Recent Searches
Clear

Learn more about our Covid-19 response.

Read More

Learn more about our Covid-19 response.

Read More

Top Key West Sailing

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.
These experiences are highly rated by travelers and have met our top quality standards.
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
On the Water
Nature and Wildlife
Sightseeing Tours
Cruises & Sailing
Extreme
Sporting Events
Snorkeling
Motor Sports
Swimming
Kayaking
More

21 results | All Key West Tours

Sort by:Featured

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

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

star-5
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
$169.95
From
$169.95
Taking safety measures

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

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

star-5
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
$69.95
From
$69.95
Taking safety measures

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

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

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.
More
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$119.95
From
$119.95
Taking safety measures

Hey, nice badge.
Experiences with this badge meet our highest quality standards and are loved by travelers like you.
Learn more
Key West Sunset Champagne Catamaran Cruise

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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.95
From
$45.95
Taking safety measures

Key West Snorkel and Sunset Sail: Rum n' Reggae

Key West Snorkel and Sunset Sail: Rum n' Reggae

star-4
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
$49.34
From
$49.34
Taking safety measures

Small-Group Key West Sunset Sail with Wine

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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$91.38
From
$91.38
Taking safety measures

Key West Sunset Sail Aboard Schooner

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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$103.20
From
$103.20
Taking safety measures

Adults only Champagne Celebration Sunset Cruise from Key West

Adults only 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.
More
  • 2 hours
  • Taking safety measures
From
$79.49
From
$79.49
Taking safety measures

Sunset Sail in Key West with Beverages Included

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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$61.46
From
$61.46
Taking safety measures

Key West Wild Dolphin Sail and Shallow-Water Snorkel

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.
More
  • 4 hours
  • Taking safety measures
From
$95.59
From
$95.59
Taking safety measures

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

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

star-5
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
  • Taking safety measures
From
$79.95
From
$79.95
Taking safety measures

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

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

star-4.5
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
$109.95
From
$109.95
Taking safety measures

Key West Day Sail Aboard Schooner

Key West Day Sail Aboard Schooner

star-5
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

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

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
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
$56.19
From
$56.19
Taking safety measures

Florida Keys Afternoon Reef Snorkel & Sail Adventure

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
More
  • 3 hours
  • Free Cancellation
From
$69.00
From
$69.00

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

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

star-4.5
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 3 hour sail is more like a private cruise than a group tour and is one of the top things to do in Key West. As we leave behind the Historic Seaport, look for Key West landmarks like the legendary Mallory Square, opulent Sunset Key and historic Fort Zachary Taylor. On reaching open water, the sails are unfurled and your adventure begins as your captain tracks dolphin pods to provide you an up-close view of these elusive creatures. With the dolphin viewing over, your cruise is just getting started! Grab a drink and relax as your captain positions the luxury catamaran for the perfect view of a famous Key West sunset. A chef’s selection of Tapas including shrimp cocktail and tuna poke are served during the sail. Choose your favorite drinks, including boutique wines and champagne perfectly paired with our Tapas – all included in the cost of your tour!
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$79.95
From
$79.95
Taking safety measures

Morning Reef Snorkel & Sail Adventure from Key West

Morning Reef Snorkel & Sail Adventure from Key West

star-5
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
$70.77
From
$70.77

Group Sunset Cruise from Duck Key

Group Sunset Cruise from Duck Key

star-5
The Solé Watersports Sunset Cruise at Hawks Cay Resort is the only Sunset Cruise in the Duck Key area. It includes cruising along the resort and homes of Duck Key, into open water and over to the uninhabited islands of Tom's Harbor. During the cruise, we'll watch for coastal birds hiding in the mangroves, pods of dolphins, and other sea life lurking in the sea grass and conclude with a Sunset Champagne Toast!
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$75.00
From
$75.00
Taking safety measures

3-Hour Private Catamaran Sunset Sail of Key West with 1 Activity

3-Hour Private Catamaran Sunset Sail of Key West with 1 Activity

star-5
Private sail with your friends, which can include either snorkeling, paddling or fishing, but always ends with some appetizers, drinks (BYOB) and a Key West Sunset! Private Single Activity Trip – Perfect to Play on the Reef or Just Sail and Enjoy the Sunset: Enjoy a traditional sailing charter Key West style, embarking from the Safe Harbour Marina on Stock Island. With a feel of “Old Key West”, the shrimp boats and local craftsmen provide a picturesque beginning to your afternoon. Once aboard you will appreciate the luxury accommodations of our charter catamaran with plenty of room to roam about. Sailing a large modern catamaran is quite easy and involves as little or as much effort as you wish to put into it. Ask to help raise the sails or take a turn at the helm if you like. The destinations for the optional activities are less than one hour away, making this 3 hour trip ideal for one of them. ○ Bring your own alcohol, beer or wine if you wish. We will keep it cold and serve you
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$799.00
per group
From
$799.00
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

Enjoy a morning sailing experience and have Schooner America 2.0 all to yourself! Let us whisk you and yours away on a glorious morning sail across the beautiful waters of Key West on your own private yacht! This 1.5 hour charter aboard the America 2.0 grants you all the luxuries of yachting on your own private schooner. Let our crew do the work as you sit back and relax and take in the sights. Soda and water included. Alcoholic beverages and food are available for purchase onboard. Due to our licensing, guests are not permitted to bring their own alcoholic beverages on their sail. At this time, we do not offer swimming, snorkeling, or diving. After booking, you will be contacted by a Classic Harbor Line representative regarding more details about your trip.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$750.00
per group
From
$750.00
per group
Taking safety measures

Filters