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The reason why this is such a great place to view the sunset is the privacy. Locals refer to it as a hidden gem, which is mainly due to poor signage. With only a little green street sign to mark the way, Fort Zachary Taylor is usually overlooked by tourists. Sunset Pier is a casual dining spot that is floating on a pier above the water. Umbrellas are set up at every table, so you will be protected from the sun until sunset. Are you looking for an all inclusive sunset viewing experience?
Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres

Since this is a private tour, you’ll have personalized attention from your guide, who will help you capture some great photos to remember this experience. Whether you’re brand new to kayaking or have done it your whole life, this guided tour will be perfect for you. Watch for wildlife in their natural habitat or coral reefs as you watch the sun set beyond the horizon. Whether you’re visiting with family or are taking a special someone out on a cruise, this option will surely be enjoyable for anyone. Despite the crowds, the weather is ideal for exploring beaches as well as enjoying sunny drives with the top down. If so, bookmark it and when you’re planning your next vacation click on any of the links below before finalizing reservations.
Sunsets Key West Style
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. Located at the tip of the Florida Keys, 165 miles from Miami, it is the perfect place to find a private sunset cruise or shared boat trip. A Key West sunset cruise is a vacation must-do that adds an unforgettable experience to any Key West visit. Champagne and sailing might not be the best mix if you’re in charge of navigating. Departing an hour before sunset from Key West, this cruise aboard a 69-foot catamaran gives the perfect view of the string of Florida Keys islands across the turquoise water. Wine, beer and sangria are also provided as part of the price and cocktails can be bought for a little extra.
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Key West Sunset Cruise with Live Island Music
There are no shortages of sailboat companies in Key West and you can easily organise a sunset sail on the day of your visit. The Appledore, America and Fury’s Commotion on the Ocean are popular sailboats. This gives you the best seat in the house for the spectacular colors of the sunset. The Sunset Deck bar offers budget friendly drink options – which include great mojitos. Picture yourself with a drink in your hand on a deck that is right on top of the water. Furthermore, live music every evening gives this place an added festive vibe.
Sunset Cruise On A Pirate Sailboat
Best In Key West wants to make your searches as relevant as possible. Nerja offers a lot of choice to visitors for wining and dining. Here are my top restaurants you can’t miss on your next visit to Nerja, Spain.
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Historic Seaport
However, if you’re looking to make your stay extra memorable then you should explore taking one of the 10 sunset cruises in Key West below. Skipjack schooners were originally designed for harvesting oysters in shallow Chesapeake Bay. Modern catamarans are adaptations of ancient Polynesian boat designs used by sea-going peoples who lived on tropical islands ringed by shallow coral reefs and lagoons. 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.
Key West Recommendations
This street, named after Florida’s first territorial governor William Pope Duval, is a great place to experience a different kind of sunset. You can grab a drink and walk along the pier, dip your toes in the ocean at the beach or chill out in one of the hammocks. Cruisin’ Tikis are the newcomers on the block with their spin on the Key West sunset experience. If you’re looking for a relaxing place to beat the crowds at sunset, then Lagerhead Beach Bar is the place for you. If you want to skip the hustle and bustle of Mallory Square, this is a great spot. If you walk out of the crowd and head past the entertainers, you will spot the back of the red-brick customs house.
What to Bring
Make sure to check out my post on the best rooftop bars in Tampa. With an open bar that includes mojitos, what better way to enjoy one of the best sunset cruises in Key West than by sitting on a 65-foot yacht and making new memories. A Key West sunset cruise with live music is a special event, to be sure, so ask around and see which charters are offering which types of music. You aren’t short of booze cruise options, from party barge to tipsy tiki. Sail on a historic schooner and enjoy tapas and wine, or feel the beats on a charter catamaran with 50 of your closest friends.
Also, don’t assume that an open bar means anything you want–most boats have limited space to carry supplies, so you won’t find the selection you will back on land. Those passengers without kids, and looking to sail aboard a schooner will find this tour as a fantastic alternative to the one listed above (#7). Complimentary beer, wine, cocktails, and sangria are provided, along with some tasty appetizers.
With a maximum of 6 people per boat, you’ll be able to spend time with your family, friends, or partner as you cruise around the harbor, admiring the setting sun. If you are planning a Key West vacation, you might wondering what you should in the evenings. In my opinion, one of the best things to do in Key West is go on a sunset cruise. In fact, Key West sunsets are so legendary, they have a nightly festival to watch them from Mallory Square. Enjoy a cruise on a spectacular Key West catamaran with departures either in the morning or late in the evening for a sunset cruise. Key West has been a popular port of call for sailors for hundreds of years.
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. This is by far our most popular and best seller when it comes to sunset cruises. Featuring headliners The Cory Heydon Band, as well as a rotating lineup of great live acts, this sunset sail totally rocks! Where else can you enjoy the sunset while dancing on the boat to live music?
It doesn’t matter if you want to find the best booze cruise Key West offers or a quiet, intimate sail–choices abound. Be sure to make your sunset sailing plans early in the day–these trips fill up as the day goes on. If you’re eyeing a private charter during a busy time of year, it’s best to make plans before you get to the island. There are plenty of options for the best sunset cruise in Key West, with many providing drinks, snacks, or dinner as you take in the sunset. The most popular options are watching the sunset on a catamaran, listening to a live band, hoisting the sail and enjoying the best of Key West. 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.
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