11 days in Portland & New York City Itinerary

11 days in Portland & New York City Itinerary

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Route & dates

11 days in Portland & New York City Itinerary

Start: San Diego
+2
Fly + foot + bus:  9​h 30​min
1
Portland
— 5 nights
Fly:  4​h 15​min
2
New York City
— 4 nights
Fly:  8​h 15​min
End: San Diego

5
nights
Portland

Portland ©
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.
Shop till you drop at Granite Hall Store and Jackson Art Studio & Gallery. Explore hidden gems such as Marginal Way Walkway and Kancamagus Highway. You'll find plenty of places to visit near Portland: Split Rock Distilling (in Newcastle), Ducktrap Bay Trading Co (in Camden) and Sweetgrass Winery and Distillery (in Union). And it doesn't end there: glide through natural beauty at Jackson Ski Touring Foundation, do a tasting at Breakwater Vineyards, brush up on your knowledge of spirits at Tamworth Distilling, and get a taste of the local shopping with Mast Cove Galleries.

To find where to stay, ratings, photos, and other tourist information, read Portland trip itinerary builder site .

San Diego to Portland is an approximately 9.5-hour flight. You can also do a combination of flight and bus; or drive. Due to the time zone difference, you'll lose 3 hours traveling from San Diego to Portland. Traveling from San Diego in February, things will get colder in Portland: highs are around 35°F and lows about 16°F. Finish up your sightseeing early on the 19th (Tue) so you can travel to New York City.

Things to do in Portland

Outdoors Shopping Museums

Side Trips

Jackson, Kennebunkport, Ricker's Hard Cider, Ducktrap Bay Trading Co, Tamworth Distilling
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Breakwater Vineyards ©
Breakwater Vineyards
Ricker's Hard Cider ©
Ricker's Hard Cider

4
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.
Shop till you drop at Fifth Avenue and Garment District. Get a sense of the local culture at The Metropolitan Museum of Art and 9/11 Memorial. The adventure continues: take in the pleasant sights at Times Square, admire the striking features of Woolworth Building, don't miss a visit to Central Park, and get a new perspective on nature at American Museum of Natural History.

To find where to stay, photos, reviews, and other tourist information, you can read our New York City journey planner.

Traveling by flight from Portland to New York City takes 4.5 hours. Alternatively, you can do a combination of flight and bus; or drive. Traveling from Portland in February, things will get a bit warmer in New York City: highs are around 46°F and lows about 29°F. Wrap up your sightseeing on the 23rd (Sat) early enough to travel back home.

Things to do in New York City

Museums Parks Shopping
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Times Square ©
Times Square
9/11 Memorial ©
9/11 Memorial

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