11 days in Florida Itinerary

11 days in Florida Itinerary

Created using Inspirock Florida holiday maker

Make it your trip
Fly
1
Key West
— 3 nights
Drive
2
Big Pine Key
— 1 night
Drive
3
Islamorada
— 1 night
Drive
4
Key Largo
— 1 night
Fly
5
Orlando
— 4 nights
Fly

S M T W T F S
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Key West

— 3 nights

Conch Republic

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.
Key West is known for museums, adventure, and wildlife. Your plan includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, browse the exhibits of Truman Little White House, stroll through Key West Butterfly & Nature Conservatory, and make a trip to Southernmost Point.

For photos, reviews, more things to do, and tourist information, read our Key West vacation maker app.

Washington to Key West is an approximately 6-hour flight. When traveling from Washington in May, plan for a bit warmer days and much hotter nights in Key West: temperatures range from 85°F by day to 77°F at night. Finish up your sightseeing early on the 24th (Mon) so you can go by car to Big Pine Key.

Things to do in Key West

Wildlife · Parks · Museums · Tours

Big Pine Key

— 1 night
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. Kick off your visit on the 25th (Tue): enjoy the sand and surf at Bahia Honda State Park and then see what you can catch with a fishing tour.

For maps, where to stay, reviews, and more tourist information, read Big Pine Key travel planner.

Getting from Key West to Big Pine Key by car takes about an hour. Other options: take a shuttle; or take a bus. Expect a daytime high around 88°F in May, and nighttime lows around 77°F. Cap off your sightseeing on the 25th (Tue) early enough to go by car to Islamorada.

Things to do in Big Pine Key

Outdoors · Wildlife · Tours · Parks

Islamorada

— 1 night

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 26th (Wed), take an in-depth tour of History of Diving Museum, then indulge your thirst for a good beer at Islamorada Brewery & Distillery, then head outdoors with Outdoor Activities, and finally sample the tasty concoctions at Florida Keys Brewing Company.

To see maps, more things to do, photos, and more tourist information, go to the Islamorada driving holiday planner.

You can drive from Big Pine Key to Islamorada in 1.5 hours. Alternatively, you can take a bus. In May, plan for daily highs up to 88°F, and evening lows to 77°F. Finish your sightseeing early on the 26th (Wed) so you can drive to Key Largo.

Things to do in Islamorada

Breweries & Distilleries · Wildlife · Tours · Outdoors

Key Largo

— 1 night

Diving Capital of the World

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.
Kick off your visit on the 27th (Thu): meet the residents at Island Dolphin Care, then see what you can catch with Florida Keys Flats Fishing, and then stroll through Spiegel Grove.

For other places to visit, reviews, traveler tips, and more tourist information, read our Key Largo trip planner.

Key Largo is just a stone's throw from Islamorada. Traveling from Islamorada in May, Key Largo is a bit cooler at night with lows of 72°F. Finish your sightseeing early on the 27th (Thu) to allow enough time to fly to Orlando.

Things to do in Key Largo

Wildlife · Parks · Tours · Outdoors

Orlando

— 4 nights

Theme Park Capital of the World

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Explore Orlando's surroundings by going to Amy Sellers Art Gallery (in Mount Dora) and Blue Heron River Tours Inc (in DeLand). Have a day of magic on the 29th (Sat) at Walt Disney World Resort. Pack the 30th (Sun) with family-friendly diversions at Universal Orlando Resort. There's more to do: get in on the family fun at SeaWorld and admire the masterpieces at Charles Hosmer Morse Museum of American Art.

Discover how to plan a Orlando trip in just a few steps with Inspirock's itinerary builder.

You can fly from Key Largo to Orlando in 3 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 88°F in May, and nighttime lows around 69°F. Wrap up your sightseeing on the 31st (Mon) to allow time to travel back home.

Things to do in Orlando

Theme Parks · Wildlife · Tours · Outdoors

Side Trips

Florida travel guide

4.4
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.