8 Breathtaking Day Trips From Boston To See The Sights And Explore

The state of Massachusetts is blessed with beautiful, natural areas which a wide range of travelers can gain satisfaction from. 

Boston itself is a vibrant, historical city with plenty of places to explore and sites to see; although, it’s beyond the city limits where you see what the state has to truly offer. 

8 Breathtaking Day Trips From Boston To See The Sights And Explore

From tranquil beaches and extravagant waterfalls to quaint towns and fishing villages, there is a range of different day trips to take in all directions from Boston. 

With all this in mind, this article will explore all the best breathtaking day trips to take from Boston, all of which are easily accessible through driving and some public transportation options. 

Let’s get straight into it! 

Boston Area Beaches

For the hot summer months, there are plenty of beaches in the Boston area to soak up some sun and cool down after a long day. 

From Portsmouth, travel south until you reach Rye, or continue or journey to the popular Hampton Beach Strip which contains many beautiful beaches and tons of restaurants. 

Located just over the Massachusetts border is Salisbury Beach, another excellent day trip spot – just over an hour north of Boston. 

Additional beautiful beaches located on Boston’s North Shore include Good Harbor and Wingaersheek beaches in Gloucester, Crane Beach in Ipswich, Plum Island in Newburyport, Revere Beach in Revere, and Singing Beach in Manchester-by-the-Sea.

Equally as beautiful are the South Shore’s beaches, one of the closest beaches being Wollaston Beach in Quincey, and many more including Nantasket Beach in Hull and Duxbury Beach in Duxbury. 

For plenty more options, you can travel south to Cape Cod for many other breathtaking beaches to visit

Portsmouth, New Hampshire

Located in New Hampshire, Portsmouth is a historical coastal city that may be small but has tons of character and many popular attractions. 

Along the docks on Bow Street, enjoy some drinks while watching the sunset at the Old Ferry Landing, Pocos, or Martingale Wharf. Alternatively, if you’re looking for a seafood dinner with a view, try Surf. And lastly, for a tasty yet casual breakfast, Colby’s is one of the best! 

Aside from the restaurants, those visiting Portsmouth can enjoy walking around Prescott Park and learning all about the history of Portsmouth in the Strawbery Banke Museum. 

Spend your evening walking around the downtown area, checking out all the local shops along the way. 

The city is ever-growing each year with many hotels and condos being built as more tourists visit the area. 

Provincetown, Massachusetts

Situated at the point of Cape Cod is Provincetown (otherwise known as “P-Town”). It is best known for its gay resort community, but also as a beautiful place to visit on a day, weekend, or longer trip.

You can get there by either driving or on a 90-minute ferry ride from Bay State Cruise Company. 

The town itself is surrounded by water with several beautiful beaches to enjoy at your leisure. During both the day and evening, take advantage of the downtown areas which have many boutiques, art galleries, restaurants, and many more to enjoy!

If you can’t make it to Provincetown, there are many Cape Cod towns within a short distance. 

Newburyport, Massachusetts

8 Breathtaking Day Trips From Boston To See The Sights And Explore

Another coastal town is Newburyport, which contains the same feel as New Hampshire or downtown Portsmouth in many respects. 

The town settled in 1635; however, of course, over the years it has been modernized and transformed. Given its location and popular beaches, such as Plum Island, Newburyport is a prime destination for tourists in the summer. 

However, it is also an ideal location to visit when in Boston during any time of the year, with many shops, restaurants, and sights to explore. 

Providence, Rhode Island

Approximately an hour’s drive south of Boston, you’ll find the city of Providence, Rhode Island, which is also known as the ‘Creative Capital’. 

Over the years, this has become an increasingly popular destination for tourists, with many popular attractions such as the annual Halloween Jack-O-Lanterns Spectacular, WaterFire – where over 80 bonfires are alighted along the three rivers of downtown Providence – or the Face of the Rainforest exhibit which takes place at the Roger Williams Park Zoo. 

During the winter months – from November through March – check out Providence Rink for Ice Bumper Cars. 

If you’re a major foodie, then you’ll love the food scene here. Talented chefs from Rhode Island’s Johnson & Wales have restaurants in the city, which include Oberlin, a seafood-focused restaurant serving small plates and tapas options. 

