Add dates

Key West Romance & special occasions

Our most recommended Key West Romance & special occasions

Key West: 2-Hour Sunset Sail on Schooner America 2.0

1. Key West: 2-Hour Sunset Sail on Schooner America 2.0

Take in the vibrant colors of Key West's fabulous sunset as you glide through the waters on one of the finest boats in the Key West Schooner Fleet. Watch the sun fade into the horizon and the stars emerge into the deep blue sky. America 2.0 features teak decks, mahogany-trimmings, and 3,600 square feet of canvas! Sit back and relax while she plies effortlessly through the crystal-clear waters off Key West, heading towards the horizon for the quintessential Florida sunset experience! Some of the sights on this sailing adventure include a view of Fort Zachary Taylor from the water, and views of the famed Sand Key Reef, Mallory Square, and Sunset Pier. Keep your eyes peeled for wildlife such as dolphins, sea turtles, and water birds – and for the famous Key West "Green Flash" at sunset. Bring your family or friends and join the courteous and professional crew for this sunset sail that completes the Key West experience in comfort and elegance.

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.

Key West: Sunset Cruise with Buffet Dinner and Open Bar

3. Key West: Sunset Cruise with Buffet Dinner and Open Bar

Climb aboard "The Party Cat" for a wonderful 2-hour cruise around the harbor.   Enjoy a freshly prepared tropical food buffet in an enclosed air-conditioned dining room. Choose from dinner options such as roast pulled pork in mojo sauce, deep fried sweet plantains, black beans and rice, marinated grilled chicken, fried fish, mixed vegetables, mashed potatoes, pasta with mini shrimp and Cuban bread and butter. Sip on your choice of tipple — margaritas, rum runners, champagne, beer, wine or spirits. After dinner, stroll upstairs to the upper deck for live music. Dance the night away or simply listen to the beat as you watch the sun set over the horizon into the Gulf of Mexico. Witness the beautiful display of colors across the night sky.

Key West: Jet Ski Island Tour with Free Second Rider

4. Key West: Jet Ski Island Tour with Free Second Rider

Climb on a brand new jet ski and set off on a thrilling island jet ski adventure. With your experienced guides, navigate through mangrove islands, stop at a local sandbar for a dip in the crystal clear waters, get a picture of the southernmost point from the water, and more. Each tour has 2 guides to ensure the complete safety of riders. The first guide sets the pace at the front, allowing all riders who want to go fast the opportunity to floor it. The second guide brings up the back, allowing the riders who want a more leisurely tour to go at their own pace. This tour has been voted the best jet ski tour in Key West. Get a great deal with a free second rider on each jet ski.

Key West: 2-Hour Sunset Sail with Live Music

5. 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.

Orlando: Mango's Tropical Cafe Dinner and Show

6. 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: • Caesar salad • Tomato bisque Entree choice of: • Mango's Churrasco Steak ($15 upcharge) • Roasted Margarita Chicken • 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 • Chocolate Ecstasy

Key West Beachside Parasailing

7. Key West Beachside Parasailing

Board the parasailing boat from Smather's Beach. Get strapped into the harness on the aft of the parasailing boat then slowly rise into the air under a beautiful red, white, and blue parasail. Get an unobstructed panoramic view of Key West from over 300 feet in the air. Slowly sink down for a cooling dip in the waters before you rise high above Key West again. Get reeled back onto the aft deck of the boat following your memorable high flying adventure.

Key West: Windjammer Sunset Cruise with Full Open Bar

8. Key West: Windjammer Sunset Cruise with Full Open Bar

Set off in search of the perfect sunset aboard the Appledore II, a 2-masted wooden schooner. Sip on your favorite drink and enjoy 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. 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.

Key West: Food Tasting and Cultural Walking Tour

9. Key West: Food Tasting and Cultural Walking Tour

Celebrate Key West's diverse and abundant local fruits of the sea. This 3-hour guided small-group experience stops at 6 tasting locations, each carefully chosen to give you an eclectic view of Key West's best restaurants along the historic seaport. Enough for a hearty lunch, tastings are served from adored local eateries, tucked-away hidden gems, and a fisherman-owned seafood market. This tour will allow you to bypass the Duval Street tourist traps and go straight to the spots that the locals frequent to eat, drink, and discover the island. As you stroll the charming side streets and docks, you will experience the island’s seaport, as well as the rich industrial history which has transformed through the generations. Your friendly and knowledgable local guides will share stories of local industry, including the colorful past and historical landmarks. Following the tour, you can explore Old Town with confidence and take advantage of recommendations on restaurants, attractions, entertainment, and cultural offerings. You'll also receive a collection of exclusive recipes, ensuring that you can enjoy memories from this tour for many years to come.

Key West: 1.5-Hour Sail on the Schooner America 2.0

10. Key West: 1.5-Hour Sail on the Schooner America 2.0

Take to the water on the schooner America 2.0, just completed in 2011. This stunning 105-foot sailboat features teak decks, mahogany trimmings, and padded bench seating. Her 3,600 square feet of sail will propel you smoothly through the waters of Key West. This exciting 1.5-hour sail features 2 complimentary alcoholic drinks for those 21 and older along with complimentary soft drinks and water. You’re encouraged to make the most of the event by bringing your own picnic lunch on board. Some of the sights you’ll see from the water include Fort Zachary Taylor, the famed Sand Key reef, Mallory Square, and Sunset Pier. Don’t forget to keep your eyes peeled for marine life such as dolphins, sea turtles, and water birds. Bring your family or friends and join the courteous and professional crew for a sail that will complete your Key West experience in comfort and style!

  • Entry tickets
  • Guided tours
  • Water activities
  • Private tours
16 activities found
Sort by:

Frequently asked questions about Key West

What top attractions are a must-see in Key West?

What are the most popular museums and exhibitions in Key West?

Other Sightseeing Options in Key West

Want to discover all there is to do in Key West? Click here for a full list.

What people are saying about Key West

Very personable and knowledgeable guide - Chris. Excellent choice of restaurants; delicious food. Great hospitality and service. Only suggestion: End the tour in an air conditioned location that participants can cool off and chill out after the tour is over.

We had a nice tour, everything was explained well and our guide really tried hard. We had a lot of fun and would do it again. This tour is also suitable for beginners

America 2.0 is beautifully kept and the crew was fantastic. We met some great people, enjoyed the snacks and beverages, and captured an amazing sunset.

Everything about this is great! Crew, vessel, service, views…highly recommend. I can not imagine anything you could possibly be disappointed with.

Excellent experience with guide Nick. This is a great way to see the island from the outside-in.