Key West Sailing Tours: Our 15 Favourites

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

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

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Top of the fleet

Spend about two hours sailing from Key West with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and chef-prepared hors d’oeuvres. A local musician provides live entertainment while you pass Mallory Square, Fort Zachary Taylor, Sunset Key, and the Key West harbor. Arrive 30 minutes early and bring a sweater.

“Wonderful experience, drinks food and music all terrific and the sunset was breathtaking. Bring a sweater”

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Key West Afternoon Snorkel Sail with Unlimited Cocktails!

2.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59Lowest fare aboard

Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef, about 7.5 miles offshore. The crew provides gear, safety instruction, and time to snorkel in shallow reef water. After swimming, enjoy included beer, wine, soft drinks, and cocktails on the return trip. The boat has restrooms and a freshwater rinse.

“The boat was great as well as the captain and mates! I didn't see a lot of fish that was a bit disappointing. Other than that it was fun!”

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

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

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

Join Danger Charters at 255 Front Street for a two-hour sunset sail with up to eight wines, five beers, soft drinks, and wine-paired hors d’oeuvres. Crews including Mary, James, Connor, and Molly are known for warm service, stories, blankets on cool evenings, and a relaxed small-boat setting.

“Great crew, excellent wine, delicious hors d’oeuvres, beautiful sunset ~ perfect evening! Plus, the limited number of guests was definitely preferred.”

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Key West Sunset Sail with Live Music, Drinks and Appetizers

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

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

Spend about two hours aboard Fury’s 65-foot catamaran as local musicians play popular cover songs, crew serve unlimited margaritas, beer, wine, champagne, soda, and seasonal appetizers. You can dance, sit in the shade, or watch the sunset near Mallory Square and Fort Zachary Taylor. Arrive early for a better seat.

“Great fun! Drinks flowed freely, great apps, but mostly awesome band & dancing under the beauty of Gods Key West sunset!!!”

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Sunset Sail in Key West with Beverages Included

5.Sunset Sail in Key West with Beverages Included

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

Sail Key West Harbor aboard Floridays’ 54-foot sailboat for about 90 minutes, with champagne, wine, margaritas, beer, and soft drinks included. The crew, including Eric, Carlo, Hunter, Chuck, Lori, and Janet, keeps the mood relaxed and personal. Expect sunset views, room to move around, and a chance of spotting dolphins.

“The boat was nice and clean. The crew was very friendly and accommodating. We had a percext view of the sunset. We enjoyed every minute of the ride.”

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

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

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

Board the replica 1851 schooner America 2.0 at Key West Bight Marina for a relaxed two-hour sunset sail. Captains such as Janet, Rae, and Dan have guided recent trips, while the crew serves beer, wine, Champagne, soda, and plated hors d’oeuvres. You’ll pass Fort Zachary, Sunset Pier, and Sand Key Lighthouse before returning to the marina.

“Sunset was enchanting and the crew was super accommodating! Captain Dan also added historical tid bits that enhanced the Key west experience. Great trip!”

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

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

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

Spend 6.5 hours aboard a 65-foot schooner with guides such as Daniel, Brian, Joe, or Captain Janet. Sail through the Key West National Wildlife Refuge, snorkel in Florida Keys waters, paddle through mangroves, and enjoy a buffet lunch with unlimited beer, wine, and soft drinks. The group is limited to 20 people.

“We really enjoyed our experience with this day excursion. The captain and the deck hands were so friendly and knowledgeable. We love that it was more intimate experience. Each of the crew members took the time to talk to all the couples on board and getting to know us . Conversation with everyone was enjoyable. Loved that it wasn’t over crowded, there was enough room for everyone to sit in the boat. The light brunch was unexpected surprise. The lunch was perfect for a day trip on the sailboat. We will definitely be coming back and booking with this company again. Well worth it. We give them 5 stars all…”

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

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

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

Set out from Key West’s Historic Seaport for a 2.5-hour catamaran cruise past Mallory Square, Fort Zachary Taylor, and Sunset Key. The crew, including captains such as Daniel and hosts such as Jordan or Gracie, serves wine, champagne, beer, soda, and small bites. Dolphins are possible, not promised.

“Wonderful experience, excellent hors d’oevres, drinks, beautiful sunset, well worth the price - would have liked to be under sail instead of engine for the trip”

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Key West Reef Snorkel & Sail Adventure

9.Key West Reef Snorkel & Sail Adventure

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

Sail from the Hyatt Centric Key West Resort aboard a 54-foot yacht, then snorkel the Florida Keys reef with gear, instruction, and drinks included. Small groups, often fewer than 24, make this a calmer choice than a large catamaran. Crew members such as Captain Owen, Chuck, Jared, Eric, and Hunter have received strong praise for their friendly help.

“It was a great tour. We were worried about the weather, but the captain decided to go on the Thanksgiving day with only 5 people on the boat. Very appreciate the decision! The staff was so nice and provided the best service and help us to prepare for snorkeling. Saw beautiful fishes and good amount of sea turtles. We really had fun time. Thank you!”

