31 days in Florida Itinerary

31 days in Florida Itinerary

Created using Inspirock Florida trip planner

Make it your trip
Fly
1
Key West
— 3 nights
Drive
2
Marathon
— 3 nights
Drive
3
Islamorada
— 1 night
Drive
4
Key Largo
— 2 nights
Drive
5
Naples
— 4 nights
Drive
6
Sanibel Island
— 2 nights
Drive
7
Sarasota
— 4 nights
Drive
8
Orlando
— 5 nights
Drive
9
Daytona Beach
— 2 nights
Drive
10
St. Augustine
— 4 nights
Drive

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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.
You'll discover tucked-away gems like Saint Mary Star of the Sea and Kayaking & Canoeing. Family-friendly places like U.S. Coast Guard Cutter Ingham Maritime Museum and Key West Historic Seaport will thrill your kids. Spend the 2nd (Sat) exploring nature at Dry Tortugas National Park. Next up on the itinerary: steep yourself in history at Key West Garden Club, make a trip to US 1 Mile Marker 0, enjoy the sand and surf at Smathers Beach, and take in the architecture and atmosphere at St. Paul's Episcopal Church.

To see ratings, maps, and other tourist information, use the Key West trip itinerary builder tool.

Orlando to Key West is an approximately 4.5-hour flight. You can also drive; or take a bus. Traveling from Orlando in January, Key West is a bit warmer at night with lows of 66°F. Finish up your sightseeing early on the 4th (Mon) so you can go by car to Marathon.

Things to do in Key West

Parks · Historic Sites · Nature · Outdoors

Marathon

— 3 nights

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.
You'll discover tucked-away gems like Crane Point Museum & Nature Center and Blue Hole. Bring the kids along to Old Seven Mile Bridge and Florida Keys Aquarium Encounters. The adventure continues: relax and rejuvenate at some of the top local wellness centers, snap pictures at Seven Mile Bridge, identify plant and animal life at National Key Deer Refuge, and kick back and relax at Sombrero Beach.

Inspirock's itinerary builder makes planning a Marathon trip simple and quick.

You can drive from Key West to Marathon in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 77°F in January, and nighttime lows around 66°F. Finish your sightseeing early on the 7th (Thu) so you can drive to Islamorada.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trip

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 8th (Fri), enjoy the sand and surf at Anne's Beach, take in the dramatic natural features at Windley Key Fossil Reef Geological State Park, get close to the beloved marine mammals with Theater of the Sea, then take an in-depth tour of History of Diving Museum, and finally relax and rejuvenate at Island Flow Yoga.

To find maps, more things to do, other places to visit, and more tourist information, go to the Islamorada trip website.

Traveling by car from Marathon to Islamorada takes an hour. Alternatively, you can take a bus. In January, daily temperatures in Islamorada can reach 77°F, while at night they dip to 66°F. Finish your sightseeing early on the 8th (Fri) so you can drive to Key Largo.

Things to do in Islamorada

Wildlife · Outdoors · Parks · Tours

Key Largo

— 2 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.
Kick off your visit on the 9th (Sat): get close to the beloved marine mammals with a swim-with-the-dolphins experience, then get a dose of the wild on Capt. Sterling's Everglades Eco-Tours, then identify plant and animal life at Molasses Reef, and finally look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center. Here are some ideas for day two: look for gifts at Robert Is Here, stroll through Anhinga Trail, then identify plant and animal life at Everglades Alligator Farm, and finally take a tour of African Queen Canal Cruise.

To find ratings, maps, where to stay, and more tourist information, use the Key Largo travel route planning app.

Key Largo is very close to Islamorada. Traveling from Islamorada in January, you can expect nighttime temperatures to be slightly colder in Key Largo, with lows of 61°F. Finish your sightseeing early on the 10th (Sun) so you can drive to Naples.

Things to do in Key Largo

Wildlife · Outdoors · Parks · Tours

Side Trips

Naples

— 4 nights
Bring the kids along to Lakes Regional Park and South Marco Beach. Venture out of the city with trips to Fort Myers (Edison and Ford Winter Estates, Manatee Park, &more), Fort Myers Beach (Times Square & Lovers Key State Park) and Speed Boats Tours (in Everglades City).

For ratings, traveler tips, more things to do, and other tourist information, use the Naples trip planning site.

Traveling by car from Key Largo to Naples takes 3 hours. Alternatively, you can take a bus. January in Naples sees daily highs of 75°F and lows of 58°F at night. Finish your sightseeing early on the 14th (Thu) so you can drive to Sanibel Island.

Things to do in Naples

Parks · Outdoors · Wildlife · Beaches

Side Trips

Sanibel Island

— 2 nights
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
On the 15th (Fri), take a memorable tour with Tours, kick back and relax at Bowman's Beach, then identify plant and animal life at Sanibel Captiva Conservation Foundation, then kick back and relax at Captiva Beach, and finally contemplate in the serene atmosphere at Captiva Chapel By-The-Sea. Get ready for a full day of sightseeing on the next day: kick back and relax at Blind Pass Beach Park, then visit a coastal fixture at Sanibel Island Lighthouse, then cruise along Sanibel Causeway, and finally see the interesting displays at The Bailey-Matthews National Shell Museum.

