Key West Cruises, Sailing & Water Tours

Key West Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours

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

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Dry Tortugas National Park Day Trip by Catamaran

4.5 star rating: Recommended 24 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 70 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 78 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

Key West Sunset Champagne and Appetizers Cruise

5 star rating: Highly Recommended 13 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

Key West Dolphin Watch and Snorkel Cruise

5 star rating: Highly Recommended 30 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 ...  Read more

Location: Key West, Florida
Duration: 3 hours

From USD $72.50

Key West Glass-Bottom Boat Tour with Sunset Option

4.5 star rating: Recommended 25 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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $46.39

Catamaran Eco-Adventure with Kayaking Tour and Snorkeling

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 ...  Read more

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

From USD $123.63

Key West Sunset Dinner Cruise

5 star rating: Highly Recommended 1 Review

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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $69.00

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 27 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

Half-Day Cruise with Kayaking and Snorkeling

5 star rating: Highly Recommended 11 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 ...  Read more

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

From USD $85.99

Key West Sunset Champagne Cruise

5 star rating: Highly Recommended 9 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

All Inclusive Water Adventure Excursion in Key West

5 star rating: Highly Recommended 3 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 Shore Excursion: Shipwreck Snorkel and Wild Dolphin Encounter

5 star rating: Highly Recommended 1 Review

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

Snorkel and Sunset Sail: Rum n' Reggae

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 ...  Read more

Location: Key West, Florida
Duration: 3 hours

From USD $48.32

90 Min Key West Harbor Sail

This 90 minute sailing trip in Key West is the best way to experience the water with friends and/or family when time is of the essence!  The captain helps ...  Read more

Location: Key West, Florida
Duration: 90 minutes

From USD $255.38

Key West Sunset Party Cruise

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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $53.16

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 of ...  Read more

Location: Key West, Florida
Duration: 4 hours

From USD $116.10

Small Group Sunset Sail with Wine

5 star rating: Highly Recommended 10 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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $86.00

Island Adventure Snorkel Kayak and Eco Tour

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 ...  Read more

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

From USD $96.70

Private Sunset Sail with Cheese Platter

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 classic ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $394.99

Private Sunset Sail with Wine and Cheese

Sunset sailing trips in Key West should be romantic with friends and/or family, and that's why we only offer private sunset sails. Our beautiful sail boat is ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $350.00

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

Schooner Appledore Key West Cruise

4 star rating: Recommended 1 Review

Enjoy a day sail or sunset sail around Key West on the Appledore II. Stretch out and relax to the sounds of internationally renowned chanteyman Geoff Kaufman, ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $39.00

Sunset Sail on Historic Schooner

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 ...  Read more

Location: Key West, Florida
Duration: 2 hours

From USD $79.00

Bugeye Backcountry Schooner Eco Tour

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

Location: Key West, Florida
Duration: 6 hours

From USD $99.99
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Only Show: Brunch Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Lunch Cruises | Night Cruises | Sailing Trips | Sunset Cruises

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