catamaran cruises florida

Tropical Sailing

Catamaran tours in miami & fort lauderdale, florida, our most popular trips.

• Most popular
• Hour Glass 2 Hours
• User All ages

Sunset Cruise Castaway the Day – Fort Lauderdale

A perfect way to end the day, taking in the breathtaking views. This Fort Lauderdale sunset cruise calls for sun dresses, sandals and chilled wine. Take advantage of one of Florida’s finest highlights upon our comfortable catamaran as we sail out to the Atlantic Ocean.

• Hour Glass 2.5 Hours

Full Moon Sunset Sail Ft. Lauderdale

Join us as we cruise along the Intracoastal waterway, you’ll be treated to a tour of the magnificent waterfront mansions and spectacular yachts.

Sunset Cruise Castaway the Day – Miami

Castaway the Day Sunset Cruise is a perfect way to end the day, cruising on the Caribbean Spirit. This Miami sunset cruise calls for sun dresses, flowered shirts, sandals, and cold refreshments.

• Hour Glass 3.5 Hours

Sail and Splash – Fort Lauderdale

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran the Spirit of Lauderdale. Sit back, relax and enjoy one of the best Fort Lauderdale boat cruises .

• Hour Glass 3 hours

Island Adventure – Miami

Enjoy an unforgettable adventure at our island destination during our day cruise from Miami. Experience the Miami lifestyle like a local on board our motor catamaran, Tranquility.

Looking for more to do? Check out these other local tours!

• Hour Glass 1 Hour

Waverunner Beach Rentals

Aloha watersports.

An excellent water sport activity for the whole family!

Seven Isles of Fort Lauderdale Tour

Blue moon outdoor center.

A sightseeing tour of the Seven Isles of Fort Lauderdale!

Kayak and SUP Rentals

2 hour – all day rentals! Choose between a single or tandem kayak, or a stand up paddleboard.

• Hour Glass 45 Min

Speedboat Tour

Thriller miami speedboat adventures.

The Thriller Speedboat Tour departs from Bayside Marketplace in Downtown Miami, Florida. The tour provides the ultimate sightseeing experience in true “Miami Vice Style”.

• Hour Glass 1.5 Hours

Parasailing

Sea rocket water adventures - ft. lauderdale.

Get ready to fly high above the Gold Coast and have a first class experience you will remember forever!

Everglades Day Safari

The Everglades Day Safari offers an in-depth, naturalist-guided day trip into the majestic Everglades! Includes an airboat ride, nature walk, mangrove wilderness boat ride and a delicious lunch!

Guided Tour – Islamorada

Key west day tours.

Welcome to a day in paradise! Enjoy a guided ecotour from Fort Lauderdale to Islamorada and back. Narrated roundtrip transportation is provided by an experienced guide.

Guided Tour – Key Largo Kayaking

Become one with our nature! Enjoy a guided ecotour from Fort Lauderdale to Key Largo and back.

Guided Tour – Key West

Enjoy a guided charter bus tour from Fort Lauderdale to Key West and back. Key West Day Tours conveniently picks up passengers in the Fort Lauderdale surrounding area and Islamorada.

What we do at Tropical Sailing

We offer two convenient locations Miami Marina at Bayside and Bahia Mar Resort in Fort Lauderdale providing great sailing access to South Florida’s finest destinations.

Our sailing and power vessels are Catamarans, that by nature of the design, provide a stable, comfortable platform with plenty of lounging space for your guests.

Our experienced staff consists of licensed Coast Guard Certified Master Captains and first mates certified in first aid and rescue. Every Captain and crew member has been hand picked for their exceptional skills and personality. Our entire staff consisting of charter specialists, captains, crew and mechanics share a passion for South Florida’s waterways, working on the water and sharing their enthusiasm with everyone they come in contact with.

During your trip, a professionally trained captain and crew will pamper your guests with tailor-made service while you cruise the world’s most desirable Caribbean destinations. Special menus can be arranged, transportation coordinated – everything necessary to assure an adventure that your group will remember for a long, long time!

Discover the ultimate in extravagance and personalized service as you step aboard our luxury crewed yachts. Stylish, spacious and elegant, our prestigious catamaran will delight you. Equipped to the highest standards, with special features and state-of-the-art electronic and water sports equipment, you can expect quality similar to that of a luxury five-star hotel.

