Top Florida Cruises &amp; Sailing - page 2

Sunset Dolphin Sail Aboard the Privateer Catamaran

Sail along St. Augustine’s picturesque coastline—and indulge in a number of generous wine samples—during this two-in-one tour. Make your own way to the dock, hop aboard the pontoon boat, and get comfortable: as you set off, you’ll see landmarks like the Castillo de San Marcos, the Bridge of Lions, and more. You’ll also taste six different wines, and will have access to the on-board bar.

Wine Tasting Cruise in St. Augustine

Scenic Hakuna Matata Sunset Cruise in West Palm Beach

The laid-back waters of the Indian River and the lavish yachts flowing along the Intracoastal Waterway set the stage for this relaxing catamaran cruise launching from Merritt Island. Native wildlife is often spotted while sailing between Cocoa Village and Ponte Vedra Beach, including dolphins, manatees, sea birds, and more. Let your captain sail you smoothly through this ecologically diverse area while you kick back with soda and snacks.

Dolphin Adventure Sail in Cocoa Beach

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

Avoid crowded bars and opt for a more fun way to listen to great music and enjoy your favorite drinks—a cruise that passes through downtown Fort Lauderdale, Port Everglades, and Las Olas Boulevard. No need to worry about expensive bar tabs—you can bring your own drinks and use the cooler boxes on the boat. The afternoon tours stop at the legendary sandbar in front of Millionaire's-mile for a swim, while the evening cruises through downtown and explores the yachts and mansions.

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Evening Boat Cruise through Downtown Ft. Lauderdale

2 Hours Swim with the Dolphins in Panama City

Sunset Sail in Key West with Beverages Included

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

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Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast to try your luck spotting dolphins, stingrays, turtles, and birds while you learn more about Key West’s waters than you ever would sailing along. Then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat.

Shark and Wildlife Viewing Adventure in Key West

Dolphin, Manatee and Sea Turtle Kayak Adventure in St. Augustine

Get ready for fun in the sun—and leave all the planning to someone else—on this half-day sailing, kayaking, and snorkeling adventure off the coast of Key West. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef teeming with marine life. Snacks, beer, wine, and soft drinks are included.

Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset

4 hours 30 minutesFree Cancellation

Cruise along Fort Lauderdale’s historic New River and enjoy a delicious barbecue dinner on this cruise. Board the Jungle Queen Riverboat and see the luxurious mansions and yachts along Millionaire’s Row, stretching from the Bahia Mar Yachting Center to the Intracoastal Waterway. The cruise travels to a tropical isle for an endless dinner offering barbecue ribs, and chicken with all the trimmings. Then experience a laugh-out-loud variety show to cap off an enjoyable and entertaining evening.

All You Can Eat BBQ Dinner and Show at Tropical Isle with Sightseeing Cruise

4 hoursFree Cancellation

See dolphins and other marine wildlife on a guided, 90-minute cruise along the bustling waters of Tampa Bay. Choose from a morning or afternoon departure time, then discover Tampa Bay’s fascinating ecosystem. Look for an abundance of wildlife that lives there — bottlenose dolphins, fish, birds, manatees, sea turtles and more — and learn how they thrive in one of the nation’s most diverse seaports, Port Tampa Bay.

1.5-hour Dolphin Sightseeing Cruise from Tampa

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

2 hours 30 minutesFree Cancellation

3 Hour Crab Island Tour from Destin Non Private with Floats

Key West Signature Sunset Sail with Live Music, Open Bar & Food

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Original Cruisin' Tikis 3hr Crab Island Sandbar Adventure

Discover the sights and marine life of Naples on a sightseeing cruise. You have the opportunity to see birds, dolphins, and, season permitting, manatees. The cruise also takes you past the area’s top mansions, Keewaydin Island, and more. Relax and learn about local history, wildlife, and celebrity real estate during on board commentary. It’s the perfect time to take unobstructed photographs of the city and its natural surroundings.

