Top Experiences in Mallory Square

Rent your own private yacht and savor the beautiful Key West waters away from the crowds. Do it all on a luxury catamaran reserved just for you! Snorkel a pristine reef, dolphin watch, jump off of the bows of the boat, sail along the Key West coastline, and enjoy cocktails with friends on your own private yacht! If the big, crowded boats are not for you, we're the perfect option for a more private sail catered specifically to your needs. Our boat is the cleanest you will find, with a spotless bathroom and an electric flush toilet. We are owner-operated so every detail of your sail is important to us. We also allow you to bring your own food and cocktails on the boat to create your own perfect experience. The S/V Liberty is a luxurious 44-ft cat, offering 5 different seating areas, so you can spread out and savor the coastline as we sail by. Bigger groups and longer charter times are available upon request. Let's go sailing!

Rent your own private yacht and savor the beautiful Key West sunset away from the crowds. Do it all on a luxury catamaran reserved just for you! Dolphin watch, jump off of the bows of the boat, sail along the Key West coastline, and enjoy cocktails with friends on your own private yacht! If the big, crowded boats are not for you, we're the perfect option for a more private sail catered specifically to your needs. Our boat is the cleanest you will find, with a spotless bathroom and an electric flush toilet. We are owner operated so every detail of your sail is important to us. We also allow you to bring your own food and cocktails on the boat to create your own perfect experience. The S/V Liberty is a luxurious 44-ft cat, offering 5 different seating areas, so you can spread out and savor the coastline as we sail by. Bigger groups and longer charter times available upon request. Let's go sailing!

Embark on a tour around the island of Key West. Your guide will be talking you through many points of interest around the island. Make sure to keep an eye out for wildlife throughout the tour. About 20 minutes before the sunset, your captain will find a quiet and private spot to watch the sun drop into the water uninterrupted by other boats, people, or land!

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.

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.

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar. Climb aboard our custom luxury catamaran for a sunset trip out into the Key West sunset. As our live performer fills the air with tropical vibes, our onboard chef will fill your plates with tropical cuisine and our bartenders will fill your cups with tropical drinks.

Dinner Menu

- Blackened Mahi with Lemon and Tartar Sauce
- Smoked Mojo Pulled Pork
- Caribbean Jerk Chicken
- Seasoned Black Beans and Tropical Yellow Rice
- Candied Sweet Plantains
- Tropical Fruit Salad
- Mixed Green Salad with Ranch or Raspberry Vinaigrette
- Caribbean Butter Corn
- Fresh Local Cuban Bread with Butter & Marmalade
- Churros Stuffed with Dulce Leche

Open Well Bar (includes: Unlimited Well Mixed Drinks, Draft Beer, Margaritas, Wine, Champagne, Rum Runners & Soft Drinks)

-Margaritas
-Rum Runners
-Well Mixed Drinks
-Draft Beer
-Wine
-Champagne
-Soft Drinks

Hop On Hop Off in Key West for one full day of an adventure. Enjoy a early morning or afternoon 3 hour Snorkel trip on a catamaran. Explore the world’s 3rd largest living coral reef. This trip is perfect for professionals and beginners. Our professional staff provide expert snorkeling instruction and equipment.
Afternoon Snorkeling includes unlimited draft beer, mixed well drinks, margaritas, rum runners, wine or champagne, once completed with snorkeling.

Early Bird Snorkel gets you to the Worlds 3rd largest living coral reef as we sail towards our destination enjoy breakfast, draft beer & unlimited mimosas. As you return you can jump on the Hop off Hop On bus and doing this tour.
Key West Aquirium
Conch Train
Sails and Rails Museum

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.

Key West is famous for it's sunsets and it doesn't get any better then on a private 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 tv and 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 is famous for it's sunsets and it doesn't get any better then on a private 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 tv and 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.

Visit the one-and-only island city of KEY WEST!

Enjoy a narrated tour on the way down, and island music on the way back.
This is way more than just a shuttle service.

HIGHLIGHTS
• See the sights in Key West
• Stay for the Key West sunset
• Plenty of Free Time
• Stops of your choosing along the way
• Designated Driver
• Narrated Tour

Do what you want in Key West! We're doing the driving!

During your free time we recommend to sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail. There's so much to do!

Sit back & enjoy the scenery as we drive down to Key West. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide.

It's more like a road trip than a tour - ask questions, point out wildlife, stop to visit the Florida Keys landmarks of your choosing and more!

