Top Florida Sailing Trips

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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

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

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

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

Private Sailing Charter in Miami

5 star rating: Highly Recommended 8 Reviews

A perfect way to enjoy a day is sailing on a beautiful 40 foot Beneteau sailboat on Biscayne Bay in Miami. The most popular charter is a sunset cruise. ... 

Location: Miami, Florida
Duration: Flexible

From USD $425.00

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

Key West Sail and Snorkel Trip from Miami

3.5 star rating: Worth doing 35 Reviews

Whether you’re an experienced snorkeler, or want to try something new and exciting, Key West is the perfect underwater destination. Your sailing and snorkeling ... 

Location: Miami, Florida
Duration: 12 hours

From USD $119.00

Sunset & Dolphin Watching Cruise in Panama City Beach

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the  Island Time sailing catamaran which departs from Treasure Island Marina in Panama ... 

Location: Panama City Beach, Florida
Duration: 2 hours

From USD $32.10

Private Sailing Trip on Biscayne Bay

5 star rating: Highly Recommended 5 Reviews

Set sail on a private 40-ft sailboat for 4 hours on Biscayne Bay with this charter from Miami. Choose from a morning, afternoon or evening sail and enjoy a ... 

Location: Miami, Florida
Duration: Flexible

From USD $425.00

Key West Sail and Snorkel Day Trip from Fort Lauderdale

4.5 star rating: Recommended 3 Reviews

Whether you’re an experienced snorkeler or you want to try something new and exciting, you’ll find Key West to be the perfect destination for fun in the ocean. ... 

Location: Fort Lauderdale, Florida
Duration: 15 hours

From USD $149.00

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

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

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

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

Private Sunset Sail in Destin

Set sail on a private cruise on either the Gulf of Mexico or Choctawhatchee Bay at sunset. With a maximum of 6 people on board, you can make this either a ... 

Location: Destin, Florida
Duration: 2 hours 30 minutes

From USD $249.99

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

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

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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