58 days in Massachusetts Itinerary

58 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner

This plan was created by another user.  Make it your plan

Route & dates

58 days in Massachusetts Itinerary

Start: San Francisco
Fly:  9​h 30​min
1
Nantucket
— 5 nights
Drive:  3​h 15​min
2
Provincetown
— 6 nights
Drive:  1​h 15​min
3
Sandwich
— 5 nights
Drive:  3​h 15​min
4
Stockbridge
— 5 nights
Drive:  2​h 30​min
5
Boston
— 8 nights
train:  45​min
6
Salem
— 3 nights
Drive:  2​h
7
Falmouth
— 3 nights
Drive:  1​h 15​min
8
Edgartown, Martha's Vineyard
— 3 nights
Drive:  2​h
9
Plymouth
— 3 nights
Drive:  1​h
10
Eastham
— 3 nights
Drive:  2​h 30​min
11
Gloucester
— 3 nights
Drive:  1​h
12
Concord
— 3 nights
Drive:  30​min
13
Cambridge
— 5 nights
Drive:  2​h 30​min
14
Orleans
— 2 nights
Drive + Fly:  9​h 15​min
End: San Francisco

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, historic sites, breweries & distilleries, and outdoors. Your plan includes some of its best attractions: examine the collection at Whaling Museum, make a trip to Brant Point Lighthouse, enjoy the sea views from Sankaty Head Lighthouse, and get engrossed in the history at Egan Maritime's Nantucket Shipwreck & Lifesaving Museum.

To see more things to do, ratings, where to stay, and more tourist information, use the Nantucket trip planner.

San Francisco to Nantucket is an approximately 9.5-hour flight. You can also do a combination of flight and ferry; or do a combination of train and flight. Due to the time zone difference, you'll lose 3 hours traveling from San Francisco to Nantucket. Traveling from San Francisco in November, expect Nantucket to be little chillier, temps between 53°F and 41°F. Finish your sightseeing early on the 6th (Wed) so you can drive to Provincetown.

Things to do in Nantucket

Historic Sites Beaches Parks
Highlights from your plan
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse
Whaling Museum ©
Whaling Museum
Great Point Light ©
Great Point Light

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.
Provincetown is known for wildlife, beaches, nightlife, trails, and museums. Your plan includes some of its best attractions: explore the galleries of Pilgrim Monument & Provincetown Museum, identify plant and animal life at Wildlife Areas, stroll through Herring Cove Beach, and get lost in a book at Provincetown Library.

To find photos, more things to do, reviews, and other tourist information, read our Provincetown day trip planning tool .

You can drive from Nantucket to Provincetown in 3.5 hours. In November, daytime highs in Provincetown are 51°F, while nighttime lows are 39°F. Cap off your sightseeing on the 12th (Tue) early enough to go by car to Sandwich.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Truro, Truro Vineyards of Cape Cod
Highlights from your plan
Race Point Beach ©
Race Point Beach
Herring Cove Beach ©
Herring Cove Beach

5
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Change things up with these side-trips from Sandwich: New Bedford Whaling Museum (in New Bedford), Yarmouth Port (Captain Bangs Hallet House Museum & Edward Gorey House) and Cape Cod Maritime Museum (in Hyannis Port). And it doesn't end there: examine the collection at Heritage Museums & Gardens, steep yourself in history at Quaker Friends Meetinghouse, enjoy the sand and surf at Sandy Neck Beach, and get curious at Sandwich Glass Museum.

To find reviews, other places to visit, where to stay, and more tourist information, refer to the Sandwich sightseeing site .

Traveling by car from Provincetown to Sandwich takes 1.5 hours. Alternatively, you can take a bus. In November, daytime highs in Sandwich are 53°F, while nighttime lows are 35°F. Finish up your sightseeing early on the 17th (Sun) so you can go by car to Stockbridge.

