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Top Experiences in Southernmost Point of the Continental USA

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Sunset Watersports

Dolphin Sighting & Snorkeling Experience in Key West

USD 64.95

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.
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Key West Boat & Jet Ski Adventures

Key West Small Group Guided Jet Ski Adventure

USD 164.95

Smaller Groups = Better Experience!

**1 Booking is 1 Jet Ski that can accommodate up to 2 riders. Ages 4+

For all you thrill-seekers and explorers, our guided Jet Ski Tours are a great way to experience Key West. Let our guide take you on a 90-minute adventure around the entire island. This 27-mile exploration is a feast for the eyes and senses. We'll make several stops along the way, checking out all of the best-known attractions the island has to offer. AND unlike other companies, our tour groups are small making for a better experience!
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Stock Island Charters

Private Sunset Cruise around Key West

USD 260

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!
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Banana Joe Tours

Small-group private Key West tour with expert guide

USD 977.18

Our Key West tour is carried out by a real tour guide with over 10 years of Florida experience, who will explain everything on the way to Key West and answer all your questions.

Of course, we have built in some points on the route where you can leave the van and go on an exploration tour on foot and take pictures.

We look forward to seeing you.

Your Banana Joe team
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Up The Keys Tours

Miami Key Largo to Key West Full-Day Private Tour

USD 260

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!
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Tripshepherd USA

Key West Walking Tour with Glass Bottom Boat Cruise

USD 233

Experience the best of Key West on our guided walking and boat tour, where you'll delve into the island's rich history and explore its stunning coastline. Begin your journey by strolling through the charming streets, learning about the indigenous peoples, Spanish settlers, and famous residents who shaped the island's identity. Visit iconic landmarks like the Truman Little White House and Hemingway's former home, soaking in their stories and architectural splendor. Then, step aboard our boat to cruise along the crystal-clear waters, where you'll enjoy panoramic views and spot vibrant marine life through the glass bottom. Whether you're captivated by history, mesmerized by nature, or simply seeking adventure, our walking and boat tour offers an immersive and unforgettable Key West experience.
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Tripshepherd USA

Key West with Glass Bottom Boat Cruise

USD 298

Embark on an unforgettable journey in Key West, where laid-back vibes meet vibrant culture. Explore the island's storied past, from its indigenous roots to its role in pivotal historic events like the Civil War and the Spanish-American War. Discover iconic landmarks like the Southernmost Point Buoy and the Ernest Hemingway Home and Museum, where literary legends once roamed. Dive into the marine wonderland of the Florida Keys with a glass bottom boat tour, marveling at colorful coral reefs and tropical fish without getting wet. Soak in stunning sunset views at Mallory Square, where street performers entertain as the sun dips below the horizon. With its blend of history, natural beauty, and endless charm, Key West offers a slice of paradise at the southernmost point of the United States.
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Florida Keys Tours and Transportation

Florida Keys Full-Day Private Tour

USD 833.34

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.

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Up The Keys Tours

Key West, Florida: Private, Customizable Walking Tour

USD 137.5

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.
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Historic Tours Of America

Key West Hop-On Hop-Off Trolley Tour

USD 55.6

The hop-on hop-off trolley tour of Key West is a fantastic way to explore this historic island. Sit back and relax while your expert tour guide turns back the pages of history to the days of Indians, pirates, wreckers and the Civil War. You’ll get a full picture of Key West on this Old Town trolley tour. FREE ADMISSSION TO THE SAILS TO RAILS MUSUEM INCLUDED WITH TICKET!
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Sunset Watersports

Key West Small-Group Jet Ski Tour

USD 162.95

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
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Sunset Watersports

Key West Small-Group Jet Ski Tour

USD 169.95

The 9:30 am Jet Ski Tour is 1 1/2 hours around Key West

Includes Free Gas, NO CHARGE for 2nd Rider, Fresh water Showers

Follow a guide on this 28 mile tour around Key West as you see the

coast line of Key West

You will see the Naval Air Station, Southern most point

Key West Harbor and much more.

If you are born after January 1st, 1988 must take a Florida Boaters Safety.

