Key West Romantic Activities, Tours & Attractions

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!

This triple combo tour gives you three amazing experiences in one package. Watch pods of local dolphins playing in their natural habitat, snorkel at a tropical reef, and last but not least witness the famous Key West sunset! This action-packed, three-for-one adventure is sure to yield magic and memories to last a lifetime. Book now!

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!

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!

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!

Hop aboard for an adventure through the most diverse underwater ecosystem in the United States with the Glass Bottom Boat Reef & Eco Tour. Enjoy traveling the tropical and sun-kissed waters of the Florida Keys on a sleek and comfortable catamaran as you scope stunning seascapes through a glass bottom. Take an underwater adventure in North America’s only living coral reef without even getting wet. See the home to elkhorn, brain coral, and hundreds of diverse fish species. Come along on a fun and informative tour of the Florida Keys on Key West's only window to the sea! Book now!

Take a thrilling ride around the beautiful Key West by jet ski. Zip through the emerald water 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!

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!

Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise in Key West, Florida. Experience some of Key West’s best musicians as you dance to the backdrop of a gorgeous, tropical sunset. Eat, drink, and be merry aboard a spacious and comfortable catamaran and take in all of the stunning sights and sounds. For an evening you'll want to last forever, set sail on this Live Music Sunset Cruise! Book today!

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!

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!

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!

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!

Treat yourself to an action-packed, 28-mile jet ski tour among the sparkling water 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.

Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Miss Valyn Catamaran. A twilight experience unlike any other, this is your opportunity to enjoy the nightlife while having the option to plunge into the depths by Florida's best reef! Take in the fleeting Key West sunset while indulging in an ambiance that only the cat delivers. Enjoy reef snorkeling, draft beer & wine on this snorkeling experience. Book your spot today!

Get out early and experience nature at its finest with a half-day island adventure complete with sailing, kayaking, and snorkeling all in one. You'll see an incredible array of birds, fish, and other regional wildlife while you explore Key West's backcountry and take in all the natural beauty around you. Live the island dream as you set sail in a 65-foot schooner, then kayak through the mangrove forests and snorkel the blue waters. Book today and let your adventure begin!

Get out on the water and experience nature at her finest with Full Day Sail, Snorkel, and Kayak Excursion complete with sailing, kayaking, and snorkeling. You'll see an incredible array of birds, fish, and other regional wildlife while you explore Key West's backcountry and take in all the beauty around you. Live the island dream as you set sail on a 65-foot Schooner, then kayak through the mangrove forests. Snorkel the blue waters in search of tropical marine species. Book this Full Day Sail, Snorkel, and Kayak Excursion today. Let your adventure begin!

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!

Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating lily pad. Enjoy this unique private adventure with family and friends, away from the crowds. Be sure to take in all of Key West's beauty while relaxing and soaking up the sun from the water. Book today and set out on a private sailing adventure.