The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn't your typical party boat—it's a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You'll enjoy a guided tasting of fine wines from around the world, along with a selection of craft and domestic beers and light hors d'oeuvres including crudites, meats, cheeses, crackers, fruit, and chocolate.

With small group sizes, there's plenty of space to move around and enjoy the view without the crowds. It's perfect for a romantic date or a fun evening with friends—upscale, but never uptight.

What really sets this trip apart is the crew. They're fun, welcoming, and passionate about what they do—ready to pour your next glass, share a story, or make sure you're having a great time. Add in a Key West sunset, and you've got one of the most unique and enjoyable evenings on the water!

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the water for a Key West sunset is like being IN the sunset itself. There is nothing quite like it. Who knows, you may get lucky enough to witness that elusive green flash!

Sunset Sail in Key West with Beverages Included

What makes Fury's Live Music Sunset Sail unique is the combination of luxury and a vibrant, immersive experience. Guests embark on a spacious 65-foot catamaran, ensuring plenty of room to enjoy breathtaking views of the world-famous Key West sunset.

The cruise stands out with its complimentary beverages—margaritas, champagne, beer, and wine—paired with a diverse selection of gourmet appetizers, catering to every taste. Live music from talented local artists adds an authentic touch, enhancing the atmosphere and making each cruise feel special.

With options to relax on the sundeck or in shaded lounges, guests can fully immerse themselves in the beauty and serenity of the Gulf. Whether for a romantic evening or a fun outing with friends, this experience captures the essence of Key West in a way that's both memorable and enchanting. It's a perfect blend of scenic beauty, culinary delights, and live entertainment!

Book July 4th for Key West's incredible fireworks display!

Key West Sunset Sail with Live Music, Drinks and Appetizers

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated hors d'oeuvres. Sit back and relax as your captain sails you effortlessly through the emerald green Key West waters and off toward the horizon for a quintessential Florida sunset experience.

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean waters while sipping a beverage. Take in views of Key West sights like Fort Zachary Taylor, Mallory Square, Sunset Pier and Sand Key Light Tower. Soda and water are complimentary. Two alcoholic beverages are included with your ticket. Additional beverages are available for purchase. 

Key West Day Sail on Schooner America 2.0 with 2 Drinks

Key West is famous for it's sunsets and it doesn't get any better then on an intimate sunset cruise aboard our custom tiki bar boats. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Tours depart an hour and fifteen minutes prior to sunset so we can get to the perfect place to watch the sunset. Our boats feature a large thatch roof for shade, bluetooth stereo, a walk in bathroom, adjustable padded bar stools and a gorgeous live edge tiki bar. You'll cruise the Key West harbor in style and view the famous sunset on your private 2 hour adventure. Keep your eyes on the horizon for a chance to see the famous Green Flash as the sun goes down.

Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure

Come see for yourself why Marathon Mermaid is voted the #1 thing to do in Marathon! Watching the sunset by water is a must-do when visiting the Keys!

Sunset Cruise

Step aboard the Pride of Key West, the island's only Glass Bottom Boat. This family-friendly tour invites you to explore North America's only living coral reef* from our state-of-the-art 65ft catamaran.
Glide over crystal-clear waters and enjoy unobstructed views of stunning coral formations, which support over 300 species of tropical fish, rays, and sea turtles. Our specially designed glass "windows to the reef" ensure continuous viewing for all passengers, allowing everyone to marvel at the rich marine life below.
Relax in the air-conditioned viewing cabin or step out onto the large sundeck for panoramic views. Our knowledgeable guides provide insights into the coral reef ecosystem and highlight fascinating marine creatures. For a truly memorable experience, join our final trip of the day to watch the sunset as you return to port—an amazing way to cap off your Key West adventure!

*In the event of unfavorable conditions, the captain may opt for an alternate location

Key West Glass-Bottom Boat Tour with Sunset Option

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide"
USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for the perfect Key West sunset sail 
Peaceful, private and exclusive! 
Your captain and mate will take you out to watch the sunset from your own private classic sailing vessel, with soft drinks, bottled water and coolers stocked with ice provided for any adult beverages you choose to bring. 
Reserve ahead, there is after all, only one High Tide sunset sail per day!
Price is for up to 6 guests, 12 guests max!.

