21 days in Florida & New York City Itinerary

21 days in Florida & New York City Itinerary

Created using Inspirock United States travel planner

Plan created by another user. Make it yours

Route & dates

1
Orlando
— 6 nights
2
New York City
— 2 nights
3
Miami Beach
— 4 nights
4
Big Pine Key
— 3 nights
5
Key West
— 4 nights

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.
Shop till you drop at The Mall at Millenia and The Artistic Hand Gallery & Studio. Appreciate the collections at Charles Hosmer Morse Museum of American Art and Timothy's Gallery. You'll find plenty of places to visit near Orlando: NASA Kennedy Space Center Visitor Complex (in Merritt Island) and Stetson Mansion (in DeLand). Next up on the itinerary: make an unforgettable trip to Walt Disney World Resort, have some family-friendly fun at The Escape Game Orlando, find something for the whole family at Universal Orlando Resort, and try out the rides at Discovery Cove.

To find ratings, where to stay, maps, and more tourist information, refer to the Orlando trip planner.

San Jose, Costa Rica to Orlando is an approximately 7-hour flight. You can also drive. You'll lose 1 hour traveling from San Jose to Orlando due to the time zone difference. Traveling from San Jose in December, you can expect nighttime temperatures to be slightly colder in Orlando, with lows of 17°C. Finish your sightseeing early on the 25th (Wed) to allow enough time to travel to New York City.

Things to do in Orlando

Theme Parks · Museums · Shopping

Side Trips

Winter Park, NASA Kennedy Space Center Visitor Complex, Stetson Mansion, The Artistic Hand Gallery & Studio
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Discovery Cove ©
Discovery Cove
Universal Orlando Resort ©
Universal Orlando Resort

2
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Start off your visit on the 26th (Thu): explore the activities along Jacqueline Kennedy Onassis Reservoir, then take a stroll through Fifth Avenue, and then admire the landmark architecture of Empire State Building. On your second day here, explore the striking landscape of Hamilton Grange National Memorial, then take a stroll through Times Square, then take a tour by water with Boat Tours & Water Sports, and finally pause for some photo ops at 9/11 Memorial.

Plan my New York City trip by asking Inpirock to come up with tips and suggestions.

You can fly from Orlando to New York City in 6.5 hours. Other options are to drive; or take a bus. Plan for colder temperatures traveling from Orlando in December, with highs in New York City at 10°C and lows at 2°C. Finish up your sightseeing early on the 27th (Fri) so you can travel to Miami Beach.

Things to do in New York City

Neighborhoods · Historic Sites · Shopping
Highlights from your plan
Fifth Avenue ©
Fifth Avenue
9/11 Memorial ©
9/11 Memorial
Times Square ©
Times Square

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.
Let the collections at Vizcaya Museum and Gardens and Britto Central capture your imagination. Head to Lincoln Road and Collins Avenuefor some retail therapy. Go for a jaunt from Miami Beach to Everglades National Park to see Shark Valley Visitor Center about 1h 10 min away. And it doesn't end there: appreciate the extensive heritage of Art Deco Historic District, see the interesting displays at Lock & Load Museum, stop by Wings Beachwear, and take a leisurely stroll along Miami Beach Boardwalk.

To find more things to do, where to stay, photos, and more tourist information, read our Miami Beach road trip tool.

You can fly from New York City to Miami Beach in 6 hours. Other options are to drive; or take a bus. Traveling from New York City in December, expect Miami Beach to be much warmer, temps between 32°C and 23°C. Wrap up your sightseeing on the 31st (Tue) to allow time to drive to Big Pine Key.

Things to do in Miami Beach

Neighborhoods · Shopping · Parks

Side Trips

Miami, Shark Valley Visitor Center
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Lincoln Road ©
Lincoln Road
Art Deco Historic District ©
Art Deco Historic District

3
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. Get some cultural insight at Shady Palm Art Gallery & Photography and History of Diving Museum. Take a break from the city and head to Bahia Honda State Park and National Key Deer Refuge. Take a break from Big Pine Key with a short trip to Islamorada Brewery & Distillery in Islamorada, about 1h 10 min away. There's more to do: look for all kinds of wild species at The Turtle Hospital.

For maps, photos, traveler tips, and more tourist information, go to the Big Pine Key road trip app.

You can drive from Miami Beach to Big Pine Key in 3 hours. Other options are to fly; or take a bus. In December, daytime highs in Big Pine Key are 31°C, while nighttime lows are 25°C. Wrap up your sightseeing on the 3rd (Fri) early enough to drive to Key West.

Things to do in Big Pine Key

Parks · Wildlife · Outdoors

Side Trips

Islamorada, Marathon
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
The Turtle Hospital ©
The Turtle Hospital

4
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.
Take a break from the city and head to Key West Butterfly & Nature Conservatory and Dolphin & Whale Watching. Let the collections at 7 Artists & Friends Gallery and Truman Little White House capture your imagination. The adventure continues: see the interesting displays at The Ernest Hemingway Home and Museum, steep yourself in history at Curry Mansion, see what you can catch with a fishing tour, and kick back and relax at Fort Zachary Taylor.

For photos, other places to visit, reviews, and more tourist information, you can read our Key West planning app.

Drive from Big Pine Key to Key West in an hour. Alternatively, you can take a bus. January in Key West sees daily highs of 28°C and lows of 22°C at night. Wrap up your sightseeing on the 7th (Tue) early enough to travel back home.

Things to do in Key West

Outdoors · Wildlife · Tours
Highlights from your plan
7 Artists & Friends Gallery ©
7 Artists & Friends Gallery
Key West Butterfly & Nature Conservatory ©
The Ernest Hemingway Home and Museum ©
The Ernest Hemingway Home and Museum

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