31 days in Florida Itinerary

31 days in Florida Itinerary

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Route & dates

31 days in Florida Itinerary

Start: Richmond
Fly:  5​h 45​min
1
Fort Walton Beach
— 3 nights
taxi + bus:  1​h 30​min
2
Panama City Beach
— 4 nights
Fly:  5​h 45​min
3
Sanibel Island
— 2 nights
Drive:  1​h 45​min
4
Marco Island
— 2 nights
ferry:  2​h 30​min
5
Key West
— 5 nights
bus:  45​min
6
Big Pine Key
— 1 night
Drive:  30​min
7
Marathon
— 3 nights
+2
shuttle + Fly + Drive:  6​h 15​min
8
St. Augustine
— 4 nights
Drive:  2​h
9
Orlando
— 6 nights
Fly:  4​h 30​min
End: Richmond

3
nights
Fort Walton Beach

Fort Walton Beach ©
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Family-friendly places like Navarre Beach and Air Force Armament Museum will thrill your kids. Step off the beaten path and head to Pensacola Beach and Henderson Beach State Park. And it doesn't end there: step off the mainland to explore Okaloosa Island, examine the collection at Garnier Post Office, take in the waterfront at Okaloosa Island Pier, and have some family-friendly fun at Escape Zone 60, Destin.

To find maps, photos, ratings, and more tourist information, use the Fort Walton Beach trip itinerary maker app .

Richmond to Fort Walton Beach is an approximately 6-hour flight. You can also do a combination of train and flight; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Richmond to Fort Walton Beach. Traveling from Richmond in September, you can expect nighttime temperatures to be somewhat warmer in Fort Walton Beach, with lows of 70°F. Wrap up your sightseeing on the 14th (Sat) to allow time to travel to Panama City Beach.

Things to do in Fort Walton Beach

Beaches Outdoors Parks

Side Trips

Destin, Pensacola Beach, Navarre Beach
Highlights from your plan
Pensacola Beach ©
Pensacola Beach
Navarre Beach ©
Navarre Beach
Henderson Beach State Park ©
Henderson Beach State Park

4
nights
Panama City Beach

Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.
Kids will enjoy Dolphin & Whale Watching and Swim with Dolphins. You'll explore the less-touristy side of things at Santa Rosa Beach and Fishing Charters & Tours. Explore the numerous day-trip ideas around Panama City Beach: Port Saint Joe (Cape San Blas & St. Joseph Peninsula State Park). Next up on the itinerary: kick back and relax at St. Andrews State Park, stroll through Panama City Beach, browse the different shops at Pier Park, and do a tasting at Panama City Beach Winery.

To find reviews, ratings, traveler tips, and tourist information, use the Panama City Beach trip planner .

Traveling by combination of taxi and bus from Fort Walton Beach to Panama City Beach takes 1.5 hours. Alternatively, you can drive. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In September, daytime highs in Panama City Beach are 89°F, while nighttime lows are 70°F. Finish up your sightseeing early on the 18th (Wed) so you can travel to Sanibel Island.

Things to do in Panama City Beach

Outdoors Beaches Parks

Side Trips

Port Saint Joe, Santa Rosa Beach, Panama City CENTER for the ARTS
Highlights from your plan
Dolphin & Whale Watching
Swim with Dolphins
St. Andrews State Park ©
St. Andrews State Park

2
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Kick off your visit on the 19th (Thu): examine the collection at The Bailey-Matthews National Shell Museum, enjoy the sand and surf at Captiva Beach, and then kick back and relax at Bowman's Beach. Get ready for a full day of sightseeing on the 20th (Fri): choose your vessel at Boat Rentals and then admire the natural beauty at Edison and Ford Winter Estates.

To see traveler tips, other places to visit, and more tourist information, refer to the Sanibel Island holiday planner .

Traveling by flight from Panama City Beach to Sanibel Island takes 6 hours. Alternatively, you can drive. In September, plan for daily highs up to 90°F, and evening lows to 74°F. Wrap up your sightseeing on the 20th (Fri) to allow time to drive to Marco Island.

Things to do in Sanibel Island

Outdoors Parks Beaches

Side Trips

Captiva Island, Edison and Ford Winter Estates
Highlights from your plan
Bowman's Beach ©
Bowman's Beach
Captiva Beach ©
Captiva Beach
Parasailing & Paragliding

2
nights
Marco Island

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. Kick off your visit on the 21st (Sat): zoom along the surf with a waterskiing or jet-skiing adventure, fly like a bird with a parasailing or paragliding tour, and then kick back and relax at South Marco Beach. Get ready for a full day of sightseeing on the 22nd (Sun): get up close to creatures of the deep with a dolphin and whale watching tour, stop by Keep In Touch, and then get some thrills on the water with a speed boat tour.

To see photos, other places to visit, where to stay, and more tourist information, read our Marco Island visit planner.

You can drive from Sanibel Island to Marco Island in 2 hours. Expect a daytime high around 89°F in September, and nighttime lows around 74°F. Wrap up your sightseeing on the 22nd (Sun) to allow time to ride a ferry to Key West.