Things to do in Sandwich

Museums Parks Historic Sites

Side Trips

Hyannis, Yarmouth Port, Osterville Village Library, New Bedford Whaling Museum, Cape Cod Maritime Museum
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum
Old King's Hwy ©
Old King's Hwy

5
nights
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. You'll find plenty of places to visit near Stockbridge: Franklin D. Roosevelt Presidential Library and Museum (in Hyde Park), Hildene, The Lincoln Family Home (in Manchester) and Walkway Over the Hudson State Historic Park (in Poughkeepsie). The adventure continues: walk around Stanley park, admire the masterpieces at The Clark Art Institute, contemplate the long history of Hancock Shaker Village, and have some family-friendly fun at The Berkshire Carousel.

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

You can drive from Sandwich to Stockbridge in 3.5 hours. Alternatively, you can take a bus; or do a combination of flight and bus. Traveling from Sandwich in November, things will get slightly colder in Stockbridge: highs are around 47°F and lows about 28°F. Finish your sightseeing early on the 22nd (Fri) to allow enough time to drive to Boston.

Things to do in Stockbridge

Museums Historic Sites Parks

Side Trips

Pittsfield, Lenox, Franklin D. Roosevelt Presidential Library and Museum, Hildene, The Lincoln Family Home, MASS MoCA
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
Stanley park ©
Stanley park

8
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.
Boston is known for historic sites, museums, parks, shopping, and nightlife. Your plan includes some of its best attractions: explore the world behind art at Museum of Fine Arts, get engrossed in the history at John F. Kennedy Presidential Museum & Library, walk around Boston Common, and make a trip to Boston Public Library.

To see photos, maps, where to stay, and tourist information, read Boston tour planner.

Getting from Stockbridge to Boston by car takes about 2.5 hours. Other options: take a bus; or take a train. Expect a bit warmer evenings in Boston when traveling from Stockbridge in November, with lows around 37°F. Finish up your sightseeing early on the 30th (Sat) so you can catch the train to Salem.

Things to do in Boston

Museums Parks Historic Sites
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Freedom Trail ©
Freedom Trail

3
nights
Salem

Salem ©
Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Kick off your visit on the 1st (Sun): have some family-friendly fun at Witch Pix, examine the collection at Peabody Essex Museum, get engrossed in the history at Salem Witch Museum, then steep yourself in history at The House of the Seven Gables, and finally go for a stroll along the water at Pickering Wharf. Get ready for a full day of sightseeing on the next day: stroll around Salem Witch Trials Memorial, then steep yourself in history at Salem Maritime National Historic Site, and then appreciate the extensive heritage of Marginal Way Walkway.

For maps, where to stay, reviews, and more tourist information, refer to the Salem day trip tool .

You can take a train from Boston to Salem in an hour. Other options are to drive; or take a bus. In November, daytime highs in Salem are 51°F, while nighttime lows are 33°F. Wrap up your sightseeing by early afternoon on the 3rd (Tue) to allow enough time to drive to Falmouth.

Things to do in Salem

Historic Sites Museums Parks

Side Trip

Marginal Way Walkway
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
The House of the Seven Gables ©
The House of the Seven Gables
Peabody Essex Museum ©
Peabody Essex Museum

3
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Falmouth is known for trails, historic sites, zoos & aquariums, beaches, and museums. Your plan includes some of its best attractions: tour the pleasant surroundings at Shining Sea Bikeway, kick back and relax at Old Silver Beach, enjoy the sea views from Nobska Point Lighthouse, and appreciate the extensive heritage of Cornelia Carey Sanctuary (The Knob).

For maps, photos, ratings, and more tourist information, read our Falmouth trip planner .

Traveling by car from Salem to Falmouth takes 2 hours. Alternatively, you can take a bus; or fly. Expect a daytime high around 46°F in December, and nighttime lows around 30°F. Wrap up your sightseeing on the 6th (Fri) to allow time to drive to Edgartown.

