Destination Summer

Whether your idea of five-star relaxation is on an island beach, at a mountain lake or in a cabin in the woods, these seasonal getaways—just a road trip away—will have you and your loved ones basking in sheer luxury no matter the direction the GPS

Surf Lodge | Montauk, New York

Why Go:
For those who dream of eternal summer, long sundrenched days filled with surf and song, the ultra hip Surf Lodge is the place to be. This nod to West Coast bohemian chic is the brainchild of owner Jayma Cardoso, who has made a name for herself having opened the super-hot nightclubs Lavo and GoldBar in New York City.  

What To Do:
When in the surf capital of the East Coast, you must surf. Don’t know how? No problem: The professional team from Coreyswave will have you standing up in no time. They say 99 percent of students stand up in their first lesson. They even include the wet suit in your rental. Not sure hanging ten is for you? Try stand-up paddleboarding; if you can keep your balance, you can do it. Surf at iconic Ditch Plains or take a free paddleboard out from the lodge and try your skill on Fort Pond Bay.

Where To Eat:
The Byron at the Surf Lodge offers up fab fare such as crab spaghetti along with summer staples like the lobster roll. Stay through the evening when the bar gets seriously clubby and often features marquee-name live bands. For those looking for a more serene dining experience, head over to the Montauk Yacht Club. Despite its name, it’s open to the public. With two superb restaurants, a private beach and a marina that houses the mega yachts that come to stay, it’s a lovely complement to the nightclub feel of the Surf Lodge. 

Insider's Tip:
Michele Ross, owner of Letarte swimwear in Greenwich, is a Surf Lodge regular. She brings her own kiteboard and teen daughter; surfing is not just for kids, you know.

The Point | Saranac Lake, New York

Why Go:
The Point in Saranac Lake is so exclusive that you won’t find it on a map; guests are provided the address only after booking (and paying). This private luxurious estate is one of the last of the Great Camps of the Adirondacks, considered by many to be the premier resort in the country. The Point was built as a private retreat for the William Avery Rockefeller family in the early 1930’s. Eleven distinctive guest rooms are spread among the four original log buildings, so even when fully booked, the property still leaves guests feeling as if they have their own Rockefeller-esque retreat.

What To Do:
Head out on a private tour of Upper Saranac Lake on the resort’s thirty-three-foot Hacker Craft. You’ll learn much about the Great Camps built by oil and steel barons in the late nineteenth and early twentieth centuries. Trust us; the salacious stories alone are worth the tour. The resort offers guests access to their fleet of boats that include canoes, mahogany electric inboards and a glass-enclosed electric boat that is used for relaxing rides, leisurely meals and, during summer, evening cocktail cruises, as some things can really only be seen from the lake. On land you can enjoy a wealth of activities including tennis, fishing and croquet.

Where To Eat:
Put on a tuxedo and head to the Great Hall, after cocktails, of course. (The Point is an all-inclusive property.) Jacket and tie are required during the week, and Wednesdays and Saturdays call for formal attire in the tradition of the great lodges of yesteryear. After dinner, guests head out to the nightly bonfire to enjoy s’mores and truffled popcorn.

Insider Tips:
No children under seventeen are allowed, and you might as well leave your iPhone at home as there are no TVs or cell service, and Wi-Fi is meted out in one small office to the truly desperate. Emily Liebert, a Westport resident and author of You Knew Me When, says: “The Point is the perfect marriage of old-world charm and modern elegance. It’s like camp for adults in the best possible way.” She suggests booking The Boathouse, if you can. It’s the most coveted room on the property. “The dramatic canopy bed and spectacular views of the lake are to die for.”

The Wauwinet | Nantucket, Massachusetts

Why Go:
Nantucket looks much as it did when the whaling industry left more than 150 years ago, and the locals wouldn’t have it any other way. The island has more homes on the National Register of Historic Places than Boston does. This “elbow of sand” off the coast of Cape Cod draws visitors looking for everything from gourmet cuisine to isolated beaches and a day of surfcasting. The Wauwinet is Nantucket’s only Relais & Chateaux property and is ideally situated at the northeast point of the island.

What To Do:
Take a ride in the hotel’s prized 1948 “Woody” (a vintage Chevy Fleetmaster station wagon) to the charming town of nearby S’conset. Rent a four-wheel drive or buy an oversand vehicle permit and cruise the beaches looking for the perfect picnic spot. (The hotel’s award- winning restaurant Topper's will pack a picnic for you.) Take a ride across the water and into town on the Wauwinet Lady for a day of shopping.