(855) 274-1023 Key West Questions? Call Us Now!

Key West Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours
Boat Tours
Catamaran Cruises
Day Cruises
Dinner Cruises
Dolphin & Whale Watching
Lunch Cruises
Sailing Trips
Sunset Cruises
Water Tours
Air, Helicopter & Balloon Tours
Airplane Tours
Boat Rentals
Boat Tours
Bus Tours
City Tours
Classes & Workshops
Cultural & Theme Tours
Day Trips
Day Trips & Excursions
Deep Sea Fishing
Dolphin Tours
Electric Car Rentals
Fishing
Flats Fishing
Food, Wine & Nightlife
Golf Cart Rentals
Hop-on Hop-off Tours
Jet Ski Tours
Kayaking
Kid Friendly
Light Tackle Fishing
Luxury & Special Occasions
Museums
Outdoor Activities
Parasailing
Private & Custom Tours
Private Charters
Sailing
Scooter Rentals
Scuba Diving
Scuba Instruction
Shore Excursions
Sightseeing Tickets & Passes
Sightseeing Tours
Snorkeling
Sunset Cruises
Tours & Sightseeing
Transfers & Ground Transport
Trolley Tours
Unique Experiences
Vehicle Rentals
Walking & Biking Tours
Walking Tours
Water Sports
Water Tours
17 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
10
10
7
Duration Clear
0
9
7
1
0
Price Clear
$0 $500+
Rating Clear
13
17
17
Specials Clear
17
10
0
0
0
Features Clear
3
17
16
0
9
2
Accessibility Clear
0
4
10
Families Clear
17
3
13

Key West Tours

Miami to Key West Day Trip with Glass Bottom Boat Cruise
Likely to Sell Out
Likely to Sell Out
4.6 (3,253)

Miami to Key West Day Trip with Glass Bottom Boat Cruise

Sightsee along the famous Overseas Highway then take a Key West Glass-Bottom Boat Cruise when you tour Key West on this great Miami to Key...

6 hours in Key West (approx.) • Hotel pickup offered • Free Cancellation
4.6 (3,253)
$159
$119
Key West Sail, Snorkel, Kayak with Sunset Option
Likely to Sell Out
Likely to Sell Out
4.9 (2,722)

Key West Sail, Snorkel, Kayak with Sunset Option

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4.5 or 6.5 hours (approx.) • Free Cancellation
4.9 (2,722)
from
$105
Key West Backcountry Safari
Likely to Sell Out
Likely to Sell Out
4.9 (2,722)

Key West Backcountry Safari

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....

4.5 or 6.5 hours (approx.) • Free Cancellation
4.9 (2,722)
from
$105
Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar
4.8 (3,786)

Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...

2 hours (approx.) • Free Cancellation
4.8 (3,786)
from
$80
Key West Sunset Dinner Cruise
4.4 (1,901)

Key West Sunset Dinner Cruise

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....

2 hours • Free Cancellation
4.4 (1,901)
from
$93
Key West Sunset Harbor Cruise
Special Offer
Special Offer
4.9 (128)

Key West Sunset Harbor Cruise

Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...

2 hours (approx.) • Hotel pickup offered • Free Cancellation
4.9 (128)
$99
$89
Sunset Sip & Sail
4.6 (416)

Sunset Sip & Sail

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

2 hours • Free Cancellation
4.6 (416)
from
$70
Key West Dolphin Watch Sunset Snorkel Cruise
Likely to Sell Out
Likely to Sell Out
4.7 (342)

Key West Dolphin Watch Sunset Snorkel Cruise

The Tours of Key WestDolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world...

3 hours • Free Cancellation
4.7 (342)
from
$70
Key West Sunset Sail Aboard Schooner America 2.0
Likely to Sell Out
Likely to Sell Out
4.9 (1,701)

Key West Sunset Sail Aboard Schooner America 2.0

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 (1,701)
from
$123
Key West Shark and Wildlife Catamaran Tour
Likely to Sell Out
Likely to Sell Out
5.0 (3,284)

Key West Shark and Wildlife Catamaran Tour

This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to...

2 hours • Free Cancellation
5.0 (3,284)
from
$99
Key West Sunset Snorkel Sail
4.8 (205)

Key West Sunset Snorkel Sail

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and...

3 hours • Free Cancellation
4.8 (205)
from
$64
Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak
4.9 (216)

Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak

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 Dolphin Watch & Snorkel
4.9 (25)

Key West Dolphin Watch & Snorkel

Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....

3 hours 30 minutes (approx.) • Hotel pickup offered • Free Cancellation
4.9 (25)
from
$99
Key West Classic Day Sail Aboard America 2.0
Likely to Sell Out
Likely to Sell Out
5.0 (210)

Key West Classic Day Sail Aboard America 2.0

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...

1 hour 30 minutes • Free Cancellation
5.0 (210)
from
$79
Key West Half-Day Fishing Charter
Likely to Sell Out
Likely to Sell Out
4.8 (478)

Key West Half-Day Fishing Charter

Fish like never before! Our custom build 64' catamaran is perfect for a more stable, relaxing ride. You'll fish for a wide variety of the...

5 hours • Free Cancellation
4.8 (478)
from
$95
Half-Day Cruise with Kayaking and Snorkeling
Likely to Sell Out
Likely to Sell Out
4.9 (2,648)

Half-Day Cruise with Kayaking and Snorkeling

This trip combines sailing, snorkeling, kayaking, and local insight in a laid-back, small-group setting. You'll sail on an authentic schooner into the calm, protected waters...

4 hours 30 minutes • Free Cancellation
4.9 (2,648)
from
$125
All Inclusive Water Adventure Excursion in Key West
Likely to Sell Out
Likely to Sell Out
4.9 (2,648)

All Inclusive Water Adventure Excursion in Key West

Tours of Key West is the only tour operator in Key West offering sailing excursions on a historic schooner into the remote backcountry of the...

6 hours 30 minutes • Free Cancellation
4.9 (2,648)
from
$159

Frequently Asked Questions

These answers are based on answers previously given to Tours of Key West customers' questions.

Key West Tours
View more

Things To Do In Key West