39 days in East Coast of USA Itinerary

39 days in East Coast of USA Itinerary

Created using Inspirock East Coast of USA travel route builder

Make it your trip
Fly
1
Charleston
— 3 nights
Fly
2
Miami
— 2 nights
Drive
3
Key Largo
— 4 nights
Drive
4
Islamorada
— 2 nights
Drive
5
Big Pine Key
— 2 nights
Drive
6
Key West
— 5 nights
Ferry
7
Fort Myers Beach
— 2 nights
Drive
8
Sarasota
— 2 nights
Drive
9
Orlando
— 5 nights
Fly
10
Washington DC
— 5 nights
Fly
11
New York City
— 6 nights
Fly

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Charleston

— 3 nights
Many visitors describe their Charleston holiday as a warm embrace by an old, dear friend--who lived about 200 years ago.
Step out of Charleston with an excursion to The Center for Birds of Prey in Awendaw--about 38 minutes away. There's still lots to do: make a trip to Drayton Hall, find your balance on the water with some of the best stand-up paddleboarding in the area, test your problem-solving skills at Elite Escape Games, and contemplate the long history of Aiken-Rhett House.

For ratings, more things to do, and other tourist information, read our Charleston holiday maker tool.

Pittsburgh to Charleston is an approximately 3.5-hour flight. You can also drive; or do a combination of train and car. Traveling from Pittsburgh in November, expect Charleston to be somewhat warmer, temps between 68°F and 49°F. Finish your sightseeing early on the 15th (Sun) to allow enough time to fly to Miami.

Things to do in Charleston

Historic Sites · Tours · Outdoors · Parks

Side Trips

Miami

— 2 nights

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Start off your visit on the 16th (Mon): admire the masterpieces at The Wolfsonian - Florida International University, get to know the fascinating history of Art Deco Historic District, then stroll through South Beach, and finally enjoy some diversion at Lock & Load Miami. Keep things going the next day: admire the natural beauty at Fairchild Tropical Botanic Garden, then admire the masterpieces at Wiener Museum of Decorative Arts (WMODA), and then test your team's savvy at America's Escape Game.

To see ratings, maps, photos, and more tourist information, read our Miami trip planning website.

Fly from Charleston to Miami in 3.5 hours. Alternatively, you can drive; or do a combination of car and train. When traveling from Charleston in November, plan for somewhat warmer days and much warmer nights in Miami: temperatures range from 82°F by day to 70°F at night. Finish your sightseeing early on the 17th (Tue) so you can drive to Key Largo.

Things to do in Miami

Parks · Fun & Games · Museums · Outdoors

Side Trips

Key Largo

— 4 nights

Diving Capital of the World

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.
Venture out of the city with trips to Homestead Miami Speedway (in Homestead) and Everglades National Park (Anhinga Trail & Mrazek Pond). And it doesn't end there: find your balance on the water with PADDLE! The Florida Keys, look for gifts at Florida Keys Key Lime Products, test your team's savvy at Kingdom Escape Games, and relax and rejuvenate at Island Time Day Spa.

To see ratings, reviews, other places to visit, and more tourist information, use the Key Largo online route maker.

Traveling by car from Miami to Key Largo takes 1.5 hours. Alternatively, you can take a bus. In November in Key Largo, expect temperatures between 81°F during the day and 68°F at night. Finish your sightseeing early on the 21st (Sat) so you can drive to Islamorada.

Things to do in Key Largo

Parks · Outdoors · Wildlife · Tours

Side Trips

Islamorada

— 2 nights

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Start off your visit on the 22nd (Sun): get the adrenaline pumping with Florida Keys Jetpacks, then indulge your thirst for a good beer at Florida Keys Brewing Company, then take a tour by water with Boat Tours & Water Sports, and finally indulge your thirst for a good beer at Islamorada Brewery & Distillery. Get ready for a full day of sightseeing on the 23rd (Mon): see the world from above with Ultimate HeliTours, stroll through The Turtle Hospital, then explore the galleries of Crane Point Museum & Nature Center, and finally kick back and relax at Sunset Park Beach.

To find photos, where to stay, reviews, and other tourist information, read our Islamorada trip itinerary planning tool.

Islamorada is very close to Key Largo. In November, plan for daily highs up to 82°F, and evening lows to 72°F. Finish your sightseeing early on the 23rd (Mon) to allow enough time to drive to Big Pine Key.

Things to do in Islamorada

Outdoors · Parks · Wildlife · Tours

Side Trips

Big Pine Key

— 2 nights
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 24th (Tue): stroll through National Key Deer Refuge and then stroll through Bahia Honda State Park. On the next day, indulge in some personalized pampering at SpaTerre at Little Palm Island Resort, add some adventure to your tour with Florida Keys Kayaks and Eco Tours, then take the plunge with Skydive Key West, and finally look for gifts at Cudjoe Sales.

For traveler tips, more things to do, ratings, and tourist information, go to the Big Pine Key day trip planning tool.

You can drive from Islamorada to Big Pine Key in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 82°F in November, and nighttime lows around 72°F. Wrap up your sightseeing on the 25th (Wed) to allow time to drive to Key West.