We look forward to sharing our love of sailing and water sports with you, your family and your friends!

See Why We're Highly Rated!

Absolutely amazing! Cannot recommend this enough! We got to see dolphins, jumping fish, the sunset, and sit with our legs on the net of the catamaran. I can’t recommend this enough! It should be an especially part of anyone’s Ft. Lauderdale vacation!

Captain E and Nick were great on this tour! We brought our grandkids and they were very attentive to them! We all had a wonderful time! We would highly recently this sunset tour! Beautiful views and great crew!

Great time with Captain E and Nick! Absolutely worth doing, especially on a hot June night! Will book again on our next Ft. Lauderdale trip.

This is hands down a must if you have a family with kids!!! Captain Joe and Danny were amazing and we all had the best time. Super accommodating and helpful and made the whole sail from start to finish a great experience! Don’t hesitate to book this excursion you won’t regret it. The price was perfection for the experience you got.

One of the best romantic dates I could ever imagine. They sailed us out in the Miami Bay (Biscayne Bay) and we got to watch the sunset. Wow! A clear 5/5

Crew on board was amazing and indulged with the participants on board. They gave great knowledge of the houses and the city in general! The cruise was relaxing and calming all together I would definitely recommend!

Beautiful views, helpful, accommodating and entertaining crew and a nice long route all made for a great value trip

• Crab Island Adventure
• Snorkel Adventure
• Sunrise Sail
• Sunset Adventure
• Dolphin Adventure
• Santa Rosa Islands
• Proposal/Anniversary
• Fireworks Adventure
• Photo Gallery
• Current Weather
• Wind Forecast
• Local Regattas
• Surf Forecast
• Sailor Slang
• What makes a good sailor?
• The Ocean Race

Exclusive Catamaran Sailing Adventures

Come explore the majestic waters of the emerald coast, catamaran sailing in the emerald coast sun..

Are you visiting the Destin, Okaloosa Island, Navarre Beach area and needing a little adventure in your life? This is what you're looking for aboard catamaran Destin Sailing Adventures. The boat is a Stiletto 27 Special Edition Catamaran, designed to provide maximum sailing pleasure and performance over a wide range of wind and sea conditions. Made for adventure and racing, so it offers plenty of excitement and comfort for any occasion. The boat is outfitted with a 20hp motor, so if the wind isn't blowing we can still get out and play! Charter comes with a local captain to take you to all the local spots, while you sit back and relax.   

We offer an array of private tours, cruises, and adventures at a reasonable price. The longer you book the more fun you can have and the more money you’ll save. These are private charters, so you won’t be with a huge crowd during these unprecedented Covid 19 times. Just you and the people you bring. Come explore Crab Island, Sunset cruises, Sailing lessons, Dolphin Tour, Snorkeling, Marriage Proposals, Birthdays, sightseeing tours, Anniversary celebrations, and more with us today.    

We are dedicated to making sure you have a great time while visiting the Emerald Coast. All trips include up to 6 Guests, Licensed Captain, cooler with ice, bean bag chairs, sound system, and a head (bathroom). Our Captain has 15 years of local experience racing/sailing along the Gulf Coast of Florida and more! Please contact us for special requests.

 One of the best catamaran sailing adventures Destin East Pass, Okaloosa Island, Santa Rosa Island, Choctawhatchee Bay has to offer!

Memorial Day

Summer is almost here!

Mins Minutes

Secs Seconds

Jetty East Snorkeling

Usually one of the busiest spots during the summer, so book your trip early to beat the crowds.

Snorkeling with a Manatee.

Early bird got the manatee this day!  

Spanish Mack

Up close and personal to a Spanish Mack doing its thing!

Pick up location

Adventure marina, okaloosa island.

1201A Miracle Strip Pkwy SE, Fort Walton Beach, FL 32548, USA

850-217-3448

"A ship is always safe at the shore, but that is not what it is built for."

Albert Einstein

Destin Sailing Adventures

1201B Miracle Strip Pkwy SE, Fort Walton Beach, Florida 32548, United States

Copyright © 2023 Destin Sailing Adventures - All Rights Reserved

AFTERNOON SUN SAIL

Life is better on the water... Come sail with us!

