Key West Sunset Cruises & Tours

Enjoy a memorable evening on the water with the Key West Sunset Dinner Cruise. Savor a fresh, tropical-inspired dinner, including roast pork with Cuban bread and fried plantains, all prepared onboard. Relax with drinks from the fully stocked bar and take in the stunning sunset views. The friendly crew ensures a comfortable experience, with indoor seating in a climate-controlled cabin. This is the perfect way to dine, drink, and dance while making unforgettable memories. Reserve your spot today for an unforgettable Key West sunset experience!

Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local landmarks and sail past Sunset Key and historic Fort Zachary Taylor as you dine on a tasty selection of varied hors d'oeuvres. Watch the sunset with your favorite drink in your hand and your loved ones by your side. Enjoy live music from local musicians! These are moments you’ll savor long after you leave town! Don't miss the boat. Book your spot today!

Embark on an unforgettable sailing adventure through the crystal-clear water of Key West with the Dolphin Watch Sunset Sail. Enjoy superbly crafted tapas like tuna poke and shrimp cocktail along with champagne, select premium wines including LaCrema, beer, and sangria as you journey to view majestic dolphins, landmark sights and the world famous Key West sunset. Get an authentic sailing experience as the captain and crew raise the sails on your luxurious catamaran and set out to find dolphins playing and frolicking in the surf and often near the boat! Book yours today!

Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise in Key West, Florida. Experience some of Key West’s best musicians as you dance to the backdrop of a gorgeous, tropical sunset. Eat, drink, and be merry aboard a spacious and comfortable catamaran and take in all of the stunning sights and sounds. For an evening you'll want to last forever, set sail on this Live Music Sunset Cruise! Book your experience today!

Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Miss Valyn Catamaran with a Sunset Snorkel Cruise in Key West, Florida. A twilight experience unlike any other, this is your opportunity to enjoy the nightlife while having the option to plunge into the depths by Florida's best reef! Take in the fleeting Key West sunset while indulging in an ambiance that only the cat delivers. Enjoy reef snorkeling, draft beer & wine on this snorkeling experience. Book your spot today!

Have you ever seen Key West at dusk on the open ocean? Just sit back on a Sunset Sip and Sail with Open Bar and Live Music and immerse yourself in the ambiance of this nightlife experience. You can dance the night away to live music while you sail the calm waters. Enjoy the best seat in the house with all of the good time essentials like draft beer, live music, open well bar, and appetizers. Book your spot now!

Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around the world. Rated one of the top two sunset tours in all of North America by Coastal Living Magazine, this luxurious Wind and Wine Sunset Sail on a historic Schooner will not disappoint. Make some new friends, enjoy tropical music, and delight your palate as you watch the sun melt into the water. Book your spot today!

Escape the hustle and bustle and experience a breathtaking sunset with a Key West Sushi & Sunset Catamaran Harbor Cruise. Your journey takes you away from commonly charted boat paths to unobstructed views and miles of turquoise waters, while snacking on delicious sushi and snacks. Travel to where the Gulf meets the Atlantic and on to the Southernmost Point of the United States. For an intimate and romantic evening that is sure to help you unwind, book a Sunset Harbor Cruise and toast to life!

Climb aboard a 65-foot historic Schooner for a luxurious experience that has been rated one of the top two sunset tours in all of North America by Coastal Living Magazine. Join this unforgettable Wind & Wine Sunset Sail in Stock Island, Florida! Embark on this journey and indulge your senses with a selection of wines and light appetizers that beautifully pair. Whether you're a wine enthusiast, a sunset lover, or simply seeking an exceptional experience, this journey promises to exceed your expectations. Book your experience today!

Leave the land behind for an evening of snorkeling and Reggae music on this Sunset Snorkel & Sail with Rum & Reggae included. The rhythmic sounds of Reggae fuse brilliantly with the vitality of your surroundings as you sail to North America’s only living reef aboard a 65-foot catamaran. Scope out the brightly colored tropical fish and corals on an underwater snorkel exploration excursion before eventually heading back to the boat to enjoy some tasty tropical rum drinks. This trip includes many exciting activities all in one trip, so embark on the Rum & Reggae Sunset Snorkel & Sail today.

If you are looking for a way to float away the day, then this Sunset Cruise on a Tiki Bar Boat is the right choice for you. Key West is famous for its glorious sunsets and this tiki cruise does not disappoint. This custom 20-foot tiki bar catamaran features a private bathroom, Bluetooth stereo, and flatscreen TV. Toast the sunset with your closest companions and favorite libation while experiencing the gorgeous scenery, cotton candy skies, turquoise water, and pure relaxation on this Sunset Cruise on a Tiki Bar Boat. Book today!

Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating lily pad. Enjoy this unique private adventure with family and friends, away from the crowds. Be sure to take in all of Key West's beauty while relaxing and soaking up the sun from the water. Book today and set out on a private sailing adventure.