Top Fort Myers Sailing Tours

Whether you’re on Spring break with your girlfriends or backpacking solo, this sunset booze cruise in Fort Myers is the perfect end to a day in paradise. It’s a bring–your-own-booze party boat, so you supply the tipples and your awesome crew take care of the rest – ice buckets, tunes, party games and, with some help from Mother Nature, that glorious Floridian sunset. Come away with lasting memories and some new drinking buddies.

Unwind after a long day aboard a relaxing sunset cruise along Fort Myers Beach. Watch as the sun starts to dip below the horizon and changes the sky from blue to several hues of oranges, reds, and pinks. Relax on the spacious catamaran with a drink in hand and watch as the scenes pass you by.

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the sun dips below the horizon. For two and a half hours, enjoy the stunning views along Fort Myers Beach and Sanibel Island, perfect for capturing unforgettable memories. With a maximum of just six guests, this intimate experience allows for a relaxed atmosphere where you can bring adult beverages and snacks while enjoying the serene waters. Sailing SW Florida since 2009, don't miss out on this popular sail that brings out the romance in everyone. Locally owned and operated by 2 licensed captains that are also husband and wife. Abundant FREE PARKING and two highly rated restaurants at the marina. - Enjoy a beautiful sunset sail with maximum of 6 guests - Cruise along the scenic shores of Fort Myers Beach and Sanibel Island - Perfect for capturing memorable photos during the golden hour - Bring your own drinks and snacks for a personalized experience

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and a myriad of sea creatures and incredible Birds! The best part is that then you can share what you have learned so we can all help to preserve the beauty of the bay and its precious Wildlife.

Leave the crowds on land behind and sail into the Gulf of Mexico on board the immaculate Orion’s Child with this small-group sailboat tour. Set off with the husband-and-wife crew and relax on board as you pass shrimp boats and waterfront homes lining the channel. Once in the gulf, the sails are raised and course set for Sanibel lighthouse or Fort Myers Beach. Spot dolphins, sea turtles, and other marine wildlife as you fly across the waves.

Party on the Florida waters with your pals during this floating BYOB tiki bar experience off Fort Myers Beach. Whether you’d rather sip and sunbathe or mix and mingle with new friends over party games, there’s plenty to enjoy while you float along on the crystal blue sea. All while your crew is on-hand to make sure everyone is staying safe while you have fun.

With limited capacity, this cruise offers a social but uncrowded setting—a laidback alternative to the busy tiki boats that cross the waterways of Fort Myers Beach at night. Enjoy a relaxed BYOB format while a captain handles navigation, so that you can focus on the atmosphere. Enjoy music and scenic views for an upbeat, unique way to experience Fort Myers after dark.

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything you need, and bring the party with custom curated playlists, Tiki-Oki, and party games. We'll stop at a secluded sandbar where you can enjoy the on board water slide, Paddleboard, and Floats. Our return trip keeps the party going.

Sail along the waterways of Fort Myers Beach and Sanibel Island aboard this relaxing cruise. Board your catamaran and enjoy a smooth sail along the blue-green waters. Pass by several landmarks including the Sanibel Island Lighthouse and Fort Myers Beach Pier. You also have the opportunity to spot local wildlife like sea turtles, dolphins, and even manatees.

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. Whether you want to dance, sing Tiki-Oki, slip down the on board water slide, or just relax and enjoy the sunset, this cruise will make all your dreams come true!

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on board sound system with Tiki-Oki, and the friendliest most fun captains around. You'll be sure to have the time of your life.