53 days in Florida Itinerary

53 days in Florida Itinerary

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Route & dates

53 days in Florida Itinerary

Start: Portland
+2
Bus + Foot + Fly:  7​h 45​min
1
Miami
— 6 nights
Drive:  1​h 15​min
2
Key Largo
— 6 nights
Drive:  45​min
3
Islamorada
— 6 nights
Drive:  45​min
4
Marathon, Florida Keys
— 6 nights
Bus:  1​h 15​min
5
Key West
— 7 nights
Ferry:  2​h 30​min
6
Marco Island
— 4 nights
Drive:  45​min
7
Naples
— 5 nights
Drive:  2​h 45​min
8
Tampa
— 5 nights
Drive:  1​h 30​min
9
Orlando
— 7 nights
Fly:  6​h
End: Portland

6
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Explore Miami's surroundings by going to Panther Ridge Conservation Center (in Wellington), Pondhawk Natural Area (in Boca Raton) and Everglades National Park (Osceola panthers, Shark Valley Visitor Center, & more). Spend the 12th (Sun) exploring nature at Everglades National Park. There's lots more to do: take in nature's colorful creations at Fairchild Tropical Botanic Garden, take a stroll through Lincoln Road, explore the world behind art at The Wolfsonian - Florida International University, and examine the collection at Lock & Load Museum.

For ratings, other places to visit, where to stay, and other tourist information, use the Miami journey planner.

Portland to Miami is an approximately 8-hour combination of bus and flight. You can also fly; or drive. Prepare for much hotter weather when traveling from Portland in January: high temperatures in Miami hover around 77°F and lows are around 63°F. Finish your sightseeing early on the 13th (Mon) to allow enough time to drive to Key Largo.

Things to do in Miami

Parks Outdoors Nature

Side Trips

Everglades National Park, Miami Beach, Pondhawk Natural Area, Panther Ridge Conservation Center, Fairchild Tropical Botanic Garden
Find places to stay Jan 7 — 13:
Highlights from your plan
Panther Ridge Conservation Center ©
Panther Ridge Conservation Center
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Fairchild Tropical Botanic Garden ©
Fairchild Tropical Botanic Garden

6
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.
Explore the numerous day-trip ideas around Key Largo: Anhinga Trail (in Everglades National Park) and Coffins Patch (in Key Colony Beach). There's still lots to do: look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, see what you can catch with a fishing tour, observe the fascinating underwater world at Island Dolphin Care, and have fun at Kiffney's Firearms and Indoor Range.

For more things to do, other places to visit, traveler tips, and other tourist information, go to the Key Largo online trip builder .

Traveling by car from Miami to Key Largo takes 1.5 hours. Alternatively, you can take a bus. January in Key Largo sees daily highs of 75°F and lows of 61°F at night. Wrap up your sightseeing on the 19th (Sun) to allow time to drive to Islamorada.

Things to do in Key Largo

Wildlife Outdoors Parks

Side Trips

Coffins Patch, Anhinga Trail
Find places to stay Jan 13 — 19:
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Anhinga Trail ©
Anhinga Trail

6
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
You'll find plenty of places to visit near Islamorada: Everglades National Park (Mrazek Pond & 99 Mile Wilderness Waterway). And it doesn't end there: take a tour by water with Boat Tours & Water Sports, contemplate the long history of Indian Key State Historic Site, head outdoors with Takedown Charters, and discover the deep blue sea with a scuba or snorkeling tour.

To find maps, reviews, and tourist information, refer to the Islamorada driving holiday app .

You can drive from Key Largo to Islamorada in an hour. Alternatively, you can do a combination of taxi and bus. January in Islamorada sees daily highs of 77°F and lows of 66°F at night. Finish your sightseeing early on the 25th (Sat) so you can drive to Marathon.

Things to do in Islamorada

Outdoors Tours Wildlife

Side Trip

Everglades National Park
Find places to stay Jan 19 — 25:
Highlights from your plan
Fishing Charters & Tours
99 Mile Wilderness Waterway ©
99 Mile Wilderness Waterway
Lignumvitae Key Botanical State Park ©

6
nights
Marathon, Florida Keys

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Explore the numerous day-trip ideas around Marathon: Big Pine Key (National Key Deer Refuge & Grimal Grove). There's lots more to do: kick back and relax at Bahia Honda State Park, snap pictures at Seven Mile Bridge, look for all kinds of wild species at Marathon Garden Club, and pause for some serene contemplation at San Pablo Catholic Church.

To find traveler tips, ratings, other places to visit, and more tourist information, read Marathon tour itinerary tool .

You can drive from Islamorada to Marathon in an hour. Another option is to take a bus. Expect a daytime high around 77°F in January, and nighttime lows around 66°F. Wrap up your sightseeing on the 31st (Fri) to allow time to take a bus to Key West.

Things to do in Marathon

Parks Wildlife Outdoors

Side Trips

Big Pine Key, Veterans Memorial Park
Find places to stay Jan 25 — 31:
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Crane Point Museum & Nature Center ©

7
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.
Spend the 3rd (Mon) exploring nature at Dry Tortugas National Park. And it doesn't end there: see the interesting displays at The Ernest Hemingway Home and Museum, contemplate the long history of Curry Mansion, look for all kinds of wild species at Wildlife Areas, and don't miss a visit to Duval Street.

