Top Key West Private and Luxury

Soak up sunset views from the water's edge, and admire a perspective many visitors miss, on this Key West sailing tour. Sample up to eight different wines and/or five different beers as you sail, and indulge in a selection of gourmet hors d'oeuvres to accompany them. As you go, learn more from your crew, and enjoy a festive and celebratory way to toast to your trip.

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle board, snorkel, or just hang out. Watch for wildlife throughout the trip such as dolphins, sea turtles, fish, birds, and much more! A cooler filled with ice and bottled water will be provided. Feel free to bring any food or alcoholic beverages.

Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Dance the evening away or relax on the sundeck or in shaded areas as you sip on a margarita, beer, or other beverages. Unlimited drinks and light appetizers are included so you don’t need to pay extra. A great standalone evening activity or the start of a night out.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, numbers are restricted to 24 so you have a spot at the rail when it’s time to capture photos of the setting sun.

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Key West, promising an unforgettable experience for all. As you sail further into the sunset, the full open bar comes to life, offering an enticing array of cocktails, wines, and spirits to complement the evening's splendor. Sip on our signature Schooner Bloody Mary or Dark & Stormy as you watch the sky ignite with color. The skilled bartenders are on hand to craft your favorite drinks, ensuring that your glass is never empty as you drink in the sights and sounds of the sea. As the schooner begins its journey back to Key West, you find yourself lost in the timeless rhythm of the sea, grateful for the opportunity to witness the beauty of a Key West sunset from the deck of a historic schooner.

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

The coast of Key West is home to sea turtles, rays, lobsters, and dolphins—if you know where to look. On this small-boat cruise, visit sites known for dolphin sightings and enjoy snorkeling in the warm waters with the chance to spot tropical fish and a diverse array of marine life. Relax on the boat’s sundeck or beneath the shade with soft drinks and snacks, and admire the views as you cruise along the scenic sandbars.

Eat your way around Key West on a food tour of “mom and pop” eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and delicious key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.

See the Key West lagoons in a whole new way. Go on a nocturnal adventure with clear kayaks and LED lights that illuminate the surroundings so you can see underwater. A local guide takes you and a small group to the best spots for a unique and memorable marine life experience lasting about 90 minutes.

Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.

Leave the tourist crowds of Key West behind for the evening and head out on the water on the historic and elegant schooner built for General Patton in the late 1930s. Cruise around the coast with the boat’s crew looking after you the whole time, and even letting you take the wheel if you want to try your hand at boating. Watch the sunset from the ocean before heading back.

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar & Sunset Cruise! This exclusive trip takes you to a beautiful sandbar, where you can lounge on our floating lily pads while our crew turns into your personal bartenders, serving up unlimited draft beer, mimosas, wine, and champagne. For those looking to explore, grab a snorkel and discover the underwater world teeming with tropical fish, stingrays, and other marine life. As the sun starts to set, we’ll cruise through the Florida Marine Sanctuary, giving you a front-row seat to Key West’s famous sunset—keep an eye out for dolphins, sea turtles & more! Savor a taste of Key West at the sandbar! Enjoy Cuban sandwiches, veggie wraps, fresh fruit, cheese & crackers, pita with hummus & more—all paired with unlimited beer, wine, mimosas & champagne. The perfect happy hour on a boat! Whether you’re here to relax, party, or explore, this trip has it all.

Cruise alongside Key West’s picturesque waterfront in style during this private sunset tour aboard a charactered tiki bar boat. Enjoy BYOB drinks in a floating, thatched bar, complete with private restroom, bluetooth-equipped television and stereo, and padded bar stools. Head past attractions like Sunset Pier, Mallory Square, Wisteria Island, and Trumbo Point, with cruises timed to capture the coastline’s famous sunsets.

For the aquatic adventure of a lifetime, cruise to North America's only living coral barrier reef. No need to go diving or snorkeling for this great view—see tropical fish, sharks, turtles, colorful coral, and other sea life from the deck of the glass-bottom boat. Opt for an evening departure to enjoy a glass of Champagne as the sun sets into the Gulf of Mexico.

Enjoy a private boat tour experience, without the hassle and costs of renting one yourself, on this half-day tour around Key West. The experience is fully customizable to your group’s interests, and can include relaxing on a sandbar, island hopping, snorkeling, dolphin watching, a sunset cruise or a combination of activities.

While most boat tours travel on small private vessels or luxury yachts, this sunset cruise takes travelers around Key West on Jolly II Rover, the only square-rigged, topsail schooner in the area. Board your ship at the historic Seaport at the corner of Elizabeth and Greene streets and sail out to see some of Key West’s best sights, including the Man O War Harbor, Christmas Tree Island, Fort Taylor, and others.

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Skipjack Resort & Marina, this serene cruise includes a complimentary champagne toast and seasonal local seafood appetizers such as fresh Florida stone crab or shrimp (when in season), offering an authentic taste of the region. Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups seeking relaxation with panoramic ocean views. Enjoy island music, warm breezes, and vibrant sunset colors as the day fades into tropical paradise. Departure times adjust seasonally to align with the actual sunset, ensuring you experience the most spectacular sky colors possible. Your confirmed departure time will be reflected in your booking confirmation.

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you on an exhilarating, up-close adventure across crystal-clear waters, winding through lush mangroves, stopping at pristine sandbars, and exploring hidden islands that are off the beaten path. This is your chance to experience Key West like never before — in a fun, fast, and eco-friendly CraigCat boat! Perfect for All Levels: Whether you're an experienced boater or a first-time adventurer, the Craigcat is easy to handle and designed for fun and comfort. With a small, nimble design, you’ll have the freedom to explore areas that larger boats or jet skis can’t reach. Up to 4 boats per tour. 2 guests max per boat. If you have 4 people in your group please make two separate bookings to accommodate your party and so forth up to 8 guests.

Try something new in Key West: parasailing. Adventure seekers who've booked this trip will love soaring over the Key West Seaport. The experience is available for singles, doubles, and even triples so it's a fantastic activity for a group of friends or a family. You'll board a state-of-the-art boat, get briefed by the crew, and then fly over the city—free as a bird.

Discover some of Key West’s deepest, darkest secrets on a ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of what is said to be one of the most haunted cities in the US. Travel down the narrow, dark streets of the Old Town at night. The wooden houses still bear the secrets of their former inhabitants. This tour is narrated by an actor playing a gravedigger.

The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast to try your luck spotting dolphins, stingrays, turtles, and birds while you learn more about Key West’s waters than you ever would sailing along. Then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat.

Take in rare birds–eye views of Key West on a parasailing adventure over Smathers Beach. With a range of departure times offered throughout the day, this tour is a popular, flexible choice for families. Your guide, who ensures that the small group has a personalized experience, takes photos and videos available for purchase after the trip.