Top Key West Sailing Trips

Cruises, Sailing & Water Tours See all

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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 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

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

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

Key West Classic Day Sail Aboard America 2.0

5 star rating: Highly Recommended 4 Reviews

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first ... 

Location: Key West, Florida
Duration: 90 minutes

From USD $59.12

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 ... 

Location: Key West, Florida
Duration: 90 minutes

From USD $255.38

Private Sail with Reef Eco Exploration

Trip starts out at Conch Harbor Marina for a 4 Hour sail. You will be taken through the National Marine Sanctuary which is home to Dolphins, Loggerhead ... 

Location: Key West, Florida
Duration: 4 hours

From USD $599.99

Key West Sunset Snorkel Sail

3 Hour Sunset Snorkel Sail See the Living Coral Reef watch the World Famous Key West Sunset Have a cool beverage.

Location: Key West, Florida
Duration: 3 hours

From USD $49.00

Mimosa Day Sail aboard Schooner America 2

Take to the water on the Schooner America 2.0, namesake off the first sailboat to win the America's Cup in 1851. This stunning 105-foot sailboat features teak ... 

Location: Key West, Florida
Duration: 90 minutes

From USD $59.12

Sunset Sip & Sail

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat . Open bar Live Music  ... 

Location: Key West, Florida
Duration: 2 hours

From USD $52.68

Private 90 Minute Customized Sailing 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 city ... 

Location: Key West, Florida
Duration: Flexible

From USD $294.99
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