Things to do in Falmouth

Parks Museums Outdoors

Side Trip

Mashpee
Highlights from your plan
Woods Hole Science Aquarium ©
Woods Hole Science Aquarium
Cornelia Carey Sanctuary (The Knob) ©
Highfield Hall & Gardens ©
Highfield Hall & Gardens

3
nights
Edgartown, Martha's Vineyard

Edgartown ©
Edgartown is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. On the 7th (Sat), visit a coastal fixture at Edgartown Lighthouse, then kick back and relax at Katama Beach/ South Beach, then take a stroll through Martha's Vineyard Camp meeting Association (MVCMA), and finally make a trip to Circuit Avenue. Keep things going the next day: head off the coast to Chappaquiddick, take in nature's colorful creations at Mytoi, then admire the striking features of Trinity Park Tabernacle, then make a trip to Flying Horses Carousel, and finally make a trip to Edgartown Books.

For traveler tips and other tourist information, go to the Edgartown road trip planning website .

Getting from Falmouth to Edgartown by car takes about 1.5 hours. In December, daily temperatures in Edgartown can reach 46°F, while at night they dip to 30°F. Wrap up your sightseeing by early afternoon on the 9th (Mon) to allow time for the car ride to Plymouth.

Things to do in Edgartown

Parks Historic Sites Nature

Side Trips

Oak Bluffs, Aquinnah Cliffs
Highlights from your plan
Katama Beach/ South Beach ©
Katama Beach/ South Beach
Trinity Park Tabernacle ©
Trinity Park Tabernacle
Edgartown Lighthouse ©
Edgartown Lighthouse

3
nights
Plymouth

Plymouth ©
Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
Plymouth is known for museums, historic sites, nature, wildlife, and parks. Your plan includes some of its best attractions: take an in-depth tour of Plimoth Plantation, explore the different monuments and memorials at Burial Hill, step off the mainland to explore Brown's Bank, and admire the majestic nature at National Monument to the Forefathers.

To see where to stay, traveler tips, and other tourist information, you can read our Plymouth trip planning site .

Traveling by car from Edgartown to Plymouth takes 2 hours. In December in Plymouth, expect temperatures between 44°F during the day and 29°F at night. Finish your sightseeing early on the 12th (Thu) so you can drive to Eastham.

Things to do in Plymouth

Museums Parks Outdoors
Highlights from your plan
Plimoth Plantation ©
Plimoth Plantation
Plymouth Rock ©
Plymouth Rock
Mayflower II ©
Mayflower II

3
nights
Eastham

Eastham ©
Eastham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Kick off your visit on the 13th (Fri): get engrossed in the history at Salt Pond Visitor Center and then stroll through Cape Cod National Seashore. Get ready for a full day of sightseeing on the 14th (Sat): stroll through Marconi Beach, tour the pleasant surroundings at Coast Guard Beach, then visit a coastal fixture at Nauset Lighthouse, and finally contemplate the long history of Captain Penniman House.

For more things to do, other places to visit, reviews, and more tourist information, you can read our Eastham trip planner .

Traveling by car from Plymouth to Eastham takes an hour. Alternatively, you can take a bus. In December in Eastham, expect temperatures between 45°F during the day and 33°F at night. On the 15th (Sun), wrap the sightseeing up by early afternoon so you can drive to Gloucester.

Things to do in Eastham

Beaches Parks Outdoors

Side Trips

Wellfleet, Cape Cod National Seashore
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Salt Pond Visitor Center ©
Salt Pond Visitor Center
Coast Guard Beach ©
Coast Guard Beach

3
nights
Gloucester

The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
Gloucester is known for wildlife, beaches, historic sites, museums, and parks. Your plan includes some of its best attractions: see majestic marine mammals with a dolphin and whale watching tour, kick back and relax at Good Harbor Beach, pause for some photo ops at Fishermen's Memorial Monument, and walk around Ravenswood Park.

To find reviews, more things to do, other places to visit, and more tourist information, you can read our Gloucester online day trip planner .

