Key West Historic District Tours & Attractions

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.
Duration: 2 hours.

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!
Duration: 1 hour 30 minutes.

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out to the Florida Marine Sanctuary for an incredible guided kayak eco tour through the mangrove isles. Keep your eyes peeled as you never know which of the over 500 marine species of wildlife you will encounter. Our expert guides will take you to the best spots to locate as many species as possible. After the kayak tour finishes we will serve lunch on the way to a local secluded sandbar. Once done with the kayak tour the bar is open. Guests will have unlimited access to our onboard soft drinks, draft beer & wine selections. Grab a beverage & explore the secluded sandbar. This trip combines all of the best things Key West has to offer. Each trip will has our master captain and two additional crew members catering to each guest.
Duration: 5 hours.

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!
Duration: 2 hours 30 minutes.

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a fun day in the sun. On the Island T’ing adventure, you’ll sail on a large catamaran away from the bustle of Key West, kayak among the natural backcountry mangrove islands in the Key West National Wildlife Refuge and view local wildlife like dolphins. A full breakfast and buffet lunch with beer, wine, soft drinks and homemade sangria, is included.
Duration: 6 hours.

Parasailing at in Key West Fl at the Key West bight

Fly high over the Key West Seaport as you parasail from State of the art parasail boats 

All crews Licensed and insured
Duration: 1 hour.

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.
Duration: 2 hours.

Introducing Squid! The quietest experience you will have on a boat while watching dolphins.
We worked with David Walworth, an MIT educated Naval Architect and Principal Engineer known for his high-efficiency catamaran designs, to build the perfect boat for our trips from scratch.

Our amazing crew are closely trained by our Honest Eco Biologists. Crew training starts on land with research and mission alignment before moving onto the water where we hone our seamanship skills and work to become as effective as possible at delivering on our Purpose.

We Work to Spread the Value of Wildlife Conservation
“People Protect What They Love.” Jacques Costeau said it, and it inspires us at Honest Eco as we work to help people discover and fall in love with the environment we are all part of.

We are continuously learning and pushing ourselves to be as environmentally responsible as possible.
Duration: 4 hours.

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.
Duration: 3 hours.

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!
Duration: 2 to 8 hours.

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour trip out to the reef, we will have you there for an hour and then a one hour journey back to our dock. We will provide instruction on how to use the equipment but recommend that you are comfortable in water over your head and that you have the ability to swim.
*We provide quality sanitized mask, snorkel, fins and flotation vest
*Professional guidance and instruction on how to use provided gear
*Fresh water hose available to rinse off after snorkeling
*Complimentary beverages to include water, soda, white wine, a selection of craft beers, margaritas, and champagne
*Floridays takes a limited number of guests so that we may provide you with the ultimate in enjoyment and service
Duration: 3 hours.

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atlantic bottlenose dolphins are the most common dolphins found around Key West. Enjoy an up-close view of dolphin pods as they swin and jump around the boat.
Duration: 2 hours 30 minutes.

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry.

Your day is spent exploring Key West’s uninhabited mangrove islands in the Key West National Wildlife Refuge. Keep an eye out for dolphins, sea turtles, manta rays and many other wildlife that call the Refuge home. Your captain knows where dolphins are frequently seen and will let you know if he spots any.

Upon reaching the mangrove islands, the schooner anchors and your exploration begins. Your day is divided between guided kayaking tours and guided snorkeling tours. The warm, shallow water is calm, sheltered by the uninhabited mangroves, making kayaking a breeze.

After your tours, come back aboard and wash off with our fresh water rinse, and relax on deck. Choose from plenty of complimentary cold drinks – frosty cold beer, wine, homemade sangria, chilled sodas and filtered water. This is the best of laid-back island living.
Duration: 5 hours.

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.
Duration: 2 hours.

Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood options) cuban sandwich & key lime pie tastings. Sample classic ingredients like Key West pink shrimp, Caribbean warm-water lobster, and fresh fish. Sip white wine after walking through the tropical neighborhood streets. This small-group tour is limited to 12 people, and you'll leave with a greater understanding of the industries that shaped our island and culture. Joining a fish lover, but not one yourself? No problem, we’ve got you covered with equally delicious substitutions.
Duration: 3 hours.

