29 days in Massachusetts Itinerary

29 days in Massachusetts Itinerary

Created using Inspirock Massachusetts journey planner

Plan created by another user. Make it yours

Route & dates

1
Boston
— 7 nights
2
Nantucket
— 5 nights
3
Provincetown
— 6 nights
4
Falmouth
— 6 nights
5
Westfield
— 4 nights

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.
Change things up with a short trip to Peabody Essex Museum in Salem (about 40 minutes away). And it doesn't end there: take in nature's colorful creations at Boston Public Garden, explore the different monuments and memorials at Mount Auburn Cemetery, browse the collection at Boston Public Library, and get engrossed in the history at Boston Tea Party Ships & Museum.

For other places to visit, more things to do, ratings, and other tourist information, go to the Boston day trip planner.

Use the Route module to find travel options from your starting location to Boston. In January, daily temperatures in Boston can reach °F, while at night they dip to °F. Finish your sightseeing early on the 13th (Mon) so you can travel to Nantucket.

Things to do in Boston

Museums Historic Sites Shopping

Side Trips

Cambridge, Peabody Essex Museum, Beanstalk Adventure Ropes Course, Brookline Booksmith
Highlights from your plan
Boston Public Garden ©
Boston Public Garden
Boston Common ©
Boston Common
North End ©
North End

5
nights
Nantucket

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, get curious at Maria Mitchell Association, see the sky in a new way at Loines Observatory, and enjoy the sea views from Great Point Light.

To find more things to do, where to stay, maps, and other tourist information, you can read our Nantucket itinerary planning app.

Traveling by combination of from Boston to Nantucket takes 3 hours. Alternatively, you can do a combination of car and ferry; or take a bus. In January, daily temperatures in Nantucket can reach °F, while at night they dip to °F. Wrap up your sightseeing on the 18th (Sat) to allow time to travel to Provincetown.

Things to do in Nantucket

Historic Sites Museums Childrens Museums
Highlights from your plan
Whaling Museum ©
Whaling Museum
Miacomet Golf Club ©
Miacomet Golf Club

6
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.
Get out of town with these interesting Provincetown side-trips: Chatham (Chatham Anglers, Chatham Railroad Museum, &more), Eastham (Salt Pond Visitor Center, Captain Penniman House, &more) and Orleans (Nauset Beach & Nauset Model Railroad Club). Next up on the itinerary: kick back and relax at Race Point Beach, stroll through Herring Cove Beach, snap pictures at Uncle Tim's Bridge, and examine the collection at Sea Space Marine Discovery Center.

To see more things to do, maps, ratings, and other tourist information, read Provincetown trip itinerary planner.

You can do a combination of ferry and taxi from Nantucket to Provincetown in 3 hours. Alternatively, you can fly; or do a combination of ferry and bus. January in Provincetown sees daily highs of °F and lows of °F at night. Wrap up your sightseeing on the 24th (Fri) to allow time to drive to Falmouth.

Things to do in Provincetown

Outdoors Beaches Parks

Side Trips

Chatham, Eastham, Orleans, Cape Cod National Seashore, Uncle Tim's Bridge
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Race Point Beach ©
Race Point Beach
Herring Cove Beach ©
Herring Cove Beach

6
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Explore the numerous day-trip ideas around Falmouth: Farm Neck Golf Club (in Oak Bluffs), Sandwich (Heritage Museums & Gardens & Old King's Hwy) and Edgartown (Edgartown Lighthouse & Katama Airfield). And it doesn't end there: grab your bike and head to Shining Sea Bikeway, explore the world behind art at Highfield Hall & Gardens, see the interesting displays at Richard C. Wheeler Bay Learning Center, and get engrossed in the history at Plimoth Plantation.

For maps, traveler tips, and tourist information, use the Falmouth trip planner.

You can drive from Provincetown to Falmouth in 2 hours. Another option is to take a bus. Expect slightly colder evenings in Falmouth when traveling from Provincetown in January, with lows around °F. Wrap up your sightseeing on the 30th (Thu) to allow time to travel to Westfield.

Things to do in Falmouth

Museums Historic Sites Outdoors

Side Trips

Plymouth, Sandwich, New Bedford, Edgartown, 9/11 Memorial-Acushnet
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Lizzie Borden House ©
Lizzie Borden House
Nobska Point Lighthouse ©
Nobska Point Lighthouse

4
nights
Westfield

Westfield ©
Westfield is a city in Hampden County, in the Pioneer Valley of western Massachusetts, United States. Change things up with these side-trips from Westfield: Maple Corner Farm Cross Country Ski Area (in Granville), Village Bike Rentals (in Adams) and Chester Railway Station (in Chester). There's lots more to do: admire the masterpieces at The Clark Art Institute, go for a walk through Concepts of Art Lenox Judaica, take in the exciting artwork at Ozzie's Glass Gallery, and learn about winemaking at Balderdash Cellars.

To find ratings, photos, more things to do, and tourist information, read Westfield trip builder tool.

Traveling by car from Falmouth to Westfield takes 2.5 hours. In January, Westfield is slightly colder than Falmouth - with highs of °F and lows of °F. Finish up your sightseeing early on the 3rd (Mon) so you can travel back home.

Things to do in Westfield

Outdoors Parks Winter Sports

Side Trips

Pittsfield, Dr. Seuss National Memorial Sculpture Garden, Ozzie's Glass Gallery, Notchview, Concepts of Art Lenox Judaica
Highlights from your plan
Ski Butternut ©
Ski Butternut
The Clark Art Institute ©
The Clark Art Institute
Otis Ridge ©
Otis Ridge

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