Adults - $60 / Children under 12 - $30

A 2 hour Sailing excursion lay back, relax, sip a delicious cold drink from our service bar and listen to a variety of music. Custom built 50 foot Catamaran. Spacious sundeck. loads of space to view. Abundant seating area. Convenient service bar Two restrooms Beer and Wine Licence Stereo Sound System Capacity 41 guests

There is no better way to sail the Gulf of Mexico waters than aboard the Kai Lani Catamaran!

View Booking Info and Availability

Arrive early for check in

DAILY SUNSET CRUISES

The perfect way to end your day or kickoff your night!

• Relaxing Sunset Sail Monday & Friday $60 for adults $30 for children (under 12)
• Sunset Sail with Live Music Tuesday, Thursday & Saturday $75 Adults and $30 for children (under 12)
• Sangria Sunday Sunset Cruise Sunday Evening $80 Adults and includes bottomless Sangria $30 Children (under 12)

Enjoy a 2 hour Sunset Sail in the Gulf of Mexico or Clearwater Bay. Whether you choose to have a few drinks and make new friends dancing to live music or enjoy a wonderful romantic cruise with that special someone, we know you'll make a memory to last a lifetime.

SPECIAL EVENT CRUISES

Join us for one of our monthly special event cruises

Our monthly event cruises feature an open bar, food and may also have live music. Many of these cruises are also partnered with non-profit organizations to increase awareness or funds. So raise a glass with your friends while helping the community!

Just some of our special events include our Valentine's day Sunset Cruise, Easter Brunch Cruise and July 4th Celebration Sail

We also have all inclusive packages available at discounted rates. These packages include other goodies like party favors for your bachelor or bachelorette party or decorations and special touches for your birthday or reunion celebration.

Please include in your email a phone number in the contact form below so one of our representatives can be in touch with you.

Contact Us for Pricing and Availability

Where are you located?

Where do i park, what about bad weather, can we bring our own alcohol, are guests required to wear life jackets, is there a restroom on the boat, what is the unlimited drink wristband, how do i pay for drinks on board if i don't have a wristband, can i host a private party on the boat.

It is best to reserve as early as possible, as last minute bookings are hard to get. We suggest a few days ahead of time. Walk-ups are welcome if you want to leave your adventure to chance of available space on one of our day trips.

Contact Info

Address 25 Causeway Blvd, Slip #49 Clearwater Beach, FL 33767

Phone (727) 446-6778

@kailanicat1 on Facebook

@kailanicatamaran on Instagram

Reservation and Charter Policies

© 2024 Kai Lani

Use code BAREFOOT for 10% off Guided Tours!

Catamaran Cruises in Key West, FL

Escape the downtown crowd - cruise with billy.

Key West’s nautical history is all based on its proximity to the world’s 3rd largest living coral reef. From pirates and privateers to ship wreckers and fisherman the draw has always been the sanctuary provided by the Florida Great Barrier Reef.  Key West’s coral rock islands trace a contiguous pathway from the Atlantic Ocean & Gulf of Mexico intersect all the way to mainland Florida. To this day our primary industry, tourism, celebrates our unique natural ecosystem in the shadow of the reef. 

Whether you want to cruise a couple of hours, island-hop all day, or see our beautiful wildlife, Billy has you covered! Bring your reef-safe sunscreen, and we’ll take care of the rest!

Ticketed Tours

• Kid Friendly!
• Clock 3.5 hours
• Info Up to 36 people
• Users All ages

Dolphin Watch & Snorkel Tour

Search for wild dolphins in their natural habitat and snorkel Key West’s backcountry waters off the Seabreeze!

• Most Popular Cruise
• Clock 2 hours
• Info Up To 38 People

Key West Sushi & Sunset Cruise

Dine on fresh sushi while taking in the famous Key West sunset. You will cruise past the southernmost point of the U.S., tropical beaches and a Civil War era Fort Zachary Taylor Historic Sate Park.

Private Experiences

• Our Newest Boat
• Clock 2 to 8 hours
• Info 1-6 People

Barefoot Private Charters

Create the perfect outing for up to 6 with a custom charter! Cast off from the island and explore the unique nature surrounding the Florida Keys!

• Clock 3 Hours
• Info 1 to 40 people

Morning Island Charter

Spend your morning at the sandbar and experience the turquoise waters surrounding Key West at a slower pace on this private charter.

