Summer Getaway on Boston's North Shore

Travel Advisor Isabel Smallman walking through vineyards in an all white outfit with a tan hat.
Curated By

Isabel Smallman

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  • Food & Wine

  • City Travel

  • Arts & Culture

  • Boston

  • USA

  • Coast

  • Relaxation

  • Foodie

A beautiful view of the Boston skyline with the vibrant blue harbor in the forefront. There are boats and trees surrounding the skyscrapers, water and industrial views.
Curator’s statement

Boston is the epicenter of surrounding summer destinations that let you move around freely while traveling like a local. Picturesque beaches, quaint downtown art districts, music festivals, historical sites and the frequent lobster roll, there is no shortage of activities for any tourist. The North Shore comes alive in the summer months and with such a vast array of activities spread throughout the region, you won't find yourself overwhelmed with congestion...there is plenty of space to explore its natural beauty on your own!

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Where to stay in Boston

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Four Seasons Hotel Boston

Nestled among the Victorian brownstone residences of Boston's Back Bay area, the Four Seasons effortlessly blends with the unique ambiance and vitality of the New England city. It boasts an indoor pool, offers views of the Boston Public Garden, and features candy vaults on every floor!

Fora Perks
  • When you book Four Seasons through Fora, you will enjoy exclusive Four Seasons Preferred Partner benefits. Your advisor will be pleased to give you more details.

Boston Harbor Hotel

A Boston mainstay at Rowes Wharf, with oversized rooms and a popular waterfront restaurant.

Fora Perks
  • $100 hotel / resort credit.

  • Welcome amenity.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

The Newbury Boston

Polished Boston hotel with stylish rooms located just steps to designer boutiques and art galleries.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

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Travel Advisor Isabel Smallman walking through vineyards in an all white outfit with a tan hat.

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Things to do in Boston

Boats standing on the seashore on the during sunset.

Beaches

With over 30 miles of coastline, we have some of the most breathtaking locations to take a swim in this mildly frigid water.

Good Harbor

Located in Gloucester, MA (about 42 minutes from Boston), this 1.4 mile beach is very popular with families because there are great tidal pools for swimming, some big waves for body surfing, and a central snack shack with an extensive menu to please everyone. On the far end of the beach is a "Joes on a Roll" food truck that just opened in 2022 to bring beach-goers some of the best lobster rolls and tater tots in town. But BEWARE of the seagulls, they will fly away with it in the blink of an eye. Additionally there is an island right off Good Harbor that (when at low tide) visitors can walk over on the sand bar and explore the area. You may even see some seals if you're lucky!

Wingaersheek

Also located in Gloucester, MA (about 43 minutes from Boston), this 0.6 mile beach is perfect for those who prefer a waveless and quiet beach with sand that stretches far out to reach the ocean as this beach seems to have an unusually long low tide...making it a favorite spot for families with small children. This beach is also a hotspot for finding sand dollars and long walks onto the private side of beach for climbing rocks.

Singing Beach

Located in Manchester By-The-Sea (about 37 minutes from Boston), this 0.5 mile beach comes to life in song as visitors shuffle their feet through the sand on this small beach. This beach is tucked away with both ends serving as a playground for kids who want to explore the conservative rocky edges for magnificent views at the top. There is a snack bar with plenty of lunch options to endure a long day at the beach. Be sure to stop at Captain Dusty's on the way out for a sweet homemade ice cream treat in the bay.

Tours

Whale Watch - The best whale encounters are just off the Gloucester coast. I recommend Cape Ann Whale Watch or 7 Seas Whale Watch.

Freedom Trail - A must for all history buffs! This 2.5 mile path through Boston highlights 16 historical sites of Boston and your colonist guide will bring history back to life as you walk through the modern streets of present-day Boston.

Salem Ghost Tour - Take the Salem high speed ferry from Boston to Salem, MA (about 45 minutes from Boston), and be your own tour guide through the spooky city streets of this famously historical place for witchcraft. Once the sun goes down, be sure to sign up for a ghost tour through the city and learn about its mysterious history as you admire its old architecture and sinister past.

Scenic Parks

Halibut Point - This state park and reservation in Rockport, MA (about 52 minutes from Boston) boasts a historic granite quarry overlooking the Atlantic Ocean with trails that are easy to navigate.

Stage Fort Park - A well-rounded park in Gloucester, MA (about 52 minutes from Boston), that offers public tennis courts, a casual restaurant, a dog park and a hidden beach (Half Moon Beach). This park is perfect for a picnic and area to hang out for live music at night during the summer months.

Plum Island - An 11-mile long barrier island (about 57 minutes from Boston), serves as a destination for beach-goers and bird watchers alike. There are three beaches to choose from and Parker River National Wildlife Refuge is a massive sanctuary to admire the migratory birds come into the area.

Live Music

Castle Hill Picnic Concert - One of the most iconic summer events of the North Shore takes place every Thursday in Ipswich, MA (about 51 minutes from Boston). Overlooking Crane Beach, the Crane Estate offers music of all genres all summer long as the community comes together to enjoy the warm weathered nights.

