Save

Private Florida Keys Tour: Explore Key West

4.9

10 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

â¢ Lots of free time in Key West
â¢ Designated driver
â¢ 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.

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

(10 Ratings)

5 stars

4 stars

3 stars

2 stars

1 star

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

Vickerydk

Jan 17, 2020

Private Tour to Key West - On Jan. 15th our party of 4 used Up The Keys to transport us to Key West and give us the opportunity to sit back, relax, and drink some adult beverages. Riding with Kim was a great find. Kim is very personable, knowledgeable, and made our trip quite enjoyable. Thanks Kim! We may see you again on a future trip.

Review provided by Tripadvisor

Diana

Mar 12, 2019

A great ride! - Kim was an excellent tour guide and driver. She explained everything we asked and things that she thought we would be interested in. She took us off the route along the way to show us a cul-de-sac that has airplane hangers instead of car garages with a very small take off strip down the middle. Who would think of that? She was friendly and enthusiastic while driving us from Marathon to Key West including the awful traffic in Key West. All 8 of us would do it again! It's worth every penny!! Thank you Kim for safely and entertainingly getting us to and from Key West!!

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

From $84

Select Date and Tickets

up to 10 guests

1 Adult