key west roadtrip
The itinerary works great flying in overnight from the west coast. After you grab your rental, the right trip for any convertible, you're headed straight to Little Havana for breakfast. A must stop at Versailles. After you're done enjoying some fine Cuban coffee and bites its road time. Get to the 1Hwy and just head on down. I made a pit stop at the Gym in Homestead to freshen-up. Then on to the first leg of the keys through Key Largo. If its in your taste, I highly suggest stopping at one of the many homemade Key Lime Pie stops along the way.
There is also several wildlife preserves, dolphin swimming and other parks if you want to take your time. It was already mid day, and a long day already including the overnight flight, so I was just enjoying the drive through to Ismamorada. I was ready for my ocean side stay and a refreshment at Amara Cay Resort. The key to staying here is its walking distance to your sunset dinner at Lazy Days. Fantastic service, vibe and seafood ocean side. And with that bed time.
Up early for some coffee, lite bite and my anticipated drive through to Key West. About 2hrs left and this is where the drive really gets cool on the open water. The convertible really earns its keep on this stretch. Save your breakfast tummy for a brunch stop in Marathon at Wooden Spoon. A classic Americana breaky spot. Just a short distance now and you'll be pulling into Key West. I actually turned my rental in because you really don't need it. And you can fly back from Key West.
I went with Margaritaville. A great stay right on the water in the Marina and walking distance to it all. Or a scooter when its time. Arriving mid day again so there's procedures to be followed: pool, refreshments then dinner. After indulging in the pool area its time for a walk and dinner right out front on the boardwalk. Keeping it easy for the first night. Bistro 245 provides the perfect sunset backdrop for your first evening. The Seared Ahi and some bubbly didnt hurt either. After I took a walk down Duval St. and had a shot at Flying Monkeys to cap the night.
Next morning after some coffee I walked over and booked a snorkel tour to get out on the water. Had some time so took a walk into town to grab another coffee and sandwich at Cuban Coffee Queen. Then back to the dock for the tour. I'll just say I loved getting out on the water and everything was enjoyable. But There really wasn't much to the snorkeling in the middle of the ocean. I'd suggest something more coastal beach excursion. That evening I had a fantastic dinning experience at Roof Top Cafe. I grabbed an outdoor balcony seat and ordered their snapper; perfecto. To continue the nicer trend of things I capped the night off with a craft cocktail at Caroline's Other Side.
The next morning was my last day and flying out in the afternoon. So I rented a scooter early to see the sights. First stop was breakfast at the 100 year+ running Pepe's Cafe. Then I looped around the island and made stops in the Southern Most Point area and the Hemingway Home. Had a margarita before my Uber to the airport. I see now what the classic nostalgia is all about with this drive and stay. Classic, comfort and character in the Keys. Cheers.
ProTip: If I did it again I'd stay in the Southern Most Point area also. This is a more relaxed rustic cottage beach vibe area. And a scooter is ideal for this place.
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