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991.
Enjoy a premium shallow snorkeling and dolphin-watching sailing excursion. Cruise on a roomy catamaran that books only to half their passenger limit for quality control.
Be ready to spot wild dolphins being WILD - hunting, playing, teaching their babies how to hunt, feed and socialize with their dolphin friends. Then to a shallow water snorkel stop at coral reefs, wrecks or the wildlife refuge - wherever the best conditions are from Mother Nature that day. The spacious catamaran offers plenty of room to relax in comfortable seats, and on a soft trampoline sundeck forward. Feel the sea breeze in your hair, and enjoy light snacks and premium drinks, all while having fun on the sparkling waters of Key West.
Duration: 4 hours.

If you’re looking for the ultimate Key West experience, join the 'Duval Crawl' pub crawl! Key West is famous for its lively bars. Join the original Key West Pub Crawl established in 2002. The only pub crawl that includes five drinks and a souvenir T-shirt!
Duration: 4 hours 30 minutes.

Dolphins are widespread in the Florida waters especially Key West as they prefer the warm waters of the tropical ocean. As we visit the Dolphin pod in the Key West Waters don't be surprised to hear their vocals in the form of clicks and whistles. Dolphins are some of Earth's most intelligent animals and very social. At times we can see pods of dolphins in the 1000's. Dolphins love to play and often we can see them Jumping out of the water. When we finish the Dolphin watch we will cruise and enjoy one of the largest reefs in the world for a fun filled snorkeling adventure. On the way back enjoy an open bar serving unlimited cold draft beer and soft drinks.

We offer this trip daily in the Morning and in sunset.


Duration: 3 hours.

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.


Duration: 2 hours.

This 1 Hour Guided Scenic Tour is not only packed with Key West’s main sights but also takes you off the beaten path. We'll go through unique and eclectic neighborhoods, from the Historic Seaport to Bahama Village, crossing along all the touristic areas. Sit back and enjoy the ride on a comfortable E-pedicab with Your Private Driver and Tour Guide! A wonderful way to relax and soak in the island vibe while learning about the history and culture of Key West. This tour Includes four stops for photo opportunities: the Little White House, Southernmost Point, Lighthouse, and Mile Marker 0. But if you wish to stop at other locations, we'll make it work for you!
Duration: 1 hour 10 minutes.

This 2 Hour Guided Scenic Tour takes you far into the island! It is not only packed with Key West’s main sights but also takes you off the beaten path and more. All the way to beautiful waterfronts, beaches, going through unique and eclectic neighborhoods, from Bahama Village to the Historic Seaport, further North to the White Street Pier, and of course crossing along all the touristic areas. Sit back and enjoy the ride on a comfortable E-pedicab with Your Private Driver and Tour Guide! A wonderful way to relax and soak in the island vibe while learning about the history and culture of Key West. This tour Includes six stops for photo opportunities: at the Little White House, Southernmost Point, Lighthouse, Mile Marker 0, the Grotto, and White Street Pier. But if you wish to stop at other locations, we'll make it work for you!
Duration: 2 hours 10 minutes.

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.
Duration: 2 hours.

Key West from Miami on a new Double Decker bus for your comfort and ease departing from South Beach. This day trip includes round-trip transport from South Beach to the center of Key West. Arrive early in the morning giving you have plenty of free time to plan solo explorations with a choice of upgrade options like Snorkeling or enjoying a glass bottom cruise. You will have over five hours of free time in Key West to explore the city independently. The trip to Key West is a beautiful scenic ride where we will cross the famous Seven Mile Bridge. You can upgrade your Key West day trip to include activities like Snorkeling, parasailing or the well know hop on hop off conch train.
Duration: 18 hours.

You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting streets of Old Town and Historic District. Experience its amazing architecture and historic sites as you learn the rich history, culture, and folklore of our beautiful island of Key West.
First-row, Historic, Cultural and Fun, the only VIP experience tour in Key West.

This tour includes a slice of famous Kermit's Key Lime Pie for each of you and a complimentary bottle of water!


Duration: 2 hours 30 minutes.

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.
Duration: 8 hours.

27 Miles and 90 Minutes of pure exhilarating watersports bliss. Your Key West Island Jet-ski Tour starts in the shallow cove, The Ibis Bay Resort dock area.

From the Gulf of Mexico to the Atlantic Ocean.....and back to the Gulf of Mexico. From sea to Ocean and back again. After your exhilarating 90-minute adventure, many guests celebrate their experience with a drink and the freshest seafood at the Stoned Crab Restaurant.
Duration: 1 hour 30 minutes.

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.
Duration: 90 to 180 minutes.

