Hamptons? Maybe Next Year: A New Yorker’s Guide to the Perfect New England Getaway


Some of my earliest memories are family trips to Cape Cod during the summer. It’s easy to romanticize such distant recollections, but on a recent trip to the area, my first time back in over 20 years, I found beaches and New England towns just as idyllic and charming as I remembered. And I was reminded of why we often made the five-hour trek from NYC: it’s worth it…worth it enough to take a long weekend, in fact. When you do, follow this guide to make the most out of your four-day New England excursion.

Day One

A bit older and wiser this time around, I came to understand why my father would anxiously mobilize the family to pack into the car and make a mad dash for the Cape in the predawn hours. I encourage you to do the same as you set off on your four-day weekend. Hit the Bourne Bridge, which crosses Cape Cod Canal from mainland Mass too late on a sunny day or a weekend, and prepare to be stuck in gridlock…for hours. A rotary on the other side of the bridge paralyzes traffic – you’re better off leaving the house bleary-eyed in the wee morning hours on a Friday, as painful as it may be.

Almost every area of Cape Cod is going to offer beautiful waterfront, so stay in Dennis Port for your first night, if not for its strategic location. Cape Cod is like a flexed arm and the town is near the elbow, offering convenient access in both directions and also to ferries that make the journey to Nantucket and Martha’s Vineyard. Dennis Port’s waterfront has resorts and restaurants that offer drink and dining options, but stay at The Platinum Pebble just up the street, a new boutique inn that features a hard to find blend of Cape quaintness with more sophisticated design and amenities.

The sitting area and bar by the pool

A guestroom at the Platinum Pebble Inn

The inn sports a simple black and white color palette and clean, uncluttered spaces that are like a crisp complement to the nautical atmosphere and the Cape’s simple beauty without appearing stark or too modern. Though the inn’s proprietors, Simon and Annabelle, have essentially gut renovated the place since buying it last year, they have also embraced the over 200-year-old property’s history, restoring some of its old furniture and preserving original floors and moldings. Its comforts and aesthetics are a pleasant addition. A leather couch, stocked bar and a flat screen television – as well as a glass tray of fresh butter cookies – make the main house’s living room a fun place to hang out after a day at the beach, and though its crystal blue pool just outside may seem like a sidebar to the ocean shore that beckons only a short distance away, its water is far warmer for a dip.

Day Two

Get an early start on Saturday and head to Provincetown. At the tip of the “fist,” P-Town is one of Cape Cod’s main destinations for shopping, dining and various sea-faring activities. A quick walk down the aptly named Commercial Street is worth the time for its collection of shops and eating. For those interested in hiking, just outside the city limits are some of the Cape’s most striking expanses of dunes and tidal inlets to explore (http://www.nps.gov/caco/index.htm). The town is also an access point to one of the region’s great natural wonders, its population of native humpback whales. Take a ride with Dolphin Fleet tours to spot humpbacks, one of the best whale species to observe as they frequently breach the surface. They don’t mind moving in close to the boat while dining as circling gulls land on their mouths to scour for stray fish stuck in their baleen.

Head back to Hyannis to catch the ferry (the last one leaves at 8:45 p.m.) for Nantucket, a must-see stop on any Cape Cod vacation. Hyannis offers a number of food options along Main Street, but visitors need not stray from the waterfront for good eating before hopping the boat. The Black Cat Summer Shack, a takeout window with a dining porch next to its more formal sister restaurant, The Black Cat Tavern, has some of the Cape’s best fried clams and fish – we may dare say some of New England’s best fried clams. Spring for the high-speed boat at Hy-Line Cruises which takes a little more out of your wallet but cuts an hour off the journey to Nantucket. Even flying along at top speed, the ferry slices through the water with the smoothness of a railroad car.

If it’s your first time there, you’ll fall in love with Nantucket immediately – as I did. The island has distinct cobblestone streets, winding roads with irresistibly cute and cozy ivy covered houses and gardens, and fine dining and shopping that are a cut above the mainland. As the price for food and accommodations will undoubtedly suggest, the island is a redoubt for the upper crust, but anyone looking for peace and serenity won’t mind paying the premium to experience its quiet shorelines and laid back and friendly vibe.

The Wauwinet Inn is about 8 miles from the town center on the island’s northern tip, but a car shuttle will be there to pick you up. Though distant by Nantucket standards, its location is an asset. Set among pastoral fields and marshland and pristine beaches, the inn is a notch more scenic and relaxing than the town center.

Enjoying the exterior areas of the Wauwinet, particularly the deck at Toppers, are well worth the short trip out of town

Day Three

Sunday morning, borrow bikes from the inn and ride the path to the seaside town of Siasconset about five miles away, a journey that takes visitors over one of the island’s most gorgeous stretches. Take a break at the historic lighthouse right before the town center and snap a few photos.

For those itching to get back into town, the Wauwinet delivers with an hourly bus that shuttles guests back and forth. But guests may not be in such a rush to leave even just for day trips. The hotel is immaculately clean and well appointed with a large outdoor area near the water lined with comfortable lounge chairs and a no cell phone policy meant to preserve the tranquility. Spend your afternoon enjoying the surroundings. Toppers, the hotel’s in-house restaurant, is also without a doubt one of the island’s best destinations for food and drink. Though the food is excellent, Toppers was even more notable to me as having, hands down, the island’s best cocktails. Any guests who visit while Mitch is tending bar will be in especially good hands.

The Union Street Inn

Spend your last overnight in town. Steps from Main Street, the historic Union Street Inn is centrally located. Its rooms are well appointed and smartly designed with a New England meets 18th Century France feel. The inn’s framed photography of classic New England sailing scenes from the 1930s is enough to inspire even the most firmly chair-bound guest to take a gander at the nearby wharf and waterfront.

Day Four

Wake up to enjoy the company of the inn’s proprietor, Ken, who knows good hospitality – he spent years in the hotel circuit in GM positions at hotels like the Royalton in NYC. His partner, Deb, was in retail at Henri Bendel, so she, too, understands the ins and outs of delivering a quality product and taking care of customers. They and their staff do just that and then some. They are knowledgeable, personable and always glad to help visitors find their way around some of the island’s less traveled attractions. The inn features its own curated walking tour, and staff conveniently collect up-to-date menus from restaurants around the island and encourage guests to peruse it and make informed dinner choices, with their help. Breakfasts are exceptionally tasty (think challah French toast, bagels and lox, fresh fruit and yogurt) and particularly pleasant, served in the inn’s homey kitchen area or on the patio outside.

If you have time for one last meal on island (whether on your third night or before you depart your final day), visit the Galley Beach restaurant, which offers an array of delicious seafood options to be enjoyed with an unparalleled view of the setting sun over the ocean. If you can get a seat right on the border of where the dining room opens up to the deck, you’ll get the best of both the indoor and outdoor dining and have a bird’s eye view at sunset.

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