Key West Special Occasion Activities, Tours & Attractions

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May 28 - Jun 3
Land-s-End-Sunset-Sail-with-Hors-d-Oeuvres-by-Sebago-Watersports

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

211 ratings
2 Hrs.
Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local landmarks and sail past Sunset Key and historic Fort Zachary Taylor as you dine on a tasty selection of varied hors d'oeuvres. Watch the sunset with your favorite drink in your hand and your loved ones by your side. Enjoy live music from local musicians! These are moments you’ll savor long after you leave town! Don't miss the boat. Book your spot today!
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Sunset-Dinner-Cruise-by-Sunset-Watersports

Key West Sunset Dinner Cruise

289 ratings
2 Hrs.
If you are looking to make memories on a glorious Key West sunset as you dine and enjoy drinks with your loved ones, then this is the perfect cruise for you. This Key West Sunset Dinner Cruise allows you to have it all. Experience a delectable dinner and drinks out at sea with a friendly crew and dine on tropical-inspired featured dishes like Roast Pork with heavenly Cuban Bread followed by fried plantains. Your meal is prepared fresh on board and your catamaran features a fully stocked bar and comfortable seating in a climate-controlled cabin. So, get out on the water and dine, drink, and dance away the day on this classic Key West Sunset Dinner Cruise. Reserve your spot today!
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Booked 2 times in last 48 hrs
Champagne-Sunset-Sail-by-Sebago-Watersports

Champagne Sunset Catamaran Cruise

100 ratings
1.5 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted sunset fade into dark as the stars give an encore unlike any other. Stretch out and enjoy a pampering of complimentary drinks with family or a special someone. Come feel the ocean breeze blow through your hair and dance across your skin as the sun sets over Key West, book your Champagne Sunset Sail today!
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Key-West-Party-Boat-Fishing-Trip

Key West Party Boat Fishing Trip (6 Hour)

23 ratings
6 Hrs.
If you're looking for the best angling adventure in Key West, then this 6 hour Party Boat Fishing Trip is the one for you! Cruise brilliant blue waters as your expert captain and crew put you on the fish! Enjoy the thrill of the catch as you reel in a shot at record-breaking snapper, grouper, cobia, amberjack, and more. Learn expert tips and tricks, as well as local secrets that will ensure you have the trip of a lifetime! Book today!
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Captains-Choice-Sunset-Sail-with-Wine-and-Tapas-Pairings

Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

114 ratings
2.5 Hrs.
Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset Sail. Enjoy superbly crafted tapas like tuna poke and shrimp cocktail along with champagne, select premium wines including LaCrema, beer, and sangria as you journey to view majestic dolphins, landmark sights and the world famous Key West sunset. Get an authentic sailing experience as the captain and crew raise the sails on your luxurious catamaran and set out to find dolphins playing and frolicking in the surf and often near the boat! Book yours today!
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Rise & Reef Snorkeling Trip With Breakfast & Unlimited Mimosas

39 ratings
3 Hrs.
Take an adventure into the depths to explore Florida's best reef on a snorkeling experience you will never forget! The Sandie Cat is Key West's newest and fastest snorkeling catamaran, which means less time wasted and more time for exploring the deep blue sea! Join the crew as they hoist the sail and get you and your family and friends out for a true Key West experience. Enjoy a complimentary breakfast, as well as unlimited mimosas (mango, strawberry & orange) & unlimited draft beer, in this all-inclusive snorkel experience. Reserve your spot today!
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Sunset-Sip-and-Sail-with-Live-Music-by-Sunset-Watersports

Sunset Sip and Sail with Open Bar and Live Music

53 ratings
2 Hrs.
Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this nightlife experience. You can dance the night away to live music while you sail the calm waters. Enjoy the best seat in the house with all of the good time essentials like draft beer, live music, open well bar, and appetizers. Book your spot now!
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Jet-Ski-Island-Tour-by-Sunset-Watersports

Jet Ski Island Tour of Key West from Cow Key Marina

30 ratings
2 Hrs.
Treat yourself to an action-packed, 28-mile Jet Ski tour among the sparkling waters of Key West and beyond. Join entertaining and experienced guides as they lead you on a scenic tour around the island that includes a slew of fantastic sights like the Southern Most Point, Key West Harbor and a local sandbar where you’ll have a chance to take a dip! Choose the last trip of the day and take in the beautiful sunset! Don't miss out on this fast-paced adventure, book yours today.
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Wind-and-Wine-Sunset-Sail-with-Danger-Charters

Wind and Wine Sunset Sail

71 ratings
2 Hrs.
Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around the world. Rated one of the top two sunset tours in all of North America by Coastal Living Magazine, this luxurious Wind and Wine Sunset Sail on a historic Schooner will not disappoint. Make some new friends, enjoy tropical music, and delight your palate as you watch the sun melt into the water. Book your spot today!
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Dip-and-Sip-Afternoon-Snorkel-Trip-by-Sunset-Watersports

Dip and Sip Afternoon Snorkel with Open Bar

53 ratings
3 Hrs.
Take an afternoon and plunge into the depths of Florida's coral reef for an amazing snorkeling experience. The Sandie Cat is Key West's newest snorkeling catamaran, which allows you to get to the reef with speed, comfort, and some serious style. Join the captain and crew, round up your group, and hit the waves for an unforgettable Key West experience packed with fun, sun, and tasty spirits. This all-inclusive trip boasts an open well bar including unlimited mimosas (mango, strawberry & orange) & a variety of soft drinks! Book your spot today!
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Schooner-Champagne-Sunset-Sail

