Best Day Trips from Boston

Located off the southern coast of Cape Cod, Martha’s Vineyard is known for its beautiful natural landscapes, charming towns, and fine dining options, making it the perfect place to relax and unwind. Discover the enchanting towns of Martha’s Vineyard, each with its own unique charm. Oak Bluffs is an ideal destination for families, offering a perfect blend of fun and history. Spend the day at the family friendly Joseph Sylvia State Beach, known for its calm waters and scenic views. Take a ride on the oldest platform carousel in the US, the Flying Horses Carousel. Stroll through the famous gingerbread cottages, where streets are lined with colorful storybook-style homes. Edgartown offers a mix of history, charm, and coastal views. Tour the Old Whaling Church, a well-preserved landmark from the island’s whaling days. Visit the Mytoi Garden, a peaceful Japanese-style garden with a koi pond and lush plantings. Take a short walk to the Edgartown Lighthouse for great views of the harbor and nearby beaches. See the multicolored clay cliffs at Moshup Beach in Aquinnah. Spend some time in Vineyard Haven and stop by the Martha’s Vineyard Museum to learn about the island’s rich history. Be sure to browse the local shops and boutiques downtown for unique island-made items and brand-name clothing. Visit the Island Alpaca farm to meet friendly alpacas and learn about life on a working alpaca farm.

How to Get to Martha's Vineyard from Boston

• By Ferry: Drive or take a bus from Boston to Woods Hole, located on Cape Cod (about 1.5–2 hours, depending on traffic). From there, take the Steamship Authority ferry to Martha’s Vineyard. This is the only ferry that accommodates vehicles, but foot passengers are also welcome. Or, take a seasonal high-speed Hy-Line Cruise ferry from Hyannis to Oak Bluffs. On average, the ferry rides take about 45 minutes.
• By Plane: Fly directly from Boston Logan International Airport to Martha’s Vineyard Airport. Several airlines offer short, direct flights (around 40 minutes), especially in the summer months.

Just a few hours from Boston, Provincetown, also known as P-town, is one of the most popular day trip destinations from Boston. This vibrant seaside town is steeped in history as the landing site of the Mayflower in 1620, commemorated by the soaring 252-foot Pilgrim Monument and the Provincetown Museum, which offers insight into the Pilgrims’ journey, Wampanoag culture, and maritime heritage. Book a Mayflower Trolley Tour for a scenic overview of the town’s historic and artistic highlights. Long celebrated as a haven for artists and the LGBTQ+ community, Provincetown is bursting with creativity and character. Visitors can stroll down lively Commercial Street, lined with art galleries, indie shops, cafes, nightclubs, and specialty boutiques. Stop by the Provincetown Art Association & Museum (PAAM), which showcases over 4,000 works by local and national artists, as well as captivating live performances. Nature lovers will find paradise on the shores of Race Point and Herring Cove beaches or on a 4x4 ride through unique landscapes with Art’s Dune Tours. For those craving even more adventure, head to Long Point Beach and Lighthouse, accessible via a peaceful hike or boat shuttle, or enjoy a whale watch or sunset cruise along Provincetown Harbor.

How to Get to Provincetown from Boston

• By Ferry: Boston Harbor City Cruises and Bay State Cruise Company operate high-speed ferries from Boston’s Seaport/Long Wharf to MacMillan Pier in Provincetown from mid‑May through mid‑October (late‑fall weekends available through early December). On average, the ferry ride from Boston to Provincetown takes about 1.5 hours.
• By Plane: Fly directly from Boston Logan International Airport to Provincetown. Cape Air offers seasonal direct flights from Logan Airport (BOS) to Provincetown Municipal Airport (about 45 minutes). 

While Salem is a popular destination year-round, the Halloween season draws visitors from around the world for its unmatched spooky atmosphere, haunted happenings, and festive events. Start your day by stepping into the eerie world of 1692 at the Salem Witch Museum, where dramatic sets and narration bring the infamous witch trials to life. Catch a live reenactment and tour a replica jail at the Witch Dungeon Museum for an even deeper dive into the past. Art and history lovers will want to explore the Peabody Essex Museum, home to global collections and historic architecture. Head to Real Pirates Salem on the waterfront to discover real treasure and artifacts from the legendary Whydah Gally shipwreck. Round out your visit with a stroll through Pioneer Village, where 17th-century life is recreated in vivid detail, and follow the Salem Heritage Trail for a self-guided tour through the city’s iconic sites, shops, and scenic spots.

Find more things to do in Salem here.

How to Get to Salem from Boston

• By Train: Take the commuter rail Newburyport/Rockport Line from North Station to Salem Station (about 35 minutes).
• By Ferry: Boston Harbor City Cruises offers ferry rides to the Salem Ferry terminal near Downtown Salem (about 50 minutes).
• By Car: Drive about 45 minutes North of Boston to Salem, MA.

Just an hour south of Boston, you’ll find the historic seaside town of Plymouth—known as “America’s Hometown”. Begin your journey at Plimoth Patuxet Museums, where immersive exhibits and costumed interpreters bring to life the stories of the Indigenous Wampanoag people and the 17th-century English settlers. Hop aboard the Mayflower II, a full-scale replica of the famous ship that carried the Pilgrims to the New World. Take a moment to visit the nearby Plymouth Rock, the landing site of the Pilgrims in 1620. A short drive away is the National Monument to the Forefathers—one of the largest solid granite monuments in the United States. For a relaxing afternoon, sample handcrafted fruit wines at Plymouth Bay Winery, where tastings come with stunning harbor views. When it’s time for dinner, indulge in authentic Brazilian cuisine at Rio’s Steakhouse, a local favorite. If you have extra time, stop by Pinehills Golf Club to play a round or enjoy the scenic course before heading back. Stop by the Plymouth County Convention & Visitors Bureau to gather maps, more recommendations, and local insights to make the most of your day trip to Plymouth.

How to Get to Plymouth from Boston

• By Train: Take the MBTA Commuter Rail Kingston Line from South Station to Kingston Station (about 1 hour 15 minutes), then a short taxi or rideshare to your Plymouth destination.
  By Bus: Plymouth & Brockton Street Railway offers direct service from Boston’s South Station to downtown Plymouth (about 1 hour 15 minutes).
  By Car: Drive about 50 minutes south of Boston to Plymouth, MA.

Skip the hassle of driving. Book a guided day trip to a nearby town with one of Boston's top tour guides.