Tours in Key West

258 results

Private Transfer from Key West Airport (EYW) to Key West Port

Book your Private Transfer from Key West Int Airport (EYW) to Key West Cruise Port. Don't go through all the hassle of waiting in a long taxi or shared shuttle queues and use our private, door-to-door airport/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 • We track your Flight • Door-to-door Service • No Hidden Charges • Clean cars & Professional drivers
20 minutes
Free Cancellation
From
$110.80

Rum Cocktail Masterclass

Step into the world of rum and discover the art of crafting exquisite cocktails at a hands-on masterclass. Whether you're a novice or a seasoned mixologist, this class offers something for everyone. Guided by expert bartenders, you'll uncover the secrets behind both classic and contemporary rum cocktails. Dive into a variety of rum styles, including two local treasures: First Legal Rum, celebrated for its smooth and rich flavor, and Pilar Dark Rum, known for its deep, complex taste with hints of caramel and spices . Master essential techniques while enjoying a fun time with friends or a unique date experience. Imagine the joy of shaking, stirring, and sipping your own creations as you toast to new skills and delicious drinks!
1 hour 30 minutes
Free Cancellation
From
$91.32

Private Transfer from Key West Port to Key West Airport (EYW)

Book your Private Transfer from Key West Cruise Port to Key West Int Airport (EYW). Don't go through all the hassle of waiting in a long taxi or shared shuttle queues and use our private, door-to-door port/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
20 minutes
Free Cancellation
From
$110.80

Eco Conscious Reef Diving with Southpoint Divers

3
Explore the only living barrier reef in America with Southpoint Divers on eco-friendly dive trips tailored for certified divers. Begin your day at your air-conditioned dive shop near the Hyatt Centric, where you’ll be equipped with top-of-the-line SCUBAPRO gear. Cruise past stunning views of Sunset Key and Fort Zachary Taylor Beach as you head to the reef. Dive into vibrant coral gardens teeming with tropical fish, turtles, and rays. With PADI-certified instructors ensuring safety and personalized attention in small groups, your underwater adventure also supports vital conservation efforts in the Florida Keys.
4 hours
Free Cancellation
From
$174.00

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.
10 hours
Free Cancellation
From
$229.99

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.
4 hours
From
$750.00

Elope in Key West Intimate Wedding 10 Guests or Less

Looking for a simple easy way to elope in Key West - look no further - our professional photographers are also officiants and so they provide a combo - they marry you then photograph this lifetime moment. Our professional will meet you at the desired location - will perform the ceremony then will photograph the format of the ceremony and some couple photos after - total event will be 1 hour - NO decor is included.
1 hour
Free Cancellation
From
$650.00

Six Fins Key West Harbor Cruise – Private Scenic Boat Tour

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.
3 hours
From
$995.00

Pontoon Boat Rental with Slides from Key West

Double Decker Pontoon Boat with slides for up to 14 passenger Rental in sunny Key West, Florida. Want a stress-free day? Hire a captain and let them handle the navigation while you focus on fun. Book now and turn your day on the water into a true paradise escape!
4 hours to 8 hours
Free Cancellation
From
$1,100.00

Private Proposal and Engagement Shoot in Key West

We take the time to review YOUR vision for this special moment in life via a conference call - we offer suggestions and then send a full confirmation with map or diagram and all aspects to make this a perfect surprise to the love of your life and your lifetime partner.
1 hour
Free Cancellation
From
$500.00

4 Hour Sunset Seasonal Tarpon Charter from Key West

On your 4-hour sunset tarpon charter, we’ll focus on targeting migrating tarpon during one of the most active feeding windows of the day. Sunset is prime time to hook into these powerful fish, and there’s often a chance to catch bonus dinner species along the way. This seasonal trip runs from April 20 to June 20 and offers a short but incredible window to connect with the fish of a lifetime. We are especially passionate about tarpon fishing—chasing these giants is what we look forward to all year. With a limit of four anglers, you'll have the space, attention, and strategy you need to make every shot count. From dialing in your presentation to managing long, high-adrenaline fights, this trip is all about making the most of a brief and unforgettable season on the water.
4 hours
Free Cancellation
From
$800.00

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.
20 minutes
Free Cancellation
From
$111.98

Ghost Tours of Cayo Hueso

walking ghost tour for an immersive, intimate experience that combines history and storytelling, offering a unique and often thrilling perspective on a city. Unlike a bus tour, walking allows you to feel the city's atmosphere, stop at specific haunted locations, and hear local secrets and stories of ordinary people, not just famous landmarks. You may even catch an orb in a photo!!!
1 hour 15 minutes
Free Cancellation
From
$40.00

Key West Bar Crawl

Dive into adventure, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let's make every day an adventure!
1 hour 30 minutes
Free Cancellation
From
$14.99

Island Maternity Bliss Photoshoot

We are able to meet your vision - whether your vision is romantic, motherly, excitement or studio art. This activity can be upgraded to studio.
1 hour
Free Cancellation
From
$550.00