Traveling by car from Eastham to Gloucester takes 2.5 hours. Alternatively, you can do a combination of bus and train; or do a combination of ferry and train. Traveling from Eastham in December, you can expect nighttime temperatures to be slightly colder in Gloucester, with lows of 27°F. Wrap up your sightseeing on the 18th (Wed) to allow time to drive to Concord.

Things to do in Gloucester

Outdoors Parks Wildlife

Side Trips

Rockport, Cogswell's Grant
Highlights from your plan
Dolphin & Whale Watching
Fishermen's Memorial Monument ©
Fishermen's Memorial Monument
Ravenswood Park ©
Ravenswood Park

3
nights
Concord

Concord ©
Concord is a town in Middlesex County, Massachusetts, in the United States. Kick off your visit on the 19th (Thu): immerse yourself in nature at Walden Pond State Reservation, browse the exhibits of Louisa May Alcott's Orchard House, then take in the views from North Bridge, and finally explore the different monuments and memorials at Sleepy Hollow Cemetery. Get ready for a full day of sightseeing on the 20th (Fri): steep yourself in history at Buckman Tavern, then walk around The Old Manse, then steep yourself in history at Minute Man National Historical Park, and finally test your problem-solving skills at popular escape rooms.

To see other places to visit, where to stay, maps, and tourist information, you can read our Concord trip planning tool .

Traveling by car from Gloucester to Concord takes an hour. Alternatively, you can take a train. In December, daily temperatures in Concord can reach 40°F, while at night they dip to 25°F. Wrap up your sightseeing by early afternoon on the 21st (Sat) to allow time for the car ride to Cambridge.

Things to do in Concord

Historic Sites Parks Nature

Side Trips

Tower Hill Botanic Garden, Room Escape Games, Buckman Tavern
Highlights from your plan
North Bridge ©
North Bridge
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House
Walden Pond State Reservation ©
Walden Pond State Reservation

5
nights
Cambridge

Cambridge ©
Best known as the location of two internationally renowned universities, Cambridge sits just across the Charles River from Boston.
Change things up with these side-trips from Cambridge: Foxwoods Resort Casino (in Mashantucket) and Upper Charles Bike Trail (in Milford). There's still lots to do: stroll the grounds of Mount Auburn Cemetery, contemplate the long history of Longfellow House Washington's Headquarters National Historic Site, learn more about the world around you at Harvard Museum of Natural History, and gain insight at Massachusetts Institute of Technology (MIT).

To find more things to do, where to stay, and more tourist information, read Cambridge trip planning app .

Cambridge is very close to Concord. Traveling from Concord in December, Cambridge is somewhat warmer at night with lows of 31°F. Cap off your sightseeing on the 26th (Thu) early enough to travel to Orleans.

Things to do in Cambridge

Museums Parks Historic Sites

Side Trips

Needham, Foxwoods Resort Casino, Lord Hobo Brewing Company, Museum of Bad Art, Upper Charles Bike Trail
Highlights from your plan
The Harvard Museum of Natural History ©
Mount Auburn Cemetery ©
Mount Auburn Cemetery
Harvard University ©
Harvard University

2
nights
Orleans

Orleans ©
Orleans is a town in Barnstable County, Massachusetts, which is co-extensive with Cape Cod. Go for a jaunt from Orleans to Chatham to see Monomoy National Wildlife Refuge about 30 minutes away. There's lots more to do: kick back and relax at Chatham Lighthouse Beach, hike along Cape Cod Rail Trail, take an in-depth tour of Chatham Marconi Maritime Center, and stroll through Nauset Beach.

For reviews, traveler tips, maps, and other tourist information, read our Orleans trip itinerary website .

You can drive from Cambridge to Orleans in 2 hours. In December, plan for daily highs up to 45°F, and evening lows to 33°F. Finish your sightseeing early on the 28th (Sat) so you can travel back home.

Things to do in Orleans

Parks Outdoors Trails

Side Trips

Chatham, Cape Cod Rail Trail
Highlights from your plan
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Monomoy National Wildlife Refuge ©
Monomoy National Wildlife Refuge
Nauset Beach ©
Nauset Beach

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