Tours are private, and include only your travel party of up to 6 people.
We customize the stops to what interests your group. We can make more, or less stops. Spend more, or less time at sights. It's YOUR day! We will make lots of suggestions, but want you to have the best experience possible so try to cater to your interests. You'll learn about many aspects of our unique history and unique eco-system. The Florida Keys is located in the middle of a National Marine Sanctuary! We have many unique and endangered animals, both on land and in our waters. And, at one point, Key West was the richest city in the state of Florida! How was THAT possible??

Want to beach hop all the way to Key West? Maybe jump off a bridge? Ya know...cause your friends are doing it! For real!

Just want to get to Key West and be pointed in the direction of the best bars? We can do that too! Adventurous enough to check out a clothing optional bar? Key West has those too!

Admission NOT included to any venue.

Embark on a flavorful journey through Key West's culinary delights. Our Caribbean Food Walking Tour takes you from the iconic Mallory Square to tasting island staples: crispy Conch Fritters, hearty Cuban Sandwiches, succulent Yellowtail Sandwiches, and the famous Key Lime Pie. This tour is a culinary adventure, blending delicious food with the rich history and culture of Key West. As you move from one tasting to the next, you'll wander past landmarks like the Mel Fisher Maritime Museum, Duval Street, and the historic district, gaining insights into the island's heritage. This experience is perfect for anyone looking to dive deep into Key West's vibrant food scene while also soaking up its historical ambiance. Whether you're an avid foodie or a curious traveler, join us for a journey that celebrates the flavors, sights, and stories of Key West, leaving you with lasting memories and a taste of the island's unique culinary landscape.

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things to do in Key West.

As we leave behind the Historic Seaport, look for Key West landmarks like the legendary Mallory Square, opulent Sunset Key and historic Fort Zachary Taylor. On reaching open water, the sails are unfurled and your adventure begins as your captain tracks dolphin pods to provide you an up-close view of these elusive creatures.

With the dolphin viewing over, your cruise is just getting started! Grab a drink and relax as your captain positions the luxury catamaran for the perfect view of a famous Key West sunset.

A chef’s selection of Tapas including shrimp cocktail are served during the sail. Choose your favorite drinks, including boutique wines and champagne perfectly paired with our Tapas – all included in the cost of your tour!

Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation.

This is private tour is customizable, meaning you can request to adjust the meeting point to better suit your day, and even request what kind of stories you'd like to hear. Perfect for wedding party, couples, family & friends, bachelor/bachelorette, birthdays, reunion, corporate groups, and more!

**If it's too far or too hot to walk, you can hop on the Duval Loop bus with your guide** It's air-conditioned with several convenient stops throughout Old Town.

The best part about your own private tour is you can ask questions and customize the tour to your interests!

Feel free to include notes in your booking about:
- what you want to know about Key West
- points of interest you'd like to include
- if you're celebrating an event
- mobility challenges or other needs we can accommodate

Total distance about 1 1/2 miles.

VOTED KEY WESTS BEST - Over 5,000 5 Star Reviews
Jet ski Tour around Key west, No Hidden Fees, Everything is included, FREE 2nd Rider, FREE Shuttle Pickup

Please check-in one hour before with your photo I.D and credit card. 

If you were born on or after January 1st, 1988 and at least 18 years of age you must take a Florida Boaters Safety test.to drive waverunners

Visit the one-and-only island city of KEY WEST!

Enjoy a narrated tour on the way down, and island music on the way back.

HIGHLIGHTS
• See the sights in Key West
• Stay for the Key West sunset
• Plenty of Free Time
• Designated Driver
• Narrated Tour

Do what you want in Key West! We're doing the driving!

Sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more!

Sit back & enjoy the scenery as we drive down to Key West. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide.

See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square

It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.

Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in paradise! While enjoying your sail remember there is plenty to see on the water’s surface or circling in the blue sky above you. Perhaps an osprey will plummet down to the water to catch its lunch or a pelican will make a splash landing near the schooner. A pod of dolphins may surface or you might spot a turtle floating by.

Talented bartenders stand ready to craft your favorite cocktails, pour glasses of fine wine, or serve up refreshing local beers. Sip on our signature Bloody Mary or Dark & Stormy as you watch the scenery drift by, or opt for a chilled glass of champagne to celebrate the beauty of the moment

Your crew will share history and natural beauty of the Florida Keys, pointing out points of interest along the coastline and sharing tales of seafaring adventures past. There's something for everyone to discover aboard the schooner.

