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We’re committed to helping you feel confident as you get back out there. Check out our flexible cancellation policies and learn what steps operators are taking to keep you safe. As conditions evolve, check local regulations for the latest information.

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77 Key West On the Water | All Key West Tours

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Schooner Key West Day and Sunset Cruises with Full BarSailing

Schooner Key West Day and Sunset Cruises with Full Bar

star-4.5
Set sail on the schooner Appledore for a scenic cruise from Key West!.  Join the crew to raise the sails, take a turn at the wheel, or just soak up views of the gorgeous Florida coast with a cocktail.. Choose a day sail for maximum sunshine, or opt for a sunset sail in the early evening, then enjoy a selection of drinks during your time on the water.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$38.95
From
$38.95
Taking safety measures

Key West Sunset Sail with Premium Wine, Champagne and Tapas PairingsDay Cruises

Key West Sunset Sail with Premium Wine, Champagne and Tapas Pairings

star-4.5
Our Captain’s Choice Sunset Sail is limited to an intimate number of passengers for an awesome experience! It’s more like a private cruise than a tour and is one of the top things to do in Key West. A chef’s selection of Tapas is served during the sail, prepared fresh daily by Sebago’s own catering kitchen. Delectable shrimp cocktail and tuna poke are Sebago’s signature dishes. Choose your favorite drinks, including boutique wines and champagne perfectly paired with our Tapas – all included in the cost of your tour! As the sun sinks lower, your captain carefully positions the boat to capture a perfect view of the fiery sky. As we leave behind the Historic Seaport, look for Key West landmarks like Mallory Square’s Sunset Celebration with its jugglers, opulent Sunset Key and the historic Fort Zachary Taylor. On reaching open water, the sails are unfurled to provide you with an authentic sailing experience. A sunset cruise Key West style with Sebago will forever linger in your memories.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$79.00
From
$79.00
Taking safety measures

Key West Sunset Sail Aboard SchoonerDay Cruises

Key West Sunset Sail Aboard Schooner

star-5
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$81.70
From
$81.70
Taking safety measures

Sunset Sail in Key West with Beverages Included Day Cruises

Sunset Sail in Key West with Beverages Included

star-5
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$61.46
From
$61.46

Key West Sunset Cruise with Live Island MusicDay Cruises

Key West Sunset Cruise with Live Island Music

star-4.5
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$58.72
From
$58.72
Taking safety measures

Key West Sunset Dinner Cruise with Tropical BuffetCity Packages

Key West Sunset Dinner Cruise with Tropical Buffet

star-4
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$67.65
From
$67.65
Taking safety measures

Rum Runner Bar Boat Tour of Key WestDay Cruises

Rum Runner Bar Boat Tour of Key West

star-3
We are the only floating bar in 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 if you book the whole boat. 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.
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  • 1 hour
  • Free Cancellation
From
$35.00
From
$35.00

Key West Sunset Champagne Catamaran CruiseCity Packages

Key West Sunset Champagne Catamaran Cruise

star-4.5
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.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Key West Shark Spotting and Wildlife Catamaran TourCity Packages

Key West Shark Spotting and Wildlife Catamaran Tour

star-5
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.
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  • 2 hours
  • Free Cancellation
From
$84.27
From
$84.27

Key West Glass-Bottom Boat Tour with Sunset OptionDay Cruises

Key West Glass-Bottom Boat Tour with Sunset Option

star-4
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 Champagne and soft drinks as the sun settles into the Gulf of Mexico.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$49.77
From
$49.77
Taking safety measures

Small-Group Key West Sunset Sail with WineDay Cruises

Small-Group Key West Sunset Sail with Wine

star-5
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$91.38
From
$91.38
Taking safety measures

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

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

star-5
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$56.19
From
$56.19
Taking safety measures

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

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

star-5
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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$56.19
From
$56.19
Taking safety measures

Champagne Celebration Sunset Cruise from Key WestWine Tasting

Champagne Celebration Sunset Cruise from Key West

star-5
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.
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  • 2 hours
  • Taking safety measures
From
$79.49
From
$79.49
Taking safety measures

