Recent Searches
Clear

Top Key West Cruises & Sailing

Saved to wishlist!
Dates
Select Dates
Sunset Cruises
Sunset Cruises
Sailing
Sailing
Catamaran Cruises
Catamaran Cruises
On the Water
On the Water
Snorkeling
Snorkeling
Glass Bottom Boat Tours
Glass Bottom Boat Tours
Day Cruises
Day Cruises
Shore Excursions
Shore Excursions
Private and Luxury
Private and Luxury
Fishing Charters & Tours
Fishing Charters & Tours
Ports of Call Tours
Ports of Call Tours
Private Sightseeing Tours
Private Sightseeing Tours
Sightseeing Tours
Sightseeing Tours
Parasailing
Parasailing
Water Tours
Water Tours
Half-day Tours
Half-day Tours
Day Trips
Day Trips
Dolphin Watching
Dolphin Watching
Boat Rentals
Boat Rentals
Sightseeing Cruises
Sightseeing Cruises
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Key West. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

54 results | All Key West Tours

Sort by: Featured

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
Likely to Sell OutLikely to Sell Out

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

star-4.5
1131
Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$89.95
From
$89.95
Taking safety measures

Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

star-4.5
496
Jam to island beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Unlimited drinks and appetizers included; multiple departure times available to suit your schedule.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$73.75
From
$73.75
Taking safety measures

Key West Sunset Champagne Catamaran Cruise

Key West Sunset Champagne Catamaran Cruise

star-4.5
334
Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$51.95
From
$51.95
Taking safety measures

Key West Sunset Dinner Cruise with Tropical Buffet

Key West Sunset Dinner Cruise with Tropical Buffet

star-4
431
Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$88.95
From
$88.95
Taking safety measures

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
Likely to Sell OutLikely to Sell Out

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar

star-5
234
Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.
More
  • 2 hours
  • Free Cancellation
From
$99.95
From
$99.95

Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

star-5
289
Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, this small group experience ensures you have a spot at the rail when it comes time to capture photos of the setting sun.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$61.46
From
$61.46
Taking safety measures

Key West Florida Reef Half-Day Snorkeling Excursion

Key West Florida Reef Half-Day Snorkeling Excursion

star-4.5
698
Enjoy an afternoon of swimming and snorkeling on this cruise off the coast of Key West. Spend a relaxing afternoon on a 69-foot catamaran headed to North America's only living coral barrier reef for the adventure of a lifetime. Pass some of Key West’s top attractions on the way, then dive right in to see more than 600 species of colorful fish, coral, and other sea life. This cruise includes professional snorkeling gear and instruction plus beer, wine, and soft drinks.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$45.95
From
$45.95
Taking safety measures

Key West Dolphin Watch and Snorkel Cruise

Key West Dolphin Watch and Snorkel Cruise

star-4.5
547
Get ready for fun in the sun on this dolphin watch and snorkeling adventure off the coast of Key West. Cruise away from the island city of Key West and see dolphins swimming alongside the boat, then jump in for a shallow-water snorkel at the Key West National Wildlife Refuge with many different species of marine life. Relax, feel the warm sea breeze and select from a variety of refreshing beverages on board the boat.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$75.20
From
$75.20
Taking safety measures

Adults only Champagne Celebration Sunset Cruise from Key West
Likely to Sell OutLikely to Sell Out

Adults only Champagne Celebration Sunset Cruise from Key West

star-5
364
Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
More
  • 2 hours
  • Taking safety measures
From
$81.40
From
$81.40
Taking safety measures

Shark and Wildlife Viewing Adventure in Key West
Likely to Sell OutLikely to Sell Out

Shark and Wildlife Viewing Adventure in Key West

star-5
764
Get up close with sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast of Key West. See dolphins, stingrays, turtles and birds and learn about Key West’s waters, and then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat. Bring a camera to capture the excitement as these super predators swarm. Cold drinks, snacks and polarized sunglasses are included on this Key West shark cruise.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$84.27
From
$84.27
Taking safety measures

Key West Glass-Bottom Boat Tour with Sunset Option

Key West Glass-Bottom Boat Tour with Sunset Option

star-3.5
222
For the aquatic adventure of a lifetime, take this cruise to North America's only living coral barrier reef. No need to go scuba diving or snorkeling for this great view — from the deck of a glass-bottom catamaran boat, see more than 600 species of tropical fish, sharks, turtles, lobsters and crabs, plus colorful coral and a vast collection of other sea life. Upgrade to a sunset cruise to enjoy a glass of Champagne as the sun settles into the Gulf of Mexico.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$53.70
From
$53.70
Taking safety measures

Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel

Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel

star-5
430
Enjoy a day of fun in the sun on the Island T’ing adventure off the coast of Key West. Sail away from the island city of Key West to the beautiful blue waters of the Gulf of Mexico on a large catamaran. Hop in a kayak and enjoy a paddle around a natural stand of mangrove. Look for dolphins, stingrays, sea turtles, manatees and more on this full-day adventure. A full breakfast and buffet lunch, plus beer, wine, soft drinks and homemade sangria are included.
More
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$124.95
From
$124.95
Taking safety measures

Key West Full-Day Power Adventure: Sailing & Watersports Package

Key West Full-Day Power Adventure: Sailing & Watersports Package

star-4.5
591
Enjoy the Key West sunshine on a full-day catamaran excursion, and take part in a range of watersports, too. As you cruise around the alluring Gulf of Mexico, gaze out at the scenery and spot local marine life. Choose from a range of activities from snorkeling and kayaking to adrenaline-fuelled parasailing or Jet Skiing. Breakfast and lunch are served on board.
More
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$209.95
From
$209.95
Taking safety measures