Schooner Champagne Sunset Sail

11 ratings
2 Hrs.
Come along on this Champagne Sunset Sail and step into luxury. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline waters to landmark sites while sampling a wide variety of complimentary drinks. Come toast to an idyllic Key West sunset on the schooner cruise that is sure to become your favorite new Key West tradition. Book yours today!
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Island-Hopper-Excursion-with-Snorkel-by-Sunset-Watersports

Key West Safari Eco Tour

12 ratings
2.5 Hrs.
Are you looking for the best kept secret in Key West?! If so, then hop in your own personal, mini speedboat and follow your knowledgeable guide into Key West's backcountry. You'll race through lush mangrove islands and see amazing marine wildlife along the way while boating in Key West's magical tropical waters. Book today and set out on an amazing adventure on the water with this Key West Safari Eco Tour!
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Sunset-Sail-Aboard-the-Historic-When-and-If

Sunset Sail Aboard the Historic When and If

20 ratings
2 Hrs.
Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s dream of sailing around the world “When and If” he was able, is available to the public for the first time in the yacht's lifetime. Sit back and experience the beautiful Key West sunset in style as the wooden schooner glides through the water driven by wind power alone. Meet the crew as they serve up a beautiful array of gourmet cheeses and share their stories of old Key West and the sea.
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Barefoot-Billy-s-Seabreeze-Sunset-Harbor-Cruise

Seabreeze Sunset Harbor Cruise with Wine and Beer

18 ratings
2 Hrs.
Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your journey takes you away from commonly charted boat paths to unobstructed views and miles of turquoise waters, while snacking on delicious sushi and snacks. Travel to where the Gulf meets the Atlantic and on to the Southernmost Point of the United States. For an intimate and romantic evening that is sure to help you unwind, book a Sunset Harbor Cruise and toast to life!
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FishMonster-Max-Half-Day-Party-Boat-Fishing

FishMonster Max Half-Day Party Boat Fishing

7 ratings
5 Hrs.
Get out on the water and enjoy Key West's newest and most luxurious party boat. FishMonster Max Half-Day Party Boat Fishing is your chance to fish the reef like never before. Cruise on this completely remodeled 64-foot twin engine catamaran, relax in the cool air-conditioned galley, or head up top for incredible 360 degree views of the ocean. Take your fish home to be enjoyed later or walk them over to any one of the numerous restaurants located along the dock and have it cooked just the way you like it! Spend your morning fishing and your evening enjoying your fresh caught dinner. This is the fishing trip of a lifetime, book today!
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2-Hour-Private-Tiki-Boat-Party

2 Hour Private Tiki Boat Party

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2 Hrs.
Join a Private Tiki Boat Party in Key West, Florida with your own custom Beachcat Tiki Boat. Glide through the gorgeous, clear Florida Keys water and take in the stunning scenery of the area around you while listening to some of your favorite tunes on an 8-speaker Bluetooth stereo system. Bring your favorite cocktail, a couple of snacks, and your most fun-loving friends for an adventure everyone will remember! Book this 2 hour Tiki Boat Party today!
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Key-West-Night-Glow-Paddle

Key West Night Glow Paddle

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45 Min.
Explore the stunning waters of Key West as you embark on an enchanting journey in a crystal clear kayak. Immerse yourself in the captivating ambiance of the night as it casts a mesmerizing glow around you. Marvel at the luminescent wonders that come to life during the nighttime hours. Whether you’re planning a romantic evening, a fun-filled adventure with friends, or a memorable family outing, this glow paddling experience is the perfect choice. Book your spot for this extraordinary nocturnal adventure and secure your clear LED kayak online today!
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2-Hour-Private-Sunset-Cruise-on-a-Tiki-Bar-Boat

2 Hour Sunset Tiki Boat Cruise

5 ratings
2 Hrs.
If you are looking for a way to float away the day, then this 2 Hour Sunset Cruise on a Tiki Bar Boat is the right choice for you. Key West is famous for its glorious sunsets and this tiki cruise does not disappoint. This custom 20 foot tiki bar catamaran features a private bathroom, Bluetooth stereo, and flatscreen TV. Toast the sunset with your closest companions and favorite libation while experiencing the gorgeous scenery, cotton candy skies, turquoise water, and pure relaxation on this 2 Hour Sunset Cruise on a Tiki Bar Boat. Book today!
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Key-West-Sandbar-Snorkeling-and-Island-Hopping

Private Key West Sandbar & Snorkeling Charter

9 ratings
4 Hrs.
Experience the beautiful Florida Keys and its lush mangroves, islands, turquoise waters, and marine life on this Private Key West Sandbar & Snorkeling Charter for up to 6 guests. Skip the usual trips with salty sailors and opt for a day with the nicest captain around. Cruise on a center console and snorkel and chill on a sandbar or opt for some island hopping fun, your trip is totally customizable. Don't miss out, book yours now!
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2-Hour-Private-Tiki-Boat-Eco-Tour

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