Long Weekend: 3 Days in Boston
I’m just back from a long weekend getaway in Boston that reminded me why fall is one of my favorite seasons to travel and how in just three days you can feel like you've truly taken in a destination so rich in history. This itinerary is perfect for a 3-day weekend taking in the major sites of the city, escaping to the coast and exploring some of the city’s best neighborhoods, from old to up-and-coming.
Day 1: Best of Boston. In the morning, get your bearings and hit the historic highlights whether by foot, trolley or boat. We opted for a self-guided walk of the Freedom Trail that takes you through the heart of the city with plenty of opportunity to great views, good eats and a true sense of the history made here. When you’re ready for lunch, head over to quaint Newbury Street where brownstones meet tree-lined streets and high-end shopping. Dine alfresco at one of the local favorites, like Stephanie’s on Newbury then walk just a few blocks to Copley Square and the beautiful Boston Public Library where you can enjoy afternoon tea and peruse the collections in this architectural gem. Just across the street slip into 19th century Trinity Church, another historic local standout. In the evening head to the North End (Bean Town’s Little Italy) for dinner at any of its cozy restaurants in this bustling neighborhood. And for dessert, make your way into Mike’s Pastry for your choice of local handmade cannolis.
Day 2: Coastal Road Trip. Rise early and head north out of the city to explore the seaside towns that beckon summer vacationers and serve up lobster rolls and a side of some serious charm. In an easy day trip, we made two stops. First in Portsmouth, NH, just an hour drive outside the city, but a big step back in time to old brick sidewalks, clever storefronts and friendly locals. Stay for a lobster roll and chowder with waterfront views, then head 30 minutes further up the coast to Kennebunkport, ME. In late September, you'll get a dose of fall colors mixed with coastal breezes and rugged coastline, and the small-town New England experience that will having you planning your next, much longer stay. Be sure to cruise up Ocean Avenue, pull over and take in rocky coastline, views of the Bush family estate and pristine Cape Cod homes all along the way.
Day 3: Neighborhoods Old & New. Boston is a city of great neighborhoods worth going off the beaten path. Be sure to leave time to explore some of the cities up-and-coming areas like SoWa (named for its location South of Washington). This eclectic area is a hotbed of art galleries, artisan events and vintage finds. On Sunday, it plays host to local vendors peddling handmade wears and decor, and serves up great local food and entertainment throughout the day. Be sure to make your way inside so as not to miss the vintage market to scour the second-hand treasures and score some truly unique finds. Now, take it from new to old and grab a ride-share to charming Cambridge for a relaxed afternoon. Start in Harvard Square where you can jump on a free student-led guided walking tour through Harvard Yard. Stroll down Massachusetts Ave and dine with the brunch crowd at sweet spots like Tatte’s Bakery & Café, then detour down nearly any street toward the Charles River where you may catch a crew team rowing by, and on Sundays from April to early November you’ll find a long portion of Memorial Drive along the water closed off for bicyclists and joggers.