Things to do in Big Pine Key

Parks · Outdoors · Beaches · Adventure

Side Trips

Key West

— 5 nights

Conch Republic

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.
Key West is known for museums, adventure, and wildlife. Your trip includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, cast your line with Key West Fishing Connection, tour the pleasant surroundings at Key West Butterfly & Nature Conservatory, and stop by Peppers of Key West.

To find reviews, traveler tips, more things to do, and tourist information, use the Key West day trip website.

Traveling by car from Big Pine Key to Key West takes an hour. Alternatively, you can take a shuttle; or take a bus. In November, daily temperatures in Key West can reach 81°F, while at night they dip to 73°F. Finish your sightseeing early on the 30th (Mon) to allow enough time to ride a ferry to Fort Myers Beach.

Things to do in Key West

Museums · Shopping · Parks · Historic Sites

Fort Myers Beach

— 2 nights
Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. Kick off your visit on the 1st (Tue): admire the natural beauty at Edison and Ford Winter Estates and then deepen your appreciation for local ecosystems through Island Time Dolphin & Shelling Cruises. Get ready for a full day of sightseeing on the next day: take in a show at Artis-Naples, then appreciate the extensive heritage of Naples Historical Society, and then tee off at LaPlaya Golf Course.

To see maps, ratings, more things to do, and tourist information, refer to the Fort Myers Beach trip builder tool.

You can ride a ferry from Key West to Fort Myers Beach in 4.5 hours. Alternatively, you can drive; or take a bus. Plan for a bit cooler nights when traveling from Key West in November since evenings lows in Fort Myers Beach dip to 63°F. Finish your sightseeing early on the 2nd (Wed) so you can drive to Sarasota.

Things to do in Fort Myers Beach

Outdoors · Tours · Historic Sites · Museums

Side Trips

Sarasota

— 2 nights
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. On the 3rd (Thu), brush up on your knowledge of spirits at Siesta Key Rum, glide through the air with Parasail Siesta, then don't miss a visit to Sarasota National Cemetery, and finally indulge your thirst for a good beer at Calusa Brewing. On the 4th (Fri), you'll have a packed day of sightseeing: take in nature's colorful creations at Gizella Kopsick Arboretum, admire the masterpieces at Duncan McClellan Gallery, and then test your problem-solving skills at Escape Rooms Unlocked.

To see more things to do, maps, and other tourist information, you can read our Sarasota online driving holiday planner.

Drive from Fort Myers Beach to Sarasota in 2 hours. Alternatively, you can take a bus. In December in Sarasota, expect temperatures between 78°F during the day and 59°F at night. Finish your sightseeing early on the 4th (Fri) to allow enough time to drive to Orlando.

Things to do in Sarasota

Breweries & Distilleries · Parks · Outdoors · Adventure

Side Trips

Orlando

— 5 nights

Theme Park Capital of the World

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.
Venture out of the city with trips to St. Johns River Tours, Inc. - Day Tours (in Astor) and Stetson Mansion (in DeLand). Have a day of magic on the 7th (Mon) at Walt Disney World Resort. Pack the 5th (Sat) with family-friendly diversions at Universal Orlando Resort. There's more to do: get in on the family fun at Universal's Islands of Adventure and make an unforgettable trip to Magic Kingdom Park.

To see maps, more things to do, and tourist information, refer to the Orlando trip planner.

Getting from Sarasota to Orlando by car takes about 2.5 hours. Other options: take a bus; or do a combination of bus and train. In December in Orlando, expect temperatures between 77°F during the day and 59°F at night. Cap off your sightseeing on the 9th (Wed) early enough to catch the flight to Washington DC.

Things to do in Orlando

Theme Parks · Outdoors · Tours · Historic Sites

Side Trips

Washington DC

— 5 nights
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Washington DC is known for museums, historic sites, and nightlife. Your trip includes some of its best attractions: explore the world behind art at National Gallery of Art, pause for some serene contemplation at Washington National Cathedral, appreciate the history behind Washington Monument, and ponder the world of politics at White House.

To see photos, more things to do, ratings, and tourist information, you can read our Washington DC trip itinerary builder tool.

You can fly from Orlando to Washington DC in 4 hours. Other options are to drive; or take a bus. Plan for much colder temperatures traveling from Orlando in December, with highs in Washington DC at 51°F and lows at 37°F. Finish up your sightseeing early on the 14th (Mon) so you can catch the flight to New York City.

Things to do in Washington DC

Museums · Parks · Zoos & Aquariums · Historic Sites

New York City

— 6 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for museums, nightlife, and shopping. Your trip includes some of its best attractions: take in panoramic vistas at Empire State Building, pause for some photo ops at Statue of Liberty National Monument, steep yourself in history at 9/11 Memorial, and admire the masterpieces at The Museum of Modern Art (MoMA).

To find maps, photos, where to stay, and tourist information, refer to the New York City trip planner.

You can fly from Washington DC to New York City in 3 hours. Alternatively, you can take a train; or drive. In December, daytime highs in New York City are 48°F, while nighttime lows are 36°F. Wrap up your sightseeing on the 20th (Sun) to allow time to fly back home.

Things to do in New York City

Museums · Parks · Historic Sites · Neighborhoods