31 days in Florida Itinerary

31 days in Florida Itinerary

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Route & dates

31 days in Florida Itinerary

Start: New York City
bus + Fly:  4​h 45​min
1
Amelia Island
— 2 nights
Drive:  1​h 30​min
2
St. Augustine
— 5 nights
Drive:  2​h
3
Orlando
— 5 nights
Fly:  4​h 15​min
4
Key West
— 5 nights
bus:  1​h 15​min
5
Marathon
— 4 nights
Drive:  45​min
6
Islamorada
— 3 nights
Drive:  3​h 30​min
7
Marco Island
— 4 nights
Drive:  1​h 30​min
8
Sanibel Island
— 2 nights
Fly + bus:  5​h 45​min
End: New York City

2
nights
Amelia Island

Amelia Island ©
The southernmost Sea Island off the coast of Florida, Amelia Island takes its name from Princess Amelia of England.
On the 1st (Mon), examine the collection at Shrimping Museum and then tour the pleasant surroundings at Fort Clinch State Park. On the next day, have fun at Pirate Playground and then stroll through Main Beach.

To see maps, where to stay, photos, and more tourist information, refer to the Amelia Island holiday maker tool .

New York City to Amelia Island is an approximately 5-hour combination of flight and taxi. You can also do a combination of train, flight, and taxi; or drive. Plan for a bit warmer temperatures traveling from New York City in October, with highs in Amelia Island at 80°F and lows at 65°F. Finish your sightseeing early on the 3rd (Wed) to allow enough time to drive to St. Augustine.

Things to do in Amelia Island

Parks Outdoors Beaches
Highlights from your plan
Fort Clinch State Park ©
Fort Clinch State Park
Pirate Playground ©
Pirate Playground

5
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Popular historic sites such as Fort Matanzas National Monument and Ponce de Leon's Fountain of Youth Archaeological Park are in your itinerary. Step out of the city life by going to St. Augustine Beach and St. Augustine Alligator Farm Zoological Park. Step out of St. Augustine to go to Ormond Beach and see Ormond Beach, which is approximately 1h 15 min away. And it doesn't end there: kick back and relax at Crescent Beach, take in the history at Mission of Nombre de Dios, take in the exciting artwork at High Tide Gallery, and see the interesting displays at St. Augustine Pirate & Treasure Museum.

For reviews, maps, where to stay, and other tourist information, go to the St. Augustine trip maker website .

You can drive from Amelia Island to St. Augustine in 1.5 hours. Alternatively, you can do a combination of taxi and bus. In October, daytime highs in St. Augustine are 80°F, while nighttime lows are 65°F. Wrap up your sightseeing on the 8th (Mon) early enough to drive to Orlando.

Things to do in St. Augustine

Parks Historic Sites Outdoors

Side Trips

Ormond Beach, Crescent Beach Public Beach
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Fort Matanzas National Monument ©
Fort Matanzas National Monument
Ormond Beach ©
Ormond Beach

5
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.
Get outdoors at Stand-Up Paddleboarding and Ponce Preserve. Bring the kids along to Walt Disney World Resort and SeaWorld Orlando. Take a break from Orlando with a short trip to Beach at Daytona Beach in Daytona Beach, about 1h 25 min away. Pack the 12th (Fri) with family-friendly diversions at Universal's Islands of Adventure. There's more to do: discover the magic at Happily Ever After Fireworks.

To find ratings, where to stay, traveler tips, and other tourist information, use the Orlando day trip tool .

You can drive from St. Augustine to Orlando in 2 hours. Another option is to take a bus. Expect a daytime high around 85°F in October, and nighttime lows around 68°F. Wrap up your sightseeing on the 13th (Sat) to allow time to travel to Key West.

Things to do in Orlando

Theme Parks Outdoors Parks

Side Trips

Beach at Daytona Beach, Stand-Up Paddleboarding, Ponce Preserve
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Beach at Daytona Beach ©
Beach at Daytona Beach
Universal's Islands of Adventure ©
Universal's Islands of Adventure

5
nights
Key West

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 Dolphin & Whale Watching and Key West Butterfly & Nature Conservatory make great kid-friendly stops. Your cultural itinerary includes sights like Key West Lighthouse and Keeper's Quarters Museum and The Basilica School of Saint Mary Star of the Sea. Spend the 14th (Sun) exploring nature at Dry Tortugas National Park. There's still lots to do: get a new perspective on things with Boat Tours & Water Sports, see the interesting displays at Mel Fisher Maritime Museum, discover the deep blue sea with a scuba or snorkeling tour, and get interesting insight from Tours.