Test has a cost (check Exclusions section) and you must arrive 1 hour early

Must Have Credit Card for Deposit and I.D.

you can take the test on line at Click Here

The only cost is mentioned under Exclusions section and you can take it as many times as you want and the license is good for 1 year.We offer this 15 minute exam 1 hour before each tour, license is good for one year
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Historic Tours Of America

Key West Shore Excursion: Key West Hop-On Hop-Off Trolley Tour

USD 55.6

When you arrive in port in Key West, take an independent, hop-on hop-off trolley tour shore excursion for the best way to explore the island. While you’re off your cruise ship, simply sit back and relax while your expert tour guide turns back the pages of history to the days of Indians, pirates, wreckers and the Civil War. You’ll get a full picture of Key West during your limited time ashore. FREE ADMISSION TO THE SAILS TO RAILS MUSEUM INCLUDED WITH TICKET!
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Florida Keys Ventures

Small-Group Walking Tour of Key West's History and Culture

USD 39.99

Meet The Locals, On Foot, At Eye Level

If you’re like us, you think of travel as more than just “going places.” You crave experience and discovery, not just monuments and museums. You want to understand what’s behind the touristic façade that most people never penetrate. That’s why the Southernmost Walking Tour is the best way to immerse you into the history and culture of Key West! When you’re on foot, the world can’t slide past you faster than you can absorb it. You’ll have time – and proximity – to get up close to the region’s culture and natural history.

Start your tour at the famous Cuban sandal factory - Kino Sandals before heading off toward the Southernmost Point of the continental United States. Along the way, our incredibly knowledgeable and well-connected local guides will show you the most popular landmarks and introduce you to local culture. By the time you’re finished, you’ll have a uniquely fun perspective of our tiny island!
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Barefoot Billy's

Key West Jet Ski Tour

USD 150

Billy started his Island Jet Ski Tour in 1992. There are many imitators, but only one Original Island Jet Ski tour! Our guides are licensed and local, so they know the waters surrounding our island like their backyard - because it is!

Our tour route changes dependant on the weather & waves of the day - we modify our tour to be comfortable and give you the longest Freeplay time possible, so you can drive it like you stole it!
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Historic Tours Of America

Key West Conch Train Tour: Explore Iconic Sights and History

USD 45.1

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!
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Florida Keys Ventures

Key West Historic District Small-Group Walking Tour

USD 46.99

Experience Historic Key West With A Small-Group Walking Tour

Ever wondered how the island of Key West was discovered and became so rich? Explore Key West’s history, lore, and legends from the ground up with an intimate walking tour. Whether you want to learn more about the island’s first industries such as shipwrecking and cigarmaking, are curious about local history, or are looking for a fun-filled walk, Key West’s Historic Districts are waiting for you!

This small-group walking tour offers both an educational experience and unparalleled delight for the lovers of history and culture. Our experienced local tour guides will lead you on an impressive stroll through the scenic streets of the Old Town where you can connect with the culture of a historic city. This unique experience is enjoyed by visitors from across the world and is a must-do while in Key West!

What to bring and to wear:
Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.

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BARBIL TOURS

Private Key West Tour in a Small Group From Miami

USD 955

Embark from Miami on a scenic drive towards the thrilling and awe-inspiring journey crossing the Seven Mile Bridge, an engineering marvel spanning the Gulf of Mexico and the Atlantic Ocean.
Enjoy the enchanting and gorgeous scenery on the Overseas Highway to Key West.
Get ready for fun in the sun on this day trip off the coast of Key West. Ride across 42 islands from Miami to Key West, then explore this island city in any number of ways during your free time. See where Ernest Hemingway used to live . Take an optional snorkeling tour with an open bar. Relax, feel the warm sea breeze and enjoy the day. Miami hotel pickup and drop-off included.

This tour will have a maximum of 5 travelers per van/SUV
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SeaEO Nautical Ventures

Half Day Luxury Boat Tour in Key West with Snorkeling

USD 700

Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring with stops like Fort Zachary Taylor Historic State Park, U.S. Coast Guard Cutter Ingham Maritime Museum, Smathers Beach, Southernmost Point of your list.
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SeaEO Nautical Ventures

31' Private Boat Charter Rental - Islamorada W/Capt up to 13ppl

USD 899

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 Islamorada 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:
⇛ Bathroom
⇛ Bluetooth / AUX audio
⇛ Children's & Infant Life Jackets
⇛ Cooler / Ice Chest
⇛ Deck / Washdown Shower
⇛ 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!
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Jupiter Legend Corporation

Miami, Key West and Fort Lauderdale 4-Day Tour from Miami

USD 790

【Premium Service】 Travel in comfort with our experienced professional Chinese speaking tour escort.