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Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

10.Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

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

Meet at 241 Front St., 30 minutes early, for a three-hour Fury catamaran trip to Key West’s living coral reef. You’ll receive instruction, mask, fins, flotation gear, and reef-safe sunscreen, then snorkel for about 30 to 40 minutes. Afterward, enjoy rum punch, beer, wine, sparkling wine, reggae music, and the sunset. Swimming ability is required.

“Super fun, super crazy ! What an experience ! It was a little intimidating but over all it was super fun.”

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Key West: Schooner Sunset Sail with Food & Drinks

11.Key West: Schooner Sunset Sail with Food & Drinks

★★★★★★★★★★4.9 · 318 reviews · 2 hours · from $122

Sail from Key West aboard the wooden schooner America 2.0 for a two-hour sunset outing. The crew serves alcoholic and non-alcoholic drinks plus a personal hors d'oeuvres plate as you pass Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier. Keep watch for dolphins, turtles, water birds, and the Green Flash.

“Amazing cruise. The crew were fantastic, the cruise very relaxing, and the setting sun beautiful to see. Many thanks, a perfect evening.”

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

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

★★★★★★★★★★4.5 · 314 reviews · 2 hours (approx.) · from $72

Sail from 201 William St. aboard the three-deck Sandie Cat for a two-hour Key West sunset cruise with live music, unlimited well drinks, beer, wine, champagne, and light appetizers. The mood can range from relaxed to lively, with open space for sunset views and a return to the same dock.

“We really enjoyed being on the water during sunset. The boat had plenty of seating for all the guests and plenty of room to move around to the best areas for views. The live violin duet was a great accompiment to the views. The free pinot grigio and food were what would be expected on this type of tour, acceptable. Great value for the price.”

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Key West: Sunset Sailing Trip with Open Bar, Food and Music

13.Key West: Sunset Sailing Trip with Open Bar, Food and Music

★★★★★★★★★★4.5 · 310 reviews · from $80

Sail from Key West’s historic seaport aboard the three-deck Sandie Cat for a two-hour sunset cruise. You’ll get open-bar drinks, light appetizers, live music, and room to move between decks. You may also help raise the sails or take a photo at the wheel.

“So much fun! Enjoyed some great music and tasty snacks! Sunset was priceless- my photo was even featured on our local weather newscast!!”

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Key West Sunset Sail Aboard Legendary Schooner Appledore

14.Key West Sunset Sail Aboard Legendary Schooner Appledore

★★★★★★★★★★5.0 · 251 reviews · 2 hours (approx.)

Set sail from Key West Historic Seaport aboard the classic wooden schooner Appledore for a 2-hour sunset trip. You can help raise the sails, enjoy beer, wine, champagne, cocktails, soda, and hors d'oeuvres, and hear sea stories from crew such as Joe, Josh, Christina, Andy, and Pablo. The boat carries no more than 36 people.

“We had a nice time and the crew did a great job with food and drinks. The sunset was very nice and the ship was beautiful. Not sure it was worth the fee, but a good time.”

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Classic Key West Schooner Sunset Sail with Full Open Bar

15.Classic Key West Schooner Sunset Sail with Full Open Bar

★★★★★★★★★★5.0 · 213 reviews · 2 hours (approx.)

Set sail from Key West’s Historic Seaport aboard a schooner limited to 22 passengers. Captain Joe, Captain Josh, Cristina, Michael, Molly, or another crew team may handle the trip. Expect a gentle cruise, cocktails, wine, beer, champagne, snacks, and views of Mallory Square, Sunset Key, Fort Zachary Taylor, and the setting sun.

“Very nice professional staff. Fun ride and really liked that only a limited number of people can be on the boat. Did not feel crowded.”

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Other ways to get on the water

Sunset Sailing Cruises Catamaran Sailing Trips Sailing and Snorkeling Trips Private Sailing Charters Island Hopping Sailing Trips Tall Ship and Schooner Sailing

Key West Sailing Tours: Our 15 Favourites

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

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

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

2.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

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

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

Key West Sunset Sail with Live Music, Drinks and Appetizers

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

Sunset Sail in Key West with Beverages Included

5.Sunset Sail in Key West with Beverages Included

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

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

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

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

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

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

Key West Reef Snorkel & Sail Adventure

9.Key West Reef Snorkel & Sail Adventure

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

10.Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

Key West: Schooner Sunset Sail with Food & Drinks

11.Key West: Schooner Sunset Sail with Food & Drinks

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

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

Key West: Sunset Sailing Trip with Open Bar, Food and Music

13.Key West: Sunset Sailing Trip with Open Bar, Food and Music

Key West Sunset Sail Aboard Legendary Schooner Appledore

14.Key West Sunset Sail Aboard Legendary Schooner Appledore

Classic Key West Schooner Sunset Sail with Full Open Bar

15.Classic Key West Schooner Sunset Sail with Full Open Bar

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