39 days in Florida Itinerary

39 days in Florida Itinerary

Created using Inspirock Florida trip planner

Make it your trip
Fly
1
Key West
— 4 nights
Drive
2
Big Pine Key
— 3 nights
Drive
3
Islamorada
— 4 nights
Drive
4
Key Largo
— 4 nights
Drive
5
Miami
— 3 nights
Drive
6
Everglades National Park
— 4 nights
Unknown
7
Marco Island
— 2 nights
Drive
8
Sarasota
— 2 nights
Drive
9
Orlando
— 6 nights
Drive
10
St. Augustine
— 2 nights
Drive
11
Fort Walton Beach
— 4 nights
Fly

S M T W T F S
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3

Key West

— 4 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 wildlife, adventure, and museums. Your plan includes some of its best attractions: see the interesting displays at The Ernest Hemingway Home and Museum, don't miss a visit to Duval Street, take an in-depth tour of Key West Firehouse Museum, and look for all kinds of wild species at Key West Butterfly & Nature Conservatory.

To see reviews, traveler tips, ratings, and tourist information, you can read our Key West trip itinerary planner.

New York City to Key West is an approximately 5-hour flight. You can also drive; or take a bus. When traveling from New York City in May, plan for a bit warmer days and warmer nights in Key West: temperatures range from 85°F by day to 77°F at night. Wrap up your sightseeing on the 28th (Fri) to allow time to drive to Big Pine Key.

Things to do in Key West

Parks · Historic Sites · Museums · Outdoors

Big Pine Key

— 3 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. Take a break from Big Pine Key with a short trip to Key West Angling in Sugarloaf Key, about 40 minutes away. There's still lots to do: see what you can catch with a fishing tour, identify plant and animal life at National Key Deer Refuge, enjoy the sea views from American Shoal Lighthouse, and relax and rejuvenate at SpaTerre at Little Palm Island Resort.

To see more things to do, other places to visit, and tourist information, you can read our Big Pine Key vacation builder tool.

Drive from Key West to Big Pine Key in an hour. Alternatively, you can take a shuttle; or take a bus. May in Big Pine Key sees daily highs of 88°F and lows of 77°F at night. Finish your sightseeing early on the 31st (Mon) to allow enough time to drive to Islamorada.

Things to do in Big Pine Key

Outdoors · Wildlife · Parks · Tours

Side Trips

Islamorada

— 4 nights

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: Marathon (San Pablo Catholic Church, Sombrero Beach, &more). Next up on the itinerary: cast your line with a fishing tour, sample the tasty concoctions at Islamorada Brewery & Distillery, get outside with Contagious Charters, and look for gifts at Petals With Pizzazz.

To find out how to plan a trip to Islamorada, use our trip itinerary maker.

Drive from Big Pine Key to Islamorada in 1.5 hours. Alternatively, you can take a bus. In May, daytime highs in Islamorada are 88°F, while nighttime lows are 77°F. Finish your sightseeing early on the 4th (Fri) so you can drive to Key Largo.

Things to do in Islamorada

Outdoors · Wildlife · Tours · Parks

Side Trip

Key Largo

— 4 nights

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: see what you can catch with Florida Keys Flats Fishing, step aboard USCG Duane, stroll through Spiegel Grove, and get up close and personal with brilliant marine life at Island Dolphin Care.

To see photos, reviews, and more tourist information, you can read our Key Largo trip itinerary planner.

Key Largo is just a short distance from Islamorada. June in Key Largo sees daily highs of 88°F and lows of 75°F at night. Cap off your sightseeing on the 8th (Tue) early enough to go by car to Miami.

Things to do in Key Largo

Parks · Wildlife · Outdoors · Tours

Miami

— 3 nights

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.
Miami is known for shopping, museums, and zoos & aquariums. Your plan includes some of its best attractions: kick back and relax at South Beach, wander the streets of Lincoln Road, contemplate the long history of Freedom Tower at Miami Dade College, and get a new perspective on things with Boat Tours & Water Sports.

To see where to stay, traveler tips, maps, and tourist information, go to the Miami online vacation planner.

You can drive from Key Largo to Miami in 1.5 hours. Alternatively, you can take a bus. In June, daytime highs in Miami are 89°F, while nighttime lows are 77°F. Finish your sightseeing early on the 11th (Fri) so you can travel to Everglades National Park.

Things to do in Miami

Parks · Historic Sites · Tours · Neighborhoods

Side Trips

Everglades National Park

— 4 nights

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. Overflow from Lake Okeechobee into the Florida Bay formed these wetlands, which are home to manatees, American crocodiles, Florida panthers, and an array of wading birds, land birds, and birds of prey.
Everglades National Park is known for wildlife, trails, and nature. Your plan includes some of its best attractions: stroll through Shark Valley Visitor Center, hike along Old Ingraham Highway, contemplate the waterfront views at Slough Slog, and look for all kinds of wild species at Nine Mile Pond Canoe Trail.

