Top Key West Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours

Only Show: Brunch Cruises | Catamaran Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Glass Bottom Boat Tours | Lunch Cruises | Night Cruises | Sailing Trips | Sunset Cruises

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Key West Sunset Champagne and Appetizers Cruise

5 star rating: Highly Recommended 48 Reviews

Admire an exquisitely painted sky during this Captain's choice sunset cruise in Key West. Create fantastic memories as you set sail on a Sebago ship, sipping ... 

Location: Key West, Florida
Duration: 2 hours

From USD $63.00

Dry Tortugas National Park Day Trip by Catamaran

5 star rating: Highly Recommended 43 Reviews

Explore beautiful tropical beaches on this full-day catamaran trip from Key West to Dry Tortugas National Park. The Dry Tortugas islands were discovered by ... 

Location: Key West, Florida
Duration: 10 hours

From USD $178.99

Key West Island T'ing: Sail, Snorkel and Kayak Adventure

5 star rating: Highly Recommended 94 Reviews

Beautiful Key West is surrounded by the sparkling blue waters of the Gulf of Mexico, making it perfect for day of fun in the sun. On the Island T’ing ... 

Location: Key West, Florida
Duration: 6 hours

From USD $112.00

Key West Dolphin Watch and Snorkel Cruise

5 star rating: Highly Recommended 44 Reviews

Get in touch with one of nature's friendliest mammals on this relaxing 3-hour dolphin cruise from Key West. Sail alongside playful dolphins and take in the ... 

Location: Key West, Florida
Duration: 3 hours

From USD $72.50

Half-Day Cruise with Kayaking and Snorkeling

5 star rating: Highly Recommended 25 Reviews

Don't miss one of the top things to do in Key West—a half-day sailing tour where you can explore the waters of the Florida Keys. You'll cruise out to a ... 

Location: Key West, Florida
Duration: 4 hours 30 minutes

From USD $86.00

Key West Sunset Dinner Cruise

4 star rating: Recommended 13 Reviews

A dinner sunset cruise in Key West is like nothing else, and this 2 hour experience offers a full tropical buffet to go along with the best sunset in the ... 

Location: Key West, Florida
Duration: 2 hours

From USD $59.00

Champagne Celebration Sunset Cruise

5 star rating: Highly Recommended 110 Reviews

Get out on Key West’s beautiful Atlantic waters to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are house ... 

Location: Key West, Florida
Duration: 2 hours

From USD $79.49

Key West Sunset Champagne Cruise

5 star rating: Highly Recommended 20 Reviews

Watch the famous Key West sunset on a 2-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy included wine, sparkling ... 

Location: Key West, Florida
Duration: 2 hours

From USD $41.00

Key West Glass-Bottom Boat Tour with Sunset Option

4.5 star rating: Recommended 38 Reviews

See the only living coral barrier reef in the continental United States on this two-hour glass-bottom boat tour from Key West! As you relax on the cruise, look ... 

Location: Key West, Florida
Duration: 2 hours

From USD $41.56

Key West Sunset Sail Aboard Schooner America 2.0

5 star rating: Highly Recommended 8 Reviews

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in great views of Mallory Square, Sunset Pier, Sand Key Light ... 

Location: Key West, Florida
Duration: 2 hours

From USD $91.38

All Inclusive Water Adventure Excursion in Key West

5 star rating: Highly Recommended 9 Reviews

This full day excursion from Key West includes all the fun things to do in the ocean - kayaking, snorkeling and sailing! You will head way back into the Key ... 

Location: Key West, Florida
Duration: 6 hours 30 minutes

From USD $129.00

Schooner Appledore Key West Cruise

5 star rating: Highly Recommended 12 Reviews

Experience sailing on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations ... 

Location: Key West, Florida
Duration: 2 hours

From USD $45.97

Key West Shark and Wildlife Catamaran Tour

5 star rating: Highly Recommended 33 Reviews

Delight in close-up views of sharks and a variety of other marine life on this 2-hour boat tour from Key West. In an eco-friendly catamaran, travel through ... 

Location: Key West, Florida
Duration: 2 hours

From USD $79.00

Key West Sunset Party Cruise

5 star rating: Highly Recommended 8 Reviews

Come sail along on an ocean breeze and enjoy some of Key West’s best musicians performing live to the backdrop of the setting sun. You’ll eat, drink and party ... 

Location: Key West, Florida
Duration: 2 hours

From USD $56.06

Island Adventure Snorkel Kayak and Tour

4 star rating: Recommended 6 Reviews

Discover a different side of Key West as you explore a secluded paradise in the Florida Keys backcountry on this Island Adventure. Tucked away between mangrove ... 

Location: Key West, Florida
Duration: 4 hours 30 minutes

From USD $106.37

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 31 Reviews

Spend a beautiful Florida day out in the clear, blue waters off Key West. On the Key West Shipwreck Snorkel and Wild Dolphin Encounter cruise, you’ll spot ... 

Location: Key West, Florida
Duration: 4 hours

From USD $95.59

Small Group Sunset Sail with Wine

5 star rating: Highly Recommended 11 Reviews

Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres. This cruise is great for a romantic evening ... 

Location: Key West, Florida
Duration: 2 hours

From USD $91.38

Sunset Sail in Key West with Cocktails and Hors d'Oeuvres

The perfect Key West sunset sail. Picture yourself on the deck of a romantic two-masted schooner. With the wind blowing in your hair, the tall ship sails into ... 

Location: Key West, Florida
Duration: 2 hours

From USD $74.00

Java Cat Sail, Kayak and Snorkel Charter

5 star rating: Highly Recommended 2 Reviews

Combine three Key West activities on this eco-adventure by chartered catamaran. Sail to the Key West National Wildlife Refuge for a guided kayaking tour of ... 

Location: Key West, Florida
Duration: 4 hours 30 minutes

From USD $123.63

Bugeye Backcountry Schooner Eco Tour

5 star rating: Highly Recommended 5 Reviews

Set sail aboard our classically-styled schooner as she departs the Historic Key West Seaport for a full day of sailing and exploration through the  pristine ... 

Location: Key West, Florida
Duration: 6 hours

From USD $99.00

Sunset Sail on Historic Schooner

5 star rating: Highly Recommended 4 Reviews

Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then Colonel George Patton "When the war is over and if I ... 

Location: Key West, Florida
Duration: 2 hours

From USD $79.00

Dart Backcountry Private Customized Charter

Dart is a 2017 Key West Dual Console boat. She is the perfect boat to venture out into the backcountry where others do not go. She is docked next to our ... 

Location: Key West, Florida
Duration: 3 hours 30 minutes

From USD $510.63

Key West Sunset Cruise

A sunset cruise in Key West is like nothing else, and this 2 hour experience offers complimentary  draft beer, wine, champagne & soft drinks.  The cruise ... 

Location: Key West, Florida
Duration: 2 hours

From USD $40.00

Key West Shore Excursion: Shipwreck Snorkel and Wild Dolphin Encounter

4 star rating: Recommended 2 Reviews

While you're in port in Key West, spend a beautiful Florida day out in the clear, blue waters on a snorkeling tour and dolphin-spotting shore excursion. Enjoy ... 

Location: Key West, Florida
Duration: 4 hours

From USD $95.59

Snorkel and Sunset Sail: Rum n' Reggae

2 star rating: It was OK, but could have been better 1 Review

This Caribbean-themed trip offers two bucket list items that Key West is famous for - a tropical coral reef and amazing sunsets. Rum punch, lively reggae and a ... 

Location: Key West, Florida
Duration: 3 hours

From USD $48.32
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