60 days in Massachusetts & Anchorage Itinerary

60 days in Massachusetts & Anchorage Itinerary

Created using Inspirock United States trip maker

Plan created by another user. Make it yours
Fly
1
Lenox
— 6 nights
Drive
2
Boston
— 9 nights
Ferry
3
Provincetown
— 7 nights
Drive
4
Hyannis
— 6 nights
Ferry
5
Nantucket
— 6 nights
Ferry
6
Oak Bluffs, Martha's Vineyard
— 6 nights
Fly
7
Anchorage
— 19 nights

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6
nights
Lenox

Lenox is an affluent town in Berkshire County, Massachusetts, United States. Get out of town with these interesting Lenox side-trips: Storrowton Village Museum (in West Springfield), Mount Greylock State Reservation (in Lanesboro) and Westfield (Grandmother's Garden & Stanley park). The adventure continues: explore the world behind art at The Clark Art Institute, head outdoors with Bartholomew's Cobble, trek along Ashuwillticook Rail Trail, and immerse yourself in nature at Skinner State Park.

To find traveler tips, where to stay, more things to do, and other tourist information, use the Lenox online driving holiday planner.

Anchorage to Lenox is an approximately 15-hour flight. You can also drive. Traveling from Anchorage to Lenox, you'll lose 4 hours due to the time zone difference. Traveling from Anchorage in July, you will find days in Lenox are a bit warmer (79°F), and nights are about the same (59°F). Finish up your sightseeing early on the 11th (Sun) so you can go by car to Boston.

Things to do in Lenox

Parks · Outdoors · Museums · Trails

Side Trips

Find places to stay Jul 5 — 11:

9
nights
Boston

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.
Explore Boston's surroundings by going to Rockport Breakwater (in Rockport), Dolphin & Whale Watching (in Gloucester) and Salem (Salem Maritime National Historic Site, Peabody Essex Museum, &more). And it doesn't end there: walk around Boston Public Garden, wander the streets of North End, observe the fascinating underwater world at New England Aquarium, and browse the different shops at Faneuil Hall Marketplace.

To see ratings, reviews, photos, and other tourist information, read Boston attractions planner.

Getting from Lenox to Boston by car takes about 2.5 hours. Other options: take a bus; or do a combination of bus and train. Traveling from Lenox in July, expect a bit warmer with lows of 67°F in Boston. Cap off your sightseeing on the 20th (Tue) early enough to catch the ferry to Provincetown.

Things to do in Boston

Museums · Historic Sites · Parks · Tours

Side Trips

Find places to stay Jul 11 — 20:

7
nights
Provincetown

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Explore Provincetown's surroundings by going to Eastham (Fort Hill Rural Historic District, Coast Guard Beach, &more). There's lots more to do: enjoy the sand and surf at Marconi Beach, tour the pleasant surroundings at Race Point Beach, look for all kinds of wild species at Wildlife Areas, and don't miss a visit to Commercial Street.

For ratings, reviews, where to stay, and more tourist information, read our Provincetown day trip tool.

Ride a ferry from Boston to Provincetown in 2.5 hours. Alternatively, you can fly; or drive. In July in Provincetown, expect temperatures between 79°F during the day and 64°F at night. Wrap up your sightseeing on the 27th (Tue) early enough to drive to Hyannis.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

Side Trips

Find places to stay Jul 20 — 27:

6
nights
Hyannis

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Explore the numerous day-trip ideas around Hyannis: Falmouth (Old Silver Beach & Shining Sea Bikeway), Nauset Beach (in Orleans) and Chatham Marconi Maritime Center (in North Chatham). The adventure continues: identify plant and animal life at Hyannis Whale Watcher Cruises, tour the pleasant surroundings at Gray's Beach, kick back and relax at Chatham Lighthouse Beach, and explore the world behind art at Sandwich Glass Museum.

To find other places to visit, ratings, maps, and more tourist information, refer to the Hyannis trip itinerary maker website.

Drive from Provincetown to Hyannis in 1.5 hours. Alternatively, you can take a bus. In July, daytime highs in Hyannis are 80°F, while nighttime lows are 66°F. Cap off your sightseeing on the 2nd (Mon) early enough to catch the ferry to Nantucket.

Things to do in Hyannis

Outdoors · Parks · Beaches · Museums

Side Trips

Find places to stay Jul 27 — Aug 2:

6
nights
Nantucket

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Nantucket is known for museums, beaches, and historic sites. Your plan includes some of its best attractions: examine the collection at Whaling Museum, enjoy the sea views from Great Point Light, tour the pleasant surroundings at Surfside Beach, and kick back and relax at Jetties Beach.

For where to stay, more things to do, traveler tips, and more tourist information, read our Nantucket travel planning site.

Traveling by ferry from Hyannis to Nantucket takes 2 hours. Alternatively, you can fly. August in Nantucket sees daily highs of 76°F and lows of 63°F at night. Wrap up your sightseeing on the 8th (Sun) early enough to ride a ferry to Oak Bluffs.

Things to do in Nantucket

Outdoors · Historic Sites · Parks · Beaches
Find places to stay Aug 2 — 8:

6
nights
Oak Bluffs, Martha's Vineyard

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. You'll find plenty of places to visit near Oak Bluffs: Menemsha Public Beach (in Menemsha) and Menemsha Hills (in Chilmark). There's still lots to do: don't miss a visit to Flying Horses Carousel, pause for some serene contemplation at Old Whaling Church, see what you can catch with Skipper, and admire the natural beauty at Mytoi.

To find photos, where to stay, maps, and other tourist information, you can read our Oak Bluffs route builder site.

Traveling by ferry from Nantucket to Oak Bluffs takes 2 hours. In August, daytime highs in Oak Bluffs are 79°F, while nighttime lows are 59°F. Wrap up your sightseeing by early afternoon on the 14th (Sat) to allow time for travel to Anchorage.

Things to do in Oak Bluffs

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Find places to stay Aug 8 — 14:

19
nights
Anchorage

The City of Lights and Flowers

Home to nearly half of Alaska's population, the port city of Anchorage covers a staggering area of over 4,900 sq km (1,900 sq mi) surrounded by mountains.
Get out of town with these interesting Anchorage side-trips: Boat Tours & Water Sports (in Whittier) and Palmer (Knik Glacier Tours, Pioneer Falls, &more). Spend the 18th (Wed) on the rails with a train tour. Make the 31st (Tue) an awe-inspiring day at Chugach State Park. There's still lots to do: see the interesting displays at Anchorage Museum at Rasmuson Center, hike along Kincaid Park, identify plant and animal life at Alaska Wildlife Conservation Center, and take an in-depth tour of Alaska Aviation Heritage Museum.

To see traveler tips, ratings, where to stay, and other tourist information, use the Anchorage day trip planner.

You can fly from Oak Bluffs to Anchorage in 14.5 hours. Alternatively, you can do a combination of ferry and car. The time zone changes from Eastern Standard Time (EST) to Alaska Standard Time (AKST), which is usually a -4 hour difference. In August, Anchorage is little chillier than Oak Bluffs - with highs of 66°F and lows of 53°F. Finish up your sightseeing early on the 2nd (Thu) so you can travel back home.

Things to do in Anchorage

Parks · Nature · Outdoors · Trails

Side Trips

Find places to stay Aug 14 — Sep 2:

Massachusetts travel guide

4.3
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.