21 days in New York City & Florida Itinerary

21 days in New York City & Florida Itinerary

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Route & dates

21 days in New York City & Florida Itinerary

Start: Jeddah
Fly:  17​h 30​min
1
New York City
— 1 night
Drive:  25​h
2
Key West
— 3 nights
Drive:  45​min
3
Big Pine Key
— 1 night
Drive:  30​min
4
Marathon
— 2 nights
Drive:  45​min
5
Islamorada
— 2 nights
Drive:  2​h
6
Miami Beach
— 2 nights
Drive:  1​h
7
Florida City
— 3 nights
Drive:  4​h 30​min
8
Siesta Key
— 1 night
Drive:  2​h 30​min
9
Orlando
— 3 nights
Fly:  21​h 30​min
End: Jeddah

1
night
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 14th (Fri): browse the exhibits of The Metropolitan Museum of Art, meet the residents at Central Park Zoo, and then appreciate the history behind 9/11 Memorial. On the next day, choose your vessel at Narwhal Yacht Charters and then make a trip to Fifth Avenue.

To see reviews, traveler tips, other places to visit, and more tourist information, refer to the New York City online trip itinerary maker .

Jeddah, Saudi Arabia to New York City is an approximately 17.5-hour flight. You can also do a combination of flight and bus. The time zone changes from Arabia Standard Time (AST) to Eastern Standard Time (EST), which is usually a -8 hour difference. Plan for colder temperatures traveling from Jeddah in December, with highs in New York City at 10°C and lows at 2°C. Wrap up your sightseeing on the 15th (Sat) early enough to travel to Key West.

Things to do in New York City

Museums Outdoors Tours
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
Fifth Avenue ©
Fifth Avenue

3
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.
Escape the urban bustle at Fort Zachary Taylor and Parasailing & Paragliding. Your inner history buff will appreciate Audubon House & Tropical Gardens and Key West Cemetery. There's lots more to do: identify plant and animal life at Key West Butterfly & Nature Conservatory, stop by Uva Wine Shop & Bar, take in the architecture and atmosphere at Saint Mary Star of the Sea, and examine the collection at The Ernest Hemingway Home and Museum.

To find photos, maps, traveler tips, and tourist information, read our Key West travel site .

You can do a combination of bus and flight from New York City to Key West in 6 hours. Other options are to fly; or drive. Traveling from New York City in December, things will get much warmer in Key West: highs are around 30°C and lows about 25°C. Finish your sightseeing early on the 19th (Wed) to allow enough time to take a bus to Big Pine Key.

Things to do in Key West

Outdoors Adventure Tours
Highlights from your plan
Stand-Up Paddleboarding
The Ernest Hemingway Home and Museum ©
Fort Zachary Taylor ©
Fort Zachary Taylor

1
night
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. Start off your visit on the 20th (Thu): admire the majestic nature at Bahia Honda State Park, then look for all kinds of wild species at National Key Deer Refuge, and then stop by Out of the Blue Gallery.

For photos and other tourist information, go to the Big Pine Key trip itinerary builder tool .

You can take a bus from Key West to Big Pine Key in an hour. Alternatively, you can drive. December in Big Pine Key sees daily highs of 31°C and lows of 25°C at night. Finish your sightseeing early on the 20th (Thu) so you can take a bus to Marathon.

Things to do in Big Pine Key

Parks Nature Outdoors
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Out of the Blue Gallery ©
Out of the Blue Gallery

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.
Start off your visit on the 21st (Fri): look for gifts at Bayshore Clothing, identify plant and animal life at Crane Point Museum & Nature Center, tour the pleasant surroundings at Sombrero Beach, then look for all kinds of wild species at The Turtle Hospital, and finally take in the views from Seven Mile Bridge. On the next day, get a new perspective on things with Boat Tours & Water Sports, then identify plant and animal life at Dolphin Research Center, and then take in the architecture and atmosphere at San Pablo Catholic Church.

To see other places to visit, maps, where to stay, and other tourist information, use the Marathon tour itinerary maker app .

Marathon is very close to Big Pine Key. December in Marathon sees daily highs of 31°C and lows of 25°C at night. Cap off your sightseeing on the 22nd (Sat) early enough to go by car to Islamorada.

Things to do in Marathon

Parks Outdoors Wildlife
Highlights from your plan
San Pablo Catholic Church ©
San Pablo Catholic Church
Sombrero Beach ©
Sombrero Beach
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center

2
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 23rd (Sun), stroll through Anne's Beach, get engrossed in the history at History of Diving Museum, and then choose your vessel at Robbie's of Islamorada. Here are some ideas for day two: look for gifts at Bella Sol Fragrance Bar and Gifts, take in the exciting artwork at Old Road Gallery, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, then get to know the fascinating history of Indian Key State Historic Site, then view the masterpieces at Michelle Nicole Lowe Art Gallery, and finally sample the tasty concoctions at Islamorada Beer Company Brewery and Tasting Room.

