16 days in New York City, New England & Washington DC Itinerary

16 days in New York City, New England & Washington DC Itinerary

Created using Inspirock United States trip planner
Make it your trip
Fly
1
New York City
— 5 nights
Fly
2
Portland
— 3 nights
Fly
3
Newport
— 2 nights
Fly
4
Washington DC
— 5 nights
Drive to Ronald Reagan Washington National Airport, Fly to Medford

S M T W T F S
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8

New York City — 5 nights

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Get some cultural insight at The Metropolitan Museum of Art and St. Patrick's Cathedral. Popular historic sites such as Franklin D. Roosevelt Presidential Library and Museum and 9/11 Memorial are in your itinerary. Explore the numerous day-trip ideas around New York City: Hyde Park (Vanderbilt Mansion National Historic Site & Home of Franklin D. Roosevelt). There's still lots to do: admire the masterpieces at The Museum of Modern Art (MoMA), get to know the fascinating history of Brooklyn Heights Promenade, go for a walk through Central Park, and admire the striking features of Rockefeller Center.

To find photos, more things to do, ratings, and tourist information, you can read our New York City trip builder website.

Medford to New York City is an approximately 9-hour flight. You can also drive; or do a combination of bus and train. The time zone difference when traveling from Medford to New York City is 3 hours. December in New York City sees daily highs of 48°F and lows of 36°F at night. Cap off your sightseeing on the 23rd (Thu) early enough to catch the flight to Portland.
Museums · Historic Sites · Parks · Tours
Side Trips

Portland — 3 nights

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Portland Museum of Art and Strawbery Banke Museum will appeal to museum buffs. Do some cultural sightseeing at Nubble Lighthouse and Victoria Mansion. And it doesn't end there: take a stroll through Old Port, admire the masterpieces at Museum of African Culture, have fun and explore at Children's Museum and Theatre of Maine, and hunt for treasures at Portland Flea-for-All.

To find traveler tips, photos, reviews, and tourist information, read Portland road trip planning app.

Traveling by flight from New York City to Portland takes 3 hours. Alternatively, you can drive; or do a combination of train and bus. Expect little chillier temperatures when traveling from New York City in December; daily highs in Portland reach 37°F and lows reach 22°F. Wrap up your sightseeing on the 26th (Sun) to allow time to fly to Newport.
Museums · Historic Sites · Childrens Museums · Neighborhoods
Side Trips

Newport — 2 nights

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Kick off your visit on the 27th (Mon): contemplate in the serene atmosphere at National Shrine of our Lady of La Salette, see what you can catch with Fish'n Tales Adventures, and then tour in style with a train tour. Keep things going the next day: tour the pleasant surroundings at Cliff Walk, see the interesting displays at The Breakers, and then admire the striking features of The Elms.

For ratings, traveler tips, other places to visit, and other tourist information, you can read our Newport trip planner.

Traveling by flight from Portland to Newport takes 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Portland in December, things will get a bit warmer in Newport: highs are around 44°F and lows about 32°F. Finish your sightseeing early on the 28th (Tue) to allow enough time to fly to Washington DC.
Historic Sites · Tours · Outdoors · Museums
Side Trip

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.
Arlington National Cemetery and National Mall will appeal to history buffs. Eschew the tourist crowds and head to Steven F. Udvar-Hazy Center and National Gallery of Art. You'll find plenty of places to visit near Washington DC: Baltimore (American Visionary Art Museum, The Walters Art Museum, &more) and National Museum of the Marine Corps (in Triangle). And it doesn't end there: take in the architecture and atmosphere at Basilica of the National Shrine of the Immaculate Conception, take a stroll through Georgetown, get engrossed in the history at United States Holocaust Memorial Museum, and admire the masterpieces at Smithsonian American Art Museum.

For maps and other tourist information, read Washington DC road trip site.

You can fly from Newport to Washington DC in 3 hours. Other options are to drive; or do a combination of bus and train. When traveling from Newport in December, plan for somewhat warmer days in Washington DC, with highs around 51°F, while nights are about the same with lows around 37°F. Cap off your sightseeing on the 2nd (Sun) early enough to travel back home.
Museums · Historic Sites · Neighborhoods · Parks
Side Trips