship of extraordinary achievement and service. Inductions have been taking place since 2011, when the Hall was in Annapolis. The Sailing Museum and National Sailing Hall of Fame has since moved to Newport, the sailing capital of the country. The number of legends in the Hall will be 135 total with this year’s class.

This year, the Induction will be held at the Chicago Yacht Club Oct. 4-5 . Tickets will be available soon on the Hall of Fame website at thesailingmuseum.org .

More information on the inductees will be available on the Hall of Fame website, as well as on its social media sites leading up to induction.

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Rock Your Yacht 2024 Owners Rendezvous — July 26-28

Join us for a raft up, sailing, food and fun! 

RSVP by June 28th, 2024 

Event Summary

Raft up on Shaw Bay off the Wye River for a Progressive Happy Hour Your boat is your stage. Your crew is your band. Costumes encouraged. Band Name, decade or genre optional. All groupies are welcome on-board!

Judges will be making their rounds so put on the tunes, break out the moves and Rock Your Yacht

• Morning Sail to St Michaels • Harbour Inn Marina and Spa • Gentleman’s Dash – unofficial race! • Spend the day poolside or sightseeing and shopping in beautiful downtown St Michaels. • Saturday evening join us for cocktails at 6:30 pm, followed by dinner and an awards ceremony

Be sure to bring your dancing shoes for the Pool-Side After Party

• Brunch and Libations before we head back to Annapolis.

Register Now

Please complete the form below and an Atlantic Cruising Yachts Representative will contact you to arrange payment.

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