8 days in Florida Keys Itinerary
8 days in Florida Keys Itinerary
Created using Inspirock Florida Keys planner
Start: Raleigh
Fly
1
Key Largo
— 2 nights
Drive
2
Islamorada
— 2 nights
Drive
3
Marathon
— 2 nights
Drive
4
Key West
— 1 night
Fly
End: Norfolk
Tue, May 17 - Tue, May 24
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Key Largo — 2 nights

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.Visiting Anhinga Trail and North Dry Rocks will get you outdoors. Discover out-of-the-way places like Swim with Dolphins and Grecian Rocks. There's lots more to do: tour the pleasant surroundings at Florida Keys Wild Bird Rehabilitation Center, enjoy the sand and surf at Harry Harris Park, admire the majestic nature at John Pennekamp Coral Reef State Park, and look for gifts at Shell World Florida Keys.
To see more things to do, reviews, where to stay, and other tourist information, use the Key Largo day trip planner.
Raleigh to Key Largo is an approximately 4-hour flight. You can also drive; or take a bus. In May, Key Largo is a bit warmer than Raleigh - with highs of 85°F and lows of 72°F. Wrap up your sightseeing on the 19th (Thu) to allow time to drive to Islamorada.
Side Trip
Highlights from your trip
Islamorada — 2 nights

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.Kick off your visit on the 20th (Fri): explore the gorgeous colors at Alligator Reef Light House, then kick back and relax at Anne's Beach, then indulge your thirst for a good beer at Florida Keys Brewing Company, and finally indulge your thirst for a good beer at Islamorada Brewery & Distillery - MM82. Here are some ideas for day two: kick back and relax at Library Beach Park, view the masterpieces at Lobster Trap Art Gift Shop and Gallery, and then discover the deep blue sea with a scuba or snorkeling tour.
To find other places to visit, more things to do, traveler tips, and more tourist information, use the Islamorada trip planner.
Islamorada is very close to Key Largo. In May, daily temperatures in Islamorada can reach 88°F, while at night they dip to 77°F. Finish your sightseeing early on the 21st (Sat) to allow enough time to drive to Marathon.
Highlights from your trip
Marathon — 2 nights

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.On the 22nd (Sun), kick back and relax at Bahia Honda State Park and then tour the pleasant surroundings at Sombrero Reef. On your second day here, enjoy the sand and surf at Sombrero Beach, see the interesting displays at Crane Point Museum & Nature Center, then learn something new at Dolphin Connection, and finally kick back and relax at Sunset Park Beach.
To find ratings, reviews, maps, and tourist information, read Marathon online driving holiday planner.
You can drive from Islamorada to Marathon in an hour. Another option is to take a bus. May in Marathon sees daily highs of 88°F and lows of 77°F at night. Finish your sightseeing early on the 23rd (Mon) to allow enough time to drive to Key West.
Side Trips
Highlights from your trip
Key West — 1 night
Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.On the 24th (Tue), get a new perspective on things with Boat Tours & Water Sports and then look for gifts at We Cycle.
To find ratings, where to stay, maps, and other tourist information, go to the Key West trip planner.
You can drive from Marathon to Key West in 1.5 hours. Another option is to take a bus. In May, plan for daily highs up to 85°F, and evening lows to 77°F. Wrap up your sightseeing on the 24th (Tue) early enough to fly back home.
Highlights from your trip
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Florida Keys travel guide
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.