Recent Searches
Clear

Top Key West Day Cruises

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

21 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
219
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 Sunset Cruise with Live Island Music
Likely to Sell OutLikely to Sell Out

Key West Sunset Cruise with Live Island Music

star-4.5
475
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

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
416
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 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
1102
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

Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

star-5
267
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 Sunset Champagne Catamaran Cruise
Likely to Sell OutLikely to Sell Out

Key West Sunset Champagne Catamaran Cruise

star-4.5
331
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

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
344
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

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
424
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 Dolphin Watch and Snorkel Cruise
Likely to Sell OutLikely to Sell Out

Key West Dolphin Watch and Snorkel Cruise

star-4.5
535
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

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
726
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 Sunset Dinner Cruise with Tropical Buffet
Likely to Sell OutLikely to Sell Out

Key West Sunset Dinner Cruise with Tropical Buffet

star-4
411
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
227
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

Rum Runner Bar Boat Tour of Key West
Likely to Sell OutLikely to Sell Out

Rum Runner Bar Boat Tour of Key West

star-4
4
We are the only floating bar on the island and we take you to places that normal tours do not, 100 year old Shipwreck, Movie boat set of Beach Bum, and we provide swimming, snorkeling, water saddles and Reef viewers. You will see Castaway Island a.k.a. Christmas Tree, Sunset Key and the crazy wildlife in, under, and around the waters of Key West. We also offer Sunset Tours. Join us from launching off the only downtown beach in Key West - Lagerheads Beach Bar. Our beach has a restaurant and drink. Along with live entertainment and lounge chairs for you to rent and stay all day. See you soon.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$39.95
From
$39.95
Taking safety measures

Half-Day Cruise from Key West with Kayaking and Snorkeling
Likely to Sell OutLikely to Sell Out

Half-Day Cruise from Key West with Kayaking and Snorkeling

star-5
691
Get ready for fun in the sun on this half-day sailing, kayaking and snorkeling adventure off the coast of Key West. Choose from a morning or afternoon excursion and set sail. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef with 600 different species of marine life. Relax, feel the warm sea breeze and enjoy the day. Snacks, beer, wine, sodas and water included.
More
  • 4 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$96.75
From
$96.75
Taking safety measures

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
  • Taking safety measures
From
$103.20
From
$103.20
Taking safety measures

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
  • Taking safety measures
From
$60.20
From
$60.20
Taking safety measures

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

Glass Bottom Boat Island Eco Adventure

star-5
19
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
  • Taking safety measures
From
$645.00
per group
From
$645.00
per group
Taking safety measures

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
7
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
  • Taking safety measures
From
$475.00
per group
From
$475.00
per group
Taking safety measures

2-Hour Private Sunset Cruise Boat in Key West

2-Hour Private Sunset Cruise Boat in Key West

star-5
5
Being aboard a private boat for sunset in Key West is a unique experience that that is unparalleled compared to a large commercial boat trip.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$325.00
per group
From
$325.00
per group
Taking safety measures

Key West Private Morning Sail on Schooner America 2.0

Key West Private Morning Sail on Schooner America 2.0

star-5
1
Getting out on the water is key when traveling in the Keys. But many sailing trips can feel crowded and impersonal. This private tour, however, lets you enjoy the experience of having your very own yacht, without the hard work. As the crew work, you can simply lay back and enjoy the views and cool breeze.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$1,032.00
per group
From
$1,032.00
per group
Taking safety measures

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
  • Taking safety measures
From
$325.00
per group
From
$325.00
per group
Taking safety measures

