Key West Cruises, Sailing & Water Tours

Key West Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours

Only Show: Day Cruises | Dolphin & Whale Watching | Night Cruises | Sailing Trips | Sunset Cruises

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Dry Tortugas National Park Day Trip by Catamaran

4.5 star rating: Recommended 14 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 ...  Read more

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 46 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 ...  Read more

Location: Key West, Florida
Duration: 6 hours

From USD $99.99

Champagne Celebration Sunset Cruise

5 star rating: Highly Recommended 57 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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $79.49

Morning and Afternoon Half Day Cruise

5 star rating: Highly Recommended 8 Reviews

Don't miss one of the top things to do in Key West! Come enjoy the Florida Keys on this kayaking, snorkeling and sailing adventure. You will cruise out to the ...  Read more

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

From USD $85.99

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 23 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 ...  Read more

Location: Key West, Florida
Duration: 4 hours

From USD $95.59

Key West Dolphin Watch and Snorkel Cruise

5 star rating: Highly Recommended 22 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 ...  Read more

Location: Key West, Florida
Duration: 3 hours

From USD $67.59

Key West Glass-Bottom Boat Tour with Sunset Option

4.5 star rating: Recommended 15 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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $46.39

Key West Shark and Wildlife Catamaran Tour

5 star rating: Highly Recommended 21 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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $78.99

Key West Schooner Champagne Sunset Sail

5 star rating: Highly Recommended 12 Reviews

View a spectacular Key West sunset from a two-masted wooden schooner on this evening sail. Travel past top Key West attractions including the Historic ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $63.39

Premium Full Day Excursion in Key West

5 star rating: Highly Recommended 2 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 ...  Read more

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

From USD $118.25

Key West Sunset Champagne and Appetizers Cruise

5 star rating: Highly Recommended 6 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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $63.39

Wind and Wine Sunset Sail

5 star rating: Highly Recommended 8 Reviews

Cruise into the sunset with wines from all around the world, Import and Domestic beers and Hors d'euvres. This cruise is great for a romantic evening or just ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $86.00

Key West Sunset Champagne Cruise

5 star rating: Highly Recommended 4 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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $38.69

4-hour Custom Charter in Key West

Set sail on a private custom charter for you and your family or small group of friends. Make great memories that last a lifetime on the clear blue waters ...  Read more

Location: Key West, Florida
Duration: 4 hours

From USD $499.99

Key West Shore Excursion: Shipwreck Snorkel and Wild Dolphin Encounter

5 star rating: Highly Recommended 1 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 ...  Read more

Location: Key West, Florida
Duration: 4 hours

From USD $95.59

Schooner When And If Sunset Sail

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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $79.00

Key West Tall Ship and Crawl

Tall Ship sailing and off Duval Street crawling that includes some hearty tastings of classic Key West inspired surf and turf rations as well as plenty ...  Read more

Location: Key West, Florida
Duration: 4 hours

From USD $116.10

Day Sail in Key West by Private Charter

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the ...  Read more

Location: Key West, Florida
Duration: Flexible

From USD $294.99

Private Snorkel and Sunset Sail Combo

Enjoy this private charter with friends or that special someone! Soak up the sun and cool off in the bright aqua waters of the Keys as you snorkel and explore ...  Read more

Location: Key West, Florida
Duration: 4 hours

From USD $594.99

Sunset Sail Private Charter

The perfect Key West sunset sail - peaceful, private and exclusive! Your captain and mate will take you out to watch the sunset from your own private ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $394.99
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Only Show: Day Cruises | Dolphin & Whale Watching | Night Cruises | Sailing Trips | Sunset Cruises

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