• Clock Varies

Seabreeze Charters

Snorkel, see Dolphin, or visit a sandbar with an open-air cruise for up to 40 people. Create the perfect escape with a private adventure aboard our 45-foot Corinthian catamaran!

Leave a review and win a chance for a free sunset cruise for two!

• Swim & Sail
• Sunset Cruise
• Private Charter
• Celebration of Life
• 4th of July Fireworks
• Holiday Boat Parade
• Cancelation Policy
• Code of Conduct
• Gift Certificates

386-871-7778

Ponce Inlet & New Smyrna ICW Catamaran Cruises

Reserve Your Cruise Today!

Photo Gallery

Fun Cat Sailing - Arabella

4958 S. Peninsula Drive, Ste. D Ponce Inlet, Florida 32127

Copyright © 2024 Fun Cat Sailing - Arabella - All Rights Reserved.

Powered by GoDaddy

This website uses cookies.

We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.

Kathleen D Sailing Catamarans   | Call or Text Now for more information 941-896-6400

Sarasota & Siesta Key

Discover the ultimate sailing experience with kathleen d sailing catamarans from our home base in sarasota and siesta key..

With Kathleen D Sailing Catamarans your unforgettable sailing adventure begins here. Conveniently located in Downtown Sarasota at Marina Jack, our prime spot ensures easy access and a seamless start to your day on the water.

Join us at Kathleen D Sailing Catamarans for the ultimate sailing experience along Sarasota’s stunning coast. For more information or to make a reservation, contact us at 941-896-6400 . Your adventure awaits!

Public & Private Sails from Sarasota & Siesta Key

Discover the joy of public sails with kathleen d sailing catamarans.

Embark on an exquisite sailing adventure tailored just for you or shared with other sea enthusiasts. Our public sails are perfect for individuals, couples, or small groups looking to experience the breathtaking beauty of Florida’s waters without chartering a full private boat. Each sail requires a minimum of four passengers, ensuring an intimate and personalized experience. At just $45 per person, per hour, plus sales tax and convenience fees, you can indulge in the serene splendor of the ocean and create memories that will last a lifetime. Don’t miss out on this unique opportunity to connect with the sea and fellow adventurers. Set sail into the horizon and let the winds guide your journey!

“Join us at Kathleen D Sailing Catamarans for the ultimate sailing experience”

For more information or to make a reservation, contact us at 941-896-6400 . Your adventure awaits!

Embark on an Exclusive Adventure with Our Private Charter Sails

Set sail on a private charter with Kathleen D Sailing Catamarans and tailor your sea journey to your personal tastes and desires. Ideal for groups seeking a more intimate and customized sailing experience, our private charters are perfect for gatherings of friends, family reunions, or special celebrations. With a minimum requirement of just four passengers, you can easily book a sail that’s designed just for you and your group. Navigate the beautiful waters at your own pace, choose your own path, and create unforgettable memories with your closest companions under the open sky. Let us help you turn a day on the water into a personalized adventure that’s as unique as you are.

Private & Public Sails Available from Sarasota & Siesta Key

Proud Partners

VISIT SARASOTA COUNTY (VSC) is the official tourism marketing entity and primary provider of visitor information for Sarasota County

For more information or to make a reservation, contact us at 941-896-6400 .

Join us at Kathleen D Sailing Catamarans for an unforgettable journey along the beautiful Sarasota coast.

Kathleen D Sailing Catamarans

2 Marina Plaza (Dock E, Slip 20) Sarasota, FL 34236

email: [email protected]

Call: 941-896-6400

What Should I Bring?

• Directions to Echo, Cruise Ship & K.W. Passenger Info

Key West Info

• Cancellation Policies, Terms and Conditions
• Catamaran Echo Videos
• Echo 2 Private Day Charters
• Echo 3 Private Day Charters
• ECHO Upgrades
• Tasting Notes
• Echo 2 Sunset Cruise
• Echo 3 Sunset Cruise

ECHO Fall 2024 specials!

Book during august and september for any future date for great promo code discounts., $200 off all echo 3 private charters – use promo code “200echo3”, $100 off all echo 2 private charters – use promo code “echofall100”, $20 off all echo 2 and echo 3 public trips (by the seat) – use promo core “echofall20”.

