8 days in Portsmouth, Cape Cod & Boston Itinerary

8 days in Portsmouth, Cape Cod & Boston Itinerary

Created using Inspirock United States visit planner

Make it your trip
Drive
1
Portsmouth
— 2 nights
Drive
2
Provincetown
— 2 nights
Ferry
3
Boston
— 3 nights
Drive

S M T W T F S
18
19
20
21
22
23
24
25
26
27
28
29
30
31

Portsmouth

— 2 nights
Portsmouth is a city in Rockingham County, New Hampshire, in the United States. Kick off your visit on the 18th (Sun): enjoy the sea views from Portsmouth Harbor Lighthouse and then don't miss a visit to Market Square. Here are some ideas for day two: stroll through Hampton Beach State Park, explore the world behind art at Currier Museum of Art, and then stroll around Prescott Park.

To see where to stay, maps, photos, and other tourist information, read our Portsmouth trip itinerary planning website.

Herndon to Portsmouth is an approximately 8-hour car ride. You can also do a combination of car and flight; or drive. Traveling from Herndon in October, you will find days in Portsmouth are little chillier (62°F), and nights are about the same (44°F). Wrap up your sightseeing by early afternoon on the 20th (Tue) to allow time for the car ride to Provincetown.

Things to do in Portsmouth

Parks · Beaches · Museums · Outdoors

Side Trips

Provincetown

— 2 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.
Start off your visit on the 20th (Tue): kick back and relax at Herring Cove Beach. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Race Point Beach, explore the activities along Provincetown Waterfront Memorial Park, then pause for some photo ops at Pilgrim Monument & Provincetown Museum, then take a leisurely stroll along MacMillan Wharf, and finally see majestic marine mammals with a dolphin and whale watching tour.

For ratings, maps, where to stay, and other tourist information, go to the Provincetown online trip itinerary maker.

Traveling by car from Portsmouth to Provincetown takes 3.5 hours. Alternatively, you can drive; or fly; or do a combination of bus and ferry. In October, daily temperatures in Provincetown can reach 63°F, while at night they dip to 49°F. On the 22nd (Thu), wrap the sightseeing up by early afternoon so you can travel to Boston.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

Boston

— 3 nights

Beantown

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, and parks. Your plan includes some of its best attractions: admire the masterpieces at Museum of Fine Arts, stroll the grounds of Granary Burying Ground, wander the streets of North End, and get engrossed in the history at Boston Tea Party Ships & Museum.

To find ratings, photos, traveler tips, and tourist information, you can read our Boston trip tool.

You can ride a ferry from Provincetown to Boston in 2.5 hours. Alternatively, you can fly; or ride a ferry; or drive. Expect a daytime high around 64°F in October, and nighttime lows around 50°F. You will leave for home on the 25th (Sun).

Things to do in Boston

Museums · Historic Sites · Parks · Neighborhoods

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.