Key West Cruises, Sailing & Water Tours

96 Results
Key West Ultimate Beach Pass with Parasailing

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass. …More

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass....

8 hours Free Cancellation
4.7 (19)
from
$107
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne …More

Likely to Sell Out
Likely to Sell Out

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne...

2 hours
4.9 (977)
from
$109
Shallow Water Snorkeling and Dolphin Watching in Key West

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s …More

Likely to Sell Out
Likely to Sell Out

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s...

4 hours
4.8 (438)
from
$109
Champagne Dolphin Sail and Reef Snorkel

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with …More

Likely to Sell Out
Likely to Sell Out

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with...

3 hours
5.0 (10)
from
$109
Classic Key West Schooner Sunset Sail with Full Open Bar

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This …More

Likely to Sell Out
Likely to Sell Out

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This...

2 hours Free Cancellation
4.9 (283)
from
$109
Key West Schooner Backcountry Eco-Tour

Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure! …More

Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!...

5 hours (approx.) Free Cancellation
4.9 (216)
from
$110
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your …More

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your...

5 hours Free Cancellation
4.9 (119)
from
$119
Key West Full-Day Catamaran Eco Tour: Sail, Kayak and Dolphin Watch

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a …More

Special Offer
Special Offer

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...

6 hours (approx.)
4.9 (558)
$125
$120
Key West Dolphin Watch and Sunset Sail on Catamaran

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of …More

Likely to Sell Out
Likely to Sell Out

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of...

3 hours Free Cancellation
4.9 (40)
from
$124
Key West Sandbar Adventure Cruise for All Ages

Wake up and start your day in paradise the right way! We will give you an experience not easily forgotten, starting with a cruise through …More

Likely to Sell Out
Likely to Sell Out

Wake up and start your day in paradise the right way! We will give you an experience not easily forgotten, starting with a cruise through...

4 hours Free Cancellation
4.9 (28)
from
$126
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key …More

Likely to Sell Out
Likely to Sell Out

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...

2 hours Free Cancellation
4.9 (1,704)
from
$127
Key West Wreckers Race Aboard Schooner America 2.0

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in …More

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in...

3 hours
4.9 (14)
from
$127
Island Sandbar Tour Catamaran Cruise in Marathon FL

Experience a classic Florida Keys sandbar adventure on a comfortable 53’ catamaran. Cruise through Boot Key Harbor and past scenic landmarks as your crew shares …More

Experience a classic Florida Keys sandbar adventure on a comfortable 53’ catamaran. Cruise through Boot Key Harbor and past scenic landmarks as your crew shares...

4 hours Free Cancellation
5.0 (9)
from
$130
Adult Only Sandbar Escape with Drinks in Key West

One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service being …More

Likely to Sell Out
Likely to Sell Out

One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service being...

4 hours Free Cancellation
4.8 (48)
from
$137
Dolphin Watching Key West and Snorkeling

This isn’t a packed tourist boat — it’s a true small-group adventure with a maximum of 6 guests. You’re not watching dolphins from far away; …More

This isn’t a packed tourist boat — it’s a true small-group adventure with a maximum of 6 guests. You’re not watching dolphins from far away;...

3 hours Free Cancellation
4.9 (49)
from
$149
Key West Dolphin Tour & Snorkeling- Small Group

Featured in National Geographic Travel - Over 2000 five-star reviews and ranked #1 on Google Maps for Key West dolphin tours. Small Groups, Big Experience …More

Featured in National Geographic Travel - Over 2000 five-star reviews and ranked #1 on Google Maps for Key West dolphin tours. Small Groups, Big Experience...

3 hours Free Cancellation
4.9 (120)
from
$149
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and …More

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and...

4 hours Free Cancellation
4.9 (576)
from
$150
Key West: Sunset Sail + Reef Snorkel & Sandbar

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • …More

Likely to Sell Out
Likely to Sell Out

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? •...

4 hours 30 minutes Free Cancellation
5.0 (56)
from
$150
All-Inclusive Sandbar Safari with Dolphin Playground Encounter

Embark on a journey like no other. This tour takes guests on an amazing journey from Key West to a secluded sandbar & then to …More

Embark on a journey like no other. This tour takes guests on an amazing journey from Key West to a secluded sandbar & then to...

5 hours Free Cancellation
4.9 (682)
from
$150
Key West's Happy Hour Sandbar & Sunset Cruise - Unlimited Drinks

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar & …More

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar &...

4 hours Free Cancellation
4.6 (42)
from
$150
Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out …More

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out...

5 hours Free Cancellation
4.9 (425)
from
$161

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These answers are based on answers previously given to Key West Private Charters customers' questions.

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