Small-Group Key West Sunset Sail with Wine
Likely to Sell OutLikely to Sell Out

Small-Group Key West Sunset Sail with Wine

star-5
436
Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers. Also included is a gourmet cheese buffet and other appetizers, like summer sausages, water crackers with brie, green apples with a honey drizzle and more. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$99.95
From
$99.95
Taking safety measures

Key West Sunset and Cocktail Cruise with Open Bar

Key West Sunset and Cocktail Cruise with Open Bar

star-5
52
After a long day of work or sightseeing, treat yourself to a relaxing 2-hour sunset cruise in Key West. Climb aboard the 47-foot catamaran and set sail along the scenic Floridian coast as the sun sinks into the water. Enjoy unlimited South Florida craft beer, California wine, and hand-crafted cocktails for the duration of the tour. A selection of fresh bread and spreads are also provided.
More
  • 2 hours
From
$75.00
From
$75.00

Key West Wild Dolphin Sail and Shallow-Water Snorkel
Likely to Sell OutLikely to Sell Out

Key West Wild Dolphin Sail and Shallow-Water Snorkel

star-4.5
210
Take a half-day sailing adventure off the coast of Key West, Florida and observe wildlife. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.
More
  • 4 hours
  • Taking safety measures
From
$97.91
From
$97.91
Taking safety measures

Key West Snorkel and Sunset Sail: Rum n' Reggae

Key West Snorkel and Sunset Sail: Rum n' Reggae

star-4
167
Combine a snorkel session on North America's only living coral reef with a Key West sunset during this catamaran cruise. Listen to lively reggae beats, snorkel using the provided equipment, and watch the sunset with a rum punch in hand.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$56.12
From
$56.12
Taking safety measures

Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings
Likely to Sell OutLikely to Sell Out

Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

star-4.5
80
Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins as well as views of Key West landmarks like the legendary Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Then, relax on the luxury catamaran to watch the sunset as nibble on tapas such as shrimp cocktail served with wine and champagne.
More
  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$79.95
From
$79.95
Taking safety measures

Key West Sunset Snorkel Sail with Open Bar, Live Music, and Appetizers

Key West Sunset Snorkel Sail with Open Bar, Live Music, and Appetizers

star-4.5
55
Combine two activities into one tour and save with this Key West sunset snorkel sail. Not only will you get to relax and listen to the music as you cruise on the Atlantic Ocean during sunset, but you’ll also get to snorkel in a nearby coral reef. Beverages and snorkel equipment are included for added convenience.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$74.95
From
$74.95
Taking safety measures

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

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

star-4.5
102
Explore the patch reefs, mangrove islands, and waterways of Key West on a 6-hour cruise and snorkeling tour aboard a wooden sailing schooner. Take a hand at the wheel on your way across the Gulf of Mexico, kayak through the mangroves, then snorkel through patch reefs and sponge gardens. This 6-hour tour includes breakfast, lunch, and access to an open bar on the return sail to Key West.
More
  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$119.95
From
$119.95
Taking safety measures

Florida Keys Afternoon Reef Snorkel & Sail Adventure

Florida Keys Afternoon Reef Snorkel & Sail Adventure

star-5
83
Explore the only living coral reef in North America on this small-group snorkeling adventure aboard a sailing yacht in Key West. You will receive instruction on how to use the equipment, but it’s recommended that participants be comfortable underwater and have the ability to swim. Common sightings include tropical fish, eels, turtles, dolphins, anemones, and urchins.
More
  • 3 hours
  • Free Cancellation
From
$79.00
From
$79.00

2-Hour Private Sunset Cruise around Key West
Likely to Sell OutLikely to Sell Out

2-Hour Private Sunset Cruise around Key West

star-5
26
Key West is famed for its sunsets but the scene in town tends to be crowded. Sidestep the big crowds by getting out onto the water on a private tour. In the company of just your party and the captain, relax as you cruise around the island and the captain points out all the important landmarks.
More
  • 2 hours
  • Free Cancellation
From
$200.00
Price varies by group size
From
$200.00
Price varies by group size

Morning Reef Snorkel & Sail Adventure from Key West

Morning Reef Snorkel & Sail Adventure from Key West

star-5
43
Sail to a gorgeous snorkeling spot off the coast of Key West to explore a coral reef home to rainbow-colored fish, anemones, eels, and more. On the hour-long sailing trip to the reef, sip included wine, beer, or soft drinks while watching for dolphins and sea turtles. The captain chooses the snorkeling spot according to each day’s conditions, ensuring the best experience for your group.
More
  • 3 hours
  • Free Cancellation
From
$79.00
From
$79.00

Sunset Sip and Sail with Open Bar, Live Music, and Appetizers from Key West

Sunset Sip and Sail with Open Bar, Live Music, and Appetizers from Key West

star-4.5
43
Planning a night out in Key West with entertainment can add up quickly. This Key West cruise saves you money by combining an open bar with musical entertainment as you sail the waters keeping an eye out for views of the sunset. Plus, it ends early enough to leave you enough time to bar hop afterward if you’d like.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$74.95
From
$74.95
Taking safety measures

Filters

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Cruises & Sailing in Key West?
Q:
What Cruises & Sailing in Key West are taking additional safety precautions?
Q:
What Cruises & Sailing in Key West are good for avoiding crowds?