10 days in Florida Keys Itinerary

10 days in Florida Keys Itinerary

Created using Inspirock Florida Keys travel planner
Make it your trip
Key West
— 5 nights
Big Pine Key
— 2 nights
Key Largo
— 2 nights


Key West — 5 nights

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.
The Ernest Hemingway Home and Museum and Truman Little White House will appeal to museum buffs. Popular historic sites such as Fort Zachary Taylor and Key West Lighthouse and Keeper's Quarters Museum are in your itinerary. There's lots more to do: discover the deep blue sea with a scuba or snorkeling tour, take in the architecture and atmosphere at Saint Mary Star of the Sea, get engrossed in the history at Key West Shipwreck Museum, and get a taste of the local shopping with Alan S. Maltz Gallery.

For more things to do, maps, where to stay, and tourist information, read our Key West trip itinerary builder tool.

Boston to Key West is an approximately 7-hour flight. You can also drive; or do a combination of train and bus. Traveling from Boston in June, things will get somewhat warmer in Key West: highs are around 88°F and lows about 79°F. Wrap up your sightseeing on the 23rd (Thu) early enough to drive to Big Pine Key.
Historic Sites · Museums · Parks · Wildlife

Big Pine Key — 2 nights

Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. On the 24th (Fri), examine the collection at Crane Point Museum & Nature Center, tour the pleasant surroundings at The Turtle Hospital, and then stroll through Bahia Honda State Park. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Sunset Park Beach, pause for some serene contemplation at San Pablo Catholic Church, and then enjoy the sand and surf at Sombrero Beach.

To see traveler tips, ratings, where to stay, and more tourist information, read our Big Pine Key trip itinerary site.

Getting from Key West to Big Pine Key by car takes about an hour. Other options: take a shuttle; or take a bus. June in Big Pine Key sees daily highs of 90°F and lows of 79°F at night. Finish up your sightseeing early on the 25th (Sat) so you can go by car to Key Largo.
Parks · Beaches · Outdoors · Wildlife
Side Trips

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.
On the 26th (Sun), take an in-depth tour of History of Diving Museum, then appreciate the extensive heritage of Indian Key State Historic Site, and then stroll through Florida Keys Wild Bird Rehabilitation Center. On the next day, immerse yourself in nature at John Pennekamp Coral Reef State Park and then discover the deep blue sea with a scuba or snorkeling tour.

For reviews, photos, ratings, and tourist information, use the Key Largo travel route website.

Drive from Big Pine Key to Key Largo in 2 hours. Alternatively, you can take a bus. In June, daytime highs in Key Largo are 88°F, while nighttime lows are 75°F. Finish up your sightseeing early on the 27th (Mon) so you can catch the flight back home.
Wildlife · Parks · Outdoors · Tours
Side Trip

Florida Keys travel guide

Scuba & Snorkeling · Landmarks · Parasailing & Paragliding
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.