14 Key West Sailing Trips to Build a Day Around

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Sail from Key West for about two hours aboard a spacious catamaran with sunset views, live local music, an open bar, shrimp, antipasti, mini tarts, and soft drinks. Arrive 30 minutes early, claim a good bow seat, and bring a sweater for breezy evenings.

“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”

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2.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59Best value

Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef. You’ll get gear, a safety briefing, and time to snorkel before the open bar begins on the ride home. Captain Brett and the Sebago crew are known for a safety-first approach, though the boat can feel busy.

“The boat, the trip and the crew were all amazing. Recommend this highly. Will definitely go on this excursion with the same company again!”

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3.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125Top rated

Board Danger Charters at 255 Front Street for a two-hour sunset sail limited to 26 people. Crew members such as Mary, Connor, Lexi, Tony, and Molly have served wines, beer, small bites, stories, and blankets while the boat heads offshore for sunset.

“The captain and crew were awesome. The wines were a great choice and the snacks were just the right amount. There was a vegan in our party and she had nothing but wine...no complaints! I recommend the danger boat..it's the best!!”

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4.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Board Fury’s 65-foot catamaran at Greene and Elizabeth Streets for two hours of live cover music, unlimited margaritas, beer, wine, Champagne, and seasonal appetizers. Sail past Mallory Square and possibly Fort Zachary Taylor while the crew picks the best route for sunset. Arrive early for seating.

“Not your usual review as our sunset cruise was cancelled by a freak raging windstorm. Just wanted to thank the team there at the pier that handled everything so professionally and quick. Rescheduling was offered but we had opt for cancellation as it was our last night in town.”

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5.Sunset Sail in Key West with Beverages Included

★★★★★★★★★★5.0 · 907 reviews · 1 hour 30 minutes (approx.) · from $79

Board Floridays at Hyatt Centric Key West for a relaxed 90-minute sail with up to 24 people. Eric, Carlo, Hunter, Janet, Chuck, Lori, and other crew members may handle the evening. Enjoy champagne, wine, margaritas, beer, and soft drinks while watching the sunset and Sunset Celebration from the water.

“There are bigger boats and longer trips and options out there for dinner cruises, etc. But we just wanted a nice 90 minute trek around the port with a small number of people on a sailboat. The bar service was a bonus to me. Captain Chuck and Lori were great hosts and were glad to let people drive the boat, take pictures of us and play tunes. We had very good weather and wind so we sailed most of the trip which is much better that motoring around IMO.”

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6.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122

Spend two hours sailing Key West aboard the replica schooner America 2.0. Captain Janet, Captain Rae, or Captain Dan may lead the trip, with crew serving plated hors d’oeuvres, beer, wine, Champagne, and soda while you pass Fort Zachary, Sunset Pier, and Sand Key Lighthouse.

“Fun and good information! Fun to learn how the boat worked! The the Keys are beautiful and the water was great.”

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7.Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

★★★★★★★★★★5.0 · 767 reviews · 6 hours 30 minutes (approx.) · from $152

Set sail from Opal Key Resort on a 65-foot schooner with a crew such as Captain Joe, Daniel, or Brian. Kayak through mangroves, snorkel in the Florida Keys National Marine Sanctuary, and enjoy a buffet lunch with unlimited beer, wine, and soft drinks.

“Best experience yet! Joe and the crew were super helpful and knowledgeable about the area. The activities and boat were clean and easy to use.”

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8.Dolphin Watching, Wine, and Tapas

★★★★★★★★★★4.5 · 699 reviews · 2 hours 30 minutes (approx.) · from $89

Set out from Key West Historic Seaport for a 2.5-hour catamaran cruise with dolphin watching, wine, beer, champagne, and chef-selected tapas. Expect views of Mallory Square, Fort Zachary Taylor, and Sunset Key. Crew members such as Captain Daniel, John, Gracie, Jordan, and Brandon have been praised for friendly service, though dolphin sightings depend on nature.

“Captain Daniel and John were outstanding and very accommodating. The tapas were exceptional, much more than we anticipated and would give the chef 5 stars!”

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9.Key West Champagne Sunset Catamaran Cruise

★★★★★★★★★★4.5 · 586 reviews · 1 hour 30 minutes (approx.) · from $59

Sail from Key West’s Historic Harbor for about 90 minutes aboard a spacious catamaran. Enjoy included champagne, wine, beer, sangria, soft drinks, and water while the captain points out sunset views, marine life, Mallory Square, and Fort Zachary Taylor. Bring a light jacket, camera, and photo ID if you drink.

“activity for a mid-sized bachelorette party: captain and crew were awesome, boat was gorgeous, bottomless cocktails, and the perfect length of time on board. event was a hit for the group and the peak of the trip!”

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10.Key West Reef Snorkel & Sail Adventure

★★★★★★★★★★4.5 · 540 reviews · 3 hours (approx.) · from $79

Sail from Hyatt Centric Key West aboard the 54-foot Floridays, then spend about 45 minutes snorkeling a Florida Keys reef. Crew members such as Captain Owen, Chuck, Jared, Eric, and Hunter have led recent trips. Gear, flotation vests, water, soda, wine, and craft beer are included.

“Crew was awesome! Great boat very knowledgeable! We went to a great spot on the reef. Highly recommend. Thank you.”

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11.Dry Tortugas National Park Day Trip by Catamaran from Key West

★★★★★★★★★★4.5 · 433 reviews · from $220

Take the Yankee Freedom III from Key West to Dry Tortugas National Park, 70 miles offshore. You’ll get breakfast, lunch, snorkeling gear, a narrated Fort Jefferson tour, and time for beaches and coral reefs. Guides such as Dan and Hollywood bring the fort’s story to life.

“Colour of the water and brief 20 minute history of fort. Ferry trip is quite long but is worth effort.”

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12.Reef Snorkel Adventure and Sunset Sail

★★★★★★★★★★4.5 · 370 reviews · 3 hours (approx.) · from $59

Join Fury Water Adventures from 241 Front Street for a three-hour Key West catamaran outing with Captain Ron and crew. Learn to snorkel over the living coral reef, then relax with rum punch, beer, wine, sparkling wine, reggae, and a sunset at sea.

“I would’ve loved to appetizers. The staff energetic was great. Your out there for 3 hours with nothing to eat”

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13.Shark and Wildlife Viewing Catamaran Tour

★★★★★★★★★★4.8 · 150 reviews · 2 hours · from $99

Join Captains Ken, Clay, and Dave Harris aboard the shaded 34-foot Tiger Cat for two hours among Key West’s backcountry wildlife. A special scent brings sharks close for safe viewing, while turtles, stingrays, dolphins, and birds may appear along the way.

“It was really interesting! All Perfect! We saw a Lots of Dolphins and found many seashells.”

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14.Afternoon Catamaran Sail and Dolphin Watch

★★★★★★★★★★4.5 · 116 reviews · 2h 30m · from $59

You’ll spend 150 minutes aboard a spacious Sebago catamaran, cruising from Key West with beer, wine, sangria, soft drinks, and water included. The English-speaking crew scans the water for Atlantic bottlenose dolphins, while two marine heads and plenty of deck space make the outing easy and comfortable.

“We did not see any dolphins, which of course was not the guides fault. I felt like we just did a circle around key west. The boat was not taken too far off the island. Glad we did the activity but have no need to do again”

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