【Safety First】Travel with thoroughly disinfected sightseeing coach and our professional well-trained tour escort.

【Unforgettable Journey】 Visit four scenic citys - Miami, Fort Lauderdale, Palm Beach, and Key West.

【Sunshine and Beach】Take a walk on South Beach as well as exploring its trendy entertainment.

【Swamp Venture】Take an airboat ride cruising through the swamp channels in the Everglades National Park.

Room Details
All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what hotel availiable on the day. The maximum occupancy per room is four travelers.

One Room Selection
If you are a party of more than four guests, please provide a separate booking.

Avoid traveling in a different bus?
If you have more than one booking, please provide all confirmation numbers once your bookings are complete.
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Historic Tours Of America

Key West Shore Excursion: Conch Tour Train

USD 45.1

When you arrive in port in Key West, take a Conch Tour Train shore excursion on your own; you’ll see the best of Key West on the tour that's been entertaining visitors to the Island City since 1958. You’ll hear legends and lore of this charming tropical paradise like stories about Henry Flagler's railroad, which arrived in Key West September 22, 1912, and forever changed the Island City. FREE ADMISSION TO THE SAILS TO RAILS MUSEUM INCLUDED WITH TICKET.
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Travel The Keys

Bahama Village Walking Tour

USD 30

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.
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Tripshepherd USA

Miami Small Group Tour from Fort Lauderdale w/Millionaire's Row

USD 239

Explore Miami - The Magic City from Fort Lauderdale with our fun and friendly local guides who will take you to witness the best views and learn about the city’s history, while immersing yourself in its Latin-American influences and beautiful white-sand beaches. There is no better way to experience the city than our best small group tours (max. 7 guests).

Enjoy the top attractions and visitor experiences while avoiding long lines and wait times, with our fully guided and narrated tours with all attraction admission fees included along with complimentary hotel pick up and drop off in Downtown Fort Lauderdale in the comfort of one of our complimentary vehicles.
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Frenchie’s E-Pedicab @ Key West Oh La La

Private E-Pedicab 2 Hours Sightseeing Tour of Old Town Key West

USD 195

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!
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Sunset Watersports

Key West Jet Ski Tour From Stock Island

USD 185.95

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 (shuttle is based on availability)

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
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Frenchie’s E-Pedicab @ Key West Oh La La

Private E-Pedicab 1/2 Hour Sightseeing Ride of Old Town Key West

USD 55

This 1/2 Hour Guided Scenic Tour is packed with Key West’s main sights. 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 the culture of Key West. This tour Includes two stops for photo opportunities: one at the Southernmost Point and one at the Mile Marker 0. But if you wish to stop at other locations, we'll make it work for you!
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Sunset Watersports

Epic Sandbar Safari With Dolphin Playground Encounter In Key West

USD 129.95

Embark on a journey like no other. This tour takes guests on an amazing journey from Key West to a secluded sandbar & then to the dolphin playground in the Florida Marine Sanctuary for some dolphin watching.

With picturesque views of the Gulf of Mexico and expert guides providing insights into the history & ecology of the area, guests can relax at the sandbar while our crew fills your cups with unlimited draft beer, wine & mimosas. Next, we will venture out future into the Sanctuary to get closer than ever to our dolphin pods. The tour includes complimentary lunch (menu below) & unlimited draft beer, mimosas & wine.

Our professional crew will make this a trip of a lifetime that you'll cherish for years to come. This trip is perfect for families, couples & solo travelers seeking a unique & unforgettable experience in the Florida Keys.
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Gray Line Miami

Key West from Fort Lauderdale Full Day Cruise

USD 99

Take a day trip from Fort Lauderdale to Key West by bus and enjoy a fun Caribbean atmosphere, street artists, outdoor cafés and more. Key West’s leafy and lively streets have plenty to offer, bus transportation begins in Fort Lauderdale once you arrive you can spend the day at leisure but if you’d like more activity, there are upgrades available! Get out on the water on a glass-bottom boat ride, snorkeling cruise or parasailing adventure, or see the attractions on dry land on the Hop-on Hop-off Trolley Tour or the Conch Train.
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Frenchie’s E-Pedicab @ Key West Oh La La

Private E-Pedicab 1 Hour Sightseeing Ride of Old Town Key West

USD 100

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!
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SeaEO Nautical Ventures

Key West Full Day Private Luxury Boat Charter

USD 899

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!