31 days in New York City & Greater Portland & Casco Bay Itinerary

31 days in New York City & Greater Portland & Casco Bay Itinerary

Created using Inspirock United States vacation builder
Make it your trip
Fly
1
New York City
— 20 nights
Drive
2
Bailey Island
— 1 night
Drive
3
Portland
— 9 nights
Bus to Boston, Fly to Tel Aviv

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New York City — 20 nights

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Explore New York City's surroundings by going to Philadelphia (Franklin Court, Wissahickon Valley Park, &more), Valley Forge National Historical Park (in Valley Forge) and Parkside Place Park (in North Wales). There's still lots to do: go for a walk through Central Park, explore the world behind art at The Metropolitan Museum of Art, walk around The High Line, and admire the landmark architecture of Grand Central Terminal.

To see maps, photos, traveler tips, and more tourist information, refer to the New York City itinerary builder site.

Tel Aviv, Israel to New York City is an approximately 13.5-hour flight. The time zone difference moving from Israel Standard Time (IST) to Eastern Standard Time (EST) is minus 7 hours. Expect little chillier evenings in New York City when traveling from Tel Aviv in June, with lows around 21°C. Finish up your sightseeing early on the 3rd (Sat) so you can travel to Bailey Island.
Museums · Parks · Historic Sites · Tours
Side Trips

Bailey Island — 1 night

Start off your visit on the 4th (Sun): take in the views from Bailey Island Bridge, stop by Land's End Gift Shop, and then hike along Giant's Stairs Trail.

For ratings, traveler tips, and tourist information, refer to the Bailey Island trip planner.

You can drive from New York City to Bailey Island in 6 hours. Alternatively, you can drive. Expect slightly colder temperatures when traveling from New York City in July; daily highs in Bailey Island reach 30°C and lows reach 19°C. Cap off your sightseeing on the 4th (Sun) early enough to go by car to Portland.
Outdoors · Parks · Trails · Shopping

Portland — 9 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.
Explore Portland's surroundings by going to Winslow Memorial Park Camping and Public Beach (in Freeport) and Yarmouth (Grist Mill Park & Royal River Park). There's still lots to do: learn the secrets of beer at The Maine Brew Bus, head outdoors with Outdoor Activities, take a stroll through Diamond Cove, and visit a coastal fixture at Portland Head Light.

To see more things to do, ratings, where to stay, and tourist information, read Portland day trip planning tool.

Traveling by car from Bailey Island to Portland takes an hour. In July, daytime highs in Portland are 30°C, while nighttime lows are 19°C. Finish up your sightseeing early on the 13th (Tue) so you can travel back home.
Parks · Outdoors · Breweries & Distilleries · Trails
Side Trips