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Top Key West Day Cruises

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8 results | All Key West Tours

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Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

star-4.5
328
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
$69.82
From
$69.82
Taking safety measures

Key West Sunset Sail Aboard Schooner

Key West Sunset Sail Aboard Schooner

star-5
170
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
$103.20
From
$103.20
Taking safety measures

Key West Glass-Bottom Boat Tour with Sunset Option

Key West Glass-Bottom Boat Tour with Sunset Option

star-4
167
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$49.77
From
$49.77
Taking safety measures

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Small-Group Key West Sunset Sail with Wine

Small-Group Key West Sunset Sail with Wine

star-5
280
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 Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

star-5
121
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
  • Taking safety measures
From
$61.46
From
$61.46
Taking safety measures

Key West Day Sail Aboard Schooner

Key West Day Sail Aboard Schooner

star-5
55
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.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$60.20
From
$60.20
Taking safety measures

Private Cruise in Florida Keys with Snorkeling Experience

Private Cruise in Florida Keys with Snorkeling Experience

We are the exclusive operator on the quiet tropical island of Duck Key. Our US Coast Guard licensed captains have over 50 years combined excursion experience in the Middle Keys and look forward to sharing our lovely paradise with you! New to snorkeling? No problem, your captain will provide all the tips to have you exploring our local sea-life in no time. We hold ourselves to a high standard and run a quality operation. With your enjoyment in mind, the private boats are clean, comfortable offering multiple seating options, and maintained regularly. After your 3 hour excursion, you’ll fall in love with the Keys!
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$622.57
per group
From
$622.57
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.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$750.00
per group
From
$750.00
per group
Taking safety measures

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