29 days in Massachusetts Itinerary

29 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner

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Make it your trip
1
Plymouth
— 14 nights
Drive
2
Chatham
— 2 nights
Drive
3
Eastham
— 2 nights
Drive
4
Dennis
— 2 nights
Drive
5
Hyannis
— 2 nights
Drive
6
Falmouth
— 3 nights
Drive
7
Provincetown
— 3 nights
Drive

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Plymouth

— 14 nights

America's Hometown

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.
Venture out of the city with trips to Chatham Marconi Maritime Center (in North Chatham), Eastham (Salt Pond Visitor Center, Coast Guard Beach, &more) and Marconi Beach (in Wellfleet). There's much more to do: examine the collection at Heritage Museums & Gardens, don't miss a visit to Old King's Hwy, engage your brain at Sandwich Glass Museum, and enjoy the sand and surf at Cape Cod National Seashore.

To find traveler tips, reviews, and other tourist information, use the Plymouth trip planner.

The Route module shows you all the different ways you can get to Plymouth. September in Plymouth sees daily highs of 75°F and lows of 55°F at night. Finish up your sightseeing early on the 17th (Thu) so you can go by car to Chatham.

Things to do in Plymouth

Museums · Parks · Historic Sites · Beaches

Side Trips

Chatham

— 2 nights
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Your day by day itinerary now includes Monomoy Island Ferry. Kick off your visit on the 18th (Fri): get a new perspective on things with Monomoy Island Ferry, then see the interesting displays at Chatham Railroad Museum, and then take in the waterfront at Chatham Pier and Fish Market. On the 19th (Sat), you'll have a packed day of sightseeing: explore the world behind art at Atwood Museum and then identify plant and animal life at Monomoy National Wildlife Refuge.

To find ratings, reviews, photos, and more tourist information, you can read our Chatham online road trip planner.

Drive from Plymouth to Chatham in an hour. Alternatively, you can take a bus. Expect a daytime high around 72°F in September, and nighttime lows around 59°F. Wrap up your sightseeing on the 19th (Sat) early enough to drive to Eastham.

Things to do in Chatham

Wildlife · Parks · Museums · Shopping

Eastham

— 2 nights
Eastham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Start off your visit on the 20th (Sun): pause for some photo ops at Eastham Windmill. Get ready for a full day of sightseeing on the 21st (Mon): enjoy the sea views from Nauset Lighthouse and then contemplate the long history of Doane Rock.

For maps, ratings, traveler tips, and tourist information, refer to the Eastham trip planning website.

Eastham is just a stone's throw from Chatham. In September, plan for daily highs up to 72°F, and evening lows to 59°F. Finish your sightseeing early on the 21st (Mon) so you can drive to Dennis.

Things to do in Eastham

Historic Sites

Dennis

— 2 nights
Dennis is a town in Barnstable County, Massachusetts, United States, located near the center of Cape Cod. Kick off your visit on the 22nd (Tue): contemplate the long history of Captain Bangs Hallet House Museum, stroll through Mayflower Beach, and then enjoy breathtaking views from Scargo Tower. On your second day here, admire the majestic nature at Nickerson State Park.

To see photos, where to stay, ratings, and tourist information, refer to the Dennis trip itinerary planner.

Dennis is very close to Eastham. Expect a daytime high around 73°F in September, and nighttime lows around 57°F. Wrap up your sightseeing by early afternoon on the 23rd (Wed) to allow time for the car ride to Hyannis.

Things to do in Dennis

Parks · Nature · Beaches · Outdoors

Side Trips

Hyannis

— 2 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
You've now added Bay Spirit Tours to your itinerary. Start off your visit on the 24th (Thu): shop like a local with Samuell Day Gallery, indulge your thirst for a good beer at Cape Cod Beer, and then take in the spiritual surroundings of St. Francis Xavier Church. Get ready for a full day of sightseeing on the 25th (Fri): take a tour by water with Bay Spirit Tours, walk around Veterans Memorial Park, and then enjoy the sand and surf at Kalmus Beach.

To find more things to do, maps, ratings, and tourist information, refer to the Hyannis tour itinerary planner.

Hyannis is very close to Dennis. September in Hyannis sees daily highs of 73°F and lows of 57°F at night. Finish your sightseeing early on the 25th (Fri) so you can drive to Falmouth.

Things to do in Hyannis

Parks · Outdoors · Historic Sites · Tours

Side Trip

Falmouth

— 3 nights
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Kick off your visit on the 26th (Sat): examine the collection at Falmouth Museums on the Green, take in nature's colorful creations at Spohr Gardens, then engage your brain at Marine Biological Laboratory, and finally snap pictures at Woods Hole Drawbridge. On your second day here, enjoy the sea views from Edgartown Lighthouse, then wander the streets of Martha's Vineyard Camp meeting Association (MVCMA), and then admire the landmark architecture of Trinity Park Tabernacle.

For more things to do, photos, maps, and other tourist information, refer to the Falmouth trip planner.

You can drive from Hyannis to Falmouth in an hour. Another option is to take a bus. In September, daily temperatures in Falmouth can reach 73°F, while at night they dip to 55°F. Wrap up your sightseeing by early afternoon on the 28th (Mon) to allow enough time to drive to Provincetown.

Things to do in Falmouth

Museums · Historic Sites · Neighborhoods · Childrens Museums

Side Trips

Provincetown

— 3 nights

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.
Your day by day itinerary now includes Dolphin Fleet Whale Watch. And it doesn't end there: browse the exhibits of Pilgrim Monument & Provincetown Museum, admire the masterpieces at Provincetown Town Hall, take in the waterfront at MacMillan Wharf, and don't miss a visit to Commercial Street.

To see maps, where to stay, more things to do, and tourist information, use the Provincetown trip planning tool.

Drive from Falmouth to Provincetown in 2 hours. Alternatively, you can take a bus. In September, daily temperatures in Provincetown can reach 71°F, while at night they dip to 57°F. On the 1st (Thu), you'll have the morning to explore before heading back home.

Things to do in Provincetown

Wildlife · Tours · Outdoors · Museums

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
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.

Cape Cod travel guide

4.4
Beaches · Dolphin & Whale Watching · Specialty Museums
Located on the southern shore of Massachusetts, Cape Cod contains some 15 towns and two islands. The arm-shaped peninsula is a popular holiday destination throughout the year because of its historical attractions, art galleries, award-winning restaurants, and a scenic coastline dotted by sandy beaches. Start your sightseeing in Provincetown, located at the very tip of the cape and famous for being the site of the first Pilgrims' landing in 1620. From there you can hit up all of the Cape's other small towns, renowned for their comfortable bed and breakfasts and distinctive cuisine of fresh fish and oyster dishes. This maritime community features more than a dozen lighthouses. Part of experiencing the Cape means a trip to its two islands--which showcase several lighthouses and numerous restaurants.