For where to stay and other tourist information, use the Sanibel Island vacation builder tool.

Drive from Naples to Sanibel Island in 1.5 hours. In January in Sanibel Island, expect temperatures between 75°F during the day and 56°F at night. Cap off your sightseeing on the 16th (Sat) early enough to go by car to Sarasota.

Things to do in Sanibel Island

Outdoors · Parks · Beaches · Wildlife

Side Trip

Sarasota

— 4 nights
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. Attractions like Crescent Beach and Treasure Island Beach make great kid-friendly stops. You'll find plenty of places to visit near Sarasota: Tampa (Sunshine Skyway Bridge & Bayshore Boulevard), Saint Pete Beach (in St. Pete Beach) and Fort De Soto Park (in Tierra Verde). There's much more to do: stroll through Caspersen Beach, get to know the fascinating history of Marie Selby Botanical Gardens, identify plant and animal life at Myakka River State Park, and admire nature's wide array of creatures at Mote Marine Laboratory & Aquarium.

To find maps, ratings, more things to do, and tourist information, read our Sarasota trip itinerary planner.

You can drive from Sanibel Island to Sarasota in 2 hours. Alternatively, you can do a combination of taxi and bus. In January, daytime highs in Sarasota are 72°F, while nighttime lows are 53°F. Finish your sightseeing early on the 20th (Wed) to allow enough time to drive to Orlando.

Things to do in Sarasota

Parks · Outdoors · Beaches · Wildlife

Side Trips

Orlando

— 5 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.
Attractions like Harry P. Leu Gardens and Crystal River make great kid-friendly stops. Eschew the tourist crowds and head to Basilica of the National Shrine of Mary, Queen of the Universe and Kissimmee Lakefront Park. Explore Orlando's surroundings by going to Nature & Wildlife Tours (in Kissimmee), Three Sisters Springs (in Crystal River) and Ellie Schiller Homosassa Springs Wildlife State Park (in Homosassa Springs). And it doesn't end there: make an unforgettable trip to Avatar Flight of Passage, try out the rides at World of Disney, take in the waterfront at Disney's Boardwalk, and don't miss a visit to Cinderella Castle.

To see more things to do, reviews, other places to visit, and tourist information, go to the Orlando online trip maker.

Getting from Sarasota to Orlando by car takes about 2.5 hours. Other options: take a bus; or do a combination of bus and train. Expect a daytime high around 71°F in January, and nighttime lows around 52°F. Finish your sightseeing early on the 25th (Mon) so you can drive to Daytona Beach.

Things to do in Orlando

Theme Parks · Parks · Wildlife · Nature

Side Trips

Daytona Beach

— 2 nights

The World's Most Famous Beach

The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
Kick off your visit on the 26th (Tue): tour the pleasant surroundings at New Smyrna Town Beach, then see majestic marine mammals with a dolphin and whale watching tour, then kick back and relax at Ormond Beach, and finally kick back and relax at Beach at Daytona Beach. On the next day, immerse yourself in nature at Blue Spring State Park, admire the striking features of Stetson Mansion, bet on your favorite at Daytona International Speedway, then look for gifts at Angell & Phelps Chocolate Factory, and finally explore the galleries of Ponce de Leon Inlet Lighthouse & Museum.

To see photos, other places to visit, where to stay, and more tourist information, you can read our Daytona Beach trip maker website.

Getting from Orlando to Daytona Beach by car takes about an hour. Other options: take a bus. In January, daytime highs in Daytona Beach are 69°F, while nighttime lows are 50°F. Finish your sightseeing early on the 27th (Wed) to allow enough time to drive to St. Augustine.

Things to do in Daytona Beach

Parks · Outdoors · Beaches · Historic Sites

Side Trips

St. Augustine

— 4 nights
St. Bring the kids along to Washington Oaks Gardens State Park and Anastasia State Park. Explore hidden gems such as National Shrine of Our Lady of La Leche at Mission Nombre de Dios and The Oldest Store Museum. Change things up with these side-trips from St. Augustine: Fernandina Beach (Fort Clinch State Park & The Golf Club at North Hampton) and Jacksonville Zoo & Gardens (in Jacksonville). Next up on the itinerary: identify plant and animal life at St. Augustine Wild Reserve, deepen your understanding at Flagler College, make a trip to St. George Street, and admire the striking features of Old Jail.

For ratings, traveler tips, more things to do, and more tourist information, read St. Augustine day trip tool.

You can drive from Daytona Beach to St. Augustine in 1.5 hours. Another option is to take a bus. January in St. Augustine sees daily highs of 65°F and lows of 49°F at night. Wrap up your sightseeing on the 31st (Sun) to allow time to drive back home.

Things to do in St. Augustine

Parks · Historic Sites · Nature · 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.