Basing yourself in Boston or Cambridge allows you to take a hub-and-spoke approach to seeing Massachusetts highlights without packing up luggage each night. On this itinerary, you’ll savor a taste of Boston and Cambridge, then set out on day trips to history-rich surrounding towns. You’ll venture in roughly chronological order: Start in Plymouth with the Pilgrims; move on to Lexington and Concord to learn about the rebellious colonists; and finally, visit the North Shore, which flourished after the Revolution. If you’re renting a car, note that you don’t need it for the full week—pick it up on (and don’t start paying for it until) Day 4.
Days 1 & 2: Boston
Begin exploring downtown Boston by walking at least part of the 2.5-mile Freedom Trail. The whole shebang can be an all-day affair, but if time is short, concentrate on the first two-thirds of the trail, from Boston Common through Faneuil Hall. Break for lunch at Faneuil Hall Marketplace, then head into the North End for a stroll on the main drag, Hanover Street, and a visit to the Paul Revere House, the oldest surviving home in downtown Boston. From there, it’s an easy walk to Long Wharf or Rowes Wharf, where you can take a sightseeing cruise or, if you want to save time and money, a water taxi ride to the Charlestown Navy Yard and back. Have dinner at Legal Sea Foods on Long Wharf, or return to the North End for Italian food.
On Day 2, prearrange tickets for a Boston Duck Tour, ideally one that leaves from the Prudential Center in the early afternoon. Be at the Museum of Fine Arts, Boston when it opens; consider taking a tour to give you an overview before you explore on your own. (The smaller Isabella Stewart Gardner Museum, a block away, is another excellent option and highly recommended.) Head to the Back Bay for lunch and your Duck Tour, then make a beeline for the retail delights of Newbury Street. Newbury dead-ends at the Public Garden, where you can unwind and perhaps go for a spin on a Swan Boat. For dinner, check out Boston’s take on French cuisine at Aquitaine Bar á Vin Bistrot, or L’Espalier if you want to pull out the stops.
Day 3: Cambridge
Start in Harvard Square with a student-led or self-guided tour of the main Harvard campus. Up next are the Harvard Art Museums, a trio of repositories for masterworks of human creation; you may prefer the Museum of Natural History, especially if children are along. Then head to lovely Brattle Street and the Longfellow House–Washington’s Headquarters. Rent a Blue Bike from any of the racks around the Square and head to the Charles River, for a meander along the well-maintained bike paths on either side of the water. For a casual evening, have dinner at Mr. Bartley’s Burger Cottage, then hit a bookstore or two; for something more fancy, go to Craigie on Main.
Day 4: Plymouth
Spend a day with the Pilgrims. Start with a 17th-century reality check at Plimoth Plantation, which opens at 9am. The hands-on activities are almost as much fun as mingling with the "settlers," who stay in character as they chat with visitors, and also interact with descendants of the Wampanoag and other Native Nations, who share their proud history and traditions. In downtown Plymouth, have lunch at the Lobster Hut, where the deck overlooks the harbor, then explore a bit, starting at Plymouth Rock. Take in some historic attractions -- the 1667 Jabez Howland House and the 1640 Sparrow House are both nearby—before returning to Boston or Cambridge for dinner.
Day 5: Lexington & Concord
Spend the morning in Lexington taking a walking tour of the historic sites and acquainting yourself with the earliest events of the Revolutionary War. Have lunch in Concord and explore the beautiful town, perhaps also visiting the Concord Museum, touring the North Bridge within Minute Man National Historical Park, and stopping at Walden Pond to dip your toes. Back in Boston, head to Top of the Hub for sunset drinks or dinner.
Day 6: Boston & Cambridge
After 2 days on the road, stick close to "home." Head to the John F. Kennedy Library and Museum, which is accessible by public transit and offers free parking (you're paying for that rental car, so you might as well get some use out of it). Spend the afternoon at the Museum of Science or the New Engalnd Aquarium, allowing enough time for an IMAX film, if that appeals to you.
Day 7: Marblehead & Salem
Begin your day on the picturesque streets of Old Town Marblehead, a top destination for both sightseeing and shopping. If your hotel room rate doesn’t include breakfast, pick up coffee and a delectable breakfast pastry at Crosby’s Marketplace. The Jeremiah Lee Mansion is a must if you enjoy house tours. Spend the afternoon in Salem, where the can’t-miss destination is the Peabody Essex Museum; if time allows, also visit the Salem Witch Museum and the House of Seven Gables. This itinerary leaves you in a handy location for returning to Boston or for heading out to explore the wonders of northern New England.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.
