Recent Searches
Clear

Top Key West Sightseeing Cruises

Saved to wishlist!
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
Select Dates
Dates
Sunset Cruises
Sailing
Day Cruises
Private and Luxury
Shore Excursions
Water Tours
Glass Bottom Boat Tours
Half-day Tours
Private Sightseeing Tours
Cruises & Sailing
On the Water
Full-day Tours
Ports of Call Tours
Likely To Sell Out
Snorkeling
Dolphin Watching
Whale Watching

19 results | All Key West Tours

Sort by: Featured

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
From
$53.70
From
$53.70

Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

star-4.5
495
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
From
$73.75
From
$73.75

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
1130
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
From
$89.95
From
$89.95

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
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
From
$61.46
From
$61.46

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
From
$51.95
From
$51.95

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
From
$81.40
From
$81.40

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
From
$124.95
From
$124.95

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
From
$88.95
From
$88.95

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
From
$75.20
From
$75.20

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
From
$84.27
From
$84.27

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

Key West Sunset Sail Aboard Schooner

Key West Sunset Sail Aboard Schooner

star-5
239
Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.
More
  • 2 hours
  • Free Cancellation
From
$103.20
From
$103.20

Key West Day Sail Aboard Schooner

Key West Day Sail Aboard Schooner

star-5
71
Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the America 2.0, a replica of the schooner that won the very first America’s Cup. Relax on padded benches and teak decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip unlimited drinks from the full onboard bar.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$60.20
From
$60.20

Glass Bottom Boat Island Eco Adventure
Likely to Sell OutLikely to Sell Out

Glass Bottom Boat Island Eco Adventure

star-5
21
Regular boat tours around Key West provide excellent views, but miss the most important view of all: the underwater world beneath the boat. This private glass-bottom boat tour provides the full, 360-degree experience of the waters around Key West. Exclusively for your group, this tour lets you create your own adventure, whether you want to snorkel the reef, explore an offshore island or simply relax on a sandbar.
More
  • 3 hours 30 minutes
  • Free Cancellation
From
$645.00
per group
From
$645.00
per group

4-Hour Private Cruise to a Sand Bar on a Boat in Key West

4-Hour Private Cruise to a Sand Bar on a Boat in Key West

star-5
10
Getting out on the water is a must-do in Key West, but big boat tours tend to be crowded. Enjoy a personalized, crowd-free experience on this private cruise. Head into the backcountry of the Florida Keys that larger boats can’t access, then anchor at a sandbar where you can swim in the clear water or relax on a floating raft.
More
  • 4 hours
  • Free Cancellation
From
$475.00
per group
From
$475.00
per group

2-Hour Private Sunset Cruise Boat in Key West

2-Hour Private Sunset Cruise Boat in Key West

star-5
5
There are plenty of sunset cruise options to choose from in Key West, but most pack guests onto large commercial boats. This private cruise is exclusively for your group, letting you avoid crowds and get the best seats to view the fabulous Key West sunset. You’ll have a tour of Key West harbor and Sunset Key, learn about the area's history and enjoy an unobstructed view of the sun dipping below the horizon.
More
  • 2 hours
  • Free Cancellation
From
$325.00
per group
From
$325.00
per group

Rum Runner Bar Boat Tour of Key West

Rum Runner Bar Boat Tour of Key West

star-4
4
Swap the busy bars of Key West for off-the-beaten-path places you wouldn't find alone. Aboard the island's only floating bar you'll learn fascinating stories about Key West while visiting a 100-year old Shipwreck, a movie set and Castaway Island. There's also opportunities for swimming, snorkeling and wildlife-watching.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$39.95
From
$39.95

2 Hour Morning Private Cruise on a Boat in Key West

2 Hour Morning Private Cruise on a Boat in Key West

Whether you bring your morning coffee or you bring bloody Mary's and mimosas, our early morning private cruise in the national wildlife refuge will start your day off in a relaxing manner.
More
  • 2 hours
  • Free Cancellation
From
$325.00
per group
From
$325.00
per group

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 Sightseeing Cruises in Key West?
Q:
What Sightseeing Cruises in Key West are taking additional safety precautions?
Q:
What Sightseeing Cruises in Key West are good for avoiding crowds?