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

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

star-5
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. Snorkel above a coral reef. 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.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$114.95
From
$114.95
Taking safety measures

Key West Wild Dolphin Sail and Shallow-Water SnorkelSailing

Key West Wild Dolphin Sail and Shallow-Water Snorkel

star-4.5
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.
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  • 4 hours
  • Taking safety measures
From
$95.59
From
$95.59
Taking safety measures

Key West Dolphin Watch Day or Sunset Snorkel CruiseSnorkeling

Key West Dolphin Watch Day or Sunset Snorkel Cruise

star-4.5
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$74.95
From
$74.95
Taking safety measures

Island Adventure Snorkel Kayak and Tour from Key WestSailing

Island Adventure Snorkel Kayak and Tour from Key West

star-4.5
Get access to a remote nature sanctuary, known only to Key West locals, during this island adventure. Choose to paddleboard, kayak, snorkel, or just lounge on the sandbar and take in the natural ambiance. Snack, lunch, and use of snorkel equipment included; wine and beer available after activities.
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  • 4 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$118.50
From
$118.50
Taking safety measures

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

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

star-4.5
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.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$89.95
From
$89.95
Taking safety measures

Key West Dolphin Watch and Snorkel CruiseSnorkeling

Key West Dolphin Watch and Snorkel Cruise

star-4.5
Get ready for fun in the sun on this dolphin watch and snorkeling adventure off the coast of Key West. Sail 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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$68.00
From
$68.00
Taking safety measures

Florida Keys Afternoon Reef Snorkel & Sail AdventureSailing

Florida Keys Afternoon Reef Snorkel & Sail Adventure

star-5
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour trip out to the reef, we will have you there for an hour and then a one hour journey back to our dock. We will provide instruction on how to use the equipment but recommend that you are comfortable in water over your head and that you have the ability to swim. *We provide quality sanitized mask, snorkel, fins and flotation vest *Complimentary beverages to include water, soda, white wine, a selection of craft beers, margaritas, flavored mimosas and champagne *Floridays takes a limited number of guests so that we may provide you with the ultimate in enjoyment and service
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  • 3 hours
  • Free Cancellation
From
$69.00
From
$69.00

Go Miami All-Inclusive Pass with Hop-on Hop-off and Zoo MiamiMountain Bike Tours

Go Miami All-Inclusive Pass with Hop-on Hop-off and Zoo Miami

star-4
The Go Miami™ Pass is an all-inclusive pass offering the best choice for maximum savings and flexibility when visiting Miami and South Beach. Choose 1-, 2-, 3-, or 5-day passes and save up to 55 percent versus paying at the gate—like a trip to the Key West Day Trip or an Everglades airboat ride, just to name a few. Each pass is good for two weeks from first use. Access on your mobile device or print and go. It’s that simple to experience some of Miami’s best attractions. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes (purchased by December 31) are valid for two year from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 30 days and/or the remaining number of attraction choices purchased.
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  • 5 days
From
$81.00
From
$81.00

Private Key West Sunset SailDay Cruises

Private Key West Sunset Sail

star-4.5
Watch the sun set and the moon rise off the coast of Key West on this private, 2-hour sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a private sailing vessel with a captain and mate. Stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset. Soft drinks are included. A cooler with ice is available to store any beverages brought on board.
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  • 2 hours
  • Free Cancellation
From
$479.99
per group
From
$479.99
per group

Afternoon Glass Bottom Boat Coral Reef Adventure from Key WestDay Cruises

Afternoon Glass Bottom Boat Coral Reef Adventure from Key West

Join us for an island adventure on our 28′ custom glass bottom boat, Looking Glass! Book just your seat or the whole boat. We’ll explore the coral reefs like you’ve never seen them before! Up close and personal, whether you decide to jump in the water and snorkel or stay on board and relax in the shade of the boat while you gaze at the many wonders of the reef through the Looking Glass. Snorkel gear is provided.
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  • 3 hours
  • Free Cancellation
From
$103.13
From
$103.13

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