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Guests can enjoy a delicious dinner aboard a state-of-the-art vessel while admiring Key West’s beautiful sunset. As you sail along the shoreline, you can take in the incredible natural beauty of the island and its historic landmarks. Climb about the world famous Party Cat catamaran for a night you won’t forget. Guests enjoy a delicious tropical food buffet made fresh in our on-board kitchen. Enjoy an unlimited open well bar & on of the island’s best live musicians as they set a true island vibe as you discover Key West’s legendary sunset.
Q: What makes a Key West Sunset Cruise so special?
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Once mostly cut off from the rest of the world, it has persevered through countless hurricanes. This trip includes an unlimited open well bar, or you can upgrade to the unlimited premium bar ticket and have access to all of your favorite premium brands. Yes, our main cabin has the seating capacity for guests and has 4 large AC units to ensure a comfortable dining atmosphere.

Catch the Key West Sunset with Tropical Food Buffet, Live Music & Open Well Bar!
In the hours leading up to dusk, head to Mallory Square and watch as it comes to life with acrobats, dancers and performers. Key West’s official currency is the U.S. dollar (USD), and ATMs are widely available. Credit cards like VISA and MasterCard are accepted most places as well.
Best Deals to Key West, Florida
This is yet another cruise that’s easy on the wallet and a couple of hours of good vibes. You can catch all kinds of exotic fish in Key West’s tropical waters, so it’s no surprise that much of the local cuisine centers on fresh seafood. Be sure to try some conch fritters and the iconic key lime pie, of course. When it comes to bars, you’ll find no shortage along lively Duval Street.
Small-Group Key West Sunset Sail with Wine
If you are, then you’re the perfect guest for the Small-Group Key West Sunset Sail with Wine Tour! This is a bit more of an intimate cruise, where the one prior to this was made for the larger crowds of people. Naturally, the idea of gliding smoothly over turquoise water under sail while toasting a perfect day with a cold beer, glass of wine, or cocktail is very tempting. A Sunset Sip & Sail or Premium Sunset Sail with Hors D’oeuvres and Full Bar will provide a perfect happy hour start for a couple planning an evening on the town. The music does vary, but typically you’ll have some jazz and smooth music to accompany you. Drinks consist of beer, soft drinks, sangria, full liquor bar, wine, champagne, and more.
Quick Answer: The 7 Best Rated Key West Sunset Sails For 2024
Known for their stability and versatility, today’s catamarans are the fastest and shallowest-running boats on the water. Visitors have been boarding boat tours out of the harbor near today’s Mallory Square since the mid-19th century. Key West sunsets are famous for highlighting nature’s grandeur as the sun sinks below the broad ocean horizon and brings on dramatic color changes of a range and intensity not seen on land.
Key West, Florida
The natural beauty and incredible climate that stays consistent pretty much year-round makes it a great place to hang out outdoors. The natural landscape, ocean, and electric sun come together for gorgeous sunsets every night, and there are many great places to watch them. Start your day in Key West with a cortadito, cafe con leche, or Cuban coffee. Coffee is taken seriously in Key West, just like in neighboring Miami, heavily influenced by the Cuban coffee tradition. Cuban Coffee Queen also serves hearty breakfasts, refreshing smoothies, and Cuban sandwiches to keep you going as you continue on your way through town.
The unobstructed fetch of the light, atmospheric moisture, and other refractory factors combine to produce awe-inspiring natural beauty. Imagine spending a beautiful evening enjoying a gourmet meal while watching the sunset over the waters of the ocean as you enjoy a luxury cruise. Amazing food, great wine, and the beautiful Florida Keys are calling. If this sounds like something that you would love to experience, Chef Brian will be waiting to welcome you aboard. If you're looking for a special way to celebrate a special occasion, a dinner cruise from Cool Key West is the perfect way to do it.
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Don’t forget to tip your barista for your morning cafe con leche, too. While on cruises to Key West, Florida, you’ll find no shortage of souvenir shacks, roadside t-shirt vendors, and Florida-related memorabilia celebrating and embracing Key West’s quirkiness. Head to Duval Street for the majority of shops, independently-owned boutiques, and galleries in the city.
When your cruise ship docks, seek out a cafe con leche and a slice of key lime pie immediately. Then set out for attractions along Duval Street or Mallory Square, both hubs for shopping and nightlife. Don’t miss the six-toed cats living at Ernest Hemingway’s famed Spanish Colonial house-turned-museum. And, of course, a photo op awaits at the Southernmost Point of the United States, a concrete buoy memorializing Key West’s geography. If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Inside Key West over a 12-month period.
Walk in the footsteps of famous Pulitzer Prize-winning author Ernest Hemingway, who lived at 907 Whitehead Street in Key West from 1931 to 1939. Come see where Hemingway wrote several critically-acclaimed short stories, plus catch sight of the six-toed cats roaming the grounds. Even in December, the forest and plants at this botanical garden in Key West retain their leaves and lush palms. The Garden describes themselves as “frost-free,” a benefit of the tropical climate. Bring the kids for an educational tour on the native plants, and don’t miss the butterfly garden. Damage from Hurricane Irma in 2017 affected the plant life, but passionate employees are working tirelessly to bring the garden back to peak fullness.
But there are also a variety of other methods to see Key West, like the Old Town Trolley. You can also rent bikes or scooters to catch the Key West breeze while you explore. For a sightseeing tour you’ll never forget, take the Conch Tour Train, which has been showing tourists around town since 1958. Before the Overseas Highway was built in 1912 to connect the various Florida Keys, Key West itself was in isolation from the rest of the world. Just 90 miles from Cuba, Key West features a huge influence of Cuban culture, particularly in its food and drink.Today, Key West’s economy is driven by tourism. It’s also known for an inclusive, close-knit LGBTQ-friendly community.
These classic ships have been sailing out of Key West for over 200 years, and guests who come aboard a Key West schooner today are in for an award-winning luxury sunset cruise. Join us for a beautiful late afternoon cruise out to the barrier reef for a refreshing dip in the crystal clear waters, then top it all off with a gorgeous sunset cruise through the harbor. Sunset Watersports is your one stop shop for Key West sunset celebrations. We have the island’s only sunset dinner cruise, an incredible sunset sailing experience or even an action packed sunset snorkeling trip.
The crew is incredibly friendly, and always attentive and there to make sure everyone has a great time. Once you board, you’ll be able to revel in amazing live entertainment, and all-you-can-eat drinks and snacks. Catch a Key West sunset from Mallory Square, a waterfront plaza facing the Gulf of Mexico. Mallory Square is the site of a long-running tradition to watch the sunset.

Enjoy cruising along the calm waters as the sky turns pink, orange, and yellow, reflecting off of the ocean. You’ll get to see Mallory Square, Sunset Key, and Key West Harbor as you sail along. From the very get-go, it’s an awesome experience thanks to the attentive and friendly staff, and positivity all-around. We should let you know that this is kind of a more upbeat experience than the others, which have a more relaxing setting. The smooth ride on the ship along with the chill music makes for a serene way to enjoy the afternoon.
The Party Cat also boasts a top sundeck perfect for sunbathing or viewing the legendary Key West sunset, depending on the trip. The top deck is also equipped with a full bar and plenty of room for our live musician on our sunset dinner cruise. A catamaran can also offer more wide-open deck space between the two hulls.
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