15 Best Cruises & Boat Tours In Key West

Concerts, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

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

/ June 4, 2026

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

Sail Key West at sunset on a large catamaran with an open bar, live local music, and filling hors d’oeuvres. Depart from Elizabeth St.

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

/ June 4, 2026

2.Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Key West sunset dinner cruise with a tropical buffet, unlimited drinks, and live music on a 65-foot yacht. See sunset from the water.

★ 4.5

“It was a great ride out and back. Captain did an awesome job. Food was good but we didn't care for the music. Sunset was amazing”

1,707 reviews2 hours (approx.)From $92.95by Sunset Watersports

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Cruises & Boat Tours, Key West, Reef Snorkeling Tours, Tour Reviews

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

/ June 4, 2026

3.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

Sail the 69-foot Marquesa to the Florida Reef for easy snorkeling, unlimited drinks after swimming, and the chance to spot dolphins.

★ 4.5

“It was exactly as we anticipated. There were a lot of people on the boat, but the staff was great and well prepared. The equipment they provided was in good condition, but I felt the water wasn't that clear and I had a hard time seeing a lot on the reef.”

1,572 reviews3 hours (approx.)From $59.00by Sebago Key West

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Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews, Wine Tours

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

/ June 4, 2026

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

Key West small-group sunset sail with up to eight wines, beer, and hors d'oeuvres on a schooner. Intimate, romantic start to night.

★ 5.0

“What an amazing experience! The wine was plentiful, the snacks were delicious, and the view of the water and sunset were unbeatable. Mary, James, and Connor were professional and friendly. All around absolutely worth doing this!”

1,366 reviews2 hours (approx.)From $125.00by Danger Charters

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Cruises & Boat Tours, Evening Experiences, Key West, Tour Reviews

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

/ June 4, 2026

5.Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Adults-only Key West sunset cruise on a small Echo catamaran with champagne-inspired drinks, gourmet cheeses, and Moët upgrades available.

★ 5.0

“This was such a wonderful experience. Having a small group made it even more special. The sunset was beautiful. The captain and crew were knowledgeable and hospitable. If you’re wondering if you should book this trip- you definitely should!”

954 reviews2 hours (approx.)From $108.91by Dolphin Echo Inc. (Catamaran Echo)

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Concerts, Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Key West Sunset Sail with Live Music, Drinks and Appetizers

/ June 4, 2026

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

A 2-hour Key West catamaran sunset sail with live music, unlimited drinks, and appetizers—plus views of Mallory Square and more.

★ 4.5

“Third trip with Fury & all were an excellent experience! We can hardly wait for our next excursion with Fury.”

952 reviews2 hours (approx.)From $79.95by Fury Water Adventures

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Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Sunset Sail in Key West with Beverages Included

/ June 4, 2026

7.Sunset Sail in Key West with Beverages Included

Key West sunset sail with included drinks. Small-group 90 minutes from Hyatt Centric; champagne, wine, margaritas, craft beer.

★ 5.0

“Very relaxing, smaller group makes it feel much more personal.”

907 reviews1 hour 30 minutes (approx.)From $79.00by Floridays

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Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Schooner Sailing, Sunset Sails & Cruises, Tour Reviews

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

/ June 4, 2026

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

Sail on a replica Key West schooner at sunset with open bar and plated hors d’oeuvres, passing Fort Zachary and classic waterfront views.

★ 5.0

“Our captain, Janet was fantastic! She made sure our experience on her ship was perfect including the sunset. Her crew Jade, Milo & Heather were super efficient in not only tending to the ship’s duties but served their guests with a huge smile. Thanks for the great experience!🌞⛵️”

804 reviews2 hours (approx.)From $122.59by Classic Harbor Line

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Canoes & Kayaks, Cruises & Boat Tours, Full-Day, Kayak Tours, Key West, Reef Snorkeling Tours, Tour Reviews

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

/ June 4, 2026

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

A full-day Key West sailing, snorkeling, and kayaking trip to the wildlife refuge, with lunch and unlimited drinks included.

★ 5.0

“Captain kid rock, James and Kylie did AMAZING!! It was so fun. Super knowledgible and friendly!! Cannot say enough great things. BOOK THIS TRIP!!”

767 reviews6 hours 30 minutes (approx.)From $152.00

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Cruises & Boat Tours, Dolphin Watching, Dolphin Watching Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews, Wine Tours

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

/ June 4, 2026

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

Key West sunset sail with dolphin watching, premium wine, champagne and tapas on a luxury catamaran, small group max 50.

★ 4.5

“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!”

699 reviews2 hours 30 minutes (approx.)From $89.00by Sebago Key West

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Cruises & Boat Tours, Dolphin Watching, Dolphin Watching Tours, Key West, Reef Snorkeling Tours, Snorkeling, Tour Reviews, Tours

Key West: Dolphin Watching and Snorkeling Eco Cruise Tour

/ June 4, 2026

11.Key West: Dolphin Watching and Snorkeling Eco Cruise Tour

Key West dolphin cruise with included snorkeling gear and drinks on a 45-foot catamaran, plus sunset timing options.

★ 4.6

“Our guides Lisa & Ivy were so friendly and informative, with great energy throughout the trip. We saw lots of dolphins and the snorkelling was a nice addition to other dolphin trips I’ve been on before. Would recommend to everyone!”

647 reviewsFrom $80by Fury Water Adventures

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Catamaran Cruises, Cruises & Boat Tours, Evening Experiences, Key West, Sailing, Sunset Sails & Cruises, Tour Reviews, Wine Tours

Key West Champagne Sunset Catamaran Cruise

/ June 4, 2026

12.Key West Champagne Sunset Catamaran Cruise

Sail Key West’s harbor to chase the champagne sunset from a 69-foot catamaran, with included drinks, a restroom, and great photo views.

★ 4.5

“So much fun and the crew is fantastic!! If you do nothing else, DO THIS! I really can’t say enough good things. It’s just a really good time.”

586 reviews1 hour 30 minutes (approx.)From $59.00by Sebago Key West

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Cruises & Boat Tours, Evening Experiences, Glass-Bottom Boat Tours, Key West, Tour Reviews, Tours

Key West Glass-Bottom Boat Tour with Sunset Option

/ June 4, 2026

13.Key West Glass-Bottom Boat Tour with Sunset Option

Glass-bottom boat over Key West’s living coral reef, with narrated marine life and optional sunset champagne cruise. Air-conditioned comfort.

★ 4.0

“Very relaxing trip out to the reef. Staff was professional and knowledgeable. I highly recommend this trip.”

576 reviews1 hour 45 minutes to 2 hours (approx.)From $69.95by Fury Water Adventures

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Cruises & Boat Tours, Key West, Reef Snorkeling Tours, Tour Reviews

Key West Reef Snorkel & Sail Adventure

/ June 4, 2026

14.Key West Reef Snorkel & Sail Adventure

Small-group sail and snorkel from Key West’s only living coral reef. Sanitized gear and drinks included. About 3 hours.

★ 4.5

“Great experience sailing for first time so relaxing and beautiful, snorkeling was awesome they made sure we had everything we needed and explained everything before hand saw dolphins on the way back couldnt have asked for a better day with this crew”

540 reviews3 hours (approx.)From $79.00by Floridays

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