Catamaran ECHO 2

Current public & private trips – book here online, (free shuttle to the echo 2 dock from the perry hotel).

Catamaran ECHO 3

Premium public and private trips – book here online, (free shuttle from downtown key west, free parking, easy uber), …is a fast and comfortable sailing machine, providing the most stable ride on the water. naturally it’s a catamaran.

And with our big bimini top, you can get all the Key West sun or shade that you want. The fresh water shower on deck comes in handy on those hot days. A private bathroom in the cabin makes a day in the wildlife refuge civilized and helps protect our tropical waters.

ECHO 2 is located at the “Key West Historic Seaport” which is downtown in Old Key West at the famous Key West Bight. The Historic Seaport “Harbor Walk” goes right around the water’s edge and leads right to ECHO’s dock along side the famous “Boat House Restaurant at Turtle Kraals”. Spend the day on the Harbor Walk before and after your ECHO trip and visit all the great shops, restaurants and bars and galleries. This is where all the locals hang out!

So come and hang out in the coolest part of town and cruise with us at Catamaran ECHO ..

ECHO'S Official Website

Wild Dolphin

Snorkeling & Sailing Adventure

Click here to read more!

Private Day Charters

Echo 2 – Downtown Key West Echo 3 – Uptown Key West

Sunset Cruise - Adults Only

Private Trips Available (all ages welcome)

Towel (day trips), Sun screen applied (no oil), Hat, Camera, Sunglasses (polarized best), a jacket in fall, winter, spring (even if you think it’s warm out), a small bag to secure your things, a few bucks and a Big Smile!

Echo Upgrades

Please reserve upgrades in advance while reserving here online, or by phone or email before the trip.

Directions, Cruise Ship & K.W. Ferry Passenger Info

Certificate of Excellence 2019

Read Reviews

Call for Reservations

1-888-579-4782.

• Name * First Last
• Email This field is for validation purposes and should be left unchanged.

Our Activities

Downtown – Key West Historic Seaport

Catamaran Echo 2 - Wild Dolphins! Snorkel & Sailing Adventure

Catamaran Echo 2 - PUBLIC Sunset & Moët Sail

Catamaran Echo 2 - PRIVATE Day Charters

Catamaran Echo 2 - PRIVATE Sunset & Moët Sail

Uptown Key West – The Perry Hotel and Marina

Catamaran Echo 3 - Uptown Sunset & Moët Sail

Catamaran echo 3 - private uptown sunset & moët sail, catamaran echo 3 - champagne dolphin sail & reef snorkel, catamaran echo 3 - premium private day charter.

ST. PETERSBURG, FL & GULF BEACHES

SAILING CATAMARAN CHARTERS

Looking for Adventure?

SUNSET CRUISES

OVERNIGHT SAILs

MEET THE SAILING CATAMARAN

Come Sail with Us!

We’re so excited to share our boat with you! Enjoy your sailing or sunset charter aboard our brand new catamaran, with its modern design, ample lounge space, and plentiful amenities perfect for chilling out and enjoying the sea.

Wiley Pixie

Schedule Your Custom Charter

Experienced captains.

Our experienced captains are knowledgeable in all the best areas of St. Petersburg and its beaches, ensuring you have a fun and safe sailing charter.

Luxury Amenities

Indulge in our many charter amenities, designed to provide the ultimate in fun, comfort, and style during your sailing adventure.

Lounge Space

Catamarans are the ultimate vibe. Relax in our spacious and comfortable lounge areas, perfect for enjoying the scenery and soaking up sun.

SUNSET CATAMARAN SAIL

Tampa Bay’s best sunset view.

Embark on a breathtaking sunset sailing cruise as you watch the sun dip below the horizon and enjoy the water at its finest. With plenty of space for you and your guests to relax and unwind, you’ll be treated to an unforgettable experience, complete with comfortable lounging areas, and all the amenities you need to enjoy a perfect evening on the water. Perfect for corporate events, birthday parties, families, groups, and proposals!

DAY CHARTER SAILS

Day Sail Packages

Enjoy a full or half day charter out on the water with our custom sail packages, where you and your friends can soak up the sun, relax on the spacious lounging areas, and take in the breathtaking ocean views. With the flexibility to customize your itinerary, you can choose from a variety of St. Petersburg’s favorite beach and water destinations to anchor at, where you can enjoy swimming, snorkeling, and other water activities.

