28 days in East Coast of USA Itinerary

28 days in East Coast of USA Itinerary

Created using Inspirock East Coast of USA tour itinerary maker

Make it your trip
Fly
1
Boston
— 2 nights
Fly
2
New York City
— 5 nights
Train
3
Washington DC
— 5 nights
Fly
4
Charleston
— 3 nights
Fly
5
Key Largo
— 1 night
Drive
6
Islamorada
— 3 nights
Drive
7
Key West
— 4 nights
Fly
8
Orlando
— 4 nights
Fly

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Boston

— 2 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Boston is known for historic sites, museums, and parks. Your plan includes some of its best attractions: explore the world behind art at Museum of Fine Arts, engage your brain at Museum of Science, pause for some photo ops at New England Holocaust Memorial, and stroll the grounds of Granary Burying Ground.

To find photos, reviews, ratings, and tourist information, read our Boston holiday builder tool.

San Diego to Boston is an approximately 7-hour flight. You can also drive; or take a bus. You'll lose 3 hours traveling from San Diego to Boston due to the time zone difference. In April, Boston is a bit cooler than San Diego - with highs of 56°F and lows of 40°F. Cap off your sightseeing on the 27th (Tue) early enough to travel to New York City.

Things to do in Boston

Museums · Historic Sites · Childrens Museums · Parks

Side Trip

New York City

— 5 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 plan includes some of its best attractions: stroll around Central Park, make a trip to Grand Central Terminal, admire the masterpieces at The Museum of Modern Art (MoMA), and admire the striking features of Empire State Building.

To see traveler tips, photos, reviews, and tourist information, read New York City trip planner.

Fly from Boston to New York City in 3.5 hours. Alternatively, you can drive; or take a train. April in New York City sees daily highs of 61°F and lows of 45°F at night. Cap off your sightseeing on the 2nd (Sun) early enough to catch the train to Washington DC.

Things to do in New York City

Museums · Parks · Historic Sites · Neighborhoods

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 plan includes some of its best attractions: explore the activities along Tidal Basin, pause for some photo ops at Washington Monument, see the interesting displays at The National Archives Museum, and get engrossed in the history at United States Holocaust Memorial Museum.

For photos, where to stay, maps, and tourist information, read our Washington DC travel route builder tool.

Traveling by train from New York City to Washington DC takes 3.5 hours. Alternatively, you can fly; or drive. Expect somewhat warmer weather when traveling from New York City in May: highs in Washington DC hover around 76°F, while lows dip to 58°F. Finish your sightseeing early on the 7th (Fri) so you can travel to Charleston.

Things to do in Washington DC

Museums · Parks · Zoos & Aquariums · Outdoors

Charleston

— 3 nights
Many visitors describe their Charleston holiday as a warm embrace by an old, dear friend--who lived about 200 years ago.
Charleston is known for parks, historic sites, and shopping. Your plan includes some of its best attractions: test your problem-solving skills at Elite Escape Games, contemplate the long history of Aiken-Rhett House, expand your understanding of the military at Fort Sumter National Monument, and admire the natural beauty at Battery & White Point Gardens.

To see photos, reviews, where to stay, and other tourist information, you can read our Charleston trip planner.

Traveling by flight from Washington DC to Charleston takes 4 hours. Alternatively, you can drive; or do a combination of train and car. Plan for a bit warmer nights when traveling from Washington DC in May since evenings lows in Charleston dip to 64°F. Finish up your sightseeing early on the 10th (Mon) so you can travel to Key Largo.

Things to do in Charleston

Historic Sites · Tours · Museums · Outdoors

Side Trips

Key Largo

— 1 night

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.
On the 11th (Tue), push the limits with Jetpack Water Flights, test your team's savvy at Kingdom Escape Games, then observe the fascinating underwater world at Island Dolphin Care, then take a tour by water with JSK Watersports, and finally identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center.

To see traveler tips, reviews, and other tourist information, go to the Key Largo trip itinerary website.

Traveling by flight from Charleston to Key Largo takes 6 hours. Alternatively, you can drive; or do a combination of car, train, and bus. Expect a bit warmer evenings in Key Largo when traveling from Charleston in May, with lows around 72°F. Wrap up your sightseeing on the 11th (Tue) early enough to drive to Islamorada.

Things to do in Key Largo

Parks · Outdoors · Tours · Zoos & Aquariums

Islamorada

— 3 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.
Get out of town with these interesting Islamorada side-trips: Marathon (Crane Point Museum & Nature Center, San Pablo Catholic Church, &more). There's much more to do: cast your line with a fishing tour, view the masterpieces at Old Road Gallery, identify plant and animal life at Alligator Reef Light House, and indulge your thirst for a good beer at Islamorada Brewery & Distillery.

To find other places to visit, where to stay, reviews, and more tourist information, read Islamorada trip itinerary website.

Islamorada is very close to Key Largo. In May in Islamorada, expect temperatures between 88°F during the day and 77°F at night. Wrap up your sightseeing on the 14th (Fri) to allow time to drive to Key West.

Things to do in Islamorada

Wildlife · Parks · Outdoors · Breweries & Distilleries

Side Trip

Key West

— 4 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.
Venture out of the city with trips to Z Flight Watersports (in Marathon) and Bahia Honda State Park (in Big Pine Key). There's lots more to do: see the interesting displays at The Ernest Hemingway Home and Museum, stroll the grounds of Key West Cemetery, view the masterpieces at Alan S. Maltz Gallery, and see the world from above with Air Adventures Helicopter Tours.

To find other places to visit, photos, ratings, and other tourist information, refer to the Key West online sightseeing planner.

You can drive from Islamorada to Key West in 2 hours. Alternatively, you can take a bus. In May, daily temperatures in Key West can reach 85°F, while at night they dip to 77°F. Finish your sightseeing early on the 18th (Tue) to allow enough time to travel to Orlando.

Things to do in Key West

Outdoors · Museums · Parks · Tours

Side Trips

Orlando

— 4 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.
Pack the 19th (Wed) with family-friendly diversions at Universal's Islands of Adventure. Plan for a day of cool, family-friendly fun on the 21st (Fri) at Discovery Cove. Next up on the itinerary: find something for the whole family at Universal Orlando Resort and make an unforgettable trip to Walt Disney World Resort.

To see maps, traveler tips, and other tourist information, use the Orlando road trip planner.

You can fly from Key West to Orlando in 4.5 hours. Alternatively, you can drive; or take a bus. Expect little chillier evenings in Orlando when traveling from Key West in May, with lows around 69°F. Finish up your sightseeing early on the 22nd (Sat) so you can travel back home.

Things to do in Orlando

Theme Parks