For where to stay, traveler tips, maps, and tourist information, read our Key West online tour planner .

You can take a bus from Marathon to Key West in 1.5 hours. Another option is to drive. In January in Key West, expect temperatures between 76°F during the day and 66°F at night. Finish up your sightseeing early on the 7th (Fri) so you can catch the ferry to Marco Island.

Things to do in Key West

Outdoors Parks Tours
Find places to stay Jan 31 — Feb 7:
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
The Ernest Hemingway Home and Museum ©

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. You'll find plenty of places to visit near Marco Island: Kirby Storter Roadside Park (in Ochopee) and Speed Boats Tours (in Everglades City). There's much more to do: see majestic marine mammals with a dolphin and whale watching tour, walk around Frank E. Mackle Park, get some thrills out on the water with a waterskiing or jet-skiing adventure, and browse the fresh offerings at Marco Island Farmers Market-Wednesday- Mid November to Mid April.

To find reviews, traveler tips, where to stay, and tourist information, read our Marco Island trip builder website .

You can ride a ferry from Key West to Marco Island in 2.5 hours. Another option is to drive. Plan for little chillier nights when traveling from Key West in February since evenings lows in Marco Island dip to 59°F. Wrap up your sightseeing on the 11th (Tue) early enough to drive to Naples.

Things to do in Marco Island

Outdoors Tours Wildlife

Side Trips

Speed Boats Tours, Kirby Storter Roadside Park
Find places to stay Feb 7 — 11:
Highlights from your plan
Dolphin & Whale Watching
Waterskiing & Jetskiing
Stand-Up Paddleboarding

5
nights
Naples

Naples is a city in Collier County, Florida, United States. Explore Naples' surroundings by going to Captain Jack Boat Tours (in Matlacha), Sanibel Island (Sanibel Island Farmer's Market, J.N. "Ding" Darling National Wildlife Refuge, & more) and List Distillery (in Fort Myers). There's still lots to do: get a new perspective on things with Boat Tours & Water Sports, admire the natural beauty at Naples Botanical Garden, contemplate the long history of Naples Historical Society, and identify plant and animal life at Shy Wolf Sanctuary Education & Experience Center.

For photos, maps, reviews, and tourist information, you can read our Naples vacation website .

Traveling by car from Marco Island to Naples takes an hour. February in Naples sees daily highs of 78°F and lows of 60°F at night. Finish your sightseeing early on the 16th (Sun) so you can drive to Tampa.

Things to do in Naples

Wildlife Tours Outdoors

Side Trips

Sanibel Island, Captain Jack Boat Tours, List Distillery
Find places to stay Feb 11 — 16:
Highlights from your plan
Dolphin & Whale Watching
Revs Institute ©
Revs Institute
Captain Jack Boat Tours ©
Captain Jack Boat Tours

5
nights
Tampa

Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
Venture out of the city with trips to Sarasota (Ted Sperling Park, Sarasota National Cemetery, & more), St. Petersburg (Duncan McClellan Gallery & Imagine Museum) and Scuba & Snorkeling (in Crystal River). There's lots more to do: get in on the family fun at Busch Gardens Tampa Bay, enjoy some diversion at Tampa Bay Sporting Clays and Archery, explore the world behind art at The Dali Museum, and see what you can catch with a fishing tour.

To find traveler tips, ratings, reviews, and tourist information, you can read our Tampa tour planning site .

Traveling by car from Naples to Tampa takes 3 hours. Alternatively, you can take a bus. In February, daytime highs in Tampa are 74°F, while nighttime lows are 57°F. Wrap up your sightseeing on the 21st (Fri) early enough to drive to Orlando.

Things to do in Tampa

Outdoors Tours Wildlife

Side Trips

Sarasota, St. Petersburg, Scuba & Snorkeling, Murielle Winery, Tampa Bay Sporting Clays and Archery
Find places to stay Feb 16 — 21:
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay

7
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.
Have a day of magic on the 28th (Fri) at Epcot. There's much more to do: make an unforgettable trip to Walt Disney World Resort, test your team's savvy at The Escape Game Orlando, don't miss a visit to Disney’s Hollywood Studios, and find something for the whole family at Universal's Islands of Adventure.

To see ratings, other places to visit, more things to do, and other tourist information, read our Orlando vacation site .

Traveling by car from Tampa to Orlando takes 1.5 hours. Alternatively, you can take a bus; or take a train. In February, plan for daily highs up to 75°F, and evening lows to 56°F. Finish your sightseeing early on the 28th (Fri) so you can travel back home.

Things to do in Orlando

Theme Parks Parks Outdoors

Side Trip

Charles Hosmer Morse Museum of American Art
Find places to stay Feb 21 — 28:
Highlights from your plan
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Magic Kingdom Park ©
Magic Kingdom Park
SeaWorld ©
SeaWorld

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