OVERNIGHT CHARTERS

Sail Under the Stars

Set sail on an unforgettable custom adventure with our overnight cruises, led by an experienced captain. Spend your nights under the stars on our 3BR/3BA catamaran, with all the amenities you need to enjoy a comfortable charter experience. From secluded anchorages to stunning sunsets and sunrises, discover the beauty of the sea and the freedom of sailing, as you explore a range of destinations from St. Petersburg to Clearwater, all the way down to Key West if you choose.

Adventure from your inbox

Top 5 Must-Visit Destinations on a Sailing Cruise from St. Petersburg, FL

Discover the best places to visit on a sailing cruise from Treasure Island, FL. Explore these breathtaking destinations, including John’s Pass Sandbar, and make your trip unforgettable!

Sunset Sailing Around Treasure Island: Your Guide to Choosing the Perfect Boat

There’s nothing quite like watching the sun dip below the horizon while out on the water. If you’re looking for a perfect way to spend an afternoon or evening in Treasure Island, sailing is an excellent option. With a number of different companies offering sunset sails, it can be tough to know which one to…

FOLLOW THAT DREAM SAILING ​​​Amelia Island Catamaran Cruises

Good things come ​from​ combining luxury and passion.

Call now to book your luxury catamaran cruise around Fernandina Beach and Amelia Island for a day you and your guests will not forget:   (904) 468-3758

Catamaran Cruises

Follow That Dream Sailing

Luxury Catamaran Cruises

We provide luxury catamaran cruises in one of the most beautiful areas of the US East Coast. With stunning landscapes and lots of wildlife to enjoy, we offer sunset and sightseeing cruises around Fernandina Beach, Amelia and Cumberland Islands, and overnight cruises to and around St. Mary's, Saint Simon's Island, Jekyll Island, Jacksonville, and St. Augustine. Join us for a memorable experience you and your guests will cherish.

Our Catamaran

Follow That Dream Catamaran

Follow That Dream , is a Lagoon 410 S2 sailing catamaran. She is 41 feet long and 24 feet wide which provides a comfortable and stable ride. You'll have lots of room to spread out and enjoy gliding on the water or to sit with friends and enjoy the experience with food and drink. Your captain and crew are highly experienced sailors and hosts and will ensure a safe and fun experience. We look forward to welcoming you aboard.

• Shell Island Snorkel & Sail

Dolphin Sunset Cruise

Fireworks cruise.

• Private Sailing Charter
• About Our Catamarans
• Meet Our Crew
• FAQ’s
• Things To Do

(850) 234-7377

5201 N. Lagoon Dr. Ste. 3 Panama City Beach, FL 32408

Let's Set Sail!

Island Time Sailing in Panama City Beach, FL

Snorkeling, sunset cruises, and dolphin tours.

The Island Time Sailing catamarans , on Panama City Beach, have been making great family memories, since 1999. We’re known for our famous “Rum Punch,” great music and a wonderful crew. This is where you can see dolphins at Shell Island , snorkel St. Andrews Bay , and enjoy the best of Panama City Beach, FL. If you’re looking for the ultimate sunset sail or perhaps an amazing snorkel trip and an unforgettable dolphin cruise, you’ve found it! We also have private sailing charter cruises for your wedding, birthday, or sailing party!

Come and experience the best sunset cruises Panama City Beach has to offer!

Catamaran Sailing Trips

Relaxing Activity Level

Shell Island Snorkel & Sail

Moderate Activity Level

Island Time Sailing Reviews

"megan benskin".

Worth every penny !! I took 4 kids ages 10 to 2 years old and they all had a blast. The crew kept my kiddos dancing and having a great time. Plenty of water time and seen dolphins and so much more. Shout of to our crew 🐬

— Megan Benskin, July 2024

More Aquatic Adventures Available

Pontoon Boat & Jet Ski Rentals, Dolphin Tours & More from our sister company website Lagoon Pontoons .

Visit Lagoon Pontoons

Island Time Sailing

5201 N. Lagoon Dr. Ste. 3 Panama City Beach , Florida 32408

©2024 Island Time Sailing. All Rights Reserved   | Privacy Policy   | Site Map     Site by KMA .

