21 days in Florida & New York City Itinerary

21 days in Florida & New York City Itinerary

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Route & dates

21 days in Florida & New York City Itinerary

Start: San Jose
Fly:  6​h 45​min
1
Orlando
— 6 nights
Fly:  6​h
2
New York City
— 2 nights
Fly:  5​h 30​min
3
Miami Beach
— 4 nights
Drive:  3​h
4
Big Pine Key
— 3 nights
bus:  45​min
5
Key West
— 4 nights
Fly:  7​h 30​min
End: San Jose

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.
Head to The Mall at Millenia and The Artistic Hand Gallery & Studiofor plenty of shopping. Museum-lovers will get to explore Charles Hosmer Morse Museum of American Art and Timothy's Gallery. Explore Orlando's surroundings by going to Stetson Mansion (in DeLand) and NASA Kennedy Space Center Visitor Complex (in Titusville). There's much more to do: laugh and play at Discovery Cove, pause for some serene contemplation at St James Roman Catholic Cathedral, make an unforgettable trip to Happily Ever After Fireworks, and get in on the family fun at Walt Disney World Resort.

For traveler tips, more things to do, reviews, and other tourist information, go to the Orlando online sightseeing planner .

San Jose, Costa Rica to Orlando is an approximately 7-hour flight. You can also drive. Due to the time zone difference, you'll lose 1 hour traveling from San Jose to Orlando. Plan for slightly colder nights when traveling from San Jose in December since evenings lows in Orlando dip to 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 Parks Museums

Side Trips

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

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.
Kick off your visit on the 26th (Thu): explore the activities along Jacqueline Kennedy Onassis Reservoir, then take a stroll through Fifth Avenue, and then don't miss a visit to Empire State Building. On the 27th (Fri), you'll have a packed day of sightseeing: explore the wealth of natural beauty at Hamilton Grange National Memorial, then take in the pleasant sights at Times Square, then take a memorable tour with Tours, and finally pause for some photo ops at 9/11 Memorial.

For reviews, photos, maps, and more tourist information, read New York City holiday builder website .

Traveling by flight from Orlando to New York City takes 6 hours. Alternatively, you can do a combination of flight and bus; or drive. Plan for cooler temperatures traveling from Orlando in December, with highs in New York City at 10°C and lows at 2°C. Finish your sightseeing early on the 27th (Fri) so you can travel to Miami Beach.

Things to do in New York City

Neighborhoods Shopping Historic Sites
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.
Visiting Shark Valley Visitor Center and South Beach will get you outdoors. Let the collections at Vizcaya Museum and Gardens and Lock & Load Museum capture your imagination. And it doesn't end there: take a stroll through Lincoln Road, explore the world behind art at The Wolfsonian - Florida International University, shop like a local with Collins Avenue, and take a leisurely stroll along Miami Beach Boardwalk.

To find reviews, photos, ratings, and tourist information, refer to the Miami Beach trip itinerary planner.

You can fly from New York City to Miami Beach in 5.5 hours. Alternatively, you can do a combination of bus and flight; or drive. Traveling from New York City in December, expect Miami Beach to be much hotter, 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
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens

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 outdoors at Bahia Honda State Park and The Turtle Hospital. Let the collections at Shady Palm Art Gallery & Photography and History of Diving Museum capture your imagination. Change things up with a short trip to Islamorada Brewery & Distillery in Islamorada (about 1h 10 min away). The adventure continues: look for all kinds of wild species at National Key Deer Refuge and add some adventure to your tour with a kayaking and canoeing tour.

To see where to stay, reviews, other places to visit, and more tourist information, read Big Pine Key trip planner.

Drive from Miami Beach to Big Pine Key in 3 hours. Alternatively, you can fly; or take a bus. Expect a daytime high around 31°C in December, and nighttime lows around 25°C. Wrap up your sightseeing on the 3rd (Fri) to allow time to take a bus to Key West.

Things to do in Big Pine Key

Parks Wildlife Nature

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.
Popular historic sites such as Fort Zachary Taylor and Truman Little White House are in your itinerary. Museum-lovers will get to explore Alan S. Maltz Gallery and The Studios of Key West. There's still lots to do: identify plant and animal life at Key West Butterfly & Nature Conservatory, see what you can catch with a fishing tour, view the masterpieces at Art On Duval Key West, and contemplate the long history of Curry Mansion.

To see reviews, photos, traveler tips, and tourist information, read our Key West trip itinerary planning site .

Traveling by bus from Big Pine Key to Key West takes an hour. Alternatively, you can drive. In January in Key West, expect temperatures between 28°C during the day and 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 Tours Wildlife
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
The Ernest Hemingway Home and Museum ©

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