Filters

What people are saying about Day Cruises in Key West

star-5
Key West Glass-Bottom Boat Tour with Sunset Option
"Ruth and Grace were very knowledgeable. We were able to talk to Grace for a little bit and she knew everything we asked about the island."..."
star-5
Key West Sunset Cruise with Live Island Music
"The band and crew were extremely friendly & fun. My sister and I enjoyed the music, breath taking views and wine."..."
star-5
Small-Group Key West Sunset Sail with Wine
"Sail was rain delayed due to the sudden downpour but it was still nice. The crew was very friendly. Would go again."..."
star-5
Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
"Had the best time. Great staff, good food, music and food. And the view was absolutely beautiful!! I would totally recommend this trip!! Well worth the money."..."
star-5
Sunset Sail in Key West with Beverages Included
"Excellent experience on the water! Wine was perfect and a great way to see Key West. This was definitely the high light of our trip."..."
star-5
Key West Sunset Champagne Catamaran Cruise
"The crew was amazing, the timing was perfect , we watched the sunset with a beautiful clear sky , we were about 30-35 people enough room for everyone. Bar service excellent"..."
star-5
Adults only Champagne Celebration Sunset Cruise from Key West
"Wonderful! Truly the highlight of our trip to key west! We were especially thankful to have just the right number of people on the boat and have a place to sit comfortably. We saw several others that packed people in like cattle. Not here. Very relaxed. Very beautiful sunset cruise! Thanks to Joe and Nikki as they did an excellent job!"..."
star-5
Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel
"Great day excursion! Got to see and experience things I never would have otherwise. Crew was fantastic. Highly recommend."..."
star-5
Key West Dolphin Watch and Snorkel Cruise
"We enjoyed seeing many dolphins on our trip! The crew, Capt Nicole and Amanda, were fantastic! Knowledgeable, friendly and fun. Couldn’t have asked for a better day on the water. We’re so glad we did this during our short trip to Key West!!"..."
star-5
Shark and Wildlife Viewing Adventure in Key West
"You go on these things and think you will be lucky to see even one shark. OMG! We saw at least twenty of them! What an experience! Definitely recommend!"..."
star-5
Key West Sunset Dinner Cruise with Tropical Buffet
"We had so much fun dancing to the wonderful live reggae music while we watched the beautiful sunset. The food was excellent and there was plenty of it. We loved being welcomed on the boat with a tasty cocktail! The staff were all friendly with smiling faces. Thank you for a great vacation memory."..."
star-5
Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
"The sunset was spectacular. The crew did and excellent job keeping everyone safe and beverages plenty."..."
star-5
Rum Runner Bar Boat Tour of Key West
"Had an absolute blast, Brian is awesome!! The boat is so cool, will definitely plan another trip with him. Also the rum was amazing."..."
star-5
Half-Day Cruise from Key West with Kayaking and Snorkeling
"Was a very fun experience! First we sailed and snorkeled after that we went kayaking, it was the perfect way to spend the day"..."
star-5
Key West Sunset Sail Aboard Schooner
"From start to finish this was an amazing sunset cruise. The staff was top notch! Loved every second!"..."
star-5
Key West Day Sail Aboard Schooner
"Beautiful day, great crew And great weather Made for a fantastic day of sailing. Highly recommend it."..."
star-5
Glass Bottom Boat Island Eco Adventure
"This was the single best charter boat experience we've ever had. Ashley, the captain, was stellar. We walked down Front Street in Key West and ended up on the pier. Then we asked around and found the Looking Glass over to the right, a couple docks over. We literally signed a form, climbed in the boat, and were on our way. She took us around the bay in Key West, pointing out points of interest, then took us to a natural sponge bed where we saw tangs and striped fishes. Then she took us to a remote island about 14 miles off shore. It had gorgeous white sand and we were able to snorkle and look for shells. She spotted a dolphin pod and we went to the spot where they were and sat for 45 minutes while they played and jumped and went under the boat! There were probably 15 dolphins with babies. Ashley is a great captain and she's fun and intelligent and interesting, but she also knows her craft. She pilots the boat very steadily so nobody got seasick. Of all the things we did in Key West, this was absolutely the highlight of the trip and worth every penny. The boat has a full cover so there's always shade, and she has a hose on board with fresh water for rinsing off. Such a Fantastic experience."..."
star-5
4-Hour Private Cruise to a Sand Bar on a Boat in Key West
"It was a great ride. Captain Rick had some great knowledge of the area. He had everything you needed for a great time!"..."
star-5
2-Hour Private Sunset Cruise Boat in Key West
"Captain Rick was extremely knowledgeable about the area and we learned a lot of local news while out on his boat! We thoroughly enjoyed our cruise."..."

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