• Book a Cruise
• Cruise Schedule
• “Cool Beans” Catamaran
• “Lil’ Beans” Pontoon
• Photos & Video
• Five-Star Reviews
• Directions & Parking

Take a Virtual Journey with Cool Beans

Choose a day-sail, champagne sunset or a private catamaran cruise below to enjoy a sailing adventure aboard our 42 foot sailing catamaran, Cool Beans .

If you’re looking for something different we can explore Keewaydin Island or one of the many other hidden treasures aboard Lil’ Beans , our luxury pontoon.

Day-Sail Cruise

Price includes a delightful escape to the beautiful waters of the Gulf of Mexico. Relax and enjoy your sailing experience on our beautiful catamaran while watching the abundant sea life and native birds of Southwest Florida.

During our day sails, we do stop for approximately 35 minutes at one of the many beautiful beaches of Southwest Florida – Keeywaydin Island, a barrier island in South Naples to swim, explore , and collect shells.

(Please note stopping at the beach is based on weather conditions. If it is too rough/choppy in the Gulf, the Captain may choose not to include a stop at the beach. Also know that to get to shore, you must swim in. We drop anchor in approx. 6 feet of water, approx. 30 yards off shore. Life jackets and floaties provided if needed. You are also welcome to stay on the boat to soak in the sun and scenery during the stop if you do not want to swim.)

• Complementary – soda, water, beer and chardonnay included
• You can also bring aboard additional food/snacks and beverages (no red wine please) on-board. Due to insurance liability, hard liquor is not allowed on our vessels.
• Smoking and Vaping are prohibited.

Gratuity Extra

Please note: 18% Gratuity will be added for parties of 7 or more.

• * Children must be at least two-years old.
• ** 24 hour prior notice cancellation policy for parties of 6 or under
• *** 48 hour prior notice cancellation policy for parties of 7 or more

Champagne Sunset Cruise

See Southwest Florida the way it was meant to be seen . . . by water! Escape from the crowds and set sail to take in our beautiful sunset. Sit back and enjoy a warm breeze in your face, a glass of champagne in your hand and the view of one of the most beautiful sunsets you will ever experience. Sail back to port and marvel at the view of the Gulf of Mexico and Naples/Marco Island beaches with the sunset lighting your way.

• Complementary – soda, water, beer and chardonnay included
• Complementary glass of champagne at sunset

Private Day-Sail or Sunset Cruise

 Would you like to have the boat to yourselves? Booking a “Private Cruise” is the perfect way to celebrate any occasion while enjoying your privacy. Choose from one of our Day Sails or our Champagne Sunset Cruises and leave the rest to us. Price includes items described above for your specific choice of cruise.

• ** 48 hour prior notice cancellation policy

Lil’ Beans Pontoon Island Beach and Sunset Adventures

Enjoy a Private 2 ½ hour Luxury Pontoon Tour for Up to 6 Guests for our Day Excursions or a 2 hour Sunset Excursion. Our Pontoons are perfect for Island hopping, up close Eco/Nature and Shelling on Keeywaydin Island. A “Must Do” while visiting SW Florida! (Sunset Charter arrives back to dock approximately 15 minutes after Sunset)

Keewaydin Island– A Deserted Barrier Island

Keewaydin Island is an 8 mile long unabridged barrier island just to the north of Marco. A fantastic sandy beach stretching the length of the island, with great shelling and opportunities to see plenty of wildlife. It serves as a sanctuary for wildlife and a popular recreational destination, especially at weekends. Keewaydin provides a great opportunity to experience Florida’s natural coast and is a vital nesting ground for Least Terns and Loggerhead Sea Turtles.

Hide-A-Way Beach/Sand Dollar Island – An Unspoiled Gulf Beach

Located just north of Tigertail Beach you’ll find Sand Dollar Island which abounds with wonderful seashells and is absolutely breathtaking and totally natural. Many of Florida’s beach-nesting shorebirds that face conservation challenges can be regularly spotted on Sand Dollar, including the Snowy Plover, Least Tern, Black Skimmer, American Oyster Catcher, and Wilson’s Plover.

• GOOD FOR CHARTERS COMPLETED BY SEPTEMBER 30 th , 2024
• * Price includes soda and water
• ** Children must be at least two-years old
• *** 48 hour prior notice cancellation policy

Groups & Special Occasions

Small intimate sunset weddings.

