The Goose's Guide to Boston & the North Shore
From Cobblestones to Coastlines
The Soul of Boston & the North Shore
Boston isn't just a city; it’s a feeling. It’s the quiet reverence of walking gas-lit streets in Beacon Hill, where centuries of American history whisper from the brick townhomes. It’s the intellectual buzz of Cambridge, the refined elegance of the Back Bay, and the unapologetic passion of a Red Sox game at Fenway. But just beyond the city's edge, a different soul emerges—the North Shore. This is where the air turns salty, the coastline gets rugged, and fiercely independent fishing villages give way to artists' colonies and stunning, wild beaches.
This is an escape of brilliant contradictions. For our flock, it’s about finding luxury in both the perfectly crafted cocktail at a chic hotel bar and the simple perfection of a lobster roll eaten on a weathered pier. We believe, as Coco Chanel did, that "Luxury must be comfortable, otherwise it is not luxury." Here, that comfort is found in the seamless transition from a world-class museum to a windswept coastal drive. We handle the details; you just have to decide whether you’re in the mood for history or the horizon.
The Lowdown:
Your New England Essentials
Where in the World: The historic heart of New England, located on the Massachusetts coast, offering a perfect pairing of a major American city with a string of charming coastal towns.
Climate & When to Flock: While summer is classic, our insider choice is early Fall (September-October). The oppressive humidity lifts, the city is vibrant with returning students, the fall foliage begins its spectacular show, and the North Shore is blissfully free of summer crowds.
Language & Lingo: English, though you'll hear the famously unique Boston accent. Don't try to imitate it; just enjoy it.
Currency: The US Dollar ($). Credit cards are accepted everywhere.
Queer-Friendliness: Boston is a very liberal and welcoming city with a long history of LGBTQ+ activism. You'll find friendly spaces throughout the city, particularly in the South End. The North Shore towns are generally welcoming and progressive.
Getting Around: In Boston, do not rent a car. The streets are a confusing, colonial-era puzzle. We’ll arrange for private drivers or you can rely on ride-sharing and the efficient subway system (the "T"). To explore the North Shore, a rental car is essential for freedom and flexibility.
Style & Packing: "Coastal Prep." For Boston, think smart-casual layers: tailored trousers or dark denim, cashmere sweaters, and stylish walking shoes. For the North Shore, lean into quality casuals: Breton-striped shirts, a good windbreaker, and boat shoes or white sneakers. Always pack a versatile blazer or jacket for evenings.
“The Goose’s Golden Egg: The best way to get from Boston to the North Shore isn’t by sitting in traffic on the highway. We recommend taking the scenic commuter ferry from Boston’s Long Wharf to Salem. It’s faster on a summer Friday, and the coastal views are a perfect transition from city to sea.”
Boston: A Mosaic of Neighborhoods
Beacon Hill: The Historic Heart
The Vibe: A preserved corner of the 19th century, with steep cobblestone streets, gas-lit alleys, and stately Federal-style townhomes that feel straight out of a storybook.
Signature Experiences: While the masses walk the Freedom Trail, we'll arrange for a private architectural historian to guide you through the hidden courtyards and exclusive private gardens of Beacon Hill. Afterwards, browse the chic, independent boutiques and antique shops along Charles Street.
Where to Stay: The Whitney Hotel offers a sophisticated, modern boutique experience that blends seamlessly with the neighborhood's historic charm.
The Table: Start your day with a classic diner breakfast at The Paramount, a neighborhood institution since 1937. For a perfect coffee and pastry, grab a seat at Tatte Bakery & Café.
Salem: Beyond the Witch Trials
The Vibe: A city of profound American history, asking visitors to look past the tourist kitsch to find a powerful story of maritime glory, architectural beauty, and the sober lessons of injustice.
Signature Experiences:
A Historian-Led Walk Through 1692: Forget the ghost tours. We'll arrange a private walk with a local historian focused on the real, harrowing story of the Witch Trials—a story of mass hysteria, misogyny, and the patriarchal power structures that targeted and condemned innocent women. The tour includes a reflective visit to the starkly beautiful Salem Witch Trials Memorial.
The Peabody Essex Museum: A world-class museum that reveals Salem's true soul as a global maritime titan. Explore its incredible collections of art and culture from around the world, including a complete, 200-year-old Chinese house brought from China and reassembled inside the museum.
The McIntire Historic District: Stroll through a stunning outdoor museum of Federal-style mansions, designed by famed architect Samuel McIntire. This is the legacy of the sea captains and merchants who brought the world's riches back to Salem.
