Southernmost Key West Historical Tour in Small Group
Travel The Keys is a guided tour and concierge company based in Key West, Florida. We offer unique historical tours in Key West, presented by a 5th generation local. Our tours present a collection of lesser known historical events and explore the cultural legacies of the Southernmost District and surrounding areas of Key West.
Key West: 22ft Premier Pontoon Rental 115 HorsePower 10 passengers
Have a blast on the half day boat rental a Premier 22 foot Pontoon 115 HorsePower. The boat holds up to 10 passengers. You can cruise in the the ocean or the bay at key west, it is only 90 miles from Cuba. Tan in the sun, dock at a sand bar.
The boat is equipped with 115 horse power, a Bimini Top, Radio and Comfortable Seats.
Remember to bring your bathing suits, sun glasses, sunscreen, towel, hats and favorite beverages.
Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling
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.
PADI Refresher Course
We make your first dive unforgettable with small groups, expert PADI instructors, and the best gear on the market - SCUBAPRO. We start you off in the pool to help build confidence and to shake the rust off. Then you will head to our air conditioned facility in downtown Key West. After a quick check-in process you’ll board our custom built dive boat, The Phoenix, conveniently docked across the street behind the Hyatt Centric Hotel. Safe, fun, eco-friendly, and outfitted with premium equipment, we can’t wait to get you back in the water!
Key West Culinary and Catamaran Reef Tour Experience
Explore the vibrant waters of Key West on this 4-hour dolphin watch and snorkeling tour aboard a luxurious catamaran. Encounter playful dolphins in their natural habitat and dive into the colorful coral reefs, guided by experienced crew. After snorkeling, indulge in a delicious Taste of Key West menu featuring local specialties like conch fritters and shrimp ceviche, complemented by an open bar of refreshing cocktails. With professional instruction and a maximum group size for personalized service, this tour promises a unique blend of marine exploration and culinary excellence.
- 4-hour tour featuring dolphin watching and guided snorkeling
- Chef-prepared menu with local favorites and an open bar
- Professional crew with extensive knowledge of local ecosystems
- Maximum group size ensures personalized attention and comfort
Sandbar Snorkel Combo Adventure
This combo tour offers two experiences in one: a peaceful sandbar visit and an exciting snorkeling session. Unlike standard trips, you’ll enjoy a well-planned itinerary that maximizes your time on the water, with expert guidance and access to prime locations.
Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres
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.
Private Transfer from Key West hotels to Key West Cruise Port
Book your Private Transfer from Key West city hotels or any address to Key West Cruise Port.
Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door-to-door city/port transfer.
Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. Meeting with a Nameplate. Door-to-door Service. No Hidden Charges. Clean cars & Professional drivers.
Dry Tortugas National Park Self-Guided Audio Tour
Explore an island paradise 70 miles west of Key West. Visit Fort Jefferson, a massive 19th-century coastal fort, and walk its brick walls while hearing stories about soldiers, prisoners, and shipwrecks. The tour even works on the ferry to this remote national park.
Snorkel in clear blue water filled with coral, tropical fish, and sea turtles. Relax on sandy beaches and look for seabirds that nest only here. Stroll through the fort’s archways, climb to the top for ocean views, and learn how the fort defended the Gulf of Mexico.
You choose what to do first—swim, explore the fort, or enjoy the beach. The tour works without internet, gives GPS directions for walking the site, and offers local tips you can keep forever.
Download the tour, take the ferry or seaplane, and explore this unique national park at your own pace—where history, nature, and crystal-clear waters meet.
*Download the Shaka Guide app to access the purchased tours*
Key West Conch and Hemingway Self-Guided Walk
Explore the vibrant spirit of the Florida Keys with the Key West Conch and Hemingway Walk.
This self-guided adventure immerses you in the rich tapestry of island life where writers like Ernest Hemingway and Tennessee Williams found their muse.
Navigate through charming streets, lively bars, and historic neighborhoods that showcase the unique blend of Caribbean, Cuban, and Conch cultures.
As you stroll at your own pace, engaging audio narratives reveal tales of resilience, creativity, and community that define this iconic island.
Discover the essence of Key West, where every corner invites you to pause, reflect, and connect with its storied past.
Key West: Morning Snorkeling Breakfast & Drinks, Conch Train
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.
Conch Train
Key West Pirate Adventure: Self-Guided Walking Tour
Journey through Key West's history on this self-guided adventure featuring swashbuckling pirate legends and maritime mysteries. Your smartphone transforms a regular walk into an epic quest, with historical puzzles, fascinating stories, and clever challenges at every stop.
Each location brings history to life — from ancient landmarks to hidden historical details you'd walk right past without the app. Solve challenges to unlock the next chapter of Key West's story.
This 1–2 hour private adventure runs 24/7. No guide needed — just your smartphone and a sense of curiosity. Available in 5+ languages.
Marathon Backcountry Fishing Charter
Experience the true beauty of the Florida Keys backcountry, gorgeous shallow flats, and abundance of fish. Marathon the hub for fishing in the Keys, great beaches, shopping, and fantastic food. Knowing like the beautiful scenery, while experiencing the thrill of a chance to catch species such as Bonefish, Tarpon, Snook and the hard fighting Permit.
Your tour is guided by a licensed Captain in a modern skiff or also called a flats boat. All the fishing rods and reels, right and left-handed and all the tackle you need, as well as all other necessities including safety equipment. Travelers that have enjoyed our fishing charters also have enjoyed
The Turtle Hospital, a tour down Seven Mile Bridge or a beautiful sunset at Sombrero Beach.