Make memories to cherish for a lifetime when you exchange wedding vows during your Cool Beans private sunset sail. Whether you have something particular in mind or need ideas, we can provide some wonderful options to assure that your wedding is everything you expect and more.

Romantic Sailing Excursions

Create the perfect moment to ask your significant other for their hand in marriage with a private cruise along the beautiful waters of Southwest Florida. Ask us how we can help to make your interlude aboard the Cool Beans a magical event to treasure for a lifetime.

Private Anniversary Cruise Celebrations

Reaffirm your love for one another alone or among special friends and loved ones aboard the Cool Beans. Your private sailing excursion is sure to be fun, romantic and memorable.

The Ultimate Birthday Private Cruise

Making a magical birthday celebration aboard the Cool Beans is one of our specialties. Whether your event is for a family daytime cruise, adventure among friends or a private sunset intimate sail, we are here to make your birthday cruise an event to remember.

Bachelorette Party

What a great way to celebrate the Bride to Be with her “Last Sail Before the Veil!” Specializing in small groups up to 20, booking a Bachelorette Party with Cool Beans Cruises will truly create a lasting memory..

Share the gift of a Cool Beans Cruise!

Use promo code:: 5DIPSIP to save $5 on Sip & Dip Catamaran Cruise!

• Most Popular!

Sunset Catamaran Cruise

2 hours | $45 per person

Quick Details

• Duration: 2 hours
• Refreshments: available for purchase on board or for pre-order
• Departing location :  138 S Flagler Dr. West Palm Beach, FL 33401

Child (12 & under)

Prepare to drink in the breathtaking south florida sunset, experience a scenic catamaran cruise in west palm beach.

Departing from the Downtown West Palm Beach docks at Clematis Street & Flagler Drive, our catamaran cruise offers a breathtaking journey along the picturesque Downtown skyline. Glide past 125 years of historic and modern architecture from the comfort of padded seats or with your feet dangling over the catamaran’s bow nets as the Atlantic waters flow beneath.

Our friendly crew is here to enhance your experience with a selection of tropical beverages, beer, wine, cocktails & mocktails and snacks. As you cruise past the Mega yachts at Rybovich, enjoy a curated mix of tropical, reggae, pop, and classic music. The adventure continues toward Peanut Island, home to the Historic Coast Guard station and John F. Kennedy’s famous 1960 bunker.

On the return trip, you’ll get up-close views of Palm Beach’s palatial mansions, the Historic Biltmore Hotel, and the iconic Breakers Hotel. Capture stunning photos of the Flagler Museum and the lush gardens of the Society of the Four Arts as we approach the dock.

Perfect for Families, Small Groups, or Couples

Whether you’re with family, a small group of friends, or enjoying a romantic outing, this cruise offers something for everyone. It’s one of the most fun experiences you can have in Palm Beach!

Comfort & Amenities :

*Covered seating area for shade lovers *Spacious deck for photos, socializing, or dancing *Onboard restroom and Coast Guard certified safety equipment *Pre-order wine & cheese options

This is not a Narrated cruise (check out our Sightseeing cruises for Narration ) but be sure to ask your crew if you would like them to point out a few of the “highlights” along the way!

(Also, be sure to check out the public Sunset Sails also available on “ Hakuna Matata ‘s” sister catamaran vessel, the NEW “Motunui” )

After your cruise, check out the dozens of restaurants, shopping and art Galleries throughout Clematis Street, CityPlace or Northwood Village. All walkable or use the FREE www.ridewpb.com shuttles.

*** CLICK HERE for our Pre-Order and Onboard Menu Options!***

*No outside beverages or food onboard the Hakuna Matata catamaran .

$3 water conservation fee applied at checkout.

Related Activities

• Partially Narrated Cruise
• Anchor Cruise
• Hour Glass 2 hours

Sightseeing Cruise

Delight in a 120 minute partially-narrated and entertaining Intracoastal Waterway Sightseeing cruise of the beautiful Palm Beaches aboard Visit Palm Beach’s 50′ Catamaran ‘Hakuna Matata’!

• Happy Hr. Time & Price!
• Hour Glass 1.5 Hours , 90 Minutes

Flamingle Happy Hour Cruise

Looking for a perfectly relaxing and fun way to end your day or begin your evening? Enjoy a happy hour cruise for all ages!