Private Key West Sunset Sail

Max 6 people. Explore the waters around Key West. This versatile boat let's you plan your own adventure. Snorkel the reef, explore an offshore island, look for dolphin and other marine life or simply relax on a sandbar with your toes in the sand! A favorite for families!

Key West: Snorkel, Sandbar & Dolphin Excursion

Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury boat, ensuring a swift and comfortable journey through the stunning turquoise waters to Dry Tortugas National Park. Revel in top-class amenities perfect for sunbathing, sightseeing, and relaxing with your private group. Discover secluded islands and pristine tropical beaches on this guided full-day adventure. History buffs will be captivated by Fort Jefferson, while outdoor enthusiasts will relish the world-class snorkeling and breathtaking natural beauty. This unique voyage combines exhilarating open-sea travel with an intimate and personalized experience, creating memories that will last a lifetime.

Dry Tortugas National Park Day Trip by Luxury Private Boat

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.

Florida Keys Sunset Cruise with Champagne Toast and Seafood

Set Sail for Tiki Revelry in Key West's Historic Seaplane Basin!
Cruise to Key West's unique Seaplane Basin. In the early 1900s, this spot buzzed with activity as seaplanes took off and landed. Today, it's a vibrant harbor where colorful houseboats bob gently, creating a charming island atmosphere.
Gear up for an afternoon of tropical fun on our 2-hour Tiki Boat Party & Mini Sandbar Escape! Let your captain navigate the turquoise waters as we head to a secluded swimming hole, the perfect setting for a tiki celebration.

Private 2-Hour Tiki Boat Party in Key West & Mini Sandbar

Ready for the most beautiful 2 hours of your Florida Keys vacation?

Forget crowded piers and noise—imagine yourself drifting peacefully as the sun melts into the beautiful water of the Florida Keys. Our 2-Hour Sunset Tiki Cruise transforms the spectacular Keys sunset into a private, moving masterpiece just for you.

The Magic of the Sunset Cruise:

Front-Row Seat to Nature's Show: Glide across the tranquil, crystal-blue waters as the sky ignites in a breathtaking palette of reds, oranges, and pinks. You'll have the best, unobstructed view of the legendary Keys sunset from the comfort of your floating tiki bar.
A Toast to Paradise: Whether you're celebrating a special occasion or simply savoring a perfect day, the sunset hour is magical. Bring your favorite beverages to toast the end of a perfect day as the stars begin to appear over the horizon.

Secure your spot now and create a memory that will glow long after the sun goes down!

Cruisin Tikis Marathon - Sunset Tiki Cruise

Our US Coast Guard licensed captains have decades of combined excursion experience in the Middle Keys and look forward to sharing our lovely paradise with you! 
Your captain will provide all the tips to have you exploring our local sea-life in no time. We hold ourselves to a high standard and run a quality operation. With your enjoyment in mind, our boats are clean and comfortable offering multiple seating options, and maintained regularly. After your 2 hour excursion, you'll fall in love with the Keys!

Florida Mom owned, voted Best in Marathon 2023, 2024

Marathon: Local Sandbar Escape 

Key West is famous for stunning sunsets, and this dinner cruise offers the perfect way to enjoy them. Savor breathtaking views as the sky transforms, while indulging in a tropical buffet, live music, and incredible vibes. It's an unforgettable evening on the water. 

Relax on a luxury catamaran with an open-air sundeck and fully air-conditioned lower cabin. Grab a drink from the open well bar as live tropical music sets the mood. Every moment is filled with beauty, flavor, and celebration as you soak in Key West's legendary charm. 

This popular cruise often sells out, so book your spot today! Don't miss your chance to experience the best of Key West – sunsets, music, and memories await on this unforgettable adventure.

Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music

Experience a classic Florida Keys sandbar adventure on a comfortable 53' catamaran. Cruise through Boot Key Harbor and past scenic landmarks as your crew shares information about the local area and points out interesting sights along the way.

