28 days in Massachusetts Itinerary

28 days in Massachusetts Itinerary

Created using Inspirock Massachusetts holiday planner

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Route & dates

28 days in Massachusetts Itinerary

Start: New York City
Drive:  3​h 30​min
1
Attleboro
— 4 nights
Drive:  1​h
2
Boston
— 7 nights
ferry:  1​h 30​min
3
Provincetown
— 4 nights
Drive:  1​h 15​min
4
Hyannis
— 4 nights
Drive:  2​h
5
Oak Bluffs, Martha's Vineyard
— 3 nights
Drive:  2​h 30​min
6
Nantucket
— 5 nights
Fly:  4​h 30​min
End: New York City

4
nights
Attleboro

Attleboro ©
Attleboro is a city in Bristol County, Massachusetts, United States. Your day-by-day itinerary now includes Capron Park Zoo. Bring the kids along to North Attleboro World War I Memorial Park and Roger Williams Park Zoo. Change things up with these side-trips from Attleboro: Lizzie Borden House (in Fall River), Colt State Park (in Bristol) and New Bedford Whaling Museum (in New Bedford). There's much more to do: have some family-friendly fun at Davis Farmland, contemplate the long history of The Stephen Hopkins House, contemplate in the serene atmosphere at National Shrine of our Lady of La Salette, and get lost in a book at Seekonk Public Library.

To see photos, traveler tips, ratings, and other tourist information, you can read our Attleboro trip itinerary site .

New York City to Attleboro is an approximately 3.5-hour car ride. Traveling from New York City in October, expect Attleboro to be a bit cooler, temps between 63°F and 44°F. Finish your sightseeing early on the 30th (Wed) to allow enough time to drive to Boston.

Things to do in Attleboro

Parks Museums Zoos & Aquariums

Side Trips

Providence, Colt State Park, Lizzie Borden House, New Bedford Whaling Museum, Indian Head Farm
Highlights from your plan
Capron Park Zoo ©
Capron Park Zoo
Davis Farmland ©
Davis Farmland
Roger Williams Park Zoo ©
Roger Williams Park Zoo

7
nights
Boston

Boston ©
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.
You'll visit kid-friendly attractions like Museum of Fine Arts and Faneuil Hall Marketplace. Change things up with these side-trips from Boston: Dolphin & Whale Watching (in Gloucester) and Salem (Salem Witch Museum, The House of the Seven Gables, & more). The adventure continues: take in nature's colorful creations at Boston Public Garden, walk around Boston Common, appreciate the extensive heritage of Freedom Trail, and traverse land and water with a duck tour.

For maps, other places to visit, where to stay, and tourist information, you can read our Boston trip itinerary builder site .

Traveling by car from Attleboro to Boston takes an hour. Expect a bit warmer evenings in Boston when traveling from Attleboro in October, with lows around 50°F. Cap off your sightseeing on the 6th (Wed) early enough to catch the ferry to Provincetown.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Salem, Concord, Dolphin & Whale Watching, Mount Auburn Cemetery
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
New England Aquarium ©
New England Aquarium

4
nights
Provincetown

Provincetown ©
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.
Bring the kids along to Cape Cod National Seashore and Race Point Beach. Venture out of the city with trips to Nauset Beach (in Orleans) and Eastham (Nauset Light Beach & Coast Guard Beach). There's much more to do: appreciate the history behind Pilgrim Monument & Provincetown Museum, enjoy the sand and surf at Long Point, tour the pleasant surroundings at Herring Cove Beach, and don't miss a visit to Commercial Street.

To see reviews, photos, and other tourist information, read Provincetown route planning app .

You can ride a ferry from Boston to Provincetown in 1.5 hours. Other options are to fly; or drive. In November, plan for daily highs up to 51°F, and evening lows to 39°F. Finish your sightseeing early on the 10th (Sun) to allow enough time to drive to Hyannis.

Things to do in Provincetown

Beaches Parks Outdoors

Side Trips

Eastham, Cape Cod National Seashore, Marconi Beach, Nauset Beach, Truro Vineyards of Cape Cod
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Nauset Beach ©
Nauset Beach
Race Point Beach ©
Race Point Beach

4
nights
Hyannis

Hyannis ©
"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Family-friendly places like Plimoth Plantation and Mayflower II will thrill your kids. Explore the numerous day-trip ideas around Hyannis: Woods Hole (Woods Hole Science Aquarium & Nobska Point Lighthouse), Falmouth (Shining Sea Bikeway, Old Silver Beach, & more) and Plymouth Rock (in Plymouth). There's still lots to do: engage your brain at Sandwich Glass Museum, see the interesting displays at Heritage Museums & Gardens, view the masterpieces at Samuell Day Gallery, and have fun and explore at Cape Cod Children's Museum.

Plan my Hyannis trip by asking Inpirock to come up with tips and suggestions.

You can drive from Provincetown to Hyannis in 1.5 hours. Another option is to take a bus. Expect a daytime high around 53°F in November, and nighttime lows around 37°F. Finish your sightseeing early on the 14th (Thu) so you can drive to Oak Bluffs.

Things to do in Hyannis

Parks Museums Outdoors

Side Trips

Falmouth, Sandwich, Plymouth, Cape Cod Children's Museum, Samuell Day Gallery
Highlights from your plan
Woods Hole Science Aquarium ©
Woods Hole Science Aquarium
Plimoth Plantation ©
Plimoth Plantation
Sandwich Glass Museum ©
Sandwich Glass Museum

3
nights
Oak Bluffs, Martha's Vineyard

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Kids will enjoy Flying Horses Carousel and Menemsha Public Beach. There's much more to do: admire the striking features of Trinity Park Tabernacle, tour the pleasant surroundings at Katama Beach/ South Beach, enjoy the sea views from Edgartown Lighthouse, and take in nature's colorful creations at Mytoi.

To see reviews, ratings, and tourist information, read Oak Bluffs tour planning tool .

Traveling by car from Hyannis to Oak Bluffs takes 2 hours. In November, daytime highs in Oak Bluffs are 53°F, while nighttime lows are 37°F. Cap off your sightseeing on the 17th (Sun) early enough to go by car to Nantucket.

Things to do in Oak Bluffs

Parks Outdoors Neighborhoods

Side Trips

Edgartown, West Tisbury, Menemsha Public Beach
Highlights from your plan
Mytoi ©
Mytoi
Flying Horses Carousel ©
Flying Horses Carousel
Menemsha Public Beach ©
Menemsha Public Beach

5
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. You'll visit kid-friendly attractions like Jetties Beach and Madaket Beach. The adventure continues: see the interesting displays at Whaling Museum, see the sky in a new way at Loines Observatory, enjoy the sea views from Sankaty Head Lighthouse, and get to know the fascinating history of Milestone Bog.

To find ratings, reviews, more things to do, and more tourist information, read Nantucket travel route planner .

Getting from Oak Bluffs to Nantucket by car takes about 2.5 hours. November in Nantucket sees daily highs of 53°F and lows of 41°F at night. Wrap up your sightseeing on the 22nd (Fri) early enough to travel back home.

Things to do in Nantucket

Historic Sites Parks Outdoors
Highlights from your plan
Great Point Light ©
Great Point Light
Jetties Beach ©
Jetties Beach
Madaket Beach ©
Madaket Beach

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