Things to do in Marco Island

Outdoors Tours Wildlife

Side Trip

Speed Boats Tours
Highlights from your plan
Dolphin & Whale Watching
South Marco Beach ©
South Marco Beach
Waterskiing & Jetskiing

5
nights
Key West

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.
Attractions like Florida Keys Eco-Discovery Center and Mel Fisher Maritime Heritage Museum make great kid-friendly stops. You'll explore the less-touristy side of things at Dry Tortugas National Park and Dolphin & Whale Watching. The adventure continues: see the interesting displays at The Ernest Hemingway Home and Museum, take an in-depth tour of Truman Little White House, get up close and personal with brilliant marine life at Key West Aquarium, and see some colorful creatures with a scuba or snorkeling tour.

To see reviews, other places to visit, traveler tips, and other tourist information, read our Key West trip planner .

Getting from Marco Island to Key West by ferry takes about 2.5 hours. Other options: drive. Plan for a bit warmer nights when traveling from Marco Island in September since evenings lows in Key West dip to 80°F. Wrap up your sightseeing on the 27th (Fri) early enough to take a bus to Big Pine Key.

Things to do in Key West

Outdoors Tours Parks
Highlights from your plan
Dolphin & Whale Watching
Florida Keys Eco-Discovery Center ©
Florida Keys Eco-Discovery Center
Mel Fisher Maritime Heritage Museum ©

1
night
Big Pine Key

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. Kick off your visit on the 28th (Sat): look for all kinds of wild species at National Key Deer Refuge, then stop by Out of the Blue Gallery, and then admire the majestic nature at Bahia Honda State Park.

To find maps, other places to visit, ratings, and more tourist information, use the Big Pine Key trip planning tool .

Take a bus from Key West to Big Pine Key in an hour. Alternatively, you can drive. September in Big Pine Key sees daily highs of 90°F and lows of 79°F at night. Wrap up your sightseeing on the 28th (Sat) to allow time to drive to Marathon.

Things to do in Big Pine Key

Parks Beaches Outdoors
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Out of the Blue Gallery ©
Out of the Blue Gallery

3
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Discover out-of-the-way places like Dolphin Research Center and Fishing Charters & Tours. Bring the kids along to Swim with Dolphins and Parasailing & Paragliding. When in Marathon, make a side trip to see Florida Keys Wild Bird Rehabilitation Center in Tavernier, approximately 58 minutes away. Next up on the itinerary: look for all kinds of wild species at The Turtle Hospital, take in the views from Seven Mile Bridge, and stroll through Sombrero Beach.

To find traveler tips, where to stay, ratings, and tourist information, read our Marathon trip builder site .

Marathon is very close to Big Pine Key. Expect a daytime high around 90°F in September, and nighttime lows around 79°F. Wrap up your sightseeing on the 1st (Tue) to allow time to travel to St. Augustine.

Things to do in Marathon

Wildlife Tours Outdoors

Side Trips

Key Largo, Fishing Charters & Tours
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Swim with Dolphins

4
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Family-friendly places like St. Augustine Beach and Ormond Beach will thrill your kids. You'll discover tucked-away gems like Jacksonville Zoo & Gardens and St. Augustine Pirate & Treasure Museum. You'll find plenty of places to visit near St. Augustine: Fernandina Beach (Fort Clinch State Park & Marlin & Barrel Distillery). There's lots more to do: kick back and relax at Vilano Beach, identify plant and animal life at St. Augustine Wild Reserve, gain insight at Flagler College, and take in the spiritual surroundings of Cathedral Basilica of St. Augustine.

For ratings, traveler tips, photos, and more tourist information, go to the St. Augustine tour itinerary tool .

Getting from Marathon to St. Augustine by combination of shuttle, flight, and car takes about 6.5 hours. Other options: drive; or do a combination of shuttle, flight, and bus. Traveling from Marathon in October, expect St. Augustine to be a bit cooler, temps between 80°F and 67°F. Finish your sightseeing early on the 5th (Sat) so you can drive to Orlando.

Things to do in St. Augustine

Parks Beaches Outdoors

Side Trips

Amelia Island, Ormond Beach, Jacksonville Zoo & Gardens
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Jacksonville Zoo & Gardens ©
Jacksonville Zoo & Gardens
Vilano Beach ©
Vilano Beach

6
nights
Orlando

Orlando ©
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.
You'll visit kid-friendly attractions like Universal Orlando Resort and SeaWorld. Step off the beaten path and head to Avatar Flight of Passage and Fun Spot America Kissimmee. Next up on the itinerary: find something for the whole family at Walt Disney World Resort, laugh and play at Discovery Cove, don't miss a visit to Cinderella Castle, and discover the magic at Magic Kingdom Park.

To find maps, traveler tips, more things to do, and other tourist information, use the Orlando sightseeing app .

You can drive from St. Augustine to Orlando in 2 hours. Alternatively, you can take a bus. Expect a daytime high around 85°F in October, and nighttime lows around 69°F. Wrap up your sightseeing on the 11th (Fri) early enough to travel back home.

Things to do in Orlando

Theme Parks Beaches Outdoors

Side Trip

Fun Spot America Kissimmee
Highlights from your plan
Universal Orlando Resort ©
Universal Orlando Resort
Walt Disney World Resort ©
Walt Disney World Resort
Universal's Islands of Adventure ©

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