16 days in Florida Itinerary

16 days in Florida Itinerary

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Route & dates

16 days in Florida Itinerary

Start: Perugia
+2
train + tram + Fly:  17​h 45​min
1
Orlando
— 1 night
Fly:  4​h 15​min
2
Key West
— 3 nights
bus:  45​min
3
Big Pine Key
— 2 nights
Drive:  30​min
4
Marathon
— 2 nights
Drive:  1​h 30​min
5
Key Largo
— 2 nights
Drive:  1​h 30​min
6
Miami Beach
— 3 nights
Fly + train:  22​h 30​min
End: Perugia

1
night
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.
Kick off your visit on the 5th (Sun): find something for the whole family at Discovery Cove. Here are some ideas for day two: make an unforgettable trip to Walt Disney World Resort.

To see photos, where to stay, ratings, and tourist information, read our Orlando vacation planner .

Perugia, Italy to Orlando is an approximately 18-hour flight. You'll gain 6 hours traveling from Perugia to Orlando due to the time zone difference. In May, Orlando is somewhat warmer than Perugia - with highs of 36°C and lows of 24°C. Finish your sightseeing early on the 6th (Mon) to allow enough time to travel to Key West.

Things to do in Orlando

Theme Parks Beaches Parks
Highlights from your plan
Discovery Cove ©
Discovery Cove
Walt Disney World Resort ©
Walt Disney World Resort

3
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.
Visit Truman Little White House and Curry Mansion for their historical value. Step out of the city life by going to Fort Zachary Taylor and Audubon House & Tropical Gardens. There's much more to do: see the interesting displays at The Ernest Hemingway Home and Museum, explore the different monuments and memorials at Key West Cemetery, visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum, and take in the architecture and atmosphere at Saint Mary Star of the Sea.

For ratings, reviews, traveler tips, and other tourist information, go to the Key West tour planner.

Traveling by flight from Orlando to Key West takes 4.5 hours. Alternatively, you can drive; or take a bus. Expect somewhat warmer evenings in Key West when traveling from Orlando in May, with lows around 29°C. Finish your sightseeing early on the 9th (Thu) so you can take a bus to Big Pine Key.

Things to do in Key West

Historic Sites Outdoors Tours
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Fishing Charters & Tours

2
nights
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 10th (Fri): view the masterpieces at Artists in Paradise Gallery, then take a tour by water with Boat Tours & Water Sports, and then admire the majestic nature at Bahia Honda State Park. Get ready for a full day of sightseeing on the 11th (Sat): identify plant and animal life at National Key Deer Refuge and then get interesting insight from Tours.

For photos, other places to visit, more things to do, and other tourist information, read our Big Pine Key sightseeing app .

Getting from Key West to Big Pine Key by bus takes about an hour. Other options: drive. In May in Big Pine Key, expect temperatures between 36°C during the day and 29°C at night. Wrap up your sightseeing on the 11th (Sat) to allow time to take a bus to Marathon.

Things to do in Big Pine Key

Outdoors Wildlife Parks
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Fishing Charters & Tours

2
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.
On the 12th (Sun), kick back and relax at Anne's Beach, get interesting insight from Tours, then contemplate the long history of Indian Key State Historic Site, and finally pause for some serene contemplation at San Pablo Catholic Church. On your second day here, enjoy the sand and surf at Sombrero Beach, identify plant and animal life at Crane Point Museum & Nature Center, then identify plant and animal life at The Turtle Hospital, and finally get all the information you need at Pigeon Key Foundation.

For maps, photos, where to stay, and more tourist information, use the Marathon route planner.

Marathon is very close to Big Pine Key. May in Marathon sees daily highs of 36°C and lows of 29°C at night. Finish your sightseeing early on the 13th (Mon) to allow enough time to drive to Key Largo.

Things to do in Marathon

Parks Historic Sites Outdoors

Side Trip

Islamorada
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
The Turtle Hospital ©
The Turtle Hospital
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center

2
nights
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.
Start off your visit on the 14th (Tue): look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, then see what you can catch with a fishing tour, then indulge your thirst for a good beer at Islamorada Beer Company Brewery and Tasting Room, and finally pause for some serene contemplation at Key Largo Baptist Church. Get ready for a full day of sightseeing on the 15th (Wed): get interesting insight from Tours and then identify plant and animal life at Anhinga Trail.

To find ratings, maps, where to stay, and more tourist information, go to the Key Largo vacation planning site .

Drive from Marathon to Key Largo in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. Plan for a bit cooler nights when traveling from Marathon in May since evenings lows in Key Largo dip to 26°C. Finish your sightseeing early on the 15th (Wed) so you can drive to Miami Beach.

Things to do in Key Largo

Wildlife Outdoors Tours

Side Trips

Islamorada, Anhinga Trail
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling

3
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.
Lincoln Road and Art Deco Historic District will appeal to history buffs. Take a break from the city and head to Shark Valley and Espanola Way. Next up on the itinerary: tour the pleasant surroundings at South Beach, see the interesting displays at Vizcaya Museum and Gardens, pause for some serene contemplation at St. Raymond Catholic Church, and take in the local highlights with Art Deco Tours.

To find where to stay, traveler tips, and tourist information, read Miami Beach route planner .

You can drive from Key Largo to Miami Beach in 1.5 hours. Alternatively, you can take a bus. In May, plan for daily highs up to 36°C, and evening lows to 27°C. Finish your sightseeing early on the 18th (Sat) to allow enough time to travel back home.

Things to do in Miami Beach

Parks Neighborhoods Historic Sites

Side Trips

Miami, Shark Valley Visitor Center, St. Raymond Catholic Church
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
South Beach ©
South Beach
Art Deco Historic District ©
Art Deco Historic District

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