Once you arrive at the sandbar, step into shallow turquoise water perfect for swimming, floating, and relaxing. Use the provided water floats and noodles, or simply unwind on deck and enjoy the sunshine and music.

This relaxed and family-friendly tour offers plenty of space to move around the boat, shaded seating, onboard restrooms, and a cooler with ice, soda, and water. Ideal for couples, families, and groups, this experience lets you enjoy Marathon's sandbars the way locals do—easygoing, fun, and surrounded by the natural beauty of the Keys.

Island Sandbar Tour Catamaran Cruise in Marathon FL

Explore the crystal-clear waters and pristine sandbar islands that surround the Florida Keys. This private sandbar charter is fully customizable—whether you're looking to relax with a drink in hand, explore the local marine sanctuary, or simply enjoy a laid-back day on the water.

Your captain will tailor the experience to your preferences, taking you to the best sandbar spots and providing everything you need for a carefree day in paradise. Enjoy sunshine, calm waters, and unforgettable views of Key West's natural beauty.

This is the ultimate way to experience the islands—your day, your way, in the heart of the Florida Keys.

Private Sandbar Charter & Island Escape in Key West

Experience Key West's waterfront the way locals do—by private boat. This harbor cruise offers a more comfortable experience, complete with narration and flexibility. With a USCG-licensed captain, you'll glide past historic forts and the Historic Seaport, Navy installations, Mallory Square, and island landmarks while hearing stories of wreckers, pirates, and poets. Choose golden-hour glow or bright daytime views, customize pace and photo stops, and savor a quiet, upscale alternative to mass tours.

✅ Explore the Historic Seaport, Mallory Square, and island landmarks
✅ See Navy installations, historic forts, and working waterfronts
✅ Learn island history from a knowledgeable USCG-licensed captain
✅ Customize the pace with photo stops, narration, or quiet relaxation
✅ Choose daytime cruises for sunshine or golden-hour evening views

This is a quiet, upscale alternative to mass tours — perfect for couples, families, and small groups seeking comfort, history, and stunning harbor scenery.

Six Fins Key West Harbor Cruise – Private Scenic Boat Tour

Experience a relaxing start to your day on a spacious 53' luxury catamaran as you cruise through the clear waters surrounding Marathon. Enjoy a complimentary morning mimosa as the crew guides you along scenic coastlines with views of the Atlantic Ocean, Boot Key, and the iconic Seven Mile Bridge.
Take a refreshing swim in calm, shallow waters and explore the sandy bottom for shells and sea life. With plenty of space on board, comfortable seating, and friendly local crew, this tour offers a peaceful and memorable way to experience the beauty of the Florida Keys.

Morning Mimosa and Swim 2hr Luxury Cruise in Marathon FL

Key West Water Fun with Snorkeling, Sunset Cruise, Dinner, Live Music and open Bar. 
Enjoy a bright and early morning snorkel Catamaran cruise departing 9 am for a full morning of Snorkeling fun. Return at 12:00pm and have 4 hours of free time before you come join us for an incredible Key West 2 hour Catamaran Sunset happy hour tropical dinner cruise with margaritas, rum runners, wine, beer and live music.

Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling

Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise departing from the historic Key West Seaport. As the sails are raised and the breeze carries you across the sparkling Gulf waters, unwind in a refined and intimate setting away from crowded party boats.

Enjoy complimentary beer, wine, champagne, and soft drinks throughout the cruise, with cocktails available for purchase. Savor a selection of hors d'oeuvres including cheese and crackers, fresh vegetables with dip, and shrimp cocktail — perfectly paired with a breathtaking Florida Keys sunset.

Watch the sky transform into vibrant shades of orange, pink, and gold as the sun dips below the horizon, creating unforgettable photo opportunities. Perfect for couples, celebrations, or anyone seeking one of the top-rated experiences in Key West. Advance reservations are highly recommended, as this popular sunset sail often sells out.

Sightseeing Cruises in Key West