30 days in Florida Itinerary

30 days in Florida Itinerary

Created using Inspirock Florida itinerary planner

Make it your trip
Fly
1
Sanibel Island
— 5 nights
Drive
2
Fort Myers Beach
— 5 nights
Drive
3
Marco Island
— 6 nights
Drive
4
Key Largo
— 3 nights
Drive
5
Key West
— 10 nights
Fly

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Sanibel Island

— 5 nights
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Sanibel Island is known for parks, beaches, and historic sites. Your trip includes some of its best attractions: stroll through J.N. "Ding" Darling National Wildlife Refuge, enjoy the sea views from Sanibel Island Lighthouse, soothe aching muscles at some of the top local wellness centers, and browse the fresh offerings at Sanibel Island Farmer's Market.

For photos, reviews, other places to visit, and tourist information, you can read our Sanibel Island trip app.

Chicago to Sanibel Island is an approximately 4.5-hour flight. You can also drive; or do a combination of bus, subway, and taxi. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Expect much hotter temperatures when traveling from Chicago in April; daily highs in Sanibel Island reach 87°F and lows reach 66°F. Wrap up your sightseeing on the 4th (Thu) early enough to drive to Fort Myers Beach.

Things to do in Sanibel Island

Outdoors · Parks · Beaches · Tours

Side Trip

Fort Myers Beach

— 5 nights
Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Explore Fort Myers Beach's surroundings by going to Barefoot Beach Preserve (in Bonita Springs), Naples (Delnor-Wiggins Pass State Park & Beer Tastings & Tours) and Fort Myers (Edison and Ford Winter Estates & Edison Park). Spend the 6th (Sat) spotting exotic species with Everglades Day Safari. And it doesn't end there: get up close to creatures of the deep with a dolphin and whale watching tour, immerse yourself in nature at Lovers Key State Park, relax and rejuvenate at some of the best spas, and take in the exciting artwork at Alliance for the Arts.

For photos, other places to visit, and tourist information, you can read our Fort Myers Beach road trip planning tool.

Fort Myers Beach is just a short distance from Sanibel Island. In May, daytime highs in Fort Myers Beach are 90°F, while nighttime lows are 69°F. Finish your sightseeing early on the 9th (Tue) to allow enough time to drive to Marco Island.

Things to do in Fort Myers Beach

Wildlife · Parks · Outdoors · Nature

Side Trips

Marco Island

— 6 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. Marco Island is known for adventure, wildlife, and beaches. Your trip includes some of its best attractions: identify plant and animal life at Wildlife Areas, enjoy the sand and surf at Keewaydin Island, tour the pleasant surroundings at Tigertail Beach, and head off the coast to Cape Romano.

To see where to stay, maps, reviews, and more tourist information, read our Marco Island travel route planner.

Traveling by car from Fort Myers Beach to Marco Island takes 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of taxi and bus. In May in Marco Island, expect temperatures between 88°F during the day and 69°F at night. Finish up your sightseeing early on the 15th (Mon) so you can go by car to Key Largo.

Things to do in Marco Island

Parks · Outdoors · Beaches · Wildlife

Key Largo

— 3 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.
Go for a jaunt from Key Largo to Grassy Key to see Dolphin Research Center about 56 minutes away. Next up on the itinerary: cast your line with a fishing tour, take a tour of African Queen Canal Cruise, indulge your thirst for a good beer at Islamorada Brewery & Distillery, and tour the pleasant surroundings at Florida Keys Wild Bird Rehabilitation Center.

To see where to stay, traveler tips, ratings, and more tourist information, go to the Key Largo online sightseeing planner.

Drive from Marco Island to Key Largo in 3 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of ferry and bus. In May, daytime highs in Key Largo are 85°F, while nighttime lows are 72°F. Cap off your sightseeing on the 18th (Thu) early enough to go by car to Key West.

Things to do in Key Largo

Wildlife · Parks · Tours · Outdoors

Side Trips

Key West

— 10 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.
You'll find plenty of places to visit near Key West: Marathon (The Turtle Hospital, Crane Point Museum & Nature Center, &more). There's still lots to do: examine the collection at The Ernest Hemingway Home and Museum, get a new perspective on things with Boat Tours & Water Sports, stroll through Key West Butterfly & Nature Conservatory, and stroll the grounds of Key West Cemetery.

To see traveler tips, maps, photos, and more tourist information, read our Key West holiday builder site.

Traveling by car from Key Largo to Key West takes 2.5 hours. Alternatively, you can take a bus. May in Key West sees daily highs of 85°F and lows of 77°F at night. You'll set off for home on the 28th (Sun).

Things to do in Key West

Museums · Parks · Historic Sites · Wildlife

Side Trip

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.