The Cabot Performing Arts Center - A historic theatre in Beverly, MA (about 32 minutes from Boston) that has recently been rejuvenated to bring guests both music and theatre performances that add a vibrance of culture and diversity to the city's downtown streets.

The Tall Ship Boston - Located on the east side of Boston, this 245' vessel offers uninterrupted views of the Boston Harbor and sunset city skyline. Live entertainment, an oyster bar, and cocktails featured at three separate custom-built bars, you will not grow bored of this stimulating experience! I will admit, the prices are very high in relation to the quality of food and drinks, but the experience itself is well worth a visit.

Downtown City Districts

Beverly - While this suburban city showcases some beautifully quaint beaches, its Cabot Street hub center is not one to miss. Explore its unique boutiques and eateries and take a coffee to go on a quick walk to Independence Park overlooking the ocean's horizon.

Gloucester - After a long beach day or whale watch, head to Main Street for a mile walk down this charming narrow stretch of art collections, thrifty outlets and bakeries.

Salem - Before a spooky ghost tour, be sure to explore Washington Street for some window shopping on Salem's cobblestone streets and pop in to some of its Witch Museum's to get a feel for its rich history of witchcraft.

Newburyport - The Market Square Historic District is one of my absolute favorite places to visit for its food trucks, live music and endless streets to explore for shopping and dining.

Lynn - Lynn has historically had a reputation for crime and violence, but has revamped its image in past years and is now famously visited by many. Central Avenue includes some popular restaurants and cafes, but my favorite activity in Lynn is hiking through the Lynn Woods Reservation. It is the second largest municipal park in Massachusetts and offers unparalleled views of the Boston skyline. From dog walks to mountain biking to horseback riding, this reservation keeps any visitor active!"

Weekend Trips

  • The Berkshires

  • Acadia National Park

  • Cape Cod

  • Martha's Vineyard

  • Kittery, ME

Places to eat & drink in Boston

People walking next to brick building during daytime

Breakfast

Depot Diner (Beverly) - Always bustling with guests of all ages (Adam Sandler loves this place!), has an extensive menu for both breakfast and lunch.

*Best coffee shop: Visit Crave for cold brew on draft, crazy breakfast sandwiches and scones.

Zeke's Place (Gloucester)- A mellow mainstay for a classic American breakfast and lunch with beautiful local art strewn around the interior.

*Best coffee shop: Castaways Vintage Cafe for homemade baked goods, açai bowls and cute retail merch.

Red's Sandwich Shop (Salem) - All American breakfast served on a hidden side street in a casual, country setting.

*Best coffee shop: Jaho Coffee Roaster and Bakery for an extensive menu of baked goods, sandwiches and even espresso martinis.

Olive's Coffee and Bakehouse (Newburyport) - Fresh pastries, great lattes and the sweetest of cinnamon rolls.

Tatte (Boston)- Feels like you're in Europe with upscale selections of quiches, pastries and coffee options.

Lunch

Joes on a Roll (Beverly) - One of my favorite lobster rolls on the North Shore! Features a family-run food truck with an extensive menu of freshly caught seafood sandwiches and homemade desserts.

Mile Marker One Restaurant (Gloucester) - Both indoor seating with glass window views of the Annisquam River and most famously, its outdoor deck seating with U-shaped bar crafting refreshing summer cocktails to wash down creative and innovative takes on veggie/meat/seafood meals.

Ledger Restaurant (Salem) - Centered on Washington Street, offers upscale dining in a historical setting.

The Deck (Newburyport) - Sitting atop the Merrimack River, this restaurant offers a great selection of seafood and tropical cocktails to sip through the afternoon.

Little Whale Oyster Bar (Boston) - Right on Newbury Street and a short walk to Prudential Center for a quick bite pit stop on your shopping stroll.

Dinner

Soma (Beverly) - Make a reservation in advance! Soma has a dark and sexy interior with classic American dishes and my favorite...their brick oven pizza is unmatched. They are notorious for a great selection of martinis as well.

Hale Street (Beverly) - Sushi Monday? Wednesday wing night? This upscale pub style restaurant is always crowded...and for good reason!

Talise (Rockport) - Also make a reservation in advance! Tucked away in Annisquam's Lobster Cove, this restaurant holds a high reputation for its seasonal menu offerings sourced from local farmer's and fishermen. Feels like a hidden gem and the servers are very knowledgable.

Antique Table (Salem) - An Italian fare situated on the water with an exceptional white table experience.

The Paddle Inn (Newburyport) - Global coastal foods with a creative take on cuisine.

*Best Breweries: Notch Brewing (Salem), Backbeat Brewing (Beverly), Old Planters Brewing (Beverly), Great Marsh Brewing (Essex) and Ipswich Brewing.

*Best Cocktails: Mile Marker One (Gloucester)

Travel Advisor Isabel Smallman walking through vineyards in an all white outfit with a tan hat.

Travel Advisor

Isabel Smallman

Get in touch with Isabel

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For more travel tips, check out Fora Advisor Julia Asselin’s guide, Things To Do & Insider Tips From A Boston Local.

This guide is part of our ongoing series on travel to Boston.