Tiki Party Boat with Slide from Key West

Set sail for adventure with our Tiki Party Boat rental, cruising the breathtaking waters! Whether you're soaking up the sun, spotting local marine life, or enjoying refreshing drinks on deck, our 14-passenger tiki boat is the perfect way to experience paradise. Complete with bar top and chairs, take your party to the sea! Want a stress-free day? Hire a captain and let them handle the navigation while you focus on fun. Book now and turn your day on the water into a true paradise escape!
4 hours
Free Cancellation
From
$775.00

Six Fins Key West Clothing Optional– Private Sandbar & Snorkeling

This is the only clothing-optional boat charter in Key West, offering a full day of sandbar relaxation, snorkeling, and wildlife encounters in complete privacy. Unlike group tours, this charter is exclusively for your party — with freedom to choose your comfort level, activities, and pace. Whether you want to sunbathe, swim, snorkel, or simply unwind in a naturist-friendly environment, this experience blends Key West’s open-minded culture with luxury and discretion. Celebrate special occasions, enjoy unique adventures, or simply unwind with space and freedom. Spot dolphins, birds, and other wildlife while swimming in turquoise waters or exploring secluded Keys backcountry. What to Expect: Professional, respectful crew ensuring comfort and privacy Refreshments, shaded seating, and snorkeling gear on board Stunning locations across the Florida Keys, from reefs to sandbars
6 hours
From
$1,670.00

Six Fins Key West Combo Charter– Private Snorkel, Sandbar, Sunset

Unlike fixed tours, this is your custom charter—open itinerary, flexible schedule, and unlimited possibilities. Your captain is a local expert who will recommend the best spots based on the weather, tides, and your interests. You might snorkel with tropical fish in the morning, anchor at a secluded sandbar for a picnic lunch, and finish the day with a dolphin encounter or sunset cruise. Every trip is one-of-a-kind, designed exclusively for you. This isn’t just a tour—it’s a private Key West adventure, built around your dreams.
6 hours
From
$1,795.00

Florida Keys Tour and Private Transportation service

2
Your tour/shuttle can go anywhere between For Lauderdale Florida and Key West! As you check out you'll have the chance to let us know where you're hoping to travel to. We'll come and pick you up and drop you off wherever is convenient for you. Reach out to us if you want us to supply a cooler with any beverages on your tour. Must have at least one adult in your party. The van holds a Maximum of 14 passenger.( Price includes up to 14 Passengers)
10 hours to 12 hours
Free Cancellation
From
$985.00

Six Fins Key West Tiki Bar Crawl by Boat – Private Cocktail Tour

This is the only tiki bar crawl in Key West done entirely by private boat, giving you a stylish, scenic, and hassle-free way to experience the island’s nightlife. Instead of walking from bar to bar, you’ll arrive by water — skipping the crowds and creating an adventure you won’t find anywhere else. Whether celebrating with friends, enjoying a special occasion, or simply wanting to sip cocktails with ocean views, this tiki bar crawl delivers a blend of island culture, local flavors, and pure Key West fun. ✨ Highlights Private tiki bar crawl by boat in Key West Visit multiple waterfront tiki bars with direct dock access Enjoy tropical cocktails, seafood, and island vibes Flexible itinerary tailored to your group Perfect for parties, celebrations, or a fun night out
4 hours
From
$1,295.00

Cudjoe Key, Florida Boat Rental Services

4
Enjoy the waters of the Florida Keys, don't have experience on the waters around Cudjoe Key? We have separate colored tracks to spots on the water on the 9" GPS.
1 day to 30 days
Free Cancellation
From
$525.00

Marathon: COMBO- Snorkel & Sandbar (Sombrero Reef)

THE ONLY 2 DESTINATION TRIP IN MARATHON. Snorkel at the iconic Sombrero Reef and relax at the secluded Molasses Key Sandbar, perfect for a day of marine exploration. This 3.5-hour tour invites you to discover the vibrant underwater world of the 3rd largest barrier reef, where you can swim among tropical fish and coral. Enjoy the convenience of snorkeling gear, a floating mat, and a power catamaran led by a licensed captain. Cooler and ice are provided for your refreshments, ensuring a comfortable outing on the water. - Explore the renowned Sombrero Reef, teeming with marine life - Unwind at the exclusive Molasses Key Sandbar, away from crowds - Includes snorkeling gear and a power catamaran with a licensed captain - Convenient cooler and ice provided for your snacks and drinks
3 hours 30 minutes
Free Cancellation
From
$139.00

Marathon: Local Sandbar Escape

4
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
2 hours
Free Cancellation
From
$119.00

Fishing the Waters of Hemingway A Key West Classic

Follow Hemingway’s wake on a private fishing charter from Key West Bight. Carries up to 6 anglers for four unforgettable hours on the blue frontier. All tackle, bait, and gear provided—plus Cuban sliders, Key West pink shrimp, and chilled coconuts. Cast for snapper, grouper, or tarpon, and toast the sea with your own rum from Schooner Wharf Bar.
4 hours
Free Cancellation
From
$179.00