Naples Sightseeing Boat Tour

Jungle Queen Riverboat 90-Minute Narrated Sightseeing Cruise in Fort Lauderdale

Harken back to yesteryear on a fun Fort Lauderdale sightseeing cruise aboard the Carrie B paddlewheeler. Sail past yachts, mansions, and cruise ships along the New River, Intracoastal Waterway, and Port Everglades. Spend time on the open sun deck, sit outside under a canopy, or in air-conditioned comfort on the main deck. The captain narrates the tour and a full-service bar and light snacks are available to purchase.

#1 VENICE OF AMERICA TOUR - Cold A/C 115' LARGEST IN LAUDERDALE!

Mega Bite Dolphin Tour Boat in Clearwater Beach

1 hourFree Cancellation

Get ready for fun in the sun on this 3-hour dolphin watch and snorkeling adventure. Sail away through the historic Grand Lagoon and see dolphins swimming alongside the boat, then jump in for a shallow-water snorkel experience to see different species of marine life. Relax, feel the warm sea breeze and enjoy a complimentary beverage on board! Our full-service bar has a variety of refreshing beverages and snacks for additional purchases. Please note our bar accepts debit/credit card transactions only. RED FLAGS DO NOT AFFECT OUR TOURS. Our tours operate in St. Andrews Bay, where conditions are often much calmer than the Gulf.

Snorkel & Dolphin Sightseeing Tour Aboard the Footloose

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

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Must-Dos in Florida

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What are people saying about Florida

Natalia_L, Sep 2026

Shell Island is a nice...

Shell Island is a nice option if you’re getting bored with just going to the beach and want to do something a little different. Definitely bring cash! Otherwise, buying drinks from the bar can be inconvenient because they can only run cards back on shore, so you may need to leave your phone or ID with them. Seeing dolphins is not guaranteed, although we were lucky and saw a family of them. I just wish we had spent more time with the dolphins because that was definitely the most exciting part. The ocean was quite wavy and dark blue, so it was actually difficult to see them unless you have very good vision. The water was wonderfully warm, which I really enjoyed. The fish weren’t particularly exciting, but it was still nice to experience a little bit of wildlife. If you swim a little farther from the boat along the rocks, keep your eyes open—we saw a really beautiful, bright blue fish there! Overall, it was a pleasant experience and something different to do, but personally, I probably wouldn’t do it again.

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

Ross_P, Sep 2026

Magical Lifetime Memories

One magical and fun adventure and a MOST to do. The crew was absolutely fantastic and I can’t say enough how they added to our lifetime memory experience making fun and enjoyable. The crew was great in pointing out the dolphins and the Captain did an amazing job maneuvering the boat to the areas where the dolphins were. And then the sunset was absolutely stunning (magical) and gave us this incredible appreciate for the creature that God has gave us. Overall it was a beautiful romantic experience for my wife and I, and will be back again.

Tropical Buffet Cruise in Clearwater Beach

TAMRA_T, Sep 2026

Greatly Surprised - Take This Excursion

This was one of the best experiences I’ve had in quite a while!! The food was great and plentiful, the drinks were free and non-stop, the DJ had everyone up and dancing (even me) and the staff was very efficient and attentive… Hands down a 10 outta 10 and the next time I visit Clearwater I’m definitely doing this dinner cruise again!! Don’t hesitate and make this purchase…

Key West Island Adventure Jet Ski Tour: Bring a Partner for Free

Abigail_D, Sep 2026

thank you!!

so much fun!! our guide was amazing and the ride was awesome. took us to a sandbar to swim, many historic sites along the way including the southernmost point bouy! 10/10 recommend as long as you can keep up with the group. also gave us access to the hotel it’s connected to and they have like 4 pools plus showers, bathrooms, and a place to eat and drink.

Miami Skyline Cruise with Biscayne Bay Views

Breanna_A, Aug 2026

Miami aqua tours is a must try!!