We invite you to take an exclusive cocktail & food taste tour on the Waterfront in Downtown Key West!
Our seasoned local guide will dive into the history of Old Fisherman’s Wharf & how it has transformed into Yacht Harbor!
Learn about the historic wrecking and rum running days of old Key West!
Sit at the bar Mel Fisher did while his treasure sat out front, on display, in the trunk of his car!
Transition into the sunset where you’ll visit the area where locals have their annual celebration for the succession of our Conch Republic from the United States!
Open your ears to live music and island vibes as you cocktail into World Famous Mallory Square’s Sunset Celebration!
Duration: 2 to 3 hours.

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!
Duration: 9 hours.

Bask in the magic of the unforgettable coastline and the Caribbean nightlife with the Miami Sightseeing Flex Pass. Save over 55% on culture, cuisine, dancing, and adventure, including Hop-On/Hop-Off Bus Tours and access to the best of Miami.
Keep the party going and save over 55% on total admission prices to some of the biggest wildlife attractions and family activities. Select from a 1, 2, 3, or 5 Day Pass, then visit as many of our partner attractions as you want. Make your choices in Miami, and the more you see the more you save!
Interact with the exotic residents of Jungle Island, see alligators up close on an Everglades Airboat Tour. Soak up the sun in South Beach, visit the Art Deco District on Ocean Drive, or eat your way through Little Havana in Calle Ocho. Shop your way through a visit to historic Ft. Lauderdale. Pass holders also receive special discounts on dining, shopping, and entertainment.
Duration: 1 to 5 days.

Where is the Best Key Lime Pie? YOU decide!

Experience the allure of the finest Key Lime Pie in Key West as you embark on a flavorful stroll along the historic waterfront harbor in Old Town Key West. Delight your palate with three enticing variations of Key Lime Pie at select local establishments, complemented by a refreshing Key Lime Cocktail of the Day. Immerse yourself in the vibrant history of Key West and its signature dessert as we wander through the charming streets, absorbing tales of the city's colorful past.

Duration: 1 hour 30 minutes.

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.
Duration: 2 hours.

Step onto our one-of-a-kind catamaran for an all-you-can-eat seafood boil and premium open bar! This trip promises a perfect blend of adventure, relaxation and excitement.

Our catamaran is designed for comfort with speacious decks, plenty of seating and shaded areas. Ideal for lounging and enjoying the scenic views of Key West's iconic turquiose waters.

Snorkel at two of Key West's prime snorkeling locations, such as Sand Key or another nearby location known for its vibrant coral and diverse marine life. Premium snorkel gear is provided and experienced guides are available for instructions perfect for all levels of experience.

After snorkeling, lounge on deck and enjoy a classic Low Country boil, a classic Southern dish. Our menu typically includes shrimp, corn on the cob, potatoes, all seasoned with a magic blend of spices, cooked together.

Expect a laid-back and enjoyable trip while unwinding with a cocktail served from our premium open bar.
Duration: 4 hours.

Picture yourself aboard our unique tiki boat, the Lazy Lady, cruising through the crystal-clear waters toward a secluded sandbar. The sun is shining bright, and the air is filled with the scent of salt and sunshine. As you approach the sandbar, the boat glides over shallow waters, revealing stretches of soft, white sand inviting you to explore.

Once you anchor, the fun begins! You can jump off the boat and wade into the warm, shallow waters, where the gentle waves lap at your feet. The atmosphere is relaxed, with laughter and conversation floating through the air. Some folks might set up beach games, while others enjoy swimming or soaking in the sun.

Time seems to slow down as you enjoy this little slice of paradise, surrounded by friends or newfound acquaintances. Whether you’re collecting seashells, taking a dip, or simply lounging in the sun, a sandbar trip on a tiki boat is a perfect blend of relaxation and adventure.
Duration: 3 hours 30 minutes.

This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There will be hors d'oeuvres passed around throughout the trip. A great way to have a private sail with your friends, family, or co-workers.
Duration: 2 hours.

Imagine gliding over gentle waves aboard the Lazy Lady, a 53-foot, one of a kind tiki boat. Soak in the vibrant colors of an iconic Key West sunset - hues of orange, pink and purple.

Sip on ice-cold beverages prepared by your friendly crew while the warm sea breeze carries the sounds of island music and laughter. The atmosphere is relaxed and festive, perfect for making new friends or sharing moments with loved ones. Expect a laid-back and enjoyable trip while unwinding with a refreshing beverage from the bar.

As the last sliver of sun disappears below the water, watch for the green flash, an enchanting touch of magic. Sail back to Key West Harbor under the star-filled sky, creating a Key West memory to last a lifetime.
Duration: 1 hour 30 minutes.