For photos, maps, ratings, and tourist information, read Everglades National Park travel itinerary planner.

Explore your travel options from Miami to Everglades National Park with the Route module. In June, plan for daily highs up to 90°F, and evening lows to 79°F. Wrap up your sightseeing on the 15th (Tue) early enough to travel to Marco Island.

Things to do in Everglades National Park

Parks · Outdoors · Trails · Nature

Marco Island

— 2 nights
Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Start off your visit on the 16th (Wed): contemplate the waterfront views at Capri Paddlecraft Park, then catch all the local highlights with Reel Kind Fishing and Tours, and then look for gifts at Keep In Touch. On your second day here, enjoy the sand and surf at Tigertail Beach, then shop like a local with Clyde Butcher's Big Cypress Gallery, and then trek along Kirby Storter Roadside Park.

To find photos, reviews, where to stay, and more tourist information, go to the Marco Island day trip planning website.

The Route module can help you plan travel from Everglades National Park to Marco Island. Plan for a bit cooler nights when traveling from Everglades National Park in June since evenings lows in Marco Island dip to 74°F. Finish up your sightseeing early on the 17th (Thu) so you can go by car to Sarasota.

Things to do in Marco Island

Outdoors · Wildlife · Parks · Tours

Side Trip

Sarasota

— 2 nights
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. Kick off your visit on the 18th (Fri): get a tailor-made plan with Catherine's Florida Charters, sample the fine beverages at Siesta Key Rum, then stroll the grounds of Sarasota National Cemetery, and finally learn about wildlife with up-close encounters at The Cat Depot. Here are some ideas for day two: examine the collection at Duncan McClellan Gallery, admire the masterpieces at Imagine Museum, then enjoy the sand and surf at Siesta Beach, and finally immerse yourself in nature at Ted Sperling Park.

For other places to visit, traveler tips, photos, and more tourist information, read Sarasota trip planner.

You can drive from Marco Island to Sarasota in 2.5 hours. Another option is to do a combination of taxi and bus. In June, daytime highs in Sarasota are 89°F, while nighttime lows are 75°F. Wrap up your sightseeing on the 19th (Sat) early enough to drive to Orlando.

Things to do in Sarasota

Outdoors · Parks · Museums · Wildlife

Side Trips

Orlando

— 6 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.
Have a day of magic on the 20th (Sun) at Walt Disney World Resort. Pack the 22nd (Tue) with family-friendly diversions at Universal's Islands of Adventure. There's still lots to do: get in on the family fun at Universal Orlando Resort, look for gifts at Tharoo & Co, admire the masterpieces at Charles Hosmer Morse Museum of American Art, and cool off at Discovery Cove.

To find ratings, traveler tips, and more tourist information, use the Orlando tour itinerary planner.

Drive from Sarasota to Orlando in 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In June, plan for daily highs up to 91°F, and evening lows to 73°F. Finish your sightseeing early on the 25th (Fri) so you can drive to St. Augustine.

Things to do in Orlando

Theme Parks · Museums · Shopping

Side Trip

St. Augustine

— 2 nights
St. Kick off your visit on the 26th (Sat): take in the exciting artwork at High Tide Gallery Art & Gifts, then get interesting insight from Tours, then identify plant and animal life at St. Augustine Wild Reserve, and finally brush up on your knowledge of spirits at St. Augustine Distillery. On your second day here, look for all kinds of wild species at St. Augustine Alligator Farm Zoological Park, visit a coastal fixture at St. Augustine Lighthouse & Maritime Museum, Inc., and then step into the grandiose world of Castillo de San Marcos National Monument.

To see more things to do, photos, maps, and tourist information, use the St. Augustine road trip planning tool.

You can drive from Orlando to St. Augustine in 2 hours. Another option is to take a bus. In June, daily temperatures in St. Augustine can reach 88°F, while at night they dip to 73°F. Wrap up your sightseeing on the 27th (Sun) to allow time to fly to Fort Walton Beach.

Things to do in St. Augustine

Wildlife · Parks · Historic Sites · Outdoors

Fort Walton Beach

— 4 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. You'll find plenty of places to visit near Fort Walton Beach: Jolly Sailing and Dolphin Cruises (in Pensacola Beach), Panama City Beach (St. Andrews State Park, Panama City Beach Winery, &more) and Pensacola (Gulf Islands, Joe Patti's Seafood Company, &more). There's still lots to do: enjoy the sand and surf at Navarre Beach and step off the mainland to explore Santa Rosa Island.

For traveler tips, more things to do, ratings, and more tourist information, go to the Fort Walton Beach online trip itinerary maker.

You can fly from St. Augustine to Fort Walton Beach in 5.5 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from St. Augustine to Fort Walton Beach. In June, daytime highs in Fort Walton Beach are 86°F, while nighttime lows are 72°F. Wrap up your sightseeing on the 1st (Thu) early enough to fly back home.

Things to do in Fort Walton Beach

Parks · Outdoors · Beaches · Nature

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.