18 days in Massachusetts Itinerary

18 days in Massachusetts Itinerary

Created using Inspirock Massachusetts holiday planner

Plan created by another user. Make it yours
1
Lenox
— 2 nights
2
Nantucket
— 4 nights
3
Oak Bluffs, Martha's Vineyard
— 3 nights
4
Provincetown
— 5 nights
5
Sandwich
— 3 nights

2
nights
Lenox

Lenox ©
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Kick off your visit on the 14th (Mon): immerse yourself in nature at Mount Greylock State Reservation, admire the masterpieces at MASS MoCA, and then admire the masterpieces at Williams College Museum of Art. Get ready for a full day of sightseeing on the next day: contemplate the long history of The Mount, Edith Wharton's Home, get a taste of the local shopping with Ozzie's Glass Gallery, then contemplate the long history of Hancock Shaker Village, and finally look for gifts at Williams & Sons Country Store.

To find traveler tips, more things to do, other places to visit, and tourist information, refer to the Lenox trip builder app.

Dubuque to Lenox is an approximately 10.5-hour combination of flight and bus. You can also drive; or do a combination of bus, subway, and train. The time zone difference when traveling from Dubuque to Lenox is 1 hour. Traveling from Dubuque in September, expect a bit cooler with lows of 49°F in Lenox. Finish your sightseeing early on the 15th (Tue) to allow enough time to travel to Nantucket.

Things to do in Lenox

Museums · Historic Sites · Wildlife

Side Trips

MASS MoCA, Williams & Sons Country Store, Mount Greylock State Reservation, Williams College Museum of Art, Ozzie's Glass Gallery
Highlights from your plan
Mount Greylock State Reservation ©
Mount Greylock State Reservation
Williams College Museum of Art ©
Williams College Museum of Art
Ozzie's Glass Gallery ©
Ozzie's Glass Gallery

4
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Discover out-of-the-way places like Brant Point Lighthouse and Sankaty Head Lighthouse. Take a break from the city and head to Madaket Beach and Surfside Beach. There's still lots to do: enjoy the sea views from Great Point Light, make a trip to Nantucket Founders Burial Ground, look for gifts at The Hub, and pause for some serene contemplation at St Paul's Episcopal Church.

To see where to stay, more things to do, photos, and tourist information, refer to the Nantucket trip maker tool.

Traveling by combination of car and ferry from Lenox to Nantucket takes 5.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus and ferry. Traveling from Lenox in September, Nantucket is a bit warmer at night with lows of 59°F. Wrap up your sightseeing on the 19th (Sat) to allow time to ride a ferry to Oak Bluffs.

Things to do in Nantucket

Outdoors · Historic Sites · Parks
Highlights from your plan
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse
Fishing Charters & Tours
Madaket Beach ©
Madaket Beach

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. Get in touch with nature at Menemsha Public Beach and Aquinnah Cliffs. Head to Chilmark Chocolates and Field Galleryfor some retail therapy. Go for a jaunt from Oak Bluffs to Aquinnah to see Gay Head Lighthouse about 40 minutes away. And it doesn't end there: enjoy the sand and surf at Oak Bluffs Town Beach, stroll through Katama Beach/ South Beach, don't miss a visit to Flying Horses Carousel, and enjoy the sea views from Edgartown Lighthouse.

To find other places to visit, photos, traveler tips, and tourist information, go to the Oak Bluffs road trip planning site.

Traveling by ferry from Nantucket to Oak Bluffs takes 2 hours. Plan for little chillier nights when traveling from Nantucket in September since evenings lows in Oak Bluffs dip to 54°F. Finish up your sightseeing early on the 22nd (Tue) so you can travel to Provincetown.

Things to do in Oak Bluffs

Parks · Outdoors · Beaches

Side Trips

Edgartown, Aquinnah, Field Gallery, Menemsha Public Beach, Chilmark Chocolates
Highlights from your plan
Menemsha Public Beach ©
Menemsha Public Beach
Gay Head Lighthouse ©
Gay Head Lighthouse
Oak Bluffs Town Beach ©
Oak Bluffs Town Beach

5
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.
You'll explore and learn at Salt Pond Visitor Center and Addison Art Gallery. Visiting Wellfleet Bay Wildlife Sanctuary and Cape Cod National Seashore will get you outdoors. Explore Provincetown's surroundings by going to Orleans (Nauset Beach & Church of the Transfiguration), Eastham (Nauset Lighthouse & Coast Guard Beach) and Ducks in the Window (in Chatham). And it doesn't end there: trek along Cape Cod Provincelands Trail, kick back and relax at Marconi Beach, get lost in a book at Provincetown Library, and cast your line with a fishing tour.

For reviews, maps, photos, and more tourist information, go to the Provincetown online trip itinerary builder.

Do a combination of ferry and car from Oak Bluffs to Provincetown in 3 hours. Alternatively, you can fly; or do a combination of ferry and bus. Expect a daytime high around 71°F in September, and nighttime lows around 57°F. Wrap up your sightseeing on the 27th (Sun) early enough to drive to Sandwich.

Things to do in Provincetown

Outdoors · Parks · Beaches

Side Trips

Wellfleet, Orleans, Eastham, Cape Cod National Seashore, Fishing Charters & Tours
Highlights from your plan
Wellfleet Bay Wildlife Sanctuary ©
Wellfleet Bay Wildlife Sanctuary
Cape Cod Provincelands Trail ©
Cape Cod Provincelands Trail
Nauset Lighthouse ©
Nauset Lighthouse

3
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Visiting Skaket Beach and Chatham Lighthouse Beach will get you outdoors. Your inner history buff will appreciate Lizzie Borden House and Nobska Point Lighthouse. Go for a jaunt from Sandwich to New Bedford to see New Bedford Whaling Museum about 38 minutes away. There's still lots to do: see the interesting displays at Heritage Museums & Gardens, grab your bike and head to Shining Sea Bikeway, and admire the majestic nature at National Monument to the Forefathers.

To find ratings, maps, and more tourist information, use the Sandwich trip itinerary website.

Traveling by car from Provincetown to Sandwich takes 1.5 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 73°F, and evening lows to 55°F. Finish your sightseeing early on the 30th (Wed) so you can travel back home.

Things to do in Sandwich

Museums · Parks · Outdoors

Side Trips

Falmouth, New Bedford Whaling Museum, Lizzie Borden House, John F Kennedy Hyannis Museum, Skaket Beach
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Skaket Beach ©
Skaket Beach
Lizzie Borden House
Lizzie Borden House

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