57 days in Florida Keys & New York City Itinerary

57 days in Florida Keys & New York City Itinerary

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Route & dates

57 days in Florida Keys & New York City Itinerary

Start: Sydney
Fly:  30​h
1
Dry Tortugas National Park
— 1 night
Travel:  3​h 45​min
2
Key West
— 9 nights
bus:  45​min
3
Big Pine Key
— 5 nights
bus:  30​min
4
Marathon
— 8 nights
Drive:  45​min
5
Islamorada
— 8 nights
Drive:  45​min
6
Key Largo
— 7 nights
Drive:  3​h 15​min
7
Duck Key
— 1 night
Drive:  2​h 15​min
8
Key Colony Beach
— 2 nights
Fly:  7​h 45​min
9
New York City
— 11 nights
Fly:  26​h
End: Sydney

1
night
Dry Tortugas National Park

Dry Tortugas National Park ©
What Dry Tortugas National Park lacks in size, it makes up for in abundance of marine life.
Kick off your visit on the 2nd (Mon): step off the mainland to explore Garden Key, then explore the striking landscape at Little Africa, and then contemplate the long history of Fort Jefferson. Get ready for a full day of sightseeing on the next day: take in the dramatic natural features at Tortugas Banks.

To find where to stay, maps, reviews, and more tourist information, refer to the Dry Tortugas National Park online tour planner .

Sydney, Australia to Dry Tortugas National Park is an approximately 30-hour flight. The time zone difference moving from Australian Eastern Standard Time (New South Wales) (AEST) to Eastern Standard Time (EST) is minus 15 hours. Expect a bit warmer evenings in Dry Tortugas National Park when traveling from Sydney in December, with lows around 25°C. On the 3rd (Tue), wrap the sightseeing up by early afternoon so you can travel to Key West.

Things to do in Dry Tortugas National Park

Parks Nature Wildlife
Highlights from your plan
Fort Jefferson ©
Fort Jefferson

9
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.
Family-friendly places like Key West Butterfly & Nature Conservatory and Fun In The Sun Key West will thrill your kids. Spend the 6th (Fri) exploring nature at Dry Tortugas National Park. Next up on the itinerary: see the interesting displays at The Ernest Hemingway Home and Museum, admire all the interesting features of Mallory Square, steep yourself in history at Curry Mansion, and shop like a local with Alan S. Maltz Gallery.

To find maps, other places to visit, where to stay, and more tourist information, use the Key West tour planner .

Use the Route module to find suitable travel options from Dry Tortugas National Park to Key West. In December in Key West, expect temperatures between 30°C during the day and 25°C at night. Finish your sightseeing early on the 12th (Thu) so you can take a bus to Big Pine Key.

Things to do in Key West

Outdoors Parks Tours
Highlights from your plan
Dolphin & Whale Watching
Key West Aquarium ©
Key West Aquarium

5
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. Bring the kids along to Bahia Honda State Park and Calusa Beach. The adventure continues: identify plant and animal life at National Key Deer Refuge, relax in the rural setting at Grimal Grove, look for gifts at Out of the Blue Gallery, and shop like a local with Artists in Paradise Gallery.

For where to stay, reviews, ratings, and other tourist information, read Big Pine Key trip itinerary planner.

You can take a bus from Key West to Big Pine Key in an hour. Alternatively, you can drive. In December, daily temperatures in Big Pine Key can reach 31°C, while at night they dip to 25°C. Cap off your sightseeing on the 17th (Tue) early enough to catcht the bus to Marathon.

Things to do in Big Pine Key

Outdoors Tours Parks
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Fishing Charters & Tours
Blue Hole ©
Blue Hole

8
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.
Family-friendly places like Pigeon Key Foundation and Marathon Garden Club will thrill your kids. Next up on the itinerary: look for all kinds of wild species at Crane Point Museum & Nature Center, tour the pleasant surroundings at Sombrero Beach, choose your vessel at Pier 68, and get outside with Gemini Dream Charters.

To find reviews, other places to visit, photos, and tourist information, read our Marathon trip planner .

Marathon is just a short distance from Big Pine Key. In December in Marathon, expect temperatures between 31°C during the day and 25°C at night. Finish your sightseeing early on the 25th (Wed) so you can drive to Islamorada.

