A Week In New England: Beacon Hill to Cape Cod to Martha’s Vineyard

That windswept whispery welcome is one of New England legacy and lore. The Atlantic coast, pebbly and perfect, that is Cape Cod quintessence. Some say the soul of such is carried in the salty air, the saltier history, the sound of sails slapping against the gale. I found it a lot less simple to define. But I brought my family, and I gave it a shot.

Flying in from the west, spending one night in Boston before ascending to the sea makes good logistical sense. Spending the night in uninspired lodging never does. In New England, where coastal come cottage style prevailed long before trend dictated they should, this is hardly a problem.

Beacon Hill Hotel and Bistro in Boston
Beacon Hill Hotel & Bistro in Boston

Brick laden and grounded in great history, the Beacon Hill Hotel & Bistro sits ever so unassumingly on Charles Street, a scenic staple in Americana and a tribute to timeless good taste. Its charms are abundant, its lure manages something both ageless and contemporary. Bearing a Bostonian Brahmin that could define a grace celebrated and cemented in museums and history books, Beacon Hill Hotel & Bistro is refinement with a hefty helping of hominess. Book early, this beauty of boutique boarding houses but twelve guest rooms and one suite, and in a mission to absorb historic Boston in as little time as you have, is idyllically located.  Families, be sure to request the Beacon Hill Suite, where you and yours can watch the Beacon Hill bustle, perched from above. A balcony above another time, where kids, if so craftily inclined, can find their way in from the fire escape on up. A bonus challenge.

Before departing Boston and heading to the New England coast, breakfast at Tatte Bakery & Café is an absolute must. My head almost exploded here. Too much perfection to take in at once. Visually it is Pinterest on steroids, aromatically it is resistance kryptonite. With the mismatched pendants, pyramids of pastries and wonderous waft of what I don’t know but please, Tatte. Let me take you home with me.

Tatte Bakery and Cafe
Tatte Bakery & Café

But first, to the sea.

Anchoring the elbow of the Cape, Wequassett Resort and Golf Club is a sun dappled hideaway so sentient in the sirens of resort retreating that comparisons could only pale. Capitalizing on a coastline that won’t quit (quite literally, the property features not one but two beaches), this sun dusted Shangri-La is the clam baking, beach combing, alfresco movie watching, and weathered wood board walk over the sea we dream New England to be. A soothing salve for whatever stressors stowed away with you, the decadence is by decree. It infuses the air and is felt in all those Five Star finishes. The Good Humor truck that makes its rounds, delivering complimentary treats throughout the day. The little private boat out to the little private island. The scent of the saltwater while watching the sails beneath the setting sun, from the Outer Bar & Grill. The balconies overlooking views that will make you emotional. Wequassett is a five-course feast in laid back luxuriating. Experientially, it is exceptional in every imaginable measure.

Wequassett Resort and Golf Club in New England
Wequassett Resort and Golf Club

And while we had visited once before, if I’m being honest, leaving isn’t any easier the second round. Which is why I highly recommend softening the blow with continued exploration of this intoxicating coast.

Boutique B&B’s are abundant, and I recommend booking one of them next, with Wequassett being the unequivocal epitome of New England resort retreating. We chose to transition from the manicured Wequassett sprawl to the something equally serene, yet more sequestered, secluded. The eastern seaboard is peppered with a plethora of lodging options, some more precious than others. We opted for a renewed relic in Wellfleet, at The Wagner at Duck Creek, a 27-room boutique hotel marrying modern amenities and an homage to heritage. White clap boards and wooden beams, skylights and white billowy bedding, all overlooking the marsh, this quiet seaside celebration of life by the bay is an education in quaint vacating, all set inside a town seemingly too adorable to be for real.

Wequassett pool and beach
Wequassett swimming pool

The property, comprised of the Captain’s House, the Carriage House, and the Cottage, is quietly, thoughtfully, delightful. Owners Erica and Leo have gone to painstaking lengths to preserve the essence and ethos of manse over marsh that turns town into temple. The softest sea blues and weathered woods set a palate pleasant enough to slow your breath and preserve what you came to absorb.

On-site dining is casual, come as you are fun. The Well Tavern + Kitchen serves east coast favorites in a setting suited for ease and memories. Cozy and clapboarded and fully house made, nothing is taken too seriously, and everything gives you reason to return. Tavern nachos, fish tacos, adult chicken fingers. This is what I’m talking about.

Wagner at Duck Creek
Wagner at Duck Creek

From Wellfleet we ferried over to the cedar shingled, white picket periwinkle wonderland that is Martha’s Vineyard. Stand back, friends. Here, hydrangeas come to multiply in cotton candy colors, blissful beaches are ubiquitous, and summer should live forever, particularly when it lives like this. On this island divine, comprised of six Adirondack decked towns, we stationed ourselves in Edgartown, at Kelley House. Anticipate muffins making mornings worth waking early for, and fresh from the oven cookies and milk to become an immediate evening ritual.