To find where to stay, ratings, and more tourist information, read our Islamorada trip itinerary tool .

Getting from Marathon to Islamorada by car takes about an hour. Other options: take a bus. Expect a daytime high around 31°C in December, and nighttime lows around 25°C. Wrap up your sightseeing on the 24th (Mon) to allow time to drive to Miami Beach.

Things to do in Islamorada

Outdoors Wildlife Adventure

Side Trip

Florida Keys Wild Bird Rehabilitation Center
Highlights from your plan
Anne's Beach ©
Anne's Beach
Robbie's of Islamorada ©
Robbie's of Islamorada

2
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.
Kick off your visit on the 25th (Tue): get a taste of the local shopping with Collins Avenue, then admire all the interesting features of Lincoln Road, then kick back and relax at South Beach, and finally take a stroll through Art Deco Historic District. On your second day here, see the interesting displays at Vizcaya Museum and Gardens, make a trip to Port of Miami, and then take a stroll through Ocean Drive.

To see traveler tips, where to stay, reviews, and other tourist information, you can read our Miami Beach trip planner .

Traveling by car from Islamorada to Miami Beach takes 2 hours. Alternatively, you can take a bus. In December in Miami Beach, expect temperatures between 32°C during the day and 23°C at night. Cap off your sightseeing on the 26th (Wed) early enough to travel to Florida City.

Things to do in Miami Beach

Neighborhoods Shopping Parks

Side Trip

Miami
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Art Deco Historic District ©
Art Deco Historic District

3
nights
Florida City

Florida City ©
Florida City is a city in Miami-Dade County, Florida, United States and is the southernmost municipality in the South Florida metropolitan area. Get some cultural insight at Flamingo and Coral Castle. Visiting Shark Valley and Anhinga Trail will get you outdoors. Change things up with a short trip to Pineland Trail in Everglades National Park (about 30 minutes away). Spend the 28th (Fri) exploring nature at Everglades National Park. The adventure continues: stop by Robert Is Here.

To see other places to visit, where to stay, and tourist information, use the Florida City itinerary planner.

Getting from Miami Beach to Florida City by car takes about an hour. In December, daily temperatures in Florida City can reach 30°C, while at night they dip to 22°C. Finish your sightseeing early on the 29th (Sat) to allow enough time to travel to Siesta Key.

Things to do in Florida City

Parks Nature Trails

Side Trips

Everglades National Park, Homestead
Highlights from your plan
Everglades National Park ©
Everglades National Park
Flamingo ©
Flamingo
Coral Castle ©
Coral Castle

1
night
Siesta Key

Siesta Key ©
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
On the 30th (Sun), enjoy the sand and surf at Siesta Beach and then enjoy the sand and surf at Crescent Beach.

To find more things to do, where to stay, reviews, and other tourist information, you can read our Siesta Key holiday planner.

Traveling by car from Florida City to Siesta Key takes 4 hours. Traveling from Florida City in December, expect slightly colder with lows of 17°C in Siesta Key. Finish your sightseeing early on the 30th (Sun) to allow enough time to drive to Orlando.

Things to do in Siesta Key

Parks Outdoors Beaches
Highlights from your plan
Crescent Beach ©
Crescent Beach
Siesta Beach ©
Siesta Beach

3
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.
Step out of Orlando to go to DeLand and see Stetson Mansion, which is approximately 58 minutes away. Pack the 1st (Tue) with family-friendly diversions at Walt Disney World Resort. Have a day of magic on the 2nd (Wed) at Disney's Animal Kingdom. It doesn't end there: buy something for everyone on your list at The Mall at Millenia and discover the magic at Happily Ever After Fireworks.

To find traveler tips, more things to do, where to stay, and more tourist information, refer to the Orlando sightseeing planner .

You can drive from Siesta Key to Orlando in 2.5 hours. Another option is to take a bus. In December in Orlando, expect temperatures between 29°C during the day and 17°C at night. Wrap up your sightseeing on the 2nd (Wed) to allow time to travel back home.

Things to do in Orlando

Theme Parks Parks Wildlife

Side Trip

Stetson Mansion
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Disney's Animal Kingdom ©
Disney's Animal Kingdom
The Mall at Millenia ©
The Mall at Millenia

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