31 days in Florida Itinerary

31 days in Florida Itinerary

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Route & dates

31 days in Florida Itinerary

Start: Philadelphia
Fly:  4​h 45​min
1
Key West
— 5 nights
bus:  1​h 15​min
2
Marathon
— 4 nights
Drive:  45​min
3
Islamorada
— 4 nights
Drive:  45​min
4
Key Largo
— 3 nights
Drive:  1​h 30​min
5
Miami Beach
— 4 nights
Drive:  2​h 15​min
6
Naples
— 4 nights
Drive:  3​h 45​min
7
Orlando
— 6 nights
Fly:  4​h 45​min
End: Philadelphia

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.
Spend the 22nd (Fri) exploring nature at Dry Tortugas National Park. There's still lots to do: examine the collection at The Ernest Hemingway Home and Museum, steep yourself in history at Truman Little White House, glide through the air with a parasailing or paragliding tour, and get a new perspective on things with Boat Tours & Water Sports.

To find other places to visit, ratings, and tourist information, read Key West trip builder website .

Philadelphia to Key West is an approximately 5-hour flight. You can also do a combination of train and flight; or drive. Traveling from Philadelphia in November, things will get much warmer in Key West: highs are around 81°F and lows about 73°F. Finish your sightseeing early on the 25th (Mon) to allow enough time to take a bus to Marathon.

Things to do in Key West

Tours Outdoors Parks
Highlights from your plan
Dolphin & Whale Watching
The Ernest Hemingway Home and Museum ©

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.
Change things up with these side-trips from Marathon: Big Pine Key (National Key Deer Refuge, Artists in Paradise Gallery, & more). There's much more to do: immerse yourself in nature at Bahia Honda State Park, pause for some serene contemplation at San Pablo Catholic Church, kick back and relax at Sombrero Beach, and relax and rejuvenate at some of the top local wellness centers.

To see reviews, photos, other places to visit, and tourist information, you can read our Marathon itinerary planner.

Traveling by bus from Key West to Marathon takes 1.5 hours. Alternatively, you can drive. In November, daily temperatures in Marathon can reach 82°F, while at night they dip to 72°F. Wrap up your sightseeing on the 29th (Fri) to allow time to drive to Islamorada.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trip

Big Pine Key
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Gemini Dream Charters ©
Gemini Dream Charters

4
nights
Islamorada

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: Everglades National Park (Nine Mile Pond Canoe Trail & Mrazek Pond). And it doesn't end there: get a new perspective on things with Boat Tours & Water Sports, sample the tasty concoctions at Florida Keys Brewing Company, look for gifts at Bella Sol Fragrance Bar and Gifts, and get outside with A Lil' Tail Charters.

To find more things to do, traveler tips, maps, and more tourist information, read our Islamorada travel route planner.

You can drive from Marathon to Islamorada in an hour. Alternatively, you can take a bus. November in Islamorada sees daily highs of 82°F and lows of 72°F at night. Wrap up your sightseeing on the 3rd (Tue) to allow time to drive to Key Largo.

Things to do in Islamorada

Outdoors Parks Wildlife

Side Trip

Everglades National Park
Highlights from your plan
Fishing Charters & Tours
Mrazek Pond ©
Mrazek Pond
Lignumvitae Key Botanical State Park ©

3
nights
Key Largo

Key Largo ©
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.
Venture out of the city with trips to Anhinga Trail (in Everglades National Park) and Homestead Miami Speedway (in Homestead). And it doesn't end there: look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, immerse yourself in nature at John Pennekamp Coral Reef State Park, enjoy some diversion at Kiffney's Firearms and Indoor Range, and get interesting insight from Tours.

For other places to visit, photos, ratings, and tourist information, read our Key Largo day trip planning website .

Traveling by car from Islamorada to Key Largo takes an hour. Alternatively, you can do a combination of bus and taxi. Traveling from Islamorada in December, expect a bit cooler with lows of 66°F in Key Largo. Wrap up your sightseeing on the 6th (Fri) to allow time to drive to Miami Beach.

Things to do in Key Largo

Parks Wildlife Outdoors

Side Trips

Anhinga Trail, Homestead Miami Speedway
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Spiegel Grove ©
Spiegel Grove

4
nights
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Explore Miami Beach's surroundings by going to Fairchild Tropical Botanic Garden (in Coral Gables) and Everglades National Park (Shark Valley Visitor Center, Gumbo Limbo Trail, & more). Next up on the itinerary: stroll through South Beach, enjoy some diversion at Lock & Load Miami, get to know the fascinating history of Art Deco Historic District, and explore the world behind art at Lowe Art Museum.

To find other places to visit, maps, reviews, and other tourist information, you can read our Miami Beach tour planner .

You can drive from Key Largo to Miami Beach in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 81°F in December, and nighttime lows around 68°F. Finish up your sightseeing early on the 10th (Tue) so you can go by car to Naples.

Things to do in Miami Beach

Parks Outdoors Nature

Side Trips

Miami, Coral Gables, Everglades National Park
Highlights from your plan
Lock & Load Museum ©
Lock & Load Museum
Shark Valley Visitor Center ©
Shark Valley Visitor Center
South Beach ©
South Beach

4
nights
Naples

Naples is a city in Collier County, Florida, United States. Explore the numerous day-trip ideas around Naples: Marco Island (Parasailing & Paragliding & Waterskiing & Jetskiing) and Sanibel Public Library (in Sanibel Island). And it doesn't end there: cast your line with a fishing tour, see majestic marine mammals with a dolphin and whale watching tour, see the interesting displays at Revs Institute, and take in nature's colorful creations at Naples Botanical Garden.

To find other places to visit, traveler tips, ratings, and other tourist information, go to the Naples day trip planning app .

Traveling by car from Miami Beach to Naples takes 2.5 hours. Alternatively, you can take a bus. Traveling from Miami Beach in December, plan for a bit cooler nights in Naples, with lows around 63°F. Finish your sightseeing early on the 14th (Sat) so you can drive to Orlando.

Things to do in Naples

Tours Outdoors Wildlife

Side Trips

Marco Island, Sanibel Public Library, Shy Wolf Sanctuary Education & Experience Center
Highlights from your plan
Fishing Charters & Tours
Dolphin & Whale Watching
Waterskiing & Jetskiing

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.
Orlando is known for theme parks, nightlife, fun & games, shopping, and museums. Your plan includes some of its best attractions: discover the magic at Walt Disney World Resort, find something for the whole family at Discovery Cove, take in nature's colorful creations at Harry P. Leu Gardens, and take in a show at Happily Ever After Fireworks.

To find maps, ratings, more things to do, and other tourist information, you can read our Orlando travel itinerary planner.

You can drive from Naples to Orlando in 4 hours. Alternatively, you can take a bus; or do a combination of bus and flight. Expect a daytime high around 77°F in December, and nighttime lows around 59°F. Finish your sightseeing early on the 20th (Fri) so you can travel back home.

Things to do in Orlando

Theme Parks Parks Beaches

Side Trips

Charles Hosmer Morse Museum of American Art, Resurrection Catholic Church
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

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