Bright whites and sapphire blues define the nautically themed décor, with suites and guest rooms making up the four freestanding buildings; the Main Hotel, the Chappy House, the Wheel House, and the Mizzentop Suites. Buoyed in botanica, each emanate a historic charm this summertime staple is infamous for. Definitely save at least one meal for The Newes From America. Post and beam ceilings, weathered brick, paper bags of sweet potato fries and pub food featuring a New England flair, it’s comfort food with an undeniable Cape quality. Yes to the onion rings.

The Kelley House, New England
The Kelley House

With its legacies of lighthouses, lobster rolls, weather beaten beauty and status as socialite retreat before such a thing existed, Martha’s Vineyard is stepping inside a town (or six) tony enough to bring you to tears, and archetypal enough to justify it. Rent a car. You need to see the island end to end.

All in, Cape Cod is an analgesic; an ineffable amalgamate of restoration and relic. Nautical nuance pervades a feel that is free floating and curative, with scenery and greenery that will steal your breath at every turn.  For a family vacation, it’s outstanding. Beach bound and breezy, cobbled streets of Kennedy playgrounds, ice cream culture, lighthouses and fried fish lined in red and white wax paper. A place painfully photogenic, where lobster and mac and cheese find their way onto most menus, where vistas don’t relent, a roving, seminal of scenic splendour, six stunning towns strung together by boundlessly beautiful backroads. An unforgettable getaway, an unregrettable choice, New England remains the insuperable classic it is reputed to be. Its legacy will always precede it. It’s actuality – it just might supersede it.

Cape Cod View
Typical Cape Cod view

The Details

Beacon Hill Hotel & Bistro, 25 Charles Street, Boston, MA 02114.

Tel: +1 800 640-3935

Website: https://beaconhillhotel.com/

Email: stay@beaconhillhotel.com

Tatte Bakery & Café, Beacon Hill, 70 Charles Street, Boston, MA 02114.

Tel: +1(617) 723-5555

Website: http://tattebakery.com/

Wequassett Resort and Golf Club, 2173 Route 28, Harwich, MA 02645.

Tel: +1(508) 784-7978

Website: https://wequassett.com/

Email: info@wequassett.com

The Wagner at Duck Creek, 70 Main Street, Wellfleet, MA 02667.

Tel: +1(508) 349-9333

Websites: www.thewagneratduckcreek.com



Email: guestservices@wagnerwellfleet.com

The Kelley House, 23 Kelley Street, Martha’s Vineyard, Edgartown, MA 02539.

Tel: +1(508) 627-7900

Website: https://kelley-house.com/

Email: info@kelley-house.com

Author Bio:

Jolie Loeb is a Luxury Lifestyle columnist based in Los Angeles.

Photographs by Jolie Loeb


  1. You’re making me homesick! I grew up in Boston, summering on the Cape, and I miss it so much. Seeing the pictures and reading your gorgeous prose reminds me that my poor kids have never spent for than 24 hours there, and we need to remedy that and let them soak up all that gorgeous scenery, food and people.

  2. These places look exquisite! We haven’t really explored this area as a family, and it wasn’t on my list. Until now! Wow.

  3. Loved your review and comments. We’re bicoastal now with a granddaughter in Providence so will save your E mail.

  4. What a fun read. Made me feel I was there. Made me want to be there. Great recommendations.

  5. Wow, I want to go to all those places!! Your descriptions and pictures are amazing, looks like paradise. The pool setting is glorious. Thanks so much for your articles, keep them coming.

  6. “Visually it is Pinterest on steroids, aromatically it is resistance kryptonite.” – Best reason to visit an establishment…EVER!

    What a beautiful itinerary. I’m going to forward to my Easterly friends!

  7. History, lush landscape and plenty of water, wonderful Inns and Hotels. Great food and plenty of outdoor activities. Hmm, what am I missing here…..sounds like heaven on earth !

  8. We will be making a college trip to Boston and will be sure to take some extra time to visit many of the wonderful establishments that you so vividly described. Your recommendations are always so enticing.

  9. We’d never been to the area before and my husband took your recommendation for Wequassett for my birthday. Far and always best bday ever! I would move in if I could!!! Then, we got to Boston and tried Tatte this am and will be back tomorrow. Every recommendation was dead on. Thank you!

  10. I would honestly turn my kids into indentured help if they let me live at the Wequassett Resort. It’s just magical. We just ate at the Tatte bakery this morning and will likely be back there tomorrow for breakfast (or maybe a late afternoon snack today).

  11. I can’t imagine a more pleasurable way to kick off a family summer vacation. The surroundings ….completely captivate. It’s soft spoken quiet elegance and local pride are music to my heart. You’ve motivated us to search for a large summer-home rental either on the Vineyard or Cape Cod. Then again Waquassett checked every box..plus others we never dreamed of.

  12. Wow! Sounds like an amazing trip. I’ll have to add it to our bucket list. The hotels and scenery look fabulous. Thanks for sharing!

  13. This part of the United States always draws me back. I love all these recommendations and be using them when my son and I travel for colleges!!

  14. This brings me back to my summer in college visiting friends on Martha’s Vineyard! Thanks for the great recommendations when I hopefully return for an east coast vacation soon!