Check in was a little confusing. It listed to look for a red umbrella and mentioned a pirate ship. I found a nice women agent and was re-reouted to the correct white umbrella where there was also a friendly man agent. We had our photo taken then got on the boat. The tour guide was very informative and witty. The tour itself was very interesting and taught us things we didn't know about Miami. There was a bar to get drinks but I didn't get anything. We were given a sheet to fill in our info for a raffle and I won!! So excited for that. :) I will definitely recommend this tour to anyone I know who comes to Miami!

#1 VENICE OF AMERICA TOUR - Cold A/C 115' LARGEST IN LAUDERDALE!

Allyson_S, Aug 2026

The cruise was fun and...

The cruise was fun and informative. Definitely a hidden gem in Ft Lauderdale! Plenty of a/c for us! We were coming from a cruise before leaving for the airport later in the afternoon. The crew held our luggage for us and made sure we were comfortable aboard the Carrie B. I would definitely recommend this to anyone visiting South Florida!

Miami Millionaires Sightseeing Cruise

Myikeon_H, Aug 2026

Fun fun fun

The boat was really fun, and the drinks were good and strong. One of my favorite parts was seeing all the beautiful houses from the water because that was really cool. I also liked that they spoke both English and Spanish, which made the experience feel welcoming. The host was funny and kept the energy up, so we had a good time throughout the ride. I would definitely recommend this boat experience to others. The only thing I would suggest is putting fans on the boat because it gets hot, and giving everyone at least one cup of ice water.

Private Boat Ride in Miami with Experienced Captain and Champagne

Sarah_S, Jul 2026

Definitely the way to see Miami!

Amazing experience! Captain Rafa and his colleague made our tour unforgettable today! We went as a family of 5 including 2 teens and a 4 year old and was throughly enjoyed by all! I mistakenly thought booking the 3 hour sandbar tour included the skyline and millionaire houses along with a stop off at the sandbar to swim in the sea, but it’s actually just time to spend in the sea at the sandbar but after talking to Rafa and paying an extra $100 to cover fuel he took us to see everything! So knowledgeable and a great way to get to know Miami! He was amazing with our 4 year old too! An experience I’m sure he will never forget! Teens loved playing their music through Bluetooth speakers too! Champagne was a great added feature too! Definitely one of the best holiday extras we’ve been on! Thank you again for a great day!

Tropical Buffet Cruise in Madeira Beach

Melisa_M, May 2026

We had a pleasant...

We had a pleasant experience on this dinner cruise. The staff was friendly and attentive, and the overall atmosphere was relaxing. The sunset views were beautiful and made the evening especially enjoyable. The food and service were good, and everything was well organized. I’d recommend it for a nice evening out on the water.

Sunset Cruise of St. Augustine

Louise_B, May 2026

St Augustine sunset cruise with dolphins

Went on St Augustine sunset boat tour with friends. Capt Evan, guide McKenzie and crew Kelly were awesome with handling the boat, interacting with the group. First let’s talk about the boat: new, clean and spacious. We were not crowded and had open space to walk around. Cash bar and fun music made for great trip. We took off from pier and immediately saw a pod of dolphins frolicking and fishing for their dinner. Guide McKenzie was very knowledgeable and shared details about dolphins, wildlife and best of all…St Augustine. The trip was a perfect 1.5-2 hr length to tour the harbor, pier and bridges. Timing was perfect to see a beautiful sunset. We got great pictures. The cost was affordable and I recommend this to anyone interested in waterfront touring. Thanks for a perfect sunset trip.

Sunset Celebration Cruise on Tropics Boat Tours

Michele_C, Apr 2026

Best way to enjoy the Sunsets of Clearwater

Enjoyed beautiful views of Clearwater & the amazing sunset. The captain was very informative & talked about the different landscapes we passed by. Also had the pleasure of watching dolphins swim right alongside of our boat. Be sure to sit on the top deck to enjoy the full skyline views!