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One goal of my recent visit to the Florida Keys was to find an additional recommendation or two in between Miami and Key West, so that one could fashion a leisurely multiday road trip along the Overseas Highway. This iconic drive strings together mangroves, tropical forests, yacht-filled marinas, fishing boat-lined piers, plush resorts and charming old seafood shacks. The highway’s view routinely opens onto the shallow islet-dotted sea surrounding the Keys, its bottom of white sand, coral reefs and turtle grass flats creating a spectacular patchwork of blues ranging from deep lapis to almost iridescent turquoise. Causeways sometimes extend for miles between islands, and driving along them can be exhilarating — especially in a convertible.
Fly into Miami and check into one of our four recommended hotels, ranging in location from Sunny Isles to Miami Beach and in style from the family-friendly Acqualina Resort to the flamboyantly theatrical Faena. Each has its merits.
Take the rest of the day to enjoy the resort of your choosing and have a sunset stroll on the beach.
The beautiful Richard Meier-designed Four Seasons Hotel at The Surf Club comprises a 12-story tower with glass curtain walls and the Mediterranean-style Surf Club.
View Hotel ListingSpend two full days in Miami. Although the metro area is well known for its beach culture and nightlife, the region offers major cultural attractions as well. I’ve enjoyed visiting world-class art museums such as the Bass and the Pérez Art Museum Miami and exploring Miami Beach’s colorful art deco architecture on a fascinating walking tour. We also once spent a memorable morning with Miami Culinary Tours tasting a variety of delicious food and drink in the Little Havana neighborhood.
Enjoy another day in the Magic City touring historic house museums, including the lavish Mediterranean-style Vizcaya Musuem and Gardens. If your trip is in early December, it may coincide with Art Week Miami, Don't miss the array of art fairs, gallery exhibitions and museum events that take place across the city.
On the way to your hotel, explore the Marathon area, which has several sites of interest, notably the Turtle Hospital. This wonderful facility dedicated to rehabilitating sick and injured sea turtles occupies a converted motel complex. The guided tours (reserve tickets in advance) are quite engaging and an excellent activity for families.
Drive on to Little Torch Key. Leave your car behind and take a motor launch south to Little Palm Island Resort. (Note that the resort doesn't allow children under 18.) The 30 oceanfront accommodations in thatched bungalow suites feature vaulted ceilings, four-poster canopy beds, separate living areas, indoor-outdoor showers and private furnished verandas. All rooms lack TVs and phones. Enjoy dinner on site.
Reached via launch from a shore station at mile marker 28.5 on Little Torch Key, the recently renovated tropical Little Palm Island Resort & Spa occupying the lush 5-acre Munson Island is half an hour north of Key West.
View Hotel ListingEnjoy your time relaxing or taking in the various amenities at Little Palm Island Resort, which include a grand spa housed within a two-story atrium, a fitness center, a private marina and a small white-sand beach. Make arrangements to enjoy snorkeling and scuba excursions, birding outings, sailing and fishing charters, and helicopter and seaplane tours.
Spend another full day on Little Palm Island.
Return by motor launch to Little Torch Key, and drive about 45 minutes to Key West. I recommend returning your rental car at the airport and taking a taxi into town. The city of Key West is pedestrian-friendly, and it’s not necessary to have a car to reach most points of interest.
Andrew Harper doesn’t have a recommended hotel in the area, but The Gardens Hotel is a friendly, traditional property with a self-service wine bar, a pool surrounded by lush botanical gardens and a perfectly central location.
Have a stroll up and down Duval Street, parts of which (especially the northern end) feel like New Orleans’ Bourbon Street. Nearby side streets are lined with charming little houses and impressive old mansions.
The Gardens Hotel is an enchanting enclave set in a walled garden and a short walk from the bustle of Key West’s main venue, Duval Street.
View Hotel ListingSpend two days enjoying Key West. Consider doing one of the walking tours I recommend, and have a look at historic sites such as Truman’s Little White House and the grand estate that belonged to Ernest Hemingway. You can also use Key West as a base for excursions. There are a range of snorkeling, diving, fishing and kayaking trips available, both private and with groups, and it could also be great fun to take the ferry to Dry Tortugas National Park, home to the impressive Fort Jefferson (you can also reach the Dry Tortugas by private seaplane).
One evening, I recommend doing a sunset cruise with the Argo Navis (you can read about our experience on the catamaran here), and on the other evening, consider taking a short ferry ride over to Sunset Key Cottages to have dinner at Latitudes, the waterfront patio of which offers magnificent sunset views (make reservations in advance).
Transfer to the Key West airport and depart on your flight home. In high season, a surprising number of cities can be reached via nonstop flights from the island.
This is a sample itinerary designed to inspire your travels. Price listed is based on two people sharing, except where noted. Flights are not included. Room categories, dates of travel and change to services may affect the starting price. Contact the Andrew Harper Travel Office to customize this journey to fit your needs.