  15. Well…this review certainly captures the essence of this amazing family vacation. While our daughters are generally incredible troopers, they too were captivated by the beauty, the food, and the ability to just slip into vacation mode easily. Vacationing on Cape Cod and Martha’s Vineyard (or Nantucket or the Maine coast) has a totally different feel than California beach vacations, Hawaii, or Mexico. You can actually feel the history around you, even pop culture history like the “Jaws” bridge sitting between Edgartown and Oak Bluffs…I would do this vacation over and over again and I hope we will!

  16. Beautiful. You really sold me on choosing Cape Cod for our next vacation! I can’t wait to visit.

  17. OMGGGGG Tatte! I want to move east just for that cafe/bakery. I bought one of the pricey sweatshirts just to bring a lasting piece of it home with me IT’S THAT GOOD. I’m grateful to now know about these other wonderful places I can visit/try on my east coast return. Now that I’m based in Toronto for a bit, it’s more than possible. Yes, yes, yes!

  18. My husband always wants us to head east for a vacation, well this sealed the deal! Looking forward to planning this vacation!

  19. Fantastic and charming. Makes me want to visit Boston and environs (despite the Patriot Fans).

  20. East coast is soon to be my new stomping grounds.
    I am so excited to visit these beautiful places.
    Great recommendations.

  21. Well, thank you- next vacation itinerary- done! This is out of a storybook. Perfect East Coast vacay for West-coasters wanting some history with our beach time.

  22. I feel I’ve died and gone to alliteration heaven!! What a sumptuous description of a very, very special place. I’ll take this article along as a guidebook.

  23. The whole trip looked amazing! Makes me want to get back to boston and then some. Thank you for bringing it to life so beautifully.

  24. I feel like Jolie is my own personal travel agent and has my trip planned out for me! She always covers the best places. Sometimes I really don’t have the destination on my radar, but she has a way of making these
    places must see for me. I love to save all of these ideas and add them to my favorites so I can check them out!

  25. What a fabulous group of places to visit. Having grown up on the North Shore outside Boston, I can truly appreciate the details that are so eloquently described. We travel back to my childhood home every summer, and we have been itching to venture out out and stay in some other places. Thank you for doing all my planning for me for me!

  26. What a wonderful article! I’ve never been, but have plenty of friends who do. I’ll forward this over to them so they can place these delightful places on their New England vacay agendas! I’m sure to score t-shirt out of the deal!

  27. I’m usually a faithful Nantucket vacationer (family there), and there’s a bit of rivalry between Nantucket and the Cape but Jolie has just convinced me to break with the tradition and stay at the Cape for awhile during next years sojourn. Too bad it’s too late for this years!

  28. Looks like perfection! Cape Cod is a Bucket List trip for me … love to know your amazing recommendations when the time comes!

  29. When I read this it makes me feel like a fool for not visiting before now. Sounds utterly dreamy. Officially on my wishlist!

  30. Sounds heavenly! Your descriptions paint the most vivid, beautiful pictures in my head. I cannot wait to take my family, walk in “your footsteps” and breathe in the beauty of each destination.

  31. This was a fun read. I felt like I was there and I feel like I want to be there. Great recommendations.

  32. What a great review. I am heading to Boston and now I have some destinations in mind. Thank you for making this look so enticing. Great review and delicious images.

  33. You brought it all back. And by “all” I mean the outrageous array of delicious food at Tatte. We stumbled upon it when walking from Brookline to Fenway Park to grab a decent bite before the game (sorry stadium-food lovers). If I hadn’t had 2 small members of the Red Sox fan club, we would have hunkered down and gone from lunch to snack to dinner. As for all the other destinations, looks like they’re in the same camp. You go there, you want to stay there and consume, or be consumed by, all that surrounds you.

  34. The relatives will not be happy. Looks like next year when we land in Boston, we’ll be heading south, not north, for our “family” vacation.

  35. Throwing my flip flops in a suitcase and following this well-heeled itinerary exactly. Will include a drive-by of the Kennedy compound, just to make sure we have all New England icon boxes checked.

  36. My family and I literally just booked our stay at Wequassett for this summer! Thank you for the informative and delightfully written review. Gonna hit all the spots you recommended. Merci. WE CAN’T WAIT!!!!

  37. FANTASTIC!!!!! You are in for SUCH a fabulous time!!!! Kids Club – I didn’t talk about that – it’s AWESOME for the 12 and under set. And the boat to the private beach – it leaves several times within the day – that beach will blow your hair back. Report back!!

  38. Thank you so much for including Wequassett Resort and Golf Club. You have a beautiful way of sharing your experiences and we were happy to have you with us. It is exciting that Cape Cod made people’s bucket lists from your story! If anyone is thinking about a vacation to the Cape, please give Wequassett a call and let us know you read about it here! Thank you!

  39. It all sounds and looks like a beautiful way to vacay! You had me at Tatte.. I’m a sucker for pretty cafes.

  40. I am from Massachusetts and this description made me homesick! Thanks for perfectly capturing the beauty and essence of New England in the summer. There’s nothing better!

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