For photos, reviews, traveler tips, and tourist information, read Key West day trip app .

You can fly from Orlando to Key West in 4.5 hours. Other options are to do a combination of train and flight; or drive. Traveling from Orlando in October, expect somewhat warmer with lows of 77°F in Key West. Cap off your sightseeing on the 18th (Thu) early enough to go by car to Marathon.

Things to do in Key West

Outdoors Tours Wildlife
Highlights from your plan
Dry Tortugas National Park ©
Dry Tortugas National Park
Dolphin & Whale Watching
Stand-Up Paddleboarding

4
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.
Your itinerary includes some good beach time at Sombrero Beach and Bahia Honda State Park. Explore hidden gems such as Dolphin Research Center and All Aboard Boat Rentals. There's much more to do: look for all kinds of wild species at The Turtle Hospital, take a memorable tour with Tours, get a new perspective on things with Boat Tours & Water Sports, and take in the views from Seven Mile Bridge.

To see more things to do, other places to visit, where to stay, and more tourist information, read our Marathon trip itinerary site .

Traveling by car from Key West to Marathon takes 1.5 hours. Alternatively, you can take a bus. In October, daily temperatures in Marathon can reach 86°F, while at night they dip to 76°F. Finish your sightseeing early on the 22nd (Mon) to allow enough time to drive to Islamorada.

Things to do in Marathon

Outdoors Wildlife Tours

Side Trip

Bahia Honda State Park
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
The Turtle Hospital ©
The Turtle Hospital
Dolphin Research Center ©
Dolphin Research Center

3
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Take a break from the city and head to Robbie's of Islamorada and Molasses Reef. Eschew the tourist crowds and head to Florida Keys Wild Bird Rehabilitation Center and A Lil' Tail Charters. And it doesn't end there: see the vivid underwater world at Spiegel Grove, indulge your thirst for a good beer at Islamorada Beer Company Brewery and Tasting Room, get a taste of the local shopping with Old Road Gallery, and tour the pleasant surroundings at Anne's Beach.

For where to stay, traveler tips, more things to do, and other tourist information, use the Islamorada day trip app .

You can drive from Marathon to Islamorada in an hour. Other options are to take a shuttle; or take a bus. October in Islamorada sees daily highs of 86°F and lows of 76°F at night. Finish your sightseeing early on the 25th (Thu) so you can drive to Marco Island.

Things to do in Islamorada

Wildlife Outdoors Parks

Side Trip

Key Largo
Highlights from your plan
Molasses Reef ©
Molasses Reef
Spiegel Grove ©
Spiegel Grove

4
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. Step off the beaten path and head to Waterskiing & Jetskiing and Nature & Wildlife Tours. Visiting Parasailing & Paragliding and Dolphin & Whale Watching will get you outdoors. Explore the numerous day-trip ideas around Marco Island: Big Cypress National Preserve (in Ochopee), Speed Boats Tours (in Everglades City) and Lowdermilk Beach (in Naples). It doesn't end there: stop by Island Trends.

For photos, traveler tips, more things to do, and other tourist information, you can read our Marco Island trip builder .

Drive from Islamorada to Marco Island in 3.5 hours. Alternatively, you can do a combination of shuttle, flight, and taxi; or do a combination of bus, flight, and taxi. Traveling from Islamorada in October, expect a bit cooler with lows of 71°F in Marco Island. Finish your sightseeing early on the 29th (Mon) so you can drive to Sanibel Island.

Things to do in Marco Island

Outdoors Tours Wildlife

Side Trips

Everglades City, Lowdermilk Beach, Big Cypress National Preserve
Highlights from your plan
Dolphin & Whale Watching
Speed Boats Tours
Waterskiing & Jetskiing

2
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Escape the urban bustle at Bowman's Beach and Fort Myers Beach. Step off the beaten path and head to Captiva Beach and Sanibel Island Lighthouse.

To see photos, more things to do, reviews, and other tourist information, go to the Sanibel Island trip maker .

You can drive from Marco Island to Sanibel Island in 1.5 hours. In October, daytime highs in Sanibel Island are 86°F, while nighttime lows are 69°F. Finish up your sightseeing early on the 31st (Wed) so you can travel back home.

Things to do in Sanibel Island

Parks Outdoors Beaches

Side Trips

Captiva Beach, Fort Myers Beach
Highlights from your plan
Bowman's Beach ©
Bowman's Beach
Captiva Beach ©
Captiva Beach
Fort Myers Beach ©
Fort Myers Beach

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