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Key West

Romance & special occasions

Our most recommended Key West Romance & Special Occasions

Key West: 2-Hour Sunset Sail with Live Music

1. Key West: 2-Hour Sunset Sail with Live Music

Set sail on a breathtaking sunset cruise aboard a spacious catamaran. Admire views of the Historic Seaport, pass jugglers and entertainers at the Mallory Square Sunset Celebration, and gaze at Fort Zachary Taylor. Enjoy unlimited drinks and appetizers on board, as well as live musical entertainment. Sail past the landmarks of Key West, as your captain positions the ship to maximize your view of the sunset. Savor a fantastic evening on the water.

Key West: Sunset Sailing Trip with Open Bar, Food and Music

2. Key West: Sunset Sailing Trip with Open Bar, Food and Music

Join a sailing experience to get you closer to the sunset than ever before. Set sail from the historic sea port of Key West and head straight out to sea for a cruise with unobstructed views of the sunset on the horizon. During the cruise, enjoy an unlimited open bar, with a wide variety of drinks on offer including rum runners, Champagne, margaritas, and draft beer. Taste a selection of finger foods, ranging from Swedish meatballs, veggie treats, cheese and crackers, pita and hummus, and meat and veggie platters. You will be sailing on one of Key West's newest sailing catamarans, the Sandie Cat. This vessel has capacity for up to 149 passengers across 3 decks, so there will always be plenty of room onboard. Grab a drink, head to the upper deck, and dance to live music as you watch the sun go down. The captain and crew will even let you help raise the sails and you can ask to have a picture taken driving the boat.

Orlando: Mango's Tropical Cafe Dinner and Show

3. Orlando: Mango's Tropical Cafe Dinner and Show

Experience authentic flavor, dynamic performances, and much more at Orlando's hottest destination in nightlife and entertainment: Mango's Tropical Café.  Dine and dance in an energy that's unmatched and electric, all in the heart of the city's famous International Drive. Enjoy a family-friendly dinner and show, featuring paramount live entertainment including a Michael Jackson tribute, a Brazilian Samba, Cuban Conga, and other Latin-inspired numbers throughout the entire breathtaking venue. Mango's live band promises to get you on your feet with lively and passionate authentic Latin music featuring congas, bongos, horns, 80's, 90's, today's hits, and more.  Savor a three-course gourmet menu of fresh "Floribbean" cuisine. Specializing in Latin and Caribbean comfort foods, as well as American favorites, Mango's serves up a one-of-a-kind dining experience for every person at your table. Menu: Starter choice of: • House salad • Caesar salad • Tomato bisque Entree choice of: • Fajita jerk seasoned chicken breast • Braised short ribs • Salmon al Limon • Plant-based penne bolognese All entrees, except the plant-based penne, are served with yellow rice, Cuban-style black beans, and plantains. Dessert choice of: • Mango coconut bread pudding • Dulce de leche chocolate cake • Mascarpone cheesecake

Key West: Snorkeling, Sunset Dinner Cruise & Open Bar

4. Key West: Snorkeling, Sunset Dinner Cruise & Open Bar

Make the most of your day in Key West with a morning snorkeling adventure at Keys Reef, located 9 miles from shore, with breakfast and unlimited mimosas and beers. Then return in the evening for a 2-hour Sunset Dinner Cruise featuring an all-you-can-eat buffet, live music, and open bar. Depart Key West in the morning on a catamaran for your snorkeling session. Sail 9 miles out to explore Keys Reef, famous for its abundance of fish. On your way to the reef, enjoy breakfast with fresh fruit, juice, muffins, and an assortment of cereals. Swim with colorful subtropical fish like yellowtail snapper, damselfish, parrotfish, and angelfish. Marvel at schools of blue-striped grunts or toothy green moray eels. See coral formations like purple sea fans, as well as crustaceans and mollusks like spiny lobsters, crabs, and conchs. After you finish exploring the underwater world, enjoy draft beer and/or mimosas on the return journey to Key West. Enjoy free time in the afternoon to explore Key West at your own pace. In the evening, check-in for your sunset dinner cruise departing from the port. Gaze out into the Gulf of Mexico, watch as the sun falls below the horizon, and maybe see the green dot – best seen on the water with a panoramic view of the setting sun. Enjoy the fantastic views from 2 decks, including an open deck on the top of the boat. Then, tuck into an all-you-can-eat buffet with an open bar. Listen to the local steel drum performer fill the air with tropical vibes, grab margaritas, rum runners, or a glass of wine as you enjoy dinner and dance with the setting sun as your backdrop.

Key West: Private Tiki Boat Sunset Cruise

5. Key West: Private Tiki Boat Sunset Cruise

Come with your friends or family for an unforgettable experience on a private tiki bar boat cruise in Key West during sunset. Enjoy your own food and drinks as the sun sets over the picture-perfect scenery. Toast to the sunset with your favorite drinks in hand and keep an eye out for the green flash as the sun meets the beautiful Caribbean water. Cruise past the world-famous Mallory Square and then just beyond Sunset Key to find the best vantage point. Your captain will point out all the sites as you cruise around the harbor and eventually return to the Historic Charter Boat Row.

Key West: Windjammer Sunset Cruise with Snacks and Drinks

6. Key West: Windjammer Sunset Cruise with Snacks and Drinks

Set off in search of the perfect sunset aboard the Appledore II, a 2-masted wooden schooner. Sip on your favorite drink and enjoy some snacks as a part of this scenic sunset tour that also takes you past some of Key West’s famous sights. With the painted sky as the backdrop, your sunset sail takes you past Key West’s historic seaport, Mallory Square’s sunset celebration, the navy mole where the big ships dock, and the civil war era Fort Zachary Taylor. Take in the sights while enjoying a glass of champagne or boutique wine, home-made sangria, an ice-cold beer, soft drinks, or something from the full cocktail bar. Savor the chef’s selection of hors d’oeuvres, cocktail shrimp, and tuna poke as well. Feel a sense of adventure as the crew hoists the sails and participate in this tradition by helping to raise the sails. When the sun begins its descent, your captain will take the boat to the perfect spot to maximize the setting sun views.

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Frequently asked questions about Key West Romance & Special Occasions

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Other Sightseeing Options in Key West

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What people are saying about Key West

It was all good everyone was friendly and helpfull in every way. The show was wonderful and the music was great !

Well worth the trip. Great music, delicious snacks, and open bar all timed perfectly to a setting sun.

The captain and crew were very friendly, sociable and safety minded. The snacks and drinks were good.

Excellent service the girl served us was soooo nice Amazing shows, food was so Good

A nice experience. Good music, drinks and food and the best sunset.