Where to Stay:
The Merchant: A chic, sophisticated boutique hotel set in a stunning historic building that was once the home of a wealthy sea captain.
The Table:
Ledger Restaurant & Bar: A high-end dining experience located in a grand, soaring former bank building from 1818. The atmosphere is as impressive as the modern New England cuisine.
The North Shore: A Salty Escape
The Vibe: A ruggedly beautiful coastline of granite cliffs, golden beaches, and charming fishing villages that have become havens for artists and artisans. This section includes the key towns of Salem, Gloucester, Rockport, and Ipswich.
Salem: Beyond the Witch Trials
The Vibe: A city of profound American history, asking visitors to look past the tourist kitsch to find a powerful story of maritime glory, architectural beauty, and the sober lessons of injustice.
Signature Experiences:
A Historian-Led Walk Through 1692: Forget the ghost tours. We'll arrange a private walk with a local historian focused on the real, harrowing story of the Witch Trials—a story of mass hysteria, misogyny, and the patriarchal power structures that targeted and condemned innocent women. The tour includes a reflective visit to the starkly beautiful Salem Witch Trials Memorial.
The Peabody Essex Museum: A world-class museum that reveals Salem's true soul as a global maritime titan. Explore its incredible collections of art and culture from around the world, including a complete, 200-year-old Chinese house brought from China and reassembled inside the museum.
The McIntire Historic District: Stroll through a stunning outdoor museum of Federal-style mansions, designed by famed architect Samuel McIntire. This is the legacy of the sea captains and merchants who brought the world's riches back to Salem.
Where to Stay:
The Merchant: A chic, sophisticated boutique hotel set in a stunning historic building that was once the home of a wealthy sea captain.
The Table:
Ledger Restaurant & Bar: A high-end dining experience located in a grand, soaring former bank building from 1818. The atmosphere is as impressive as the modern New England cuisine.
Rockport, Gloucester & Ipswich: Coastal Charm
The Vibe: This is the quintessential New England you've been dreaming of. A string of fiercely independent towns where the smell of salt hangs in the air, lobster boats bob in the harbor, and art galleries line streets once walked by sea captains.
Signature Experiences:
A Private Schooner Sail from Gloucester: See the coast as it was meant to be seen—from the water. We'll charter a beautiful schooner for a sunset sail out of America's oldest seaport.
Crane Beach at Low Tide: This pristine, protected beach in Ipswich offers vast expanses of sand and dunes. We recommend a visit on a weekday morning at low tide for a meditative and profoundly beautiful walk.
Antique Hunting in Essex: The small town of Essex boasts the highest concentration of antique shops in the country. We can arrange for a private guide to help you navigate the best shops.
Where to Stay:
Blue Inn on the Beach (Plum Island): For a true toes-in-the-sand experience, this boutique hotel offers chic, oceanfront rooms on a beautifully remote barrier island.
The Addison Choate (Rockport): A stunningly renovated and designed boutique hotel in the heart of Rockport, offering a modern, luxurious take on the classic New England inn.
The Table:
The Clam Box of Ipswich: An iconic, can't-miss institution. This is the "real deal" for classic New England fried clams and seafood.
Woodman's of Essex: Another local legend, claiming to have invented the fried clam. A no-frills spot to enjoy a lobster bake on a picnic table by the salt marsh.
“The Goose’s Golden Egg: On your way up the coast, make a quick detour to Ingaldsby Farm in Boxford. It’s a generations-old farm stand where you can pick up the best apple cider donuts and local produce—the perfect snack for your coastal drive.”
The Goose’s Hidden Gem
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Many visitors drive the coast, but the real secret is to experience it by water. The ultimate North Shore day involves taking a morning ferry to the Isles of Shoals, a rugged archipelago nine miles off the coast. Here, you can explore the dramatic, windswept landscape that inspired so many artists, feel the raw power of the Atlantic, and then return to the mainland for a fresh seafood dinner in Portsmouth, New Hampshire, just over the border. It’s a journey that captures the true, salty soul of New England.”
A Note from Our Founder
Some places are just in your bones. For me, that's New England. From my days studying Anthropology at Boston University to my time at Boston Consulting Group, this region has been the backdrop to my life's story. I've explored every inch of the coastline from Connecticut to Canada, and while I may be a California girl by birth, I will forever be a proud Masshole at heart. This guide is my love letter to the place that shaped me—its history, its beauty, and its unpretentious soul. I can't wait to share it with you.
Your Adventure Awaits
This is just the beginning. We’re here to handle every detail, from the flight to the fondue, ensuring your journey is as seamless as it is unforgettable. It's time to see more, feel more, and be more.