South Shore summer weekend getaway guide

Just a hop, skip, and a jump away from Boston, Plymouth offers a means to every end.

White Horse Beach, Plymouth, Mass. –The Pinehills

Longing for a nearby weekend adventure? Take a trip to the relaxing and historic South Shore of Massachusetts. Whether you are captivated by the tall pines and lengthy trails, or prefer to lie in a chaise by the pool, there’s a place for you. There are many options to choose from when visiting the South Shore, from small inns to lavish lodging to long-term residences. The staples, however, are all alike: quaint luxury, sips of lemonade in the sun, and the simplicity of life at the beach.

Check out our weekend guide for a few easy days of vacation on the South Shore.


Friday: arrive + unwind

The Mayflower II, downtown Plymouth, Mass.
The Mayflower II, downtown Plymouth, Mass. —Shutterstock

Afternoon  Head down to the South Shore after work on Friday via car (about 1.25 hours from Boston) or hop on the Plymouth/Kingston commuter rail (about 1.5 hours from Boston) and arrive just in time for dinner.

Evening → Wine and dine with a view at one of many beachside bars and restaurants in downtown Plymouth. Try Anna’s Harborside Grille for a more upscale option or the Cabby Shack for an authentic New England lobster roll and fun outdoor deck. Both venues sit just feet away from the Mayflower II. After dinner, promenade down the beach, enjoy the sand between your toes, and feel the cool ocean breeze.

Then check-in at the romantic, French manor-inspired Mirbeau Inn & Spa at The Pinehills—recently voted among the top 100 resort hotels in the world by readers of Condé Nast Traveler.

Saturday: set out on an adventure

Wake up feeling rested and ready to start your first full day of exploration.

Morning Head out for a morning round of golf, or a spin around on a kayak on one of the many ponds in Plymouth—all before enjoying a stack of homemade blueberry pancakes at the new Café Roo at The Pinehills.


Two of golf’s hidden gems are set among the natural beauty at The Pinehills: the Rees Jones and the Nicklaus Design courses of Pinehills Golf Club. Ranked among the top-10 championship courses in the state by GolfWeek, these 18-hole, daily fee golf courses are open to the public.

Daily fee golf course at The Pinehills
Daily fee golf course at The Pinehills —The Pinehills

Afternoon Before you head out of The Pinehills, pack a lunch with provisions from The Market, then start discovering the miles of trails accessible by bike or foot through acres of preserved “kettles” and “kames” at nearby Miles Standish State Park. Walking what are more commonly known as “valleys” and “hills,” carved out more than 25,000 years ago by the last glacial ice sheet, makes for a heart-pumping afternoon.

the village
Shop around in downtown Plymouth

Evening After all that fresh air and exercise, check out the shops – Setting the Space and Sylvia’s by the Sea, at The Pinehills Village Green, or if you are feeling more energetic, explore the excellent variety of shopping in downtown Plymouth. As the sun sets, make your way via the oldest unpaved, continuously used road in the nation, Old Sandwich Road, to the Rye Tavern for dinner.

The Rye Tavern at The Pinehills
The Rye Tavern at The Pinehills

Formerly known as the Old Cornish Tavern, The Rye Tavern, built more than 300 years ago, boasts delicious farm-to-table cuisine with ingredients cultivated as close by as their own garden. Enjoy the patio seating, the outdoor bar, or a seat by the outdoor fireplace.

Sunday: look forward to a fun day ahead

Spa Mirbeau —The Pinehills

Morning Have a lazy and restful morning with a relaxing visit at Spa Mirbeau, followed by brunch at The Bistro & Wine Bar.


Afternoon Following brunch head over to the historic sites that are so plentiful on the South Shore. Our nation was born here. You’ll see Plymouth Rock, Plimoth Plantation, Pilgrim Hall Museum, or the Mayflower II, to name a few. After absorbing Plymouth’s rich colonial history, kick back at the Plymouth Bay Winery or Mayflower Brewing Company. If you bring the kids, try Peaceful Meadows or Ziggy’s for an ice cream snack, instead.

Evening Before you go, don’t forget to indulge in some New England seafood. Every New England town has its own best lobster roll, so before setting off back to Boston or from wherever you hail, make sure to pick up a couple of rolls from the Lobster Hut.



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