Private Florida Keys Tour: Explore Key West
4.9
12 Ratings
Up The Keys

Embark on a private Florida Keys tour and explore the vibrant island city of Key West. Enjoy a narrated tour, designated driver, and plenty of free time to sightsee, dine, and experience the sunset. It’s a road trip adventure with a local guide!

Duration: 8 hours
Cancellation: 1 day learn more
Highlights
  • Up The Keys - HIGHLIGHTS
    • Lots of free time in Key West
    • Designated driver
    • Narrated tour

It’s not an ordinary sightseeing tour. It’s an extraordinary road trip among friends who just haven’t met yet. You depart Marathon in a comfortable 15-passenger, air-conditioned van, and you’ll travel over 20+ bridges on the Overseas Highway. Your driver is also your friendly local tour guide that entertains you with interesting stories and fun facts with a headset microphone set to a comfortable audio level. You are encouraged to ask questions and make comments and observe the wildlife and interesting sightings along the way.

See the Southernmost Point, Hemingway’s House, Mile Marker Zero, Sloppy Joe’s, and Mallory Square and then enjoy approximately 3 hours of free time in Key West to do whatever it is you want. Add a sunset sail, Key West attraction, or a dinner cruise to enhance your experience. We’ll provide you with a list of suggested places to go and things to do. Arrive back in Marathon about 2 hours after sunset.

You’ll be picked up at your accommodations in Marathon or other specified location of your choosing. You’ll receive an email with your pick-up time the day before your tour.

  • The Overseas Highway - Experience the spectacular views along the Overseas Highway from the comfort of our customized touring van with panoramic windows.
  • Key West - HIGHLIGHTS
    • World-Famous Key West Sunset
    • See Key West’s iconic attractions
    • Lots of free time in Key West

See the Southernmost Point, Hemingway’s House, Mile Marker Zero, Sloppy Joe’s, and Mallory Square and then enjoy approximately 3 hours of free time in Key West to do whatever it is you want. Add a sunset sail, Key West attraction, or a dinner cruise to enhance your experience. We’ll provide you with a list of suggested places to go and things to do.

You’ll be picked up at your accommodations in Marathon or other specified location of your choosing. You’ll receive an email with your pick-up time the day before your tour.

  • Seven Mile Bridge - We’ll drive over the iconic 7-Mile Bridge & revel at the 1912 historic original, which was the longest bridge in the world when it was built.
  • Mallory Square - Your guide will show you where Mallory Square is located so you can opt in for the nightly Sunset Celebration.
  • Key West Historic Seaport - We’ll drop you off at the Historic Seaport so you can enjoy your free time from a convenient location. Duval Street & Sloppy Joe’s is only 2 blocks away!
What's Included
  • Hotel pickup and drop-off
  • Local Driver/Professional Tour Guide
  • Live commentary on board
What's Not Included
  • Gratuities
Additional Information

Explore the unique island town of KEY WEST!

Take pleasure in a guided journey on our way there, and delight in island rhythms during our return trip.

FEATURES
• Take in the sights around Key West
• Experience a Key West sunset
• Plenty of Leisure Time
• Appointed Driver
• Guided Tour

Experience Key West your way! The driving is on us!

Tours, unwind during happy hour, enjoy a delicious meal, visit Mallory Square at dusk, embark on a sunset sail, among other activities!

Relax and admire the beautiful landscape as we cruise down to Key West. Discover the history, culture, and nature of the Florida Keys & Key West from a knowledgeable local guide.

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

Imagine it more as an adventurous trip rather than a standard tour - feel free to ask questions, highlight wildlife, and make new acquaintances.

