29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida journey planner

Plan created by another user. Make it yours
Fly
1
Key West
— 5 nights
Drive
2
Big Pine Key
— 3 nights
Drive
3
Islamorada
— 4 nights
Drive
4
Key Largo
— 3 nights
Bus
5
Everglades National Park
— 4 nights
Train
6
Miami
— 4 nights
Fly
7
Orlando
— 5 nights
Fly

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5
nights
Key West

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.
Spend the 16th (Sat) exploring nature at Dry Tortugas National Park. There's lots more to do: see the interesting displays at The Ernest Hemingway Home and Museum, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, steep yourself in history at Curry Mansion, and get a taste of the local shopping with Alan S. Maltz Gallery.

To see where to stay, reviews, maps, and tourist information, read Key West route maker.

Rochester to Key West is an approximately 7.5-hour flight. You can also drive; or do a combination of train and bus. Traveling from Rochester in January, expect Key West to be much hotter, temps between 76°F and 66°F. Wrap up your sightseeing on the 20th (Wed) early enough to drive to Big Pine Key.

Things to do in Key West

Parks · Historic Sites · Outdoors · Nature

3
nights
Big Pine Key

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. Big Pine Key is known for beaches, wildlife, and adventure. Your plan includes some of its best attractions: identify plant and animal life at National Key Deer Refuge, indulge in some personalized pampering at SpaTerre at Little Palm Island Resort, get interesting insight from Florida Keys Kayaks and Eco Tours, and enjoy the sea views from American Shoal Lighthouse.

To see where to stay, maps, reviews, and more tourist information, read Big Pine Key trip itinerary planner.

You can drive from Key West to Big Pine Key in an hour. Other options are to take a shuttle; or take a bus. Expect a daytime high around 77°F in January, and nighttime lows around 66°F. Finish your sightseeing early on the 23rd (Sat) to allow enough time to drive to Islamorada.

Things to do in Big Pine Key

Parks · Wildlife · Outdoors · Beaches

Side Trips

4
nights
Islamorada

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.
Change things up with these side-trips from Islamorada: Ultimate HeliTours (in Marathon Shores) and Marathon (Sombrero Beach, The Turtle Hospital, &more). The adventure continues: add some adventure to your tour with The Kayak Shack, get engrossed in the history at History of Diving Museum, see the interesting displays at Florida Keys History & Discovery Center, and sample the tasty concoctions at Islamorada Brewery & Distillery.

To find reviews, traveler tips, photos, and more tourist information, go to the Islamorada tour itinerary planner.

Traveling by car from Big Pine Key to Islamorada takes 1.5 hours. Alternatively, you can take a bus. In January, plan for daily highs up to 77°F, and evening lows to 66°F. Cap off your sightseeing on the 27th (Wed) early enough to go by car to Key Largo.

Things to do in Islamorada

Parks · Wildlife · Historic Sites · Museums

Side Trip

3
nights
Key Largo

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.
Key Largo is known for wildlife, nature, and adventure. Your plan includes some of its best attractions: look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, get the adrenaline pumping with Jetpack Water Flights, immerse yourself in nature at John Pennekamp Coral Reef State Park, and test your team's savvy at Kingdom Escape Games.

For where to stay, ratings, maps, and other tourist information, you can read our Key Largo trip itinerary planning site.

Key Largo is very close to Islamorada. Traveling from Islamorada in January, plan for slightly colder nights in Key Largo, with lows around 61°F. Finish your sightseeing early on the 30th (Sat) so you can take a bus to Everglades National Park.

Things to do in Key Largo

Parks · Outdoors · Tours · Wildlife

4
nights
Everglades National Park

Largest Subtropical Wilderness in the United States

A vast expanse of pristine wetlands, Everglades National Park holds the distinction of being the largest tropical wilderness in the U.S.
On the 2nd (Tue), spend an adventurous day with Florida Outdoor Adventures - Guided Everglades Kayak Tours. Next up on the itinerary: hike along Gumbo Limbo Trail, stroll through 99 Mile Wilderness Waterway, identify plant and animal life at Shark Valley Visitor Center, and explore the activities along Slough Slog.

To see more things to do, where to stay, and tourist information, refer to the Everglades National Park trip itinerary planning site.

You can take a bus from Key Largo to Everglades National Park in 2.5 hours. In January, daytime highs in Everglades National Park are 77°F, while nighttime lows are 66°F. Cap off your sightseeing on the 3rd (Wed) early enough to catch the train to Miami.

Things to do in Everglades National Park

Parks · Outdoors · Trails · Nature

4
nights
Miami

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Take a break from Miami with a short trip to West Palm Beach Food Tours in West Palm Beach, about 1h 20 min away. And it doesn't end there: admire the natural beauty at Fairchild Tropical Botanic Garden, see the interesting displays at Vizcaya Museum and Gardens, get the lay of the land with Art Deco Walks, and test your team's savvy at South Beach Room Escape.

For photos, traveler tips, other places to visit, and tourist information, go to the Miami trip builder app.

You can take a train from Everglades National Park to Miami in 2.5 hours. Alternatively, you can take a bus. February in Miami sees daily highs of 79°F and lows of 65°F at night. Wrap up your sightseeing on the 7th (Sun) early enough to travel to Orlando.

Things to do in Miami

Tours · Parks · Outdoors · Neighborhoods

Side Trips

5
nights
Orlando

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.
Have a day of magic on the 8th (Mon) at Walt Disney World Resort. Have a day of magic on the 12th (Fri) at Disney's Animal Kingdom. The adventure continues: get in on the family fun at Universal Orlando Resort, take in the architecture and atmosphere at St James Roman Catholic Cathedral, and admire the masterpieces at Charles Hosmer Morse Museum of American Art.

For where to stay, ratings, photos, and more tourist information, refer to the Orlando trip planner.

Getting from Miami to Orlando by flight takes about 3.5 hours. Other options: drive; or take a bus. Expect a bit cooler evenings in Orlando when traveling from Miami in February, with lows around 56°F. Finish your sightseeing early on the 12th (Fri) so you can travel back home.

Things to do in Orlando

Theme Parks · Museums · Historic Sites

Side Trip

Florida travel guide

4.3
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.