4 days in Florida Itinerary

4 days in Florida Itinerary

Created using Inspirock Florida travel route planner

Make it your trip
Fly
1
Key West
— 1 day
Drive
2
Marathon
— 1 night
Bus to Key West, Fly to Orlando
3
Orlando
— 1 night
Drive
4
St. Augustine
— 1 night
Fly

S M T W T F S
16
17
18
19
20
21
22

Key West

— 1 day

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.
Start off your visit on the 17th (Mon): look for gifts at We Cycle, contemplate the long history of Key West Garden Club, then visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum, then stroll the grounds of Key West Cemetery, and finally relax and rejuvenate at some of the best spas.

To find more things to do, ratings, other places to visit, and more tourist information, you can read our Key West holiday planner.

New York City to Key West is an approximately 5-hour flight. You can also drive; or take a bus. Expect a bit warmer weather when traveling from New York City in May: highs in Key West hover around 85°F, while lows dip to 77°F. Finish your sightseeing early on the 17th (Mon) so you can drive to Marathon.

Things to do in Key West

Spas · Shopping · Historic Sites · Parks

Marathon

— 1 night

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Kick off your visit on the 18th (Tue): stroll through Sombrero Beach, then stroll through The Turtle Hospital, and then enjoy the sand and surf at Bahia Honda State Park.

For photos, reviews, traveler tips, and other tourist information, use the Marathon trip website.

Getting from Key West to Marathon by car takes about 1.5 hours. Other options: take a bus. In May in Marathon, expect temperatures between 88°F during the day and 77°F at night. Finish your sightseeing early on the 18th (Tue) so you can travel to Orlando.

Things to do in Marathon

Parks · Beaches · Outdoors · Wildlife

Side Trip

Orlando

— 1 night

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.
Start off your visit on the 19th (Wed): get some fabulous bargains at Orlando Vineland Premium Outlets, look for gifts at World of Disney, and then buy something for everyone on your list at The Florida Mall.

To find ratings, maps, traveler tips, and other tourist information, go to the Orlando trip itinerary maker site.

You can do a combination of bus and flight from Marathon to Orlando in 4.5 hours. Other options are to drive; or take a bus. Plan for little chillier nights when traveling from Marathon in May since evenings lows in Orlando dip to 69°F. Finish up your sightseeing early on the 19th (Wed) so you can go by car to St. Augustine.

Things to do in Orlando

Shopping · Theme Parks

St. Augustine

— 1 night
St. Kick off your visit on the 20th (Thu): deepen your understanding at Flagler College, then stop by Whetstone Chocolates Tasting Tour, then do a tasting at San Sebastian Winery, and finally enjoy the sand and surf at St. Augustine Beach.

For other places to visit, maps, ratings, and other tourist information, use the St. Augustine day trip planner.

Getting from Orlando to St. Augustine by car takes about 2 hours. Other options: take a bus. Traveling from Orlando in May, expect nights in St. Augustine to be about the same, around 67°F, while days are slightly colder, around 83°F. Finish your sightseeing early on the 20th (Thu) to allow enough time to fly back home.

Things to do in St. Augustine

Parks · Beaches · Wineries · Outdoors

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.