Itinerary Highlights

  • Visit world-class museums in Miami
  • Take a culinary tour
  • Explore Little Havana
  • Stop in Everglades National Park
  • Visit the Turtle Hospital in Marathon
  • Enjoy a walking tour of Key West
  • Take a sunset cruise

Follow in Our Footsteps

Editor’s Itinerary

Florida Keys
Duration: 12 Days

Sun, Surf and Seafood in the Sunshine State

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.

It’s certainly possible to drive from Miami to Key West in a single day, but it does seem a shame not to pause once or twice to enjoy the extraordinary places in between. This would be my ideal 12-day itinerary.

Day 1

Arrive in Miami

Fly into Miami and check into one of our six recommended hotels, ranging in location from Sunny Isles to South Beach and in style from the flamboyantly theatrical Faena to the more traditional and tranquil Betsy. 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.

Stay Overnight

Four Seasons Hotel at The Surf Club

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.

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Days 2 - 3

Explore Miami

Spend 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.

Stay Overnight

Four Seasons Hotel at The Surf Club

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.

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Day 4

Miami to Marathon

If you haven’t already, rent a car and drive south from Miami. You might make a detour into Everglades National Park (guided tours are available), or depart the mainland and start your drive along the Overseas Highway.

It takes about two hours to reach Islamorada, where the marina-view terrace of the Square Grouper is a fine place to break for a casual lunch.

It’s another 45 minutes or so to the 199-room Isla Bella Beach Resort at the far end of Marathon.

Check in to your spacious accommodation (all rooms have water views) and spend the rest of the afternoon relaxing by the pool or in an umbrella-shaded lounger along the beach. Have dinner tonight on the waterfront patio of the resort’s Italian-inflected Il Postino restaurant. Time your reservation to start about 30 minutes before sunset.

Stay Overnight

Isla Bella Beach Resort

The family-friendly Isla Bella Beach Resort is located an hour from Key West and two and a half hours from Miami.

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Days 5 - 6

Marathon

Take two days (or just one, if time is short) to relax at Isla Bella Beach Resort and explore the Marathon area. The hotel can arrange for a variety of activities including snorkeling, scuba diving and deep-sea fishing. Marathon also has sites of interest, notably the Turtle Hospital. About five minutes from Isla Bella, 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.

Stay Overnight

Isla Bella Beach Resort

The family-friendly Isla Bella Beach Resort is located an hour from Key West and two and a half hours from Miami.

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Day 7

Marathon to Little Palm Island

Depart Isla Bella late this morning and drive about 30 minutes to Little Torch Key. Leave your car behind and take a motor launch south to Little Palm Island Resort. All 30 of its thatched bungalows, as well as its public spaces, have been recently renovated. The 5-acre island is very popular with honeymooners and other couples, but it’s not ideal for families (guests under 18 are not permitted).

Stay Overnight

Little Palm Island Resort & Spa

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.

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Day 8

Little Palm Island

Spend a full day on Little Palm Island. You might also take advantage of its grand spa, or do a snorkeling or birding excursion, or do nothing at all.

Stay Overnight

Little Palm Island Resort & Spa

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.

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Day 9

Little Palm Island to Key West

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.

Check in at The Gardens Hotel, ideally into one of the Cottages or large suites. This friendly traditional property has 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.

Stay Overnight

The Gardens Hotel

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.

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Days 10 - 11

Key West

Spend 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).

Stay Overnight

The Gardens Hotel

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 Listing
Day 11

Depart

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.