Key West Adventures is located on a beautiful four-mile, by one-mile long island that offers guests a living and breathing museum of American History crisscrossed with modern-day creativity. There are narrow streets, named for pioneers and presidents, lined with Victorian mansions dating back to the 1830s when Key West was America’s wealthiest city. Guests can ride along the Atlantic Ocean on South Roosevelt Boulevard then zigzag their way towards the southernmost point in the continental U.S. in a Polaris Slingshot. Guests can explore Old Town like a celebrity by cruising northbound on historic Duval Street as they slowly roll a mile and a half through thumbs up and picture takers as they solo parade towards Front Street and Mallory Square. Here, guests can drive in all directions through Old Town and explore the iconic area. See the famous Key West lighthouse across the street from Ernest Hemingway’s house. A little further into Key West guests will find President Truman’s Little White house. The Oldest House can also be spotted along this route. Guests will turn heads and catch eyes as they pass by Sloppy Joe’s Margaritaville, Captain Tony’s and Irish Kevin’s. Don’t just see Key West, be Key West.


(305) 293-3555

3424 N Roosevelt Boulevard
Key West, FL
33040 United States


Ride Type: On-Road
Vehicle Types: Slingshot
Duration: half-day, full-day, multi-day
Level: All Levels


Drivers must be 25 years of age or older. Specific Outfitter or state regulations may supersede guidelines, please confirm with the local Outfitter.


Seasonality: Spring, Summer, Fall, Winter
Terrain Type: Road


Flight: Fly directly to Key West. Delta, American, United all have routes to the island. We have rental cars available in Key West. Jeep Wranglers, Mini Coopers convertibles, economical Jeep Renegade 4 doors. Fly into FTL - Grab a convertible Jeep Wrangler Rental from us at our affiliate Gold Coast Car Rental. Fly into MIA - Grab a Hertz or Enterprise one way rental. (sorry we're not in MIA yet) Private Plane/Jet - Arrange a Slingshot or Jeep rental through Signature Flight Support EYW. Call us at 305-293-3555 or book online.

Ground Transportation: From Southwest Florida, take the Key West Express fro FT Myers or Naples. We will meet you at the dock. By Private boat/yacht - call us to arrange pickup at your Key West area marina. By RV to one of the many RV parks - leave your Toad at home - free delivery and pickup at Key West Area RV parks (up to Blue Water) Delivery fees apply to RV parks up the Keys, but we can still get it done.


Old Town –Margaritaville, Ocean Key, Pier House, Curry Mansion or the Gardens Hotel. https://www.currymansion.com New Town –Parrot Key, Havana Cabana, equipped with a great pool, Laureate or 24 North. South Shore - Sheraton Inn and Suites or the Doubletree. Stock Island - Perry Hotel, Oceans Edge and the new Key West Harbor Yacht Club. The Key West Harbor Yacht Club only has a few rooms but it is very cool!


Lunch: Eaton Seafood Market has the freshest fish and Stone Crabs when in season. Their Lobster roll is famous, and rightfully so. They possibly have the best fish dip on the island, and this is where locals get their tuna, grouper and snapper.
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Dinner: Salute! On the Beach on the Atlantic Side at Higgs Beach located on Atlantic Boulevard on Reynolds Street. There is beachside dining and ample parking located here. Try the pie in the Key of Lime here.
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Mallory Square is the Historic Seaport district that welcomes a sunset celebration. There is parking available. There are live performances, jugglers, musicians, acrobats and people to watch. Enjoy the sunset from sea level and keep an eye out for the Green Flash.
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Polaris Adventures focuses on the safety of every rider, from vehicle overviews & training before every ride to a modern check out process, our outfitters are there to make sure you have a safe, memorable, adventure.

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Get in touch with any of our Outfitters directly to learn more about their adventures, requirements or how to build your perfect getaway. You can find their contact info above.

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Key West, FL

Starting at $125