Location
Up The Keys
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(12 Ratings)
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1 star
Lindasb4406qy
Jul 21, 2024
Great all day tour and entertainment - Scott picked us up at our accommodations mid morning and proceeded to WOW us all day. He gave us many options for our trip down to Key West. We had a terrific water front lunch, saw numerous Key deer and loved the bridge view vistas on the Overseas Highway. We toured Key West and had time on our own for shopping and watching the Mallory Square antics. We were four couples and we managed to wear our selves out. Scot was available to assist us at a moments notice and we enjoyed spending time with him and his stories during the drive and during the meals. After our busy day, we were thrilled to not have to drive back to Marathon on our own! Highly recommend this company. They are terrific to work with and will make sure that your trip exceeds your expectations!! Book your tour with Up The Keys and you will not be disappointed.
Review provided by Tripadvisor
Tisha_k
Jun 14, 2024
Worth the trip. - Scott was very knowledgeable about the area. He was very personable and made the trip enjoyable. Would highly recommend.
Review provided by Viator
Mstau002
Sep 4, 2023
Great day with friendly owners! - Our group of friends had a blast! Maddie was so accommodating and kind to book with and Scott made sure our trip went smoothly. Great communication and comfortable vehicle to explore the keys in!
Review provided by Tripadvisor
Damorelli
Mar 9, 2023
Great Tour for First Time Visitors to Key West - We spent a fun afternoon with Maddy. She introduced us to places that we had not visited, despite this being our 4th trip to KW. She is a gracious, typically nice Canadian who aims to please. I wouldn’t hesitate to recommend this company to give you a tour of the area. We saw many key deer, a couple of huge alligators and walked the historic bridges of the Keys. She also offered some recommendations of other things to see, restaurants, etc. we were offered cold water and granola bar during the tour. The van is comfortable and very nice. She offered to stop at a local coffee shop to grab some coffee but we had just eaten lunch before the tour. Put this tour on your to do list, especially if it’s your first trip to the Keys.
Review provided by Tripadvisor
Mattsh1220ks
Jul 5, 2022
Great Private Booze Cruise - We booked a private trip for 10 of us from Key West up to Marathon with 4 other stops on various keys for our own personal booze cruise. Maddy was awesome helping me choose some fun sites for our group. The van was prompt on pickup and was very open to letting us navigate our day if we wanted to make any last minute changes. I would definitely recommend!
Review provided by Tripadvisor
Sharon_j
Feb 16, 2022
Great experience - Meghan was so friendly and informative. We learned a lot of local history from her. Her tips of where to go on the island were spot on. Mikey was very accommodating and friendly. He got us home safe and sound. Highly recommend!
Review provided by Viator
Schoppek
Sep 24, 2021
Z Brew Krewe - Pub Crawl - Kim is AWESOME!! She took a large group of us from Key West up to the two Breweries in Islamorada. We made a lot of pits stops along the way and back ... She kept us on task and told us a lot about the areas and sites as we made the drive. I HIGHLY recommend contacting Kim if your needing a tour guide/driver. KIM ROCKS!!!
Review provided by Tripadvisor
Craig
Sep 22, 2021
Awesome Brewery Tour with Up The Keys - Kim is the best. She picked up our group of 10 adults and took us to our choice of breweries and bars up the Keys. She was entertaining and kept us informed of where we were and lots of great information.
Review provided by Tripadvisor
Laurenm877
Feb 19, 2021
Flexible and Fun Nature Tour - Even though UTK is based in Key West, the driver kindly agreed to pick us up from our hotel in Marathon. He was knowledgeable, kind, and fun to chat with throughout the tour. He made sure that we got to see all of the cool stuff the Keys has to offer, including the history of bridges, finding Key deer in the backroads of Big Pine Key, and pointing out the gator at Blue Hole. This is a great trip! Even though my husband and I were the only two who booked that day, they still did the trip no problem. Highly recommend to get a little taste of the Keys out in nature.
Review provided by Tripadvisor
802lauraz
May 9, 2022
Nice to be driven! - This was a private tour, meaning just the two of us were on the 15 person van. We rented a car for our Keys trip, so it was kinda odd that we did this. I thought it was more of a "party" trip with others. For some reason, I also thought beverages were included; they are not, except water. The driver was wonderful and knew lots about the Keys and Key West in particular. You don't actually stop anywhere though. You get driven past the sight seeing highlights in Key West, which helps you get the lay of the land. Hours of free time and sun set watching on your own. Key West is plenty walkable so it was fun. I just wouldn't spend this much money to be driven anywhere again. To be clear, although I was confused on what the tour involved, the tour company called me the day before and made it clear we would not be stopping anywhere, just driving past sites.
Review provided by Tripadvisor
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up to 10 guests
1 Adult
September 2024
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