Alternatively, for some Italian food, check out Federal Hill, known to the locals as the Little Italy of Providence. Another reputable sport is The Dorrance, situated with a converted bank that serves globally-inspired New England dishes. 

When in town, you can’t leave without stopping at PVDonuts for some delicious and unique brioche donuts that come in an array of fun flavors and toppings such as butterscotch crunch, brown butter brownie, and fruit pebbles. 

Looking to extend your time in the city, then check out some of these popular hotels including The Dean, which was designed around the city’s culture and history, as well as the Providence Biltmore, an intricately historic building designed and delivered by New York’s Grand Central Terminal architects, and, finally, the Hotel Providence, another option located in the center of the city, great for travelers near and far. 

Martha’s Vineyard And Nantucket, Massachusetts

Just off the coast of Massachusetts, you’ll find Martha’s Vineyard and Nantucket – two popular tourist destinations, especially in the summer. 

Both are ideal for day trips from Boston, especially Martha’s Vineyard which is only a short ferry ride away. 

Over the winter months, both islands tend to be quieter, so plan your vacation accordingly. 

You’ll be dropped off in Vineyard Haven where you’ll find plenty of shops and restaurants to explore. From here, you can head to Oak Bluffs towards the 318 colorful Gingerbread Cottages at Wesleyan Groven; just off of Circuit Street. 

If you’re planning on taking your car, or even a bicycle, this makes it easier to explore the downtown areas and the island’s beaches. 

While Martha’s Vineyard and Nantucket are both islands; they both have different vibes. For one, Nantucket is smaller and you’ll find picture-worthy homes covered in hydrangeas and cobblestoned downtown streets. 

Of course, you’ll find plenty of beautiful beaches and vibrant shops, boutiques, and art galleries throughout the island. For a taste of local beer, check out Cisco Brewers which has become popular throughout New England.

Likewise, at one of the downtown bars, try a Nantucket-original Triple Eight Blueberry Vodka.

Nashoba Valley Winery & Other Vineyards

While New England may not be a full-blown wine country like others, many family-owned vineyards make for an enjoyable day trip.  No matter where you’re staying, there is sure to be at least one within driving distance. 

From Boston, your best option is the Nashoba Valley Winery, here you can sample some delicious wines, as well as pick your own apples, peaches, and nectarines when in season, and then spend your evening enjoying some farm-to-table food at J’s Restaurant. 

Furnace Brook Winery is another fine option in the Berkshires, Massachusetts – approximately 2.5 hours drive from Boston. 

Approximately an hour north of the city, you’ll find South Hampton, New Hampshire’s Jewell Towne Vineyards. 

When in Rhode Island, visit Carolyn’s Sakonnet Vineyard or Verde Vineyards.

Likewise, while making your way into Connecticut, head through the Connecticut Wine Trail and visit the Lost Acres Vineyard located in North Granby, Sharpe Hill Vineyard in Pomfret, and Arrigoni Winery in Portland. 

Newport, Rhode Island

Another popular coastal town is Newport, Rhode Island, just a short drive away from Boston. It contains all the makings for a fun-filled, perfect day trip with many beaches and Gilded age mansions to explore and many paths along the notable Cliff Walk to enjoy. 

Similarly, explore the popular Brick Market Place, a downtown area featuring over 25 shops and many eateries. 

Likewise, got many car lovers among the gang? Then you’ll want to check out the Newport Car Museum, located close by Portsmouth, it’s the perfect way to spend any rainy days. 

Popular restaurants in Newport include Winner Winner, The White Horse Tavern, The Black Pearl, America’s oldest Taverns, Mission Burger, and Scarpetta Newport. 

Looking to extend your trip to Newport? Spent the night in one of the town’s top hotels and resorts including Gurney’s Newport Resort & Marina, Forty 1° North, The Chanler at Cliff Walk, and The Vanderbilt. 

Final Thoughts

Boston is packed with culture and history with plenty of activities to make the most out of a trip; however, it isn’t until you escape the city that you’ll find the true beauty of the state.

From stunning coastlines to vibrant vineyards, hopefully, this guide has provided you with some breathtaking day trips from Boston. 

Mylene Mace