Top Fort Myers Cruises & Sailing

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.

Sip a drink and relax while the crew sails to their favorite scenic spots around the beach. You’ll get stunning views of the sunset over the water and have a chance to spot a host of local wildlife, from dolphins to manatees, while you enjoy the ride. Make memories that will last a lifetime on your next Fort Myers trip with the help of this friendly crew.

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.

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.

Come aboard this tiki boat and set sail for fun from Fort Myers Beach with your captain on this group cruise. Look out for dolphins, manatees, and other marine wildlife while you coast through the Florida waters and sip a chilled drink. The covered catamaran has plenty of space and shade so you can protect yourself from the Florida sun.

Climb aboard our custom round tiki boat for a 90-minute public cruise that blends tropical vibes with easygoing fun. Bring your favorite beverages (cooler and ice provided), settle into plush wrap-around seating under a shaded bamboo canopy, and let your expert captain navigate the calm waters. With a full stand-up bathroom onboard, you can stay refreshed and comfortable without missing a moment of the action. Drift through mangrove-lined backwaters and scan the bay for local wildlife—dolphins, manatees, rays, and coastal birds—though sightings aren’t guaranteed, the search is part of the fun. Our premium sound system lets you set the mood with Bluetooth and aux hookup. This floating tiki bar boat delivers pure Florida fun in a friendly, social atmosphere.

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.

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.

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on our public activities or having an intimate celebration with your chosen ones on private outings. Fancy a tipple while the waves lap around you? Bring your beverage of choice – just remember, BYOB! Safety and fun go hand-in-hand at Tiki Pub. Every voyage is captained by our experienced crew, ensuring your adventure is smooth sailing from start to finish. Plus, for those looking to have a blast without splashing too much cash, we offer a wallet-friendly option to revel in Fort Myers' captivating waterways.

Captain Lauren with SWFL Party Pontoon is a marine biologist with years on the water in the area. Tours are catered to the group on board, so whether you want to just relax, shell, learn about the area, we have you covered. Floaties and beach games (and sand castle making toys for the kids) are always included. If you want to snorkel, we do not provide gear, but that can be done at some of the beaches. Book direct for more info or other tours.

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.

Come aboard The Oasis and leave your worries on land! Bring your favorite drinks (cans only) and experience Charlotte Harbor’s most relaxing way to meet the locals—our playful bottlenose dolphins. We keep drinks ice-cold in a jumbo cooler and provide cups, plates, napkins, and a private electric-flush restroom. Lounge under the tiki roof or stretch out on plush seating while island tunes roll. This isn’t just a boat ride—it’s a naturalist-led eco tour. Learn how dolphins hunt and raise calves as we slow for respectful viewing (sightings common, never guaranteed). Watch for seasonal manatees, ospreys, pelicans, rays, snook, and the mangrove nurseries that power this estuary. Kids (and curious adults) love our discovery bucket—conch shells, captain’s spyglasses, fossils, and skeleton models bring the ecosystem to life. You’ll leave with new facts, great photos, and that vacation feeling.

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 your worries on land. The Oasis is bringing sunset views, island tunes, LED lights, and plush lounge seating for up to 30 guests. Custom-built to bring the ultimate Jimmy Buffet style cruise to you. Construction on The Oasis finished in January of 2024, making it the latest and greatest tiki boat on the harbor. When you have to take a liki on the tiki there's a fully enclosed and private restroom with an electric flushing toilet. Chill in the shade under our Tiki Thatched roof, or sit up front to catch some sun and work on your tan. When the sun goes down, dance under the LED lights and move to the sounds of our Oasis surround sound system. We have full Bluetooth capabilities, so feel free to request a song! Both adults and children may join us. Please leave all pets/animals at home as they are not allowed onboard. No Smoking or Drugs allowed onboard at any time.

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.

Explore the stunning waters of the Gulf of Mexico and Pine Island Sound on a private, fully customizable boating adventure. Guided by Captain Jenni, the island’s only female captain, you'll visit secluded islands accessible only by boat, search for marine wildlife, snorkel in crystal-clear waters, and collect shells along pristine beaches. Customize your day with a stop at the waterfront restaurant on Cabbage Key, discover hidden coastal gems, and learn about the area's fascinating history and local culture from a lifelong resident. Perfect for families, couples, and adventure seekers of all ages, this unforgettable experience combines sightseeing, wildlife, relaxation, and exploration in one memorable day.

Get up close and personal to Florida’s wildlife on a paddleboard tour through Fort Myers. Get your gear and slowly navigate the waterways in search of West Indian manatees, dolphins, sea turtles, pelicans, and many more species. Stop to search for seashells at a nearby beach and take in the coastal views before heading back to the launch point.

Capt. Mike, a Snook Bight Marina Fishing Pro staff guide, is happy to assist you in every way from baiting your hook, casting and cleaning any fish within the legal-size limit. If you are a nature lover we can see dolphins any time of year near Fort Myers Beach. In the summer months, there are also excellent opportunities to spot manatees. 4 hours of fishing fun, we fish within 3 miles of shore and travel time between spots is anywhere from a few minutes to 20 to take advantage of optimal fishing conditions. The boat is stable, has partial shade, a small bathroom, and an iced cooler on board for your favorite food and drinks that you provide. Or there is room for your own cooler. We are handicap accessible and limited to 6 passengers max. We provide everything you will need for fishing, you just bring food and drinks.

Cast your line in Florida’s abundant waterways and enjoy a relaxing boat day with this private charter service. Board your vessel with your group and choose to fish in the back bays to target snook, redfish, and trout, or offshore for snapper, grouper, mackerel, and shark. This tour is completely customizable to your group’s interests and skill levels.

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!

Sun-N-FunTours & Charters offers one of the few opportunities to take out your entire family or larger groups on a private tour. Your boat is very spacious and includes a head/changing room onboard. The Captain is very knowledgeable of the local waters, wildlife and history in the area.

We’re not just another tiki boat—we’re your locally owned and operated island escape. Unlike the “cookie-cutter” tours, we keep it personal with private, custom trips for 4 to 12 guests, so your group always gets the boat to themselves. Our captains don’t just drive the boat—they interact, share local stories, and make sure you’re having a blast from start to finish. We’re proud to be independently owned, which means we focus on people, not policies. Whether you’re here for a sunset cruise, dolphin spotting, or just to party with friends, every tour is tailored to your vibe. Add in our roomy tiki boat, and the best BYOB setup on Fort Myers Beach—and you’ll see why memories made with us last long after the sun goes down.

Take a ride along the waterways of Fort Myers Beach aboard a private tiki boat during this excursion. Sit and relax on the comfortable vessel, that offers both shaded and unshaded seating, and keep your eyes peeled for local wildlife, mainly the playful dolphins. You can also bring your own drinks and snacks on board to really make the experience your own.