Key West Senior Friendly Activities, Tours & Attractions

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Jun 12 - Jun 18
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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Half-Day-Key-West-Ultimate-Sandbar-Adventure-with-Mangrove-Kayak-Eco-Tour

Half-Day Key West Ultimate Sandbar Adventure with Mangrove Kayak Eco Tour

1 rating
6 Hrs.
Enjoy the ultimate combination of adventure, rest, and relaxation on this Half Day Key West Ultimate Sandbar Adventure with Mangrove Kayak Eco Tour. Cruise out to the Florida Marine Sanctuary for an incredible guided kayak eco tour through the mangrove isles and keep your eyes open wide as you never know which of the over 500 marine species of wildlife you will encounter. Your expert guides will take you to the best spots! After the kayak tour, have lunch on the way to a local secluded sandbar and then when you're all done on the kayak tour, the bar is open!! You will have unlimited access of soft drinks, draft beer, and wine selections. Grab a beverage and explore the secluded sandbar. Each trip will have a master captain and two additional crew members catering to your every need. Leave your stress behind and book this amazing sandbar adventure today!
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Barefoot-Billy-s-Seabreeze-Dolphin-and-Snorkel-Tour

Seabreeze Dolphin & Snorkel Tour

18 ratings
3.5 Hrs.
Be on the lookout for Key West’s magnificent dolphins while cruising the crystal clear backcountry waters of the Gulf of Mexico. On this family-friendly outing filled with amenities, observe dolphins and other Key West wildlife mingling in their natural habitat among deserted tropical islands. Don't forget to dive in and snorkel Key West's warm, gentle water to see all the ocean has to offer with a Seabreeze Dolphin & Snorkel Tour. Book 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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Jet-Ski-Island-Tour-from-Parrot-Key

Jet Ski Island Tour from Parrot Key

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1.5 Hrs.
Take a thrilling ride around the beautiful Key West by jet ski. Zip through the emerald waters and forget about your worries. See different sites such as, the Southernmost Point, Key West Harbor, and a local sandbar where you will have a chance to take a dip. While on the water, you may even catch a glimpse of bottlenose dolphins, pelicans, and many more marine animals in their natural habitats. Don't miss your bragging rights, book this thrilling Jet Ski Tour today!
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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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Conch-Tour-Train-Key-West

Hop On Hop Off Conch Tour Train Key West

12 ratings
Take a train ride through time and learn the legacy of Old Town from the Conch's themselves on this Hop On Hop Off Conch Tour Train in Key West. Be taken back in history where you'll discover the most famous sights. Your native tour guide will delight and enlighten you with interesting tales of yesteryears. All Aboard! It's time for you to learn about the magic and charm of Key West, get your seat on the Conch Tour Train today!
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Morning-Reef-Snorkel-and-Sail-by-Sebago-Watersports

Morning Reef Snorkel and Sail in Key West

32 ratings
3 Hrs.
Begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. First, you’ll sail seven miles off Key West’s majestic coast to the shallow Caribbean water of the Florida Keys Reef. Imagine yourself swimming in warm tropical waters with swarms of vibrant colorful fish all around you. Set off on an adventure and book your Morning Reef Snorkel with Sebago Watersports today.
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Key-West-Sunset-Sail-on-America-2-0-by-Classic-Harbor-Line

Key West Sunset Sail on America 2.0

45 ratings
2 Hrs.
Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green Flash." Experience the magic and romance of sailing at dusk as you sip champagne and watch for dolphins and other marine wildlife in the surf. Your friendly captain and crew will teach you the basics of sailing and even let you take the wheel. So, take a turn at the helm of one of the fastest schooners in the United States, book today!
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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

8 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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Booked 2 times in last 48 hrs
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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Day-Sail-Aboard-Schooner-America-2-0-by-Classic-Harbor-Line

Day Sail Aboard Schooner America 2.0

17 ratings
1.5 Hrs.
Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating for the whole family. The sights you’ll see along the way include a waterside view of Fort Zachary Taylor, the famed Sand Key Lighthouse, Mallory Square, and Sunset Pier. So sit back and feel the warm breeze dance across your skin as you watch the sights of the beautiful waters around Key West. Book your spot today!
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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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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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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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Guided-Backcountry-Paddle-Tour-with-Key-West-Eco-Tours

Guided Backcountry Paddle Tour

14 ratings
2 Hrs.
Adventure out and join this Guided Backcountry Paddle Tour of Key West's lush island mangroves. Choose from a paddleboard or kayak and enjoy the sheltered, calm water of the mangrove ecosystem. See the wonders of this unique habitat as your experienced nature guide highlights the plants, animals, and marine-life it contains. If you seek a relaxing and authentic retreat, book this unique paddle adventure today.
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Guided-Old-Town-Bike-Tour-with-Key-Lime-Bike-Tours

Guided Old Town Bike Tour of Key West

24 ratings
3 Hrs.
Slow down and explore the best from Old Key West on a guided bicycle tour! This leisurely ride will teach you all about the history, architecture, and culture of America's southernmost city. This tour hits all the local hotspots, provides great photo opportunities, and includes a complimentary slice of Key Lime Pie at the end of your trip! Book this tour today!
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