Key West Airport (EYW) to Key West - Arrival Private Transfer
Book your private arrival transfer from Key West Int Airport (EYW) to Key West hotels.
Avoid the hassle of waiting in long taxi or shared shuttle queues and use our private, door-to-door airport transfer.
Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination.
• We track your flight.
• Our driver greets you with a name plate.
• We provide door-to-door service.
• There are no hidden charges.
• We use clean cars and professional drivers.
Key West: Nautic Star 21 Ft Speed Boat 21ft 115 Horse Power Speedboat-6 Pass
Have a blast on the half day boat rental a 21ft Nautic Star speed boat. The boat holds up to 6 passengers. You can cruise in the the ocean or the bay at key west, it is only 90 miles from Cuba. Tan in the sun, dock at a sand bar.
The boat is equipped with 60 horse power, a Bimini Top, Radio and Comfortable Seats.
Remember to bring your bathing suits, sun glasses, sunscreen, towel, hats and favorite beverages.
A Self-Guided Tour of Key West's Legends and Sights
Slip into Jimmy Buffett and Hemingway’s sandals and see iconic island sights on this self-guided audio tour.
Key West’s quirky island lifestyle has attracted larger-than-life characters, including author Ernest Hemingway, singer Jimmy Buffet, and treasure hunter Mel Fisher. On this walking tour, you’ll hear about the legendary people the island has attracted over the years and see where they made history.
Your guide is none other than Frank Everhart, the Schooner Wharf Bar’s very own comedic magician, whose tales are as captivating as the history they’re woven from.
Frank, with his intimate knowledge and personal anecdotes, will show you the museums, bars and often-overlooked corners where treasure hunters, eccentrics, and unforgettable locals left their mark. You’ll even see Jimmy Buffet’s first home and his Key West recording studio, Shrimpboat Sound Studio.
Key West Airport (EYW) to Key West - Arrival Private Transfer
Book your Private Arrival Transfer from Key West Int Airport (EYW) to Key West hotels.
Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airport transfer.
Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.
• Meeting with a Nameplate
• We track your Flight
• Door-to-door Service
• No Hidden Charges
• Clean cars & Professional drivers
Snorkeling and Catamaran Adventure in Key West
Sail from Key West Bight aboard Papa’s Cat, a 48-ft catamaran inspired by Hemingway’s island spirit. Dive vibrant reefs, drift over sugar-white sandbars, and sip fresh coconuts as you soak up
the sun. With snorkel gear, towels, sunscreen, Cuban sliders, and Key West pink shrimp included, this private four-hour charter for up to 10 guests captures the easygoing magic of Key West—equal parts exploration and relaxation.
Key West to Key West Airport (EYW) - Departure Private Transfer
Book your private departure transfer from Key West hotels to Key West Int Airport (EYW).
Don't go through all the hassle of waiting in a long taxi or shared shuttle queue and use our private, door-to-door airport transfer.
Your driver will be waiting for you at a scheduled time, and you will travel comfortably to your destination. Meeting with a Nameplate and we will track your flight. We offer Door-to-door service. There is no hidden charges and we have clean cars and professional drivers
Private Fun Fishing Charter
This experience combines the thrill of fishing with a relaxed, fun atmosphere. You’ll be guided by a seasoned captain who knows the best local fishing spots—hidden honey holes full of fish and stories. Unlike typical charters, we offer hands-on tips for beginners and seasoned anglers alike, ensuring everyone learns something new while having a great time. It’s more than just fishing—it’s an adventure filled with laughter, connection, and unforgettable moments on the water.
Bahama Village Walking Tour
Tours will begin at the corridor of the Southernmost District near the Key West Lighthouse and the home of the infamous author Ernest Hemingway. We will proceed through the Southernmost District and continue onto the neighborhood where the historic "Bahama Village" remains. Your experience will be provided by a fifth generation native of Key West and will include the history, folklore and architecture of traditional Key West.
Marathon: Sunset Beach Party at the Sandbar
* US Coast Guard licensed Master Captain and Mate provided for your safety & comfort
* Open bow and comfortable cushioned perimeter seating
* Lots of shade available* Premium Bluetooth marine sound system with island vibe music
* Enjoy cruising the Keys waters in comfort
* Beautiful Florida Keys sunset from the water
* Enjoy the relaxing Sandbar
* Family friendly / fun for all ages
* Make everlasting memories!
Key West: Smathers Beach & activities with a Sunset Catamaran & Open Bar
Fun in the sun when you make it over to Smathers Beachand have the best day with unlimited use of water activities. Go kayaking, paddle boarding, sailing or just seat in your beach chair and umbrella and enjoy the sun. Make sure to be at the check in for you sunset cruise with live music and open bar no later than 4:15 check in for a 5pm departure. On the 2 hour Sunset cruise you will have an open well bar which includes rum-runners, margaritas, mixed drinks, draft beer, wine, champagne & soft drinks. We will service finger food appetizers like Jamaican jerk chicken sliders on Hawaiian rolls, BBQ meatballs, veggie trays, cheese & cracker trays, Pita & hummus.
A Snorkel Tour with a Twist of History, Marathon, Florida Keys
Experience premier snorkeling in the Florida Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat for the USS Roosevelt. Set off on a scenic excursion past Marathon’s iconic landmarks while we share fascinating stories of the Keys’ historic past. Then, explore vibrant reefs teeming with marine life, or simply relax on the water and take in the views. Even if you’re less adventurous or prefer to stay dry, there’s plenty to enjoy—this is a tour that truly lets everyone in your group experience the magic of the Keys. This unique adventure is quickly becoming a Florida Keys tradition for visitors who want history, scenery, and unforgettable snorkeling.