Looking for the perfect way to end your day? Join us on the Seabreeze and ride in comfort with this relaxing, catered cruise into the horizon on Key West’s gentle seas. Relax in the shade under the bimini or sunbathe on the bow to take in that last bit of sunshine. Sunset Cruises are a Key West luxury with our panoramic views of the sun melting into tropical waters – and the best way to enjoy it is with good food and great drinks!

Departing from the Garrison Bight Marina, your sunset cruise will take you on a unique path away from the rush of boats leaving downtown. This exclusive cruise is a great way to start your night out, celebrate a special occasion, or bring your stay to a close with an easy-going route through the Key West Harbor and the Gulf of Mexico.

We operate year-round at reduced capacity for a more intimate experience for our guests. You’ll get to know our crew and maybe meet some friends along the way. We also have a full marine head (bathroom) for your convenience.

Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy included wine, sparkling wine, beer, sangria or margaritas on board the boat. . As you sail through the water, admire views of the island with a cold beverage in hand — the perfect way to end a beautiful day in paradise.

Experience the best of Key West on the famous Conch Tour Train! One of Florida’s most popular attractions, the Conch Tour Train has been entertaining visitors to the ‘Island City’ for decades. Learn about the history of the train, a tribute to Henry Flagler's engineering miracle when he brought the railroad to Key West in 1912, and explore this charming tropical paradise on a leisurely train ride around the island! FREE Admission to the Sails to Rails Museum included with ticket!

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!

Hop on a bus that will take you on a great adventure to Key West, a Tropical Paradise in US. Enjoy the ride along the Florida Keys and the amazing colorful waters of the Atlantic Ocean and the Gulf of Mexico.There will be only one brief stop for breakfast / bathroom in Key Largo.

Once you get there, you will have 6 hours to experience the caribbean atmosphere of the island.

Dive in the blue waters of Key West Coral Reef for 3 hours in a luxury catamaran with unlimited alcoholic and non alcoholic drinks included, sanitized snorkeling gear is also included.

  Don't forget to try some of the typical things in Key West; like the Key Lime Pie, the Conch Fritters and others. 

  At 5:45 pm, it's time to return back ; our bus will depart from 908 Caroline Street; same place where you were dropped off in the morning. This time the trip is non-stop; you will be back at your hotel between 9:00 -10:00 pm ( depending on hotel location).

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and feasting on shrimp cocktail on your way to the best sunset viewing spot. You'll enjoy twilight views of the island as you watch the famous Key West sunset from the water.

Now featuring live music from local Key West Musicians!

See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with this affordable walking tour.

• Find out how the town nearly went bankrupt before reinventing itself as ‘The Conch Republic’ in the 1900s
• Hear from producer Ed Owen, a seasoned Key West traveller and tour guide
• Do it all in 90 minutes or linger at stops along the way with complete control over when you start and finish
• Get unlimited use before your booking date and after it
• Use the virtual tour option at home
• This tour does not enter or include entry to any of the attractions mentioned en route

Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code.

The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.

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.

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!.

On our Secret Food Tour: Key West Old Town, we'll walk far from the tourist traps of Duval to show you the real city and its best food. You'll gain insight into how the diverse cultural influences of Key West have shaped the island into a unique destination that's globally renowned for its exceptional gastronomic experiences. Our local guides will take you on a journey to explore the history and culture of "The Key to the Caribbean," sharing their passion and passing down stories that have been told from generation to generation.

You'll discover the oral history of Key West's prosperity and how treasures transformed this small island into a worldwide attraction.

Enjoy traditional Key West bites, taste the freshness of ingredients that only a coastal city can offer, and uncover flavors you won't find anywhere else in the world. Plus there’s our amazing secret dish that you can only find about it on the day!

Our captains, boats, and fact we customize every trip to every clients dream day is what sets us apart and why we dominate other charter companies. There is a reason people stay at the Ritz-Carlton, though there is a motel 6 right up the road, and that's the type of experience we aim to provide.

Discover the magic of Florida Keys aboard a luxurious private boat charter, accommodating up to 13 guests. Perfect for a range of activities—snorkeling, exploring local sandbars, island-hopping, or even a special proposal—our boat offers something for everyone.

Features:
⇛ Air Condition
⇛ Bathroom
⇛ Bluetooth / AUX audio
⇛ Children's & Infant Life Jackets
⇛ Cooler / Ice Chest
⇛ Deck / Washdown Shower
⇛ Depth & Fish Finder
⇛ Enclosed Cabin to escape the sun, weather, or just take a break
⇛ Large Sunpad to Sunbathe
⇛ Refrigerator
⇛ Stateroom for Infants & Children to Lay Down
⇛ Sunroof
⇛ Swim ladder

Join us for a trip by booking today!