19 days in Florida Keys Itinerary

Created using Inspirock Florida Keys trip maker
Make it your trip
Fly
1
Islamorada
— 3 nights
Drive
2
Marathon
— 5 nights
Drive
3
Key West
— 5 nights
Drive
4
Key Largo
— 5 nights
Fly

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Islamorada — 3 nights

The Village of Islands

Islamorada is known for wildlife, adventure, and museums. Your trip includes some of its best attractions: take a tour by water with Boat Tours & Water Sports, sample the tasty concoctions at Florida Keys Brewing Company, immerse yourself in nature at Lignumvitae Key Botanical State Park, and step off the mainland to explore Windley Key.

To find reviews, photos, more things to do, and more tourist information, you can read our Islamorada trip planner.

Sao Paulo, Brazil to Islamorada is an approximately 11.5-hour flight. Traveling from Sao Paulo to Islamorada, you'll gain 2 hours due to the time zone difference. Plan for somewhat warmer temperatures traveling from Sao Paulo in May, with highs in Islamorada at 36°C and lows at 29°C. Finish your sightseeing early on the 6th (Sat) so you can drive to Marathon.
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Parks · Nature · Breweries & Distilleries · Museums

Marathon — 5 nights

Heart of the Florida Keys

Get out of town with these interesting Marathon side-trips: Fishing Charters & Tours (in Big Pine Key) and SpaTerre at Little Palm Island Resort (in Little Torch Key). There's lots more to do: steep yourself in history at Pigeon Key, snap pictures at Seven Mile Bridge, enjoy the sand and surf at Sombrero Beach, and stroll through Bahia Honda State Park.

For traveler tips, where to stay, maps, and tourist information, you can read our Marathon online trip itinerary builder.

Drive from Islamorada to Marathon in an hour. Alternatively, you can take a bus. In May in Marathon, expect temperatures between 36°C during the day and 29°C at night. Finish up your sightseeing early on the 11th (Thu) so you can go by car to Key West.
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Parks · Wildlife · Outdoors · Beaches
Side Trips

Key West — 5 nights

Conch Republic

Key West is known for sightseeing, wildlife, and adventure. Your trip includes some of its best attractions: see the interesting displays at The Ernest Hemingway Home and Museum, see some colorful creatures with a scuba or snorkeling tour, take in the waterfront at Mallory Square, and take an in-depth tour of Key West Firehouse Museum.

For photos, maps, where to stay, and other tourist information, you can read our Key West holiday planner.

You can drive from Marathon to Key West in 1.5 hours. Alternatively, you can take a bus. May in Key West sees daily highs of 34°C and lows of 29°C at night. Finish your sightseeing early on the 16th (Tue) to allow enough time to drive to Key Largo.
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Parks · Museums · Outdoors · Historic Sites

Key Largo — 5 nights

Diving Capital of the World

Key Largo is known for wildlife, nature, and adventure. Your trip includes some of its best attractions: discover the deep blue sea with a scuba or snorkeling tour, take a tour of USCG Duane, admire the majestic nature at John Pennekamp Coral Reef State Park, and stroll through Spiegel Grove.

Planning Key Largo trip won't be overwhelming when you use Inspirock's itinerary maker.

You can drive from Key West to Key Largo in 2.5 hours. Another option is to take a bus. Traveling from Key West in May, Key Largo is little chillier at night with lows of 26°C. You will leave for home on the 21st (Sun).
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Wildlife · Parks · Tours · Outdoors

Florida Keys travel guide

4.3
Scuba & Snorkeling · Parasailing & Paragliding · Landmarks
An archipelago of about 1,700 islands extending in a gentle arc south and southwest of Florida's mainland, the Florida Keys divide the Atlantic from the Gulf of Mexico. Many visitors on vacation come to scuba dive in the coral reefs, fossilized and exposed as sea levels declined over thousands of years. In addition to being one of the world's top diving and fishing spots, the Keys feature hundreds of shops, restaurants, bars, and various tourist attractions, most of them crowded all year long with visitors on vacation. To soak up the Keys' atmosphere and discover writer Ernest Hemingway's former haunts, drive from one island to the other all the way to Key West, located just 140 km (90 mi) from Cuba.
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