Key West Sunset Cruises & Sunset Sails

Table Of Content

• Your Trip Includes
• 🌅 The 7 Best Key West Sunset Dinner Cruises [2024 Reviews]
• Q: What makes a Key West Sunset Cruise so special?
• Q: What kind of wine is served on the Key West Wind & Wine Sunset Sail?
• KEY WEST'S FAMOUS
• Key West Sunset Snorkel with Unlimited Draft Beer & Wine
• Boat Features
• INCREDIBLE Things to Do in Hilo, Hawaii (& Nearby)

For a sunset sailing cruise from Key West that runs throughout the year, there’s the Sandie Cat, a modern, three-deck catamaran with space for up to 150 people. The sails are often raised on this catamaran cruise, while the ambience is set by the live music on board. Key West conjures up images of Caribbean culture, taking a catamaran cruise through the balmy Gulf of Mexico, magnificent marine life and Ernest Hemingway fishing with a cold beer in hand.

Your Trip Includes

Experience the incredible Key West sunset with just your loved ones, as you spend 2 hours passing by the iconic Key West landmarks. It also happens to be one of the busiest booze cruises in Key West that has a solid reputation for its energetic crew and entertainment. Dance the evening away while enjoying a full open bar that includes beer, sodas, wine and sparkling wine. The classic schooner offers visitors a romantic vessel to enjoy watching the spectacular Key West sunset. With gorgeous hors d’oeuvres provided as you sail around iconic Key West landmarks such as Mallory Square which also happens to be the birthplace of watching sunsets in Key West. Chef Brian is also available for catering private parties or weddings.

🌅 The 7 Best Key West Sunset Dinner Cruises [2024 Reviews]

Join us for a beautiful late afternoon cruise out to the reef, a refreshing dip in the crystal clear waters, then top it all off with a gorgeous sunset as you cruise back. For an active family, or anyone who enjoys the water, taking an afternoon snorkeling trip that winds down with a beautiful sunset (and beverages) offers the best of both worlds. Nature lovers should try a Glass-Bottom Boat Tour Sunset Combo or take the Dolphin Watch Sunset Snorkel Cruise. The custom of celebrating the amazingly colorful ocean sunsets took hold, and now Mallory Square and the Key West sunsets are both world famous. Enjoy the Key West sunset from the catamaran as you enjoy freshly prepared tapas and snacks.

Q: What makes a Key West Sunset Cruise so special?

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.

The Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres is all that and more. The local musicians are very talented and entertaining, setting the tone for a fun evening as you watch the sun set with the electric colors spreading across the sky. For each tour, our professional crew provides a thorough briefing for how to move around catamaran decks safely. Whether you're a seasoned sailor or on a boat for the first time, we've got you covered. Join us for one of the most memorable nights on the water, Key West’s Lighted Boat Parade. With live commentary and information about the island of Key West, the Key West cruise takes in the landmarks of Key West and one of the most spectacular sunsets in the Florida Keys.

You can expect to pay between $50 – $100 per person for a sunset cruise in Key West. Check out the next section where I jump into this a bit more. Almost every single sunset cruise in Key West will leave from the Key West Historic Seaport shown in the map below. This seaport is just outside of historic Old Town, so if you are staying nearby, walking shouldn’t be a problem. Sail into the sunset with food, bubbly, wilderness and a little culture all thrown in together on these five elegant Key West cruises. The band plays everything from reggae to rock, and the crowd can get a bit lively!

Key West Sunset Snorkel with Unlimited Draft Beer & Wine

The ability to skim through the shallows and land directly on the beach was critical. Known for their stability and versatility, today’s catamarans are the fastest and shallowest-running boats on the water. Sebago has operated its Key West Sunset Champagne Catamaran Cruise for a number of years and is one of the top-rated Key West sunset cruises. Experience a 69-foot catamaran with an open bar that includes views across the Gulf of Mexico & Atlantic Ocean. Does dancing to some island grooves from local musicians while you eat, drink, and enjoy a beautiful sunset on the water sound like a good time to you?

Boat Features

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. 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.

It makes sense, then, that tons of tourists flock here every year. 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 Cool Key West over a 12-month period. Then you definitely need to check out some of the best rooftop bars the city has to offer. Entertainment and a satisfying customer experience are our priority. Brian Kirkpatrick has been a  professional chef for the past thirty-five years. He has lived in Key West for the last ten years, and formerly worked as a sous chef for the Marquesa Hotel, one of Key West four star hotels.

All the boats used for these popular Key West Sunset Cruises are top-of-the-line designs built for safety, comfort, and fun on the waters around Key West. The United States Coast Guard regularly inspects every Key West Sunset Cruise boat, and all required safety equipment is aboard and properly updated at all times. This is luxury sunset cruising at its best, with expert local captains and crew members, high-tech navigation gear, and the latest in quiet, efficient, low-emission engines. Plus, there are those added touches to enjoy like room for cocktail and wine service, deck space for top local musicians to perform, and even a bit of space to dance on some cruises.

This boat is one of the smallest ones of any sunset cruise we’ve seen in Key West, however, this offers a more intimate experience that’s great for sharing with your loved one(s). The captain and crew do a great job of keeping you entertained while making sure everyone is tended to properly. Grab a tropical mixed drink and dance to a live performance from one of Key West’s best entertainers while enjoying a legendary Key West sunset.

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I’ve seen people in jean shorts and flip flops, but most people dress in resort casual. 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. The smooth ride on the ship along with the chill music makes for a serene way to enjoy the afternoon. Are you looking for a calm, relaxing cruise tour instead of a party cruise? There are plenty of both in Key West, and this one falls into the category of the former, despite the ship being called “The Party Cat”.

The top deck is also equipped with a full bar and plenty of room to host a DJ or live music. As you sail, make sure to take advantage of the unlimited snacks and ice-cold water onboard. On here, you won’t be hearing any music or rowdy environments. This tour is designed to be peaceful and allow you to take in the experience of sailing while enjoying the natural beauty around you. Enjoy unlimited appetizers, beer, margaritas, wine, sangria, champagne – whatever you feel like having!

Enjoy a mouthwatering tropical food buffet while you sip on refreshing drinks. As you step aboard, grab a tropical beverage and let the rhythmic beats of our local steel drum performer transport you to a tropical paradise. Enjoy unbeatable views of the sunset along with an amazing tropical food buffet served by our staff. Grab a tropical beverage and groove into the sunset as our local steel drum performer fills the air with tropical vibes. Depart the harbor in the late afternoon to enjoy an evening on the water, or combine dolphin watching, snorkeling, or a glass-bottom boat tour with sunset and the perfect end to another day in paradise. 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.

Drinks consist of beer, soft drinks, sangria, full liquor bar, wine, champagne, and more. Once you set sail, you’ll be served a choice of wine, 4 different kinds of beers, along with delicious charcuterie selections such as a wonderful cheese, cracker, meat, and olives plate. This smooth ride is luxurious, a load of fun, and one of the best ways to watch the sun go down on the island. Meet up around 4 pm along with the rest of your group to board the ship. You’re immediately greeted by the crew, who are super friendly and make the experience that much better.

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The unobstructed fetch of the light, atmospheric moisture, and other refractory factors combine to produce awe-inspiring natural beauty. One of the top-rated and best sunset cruises in Key West is the Key West Sunset Sail with Full Bar and Live Music. Set sail in the late afternoon and enjoy terrific live music, a full open bar, and plenty of delicious hors d’oeuvres. 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.