Things to do in Marathon

Outdoors Tours Wildlife
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Pigeon Key Foundation ©
Pigeon Key Foundation
Crane Point Museum & Nature Center ©

8
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
You'll visit kid-friendly attractions like Robbie's of Islamorada and Windley Key Fossil Reef Geological State Park. There's still lots to do: sample the tasty concoctions at Florida Keys Brewing Company, immerse yourself in nature at Lignumvitae Key Botanical State Park, take a tour by water with Bayside Boat Rentals, and get outside with Satisfaction Charters Inc..

To see traveler tips, reviews, maps, and tourist information, read Islamorada itinerary builder app .

You can drive from Marathon to Islamorada in an hour. Alternatively, you can take a bus. In December, daily temperatures in Islamorada can reach 31°C, while at night they dip to 25°C. Finish your sightseeing early on the 2nd (Thu) so you can drive to Key Largo.

Things to do in Islamorada

Outdoors Tours Transportation
Highlights from your plan
Robbie's of Islamorada ©
Robbie's of Islamorada
Anne's Beach ©
Anne's Beach
Parasailing & Paragliding

7
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.
Bring the kids along to Florida Keys Wild Bird Rehabilitation Center and Island Dolphin Care. Spend the 7th (Tue) peacefully gliding across the water with some of the best stand-up paddleboarding in the area. The adventure continues: see the vivid underwater world at Spiegel Grove, identify plant and animal life at Key Largo Undersea Park, admire nature's wide array of creatures at Dolphins Plus Marine Mammal Responder, and discover the deep blue sea with a scuba or snorkeling tour.

To see where to stay, photos, maps, and other tourist information, read Key Largo trip planner.

You can drive from Islamorada to Key Largo in an hour. Alternatively, you can do a combination of bus and taxi. Expect a bit cooler evenings in Key Largo when traveling from Islamorada in January, with lows around 19°C. Wrap up your sightseeing on the 9th (Thu) early enough to travel to Duck Key.

Things to do in Key Largo

Wildlife Parks Tours
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Key Largo Fishing Adventures ©
Key Largo Fishing Adventures

1
night
Duck Key

Duck Key ©
Duck Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the middle Florida Keys. On the 10th (Fri), immerse yourself in nature at Long Key State Park and then do sightseeing your way with Fish 'N Fun Boat Rentals.

For ratings, photos, where to stay, and other tourist information, go to the Duck Key online journey planner .

Getting from Key Largo to Duck Key by car takes about 1.5 hours. In January, plan for daily highs up to 29°C, and evening lows to 22°C. Wrap up your sightseeing on the 10th (Fri) early enough to travel to Key Colony Beach.

Things to do in Duck Key

Wildlife Tours Outdoors

Side Trip

Long Key State Park
Highlights from your plan
Long Key State Park ©
Long Key State Park

2
nights
Key Colony Beach

Key Colony Beach is a municipality in the middle of the Florida Keys, Monroe County, Florida, United States. Start off your visit on the 11th (Sat): enjoy the sand and surf at Sunset Park Beach and then take a memorable tour with Tours. On the 12th (Sun), you'll have a packed day of sightseeing: choose your vessel at Vacation boat rentals and then identify plant and animal life at Coffins Patch.

To see reviews, maps, other places to visit, and other tourist information, refer to the Key Colony Beach holiday maker site .

Key Colony Beach is very close to Duck Key. January in Key Colony Beach sees daily highs of 29°C and lows of 22°C at night. Finish your sightseeing early on the 12th (Sun) to allow enough time to travel to New York City.

Things to do in Key Colony Beach

Outdoors Wildlife Tours
Highlights from your plan
Fishing Charters & Tours
Coffins Patch ©
Coffins Patch
Vacation boat rentals ©
Vacation boat rentals

11
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.
Bring the kids along to Central Park and American Museum of Natural History. Go for a jaunt from New York City to Bronx to see Bronx Zoo about 36 minutes away. There's much more to do: don't miss a visit to The Metropolitan Museum of Art, browse the exhibits of 9/11 Memorial, admire the striking features of Rockefeller Center, and explore and take pictures at The High Line.

To find photos, other places to visit, more things to do, and other tourist information, use the New York City trip builder site .

The Route module can help you plan travel from Key Colony Beach to New York City. In January, New York City is much colder than Key Colony Beach - with highs of 5°C and lows of -5°C. Wrap up your sightseeing by early afternoon on the 24th (Fri) to allow time for travel back home.

Things to do in New York City

Museums Parks Historic Sites

Side Trips

Bronx Zoo, Brooklyn Botanic Garden
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Statue of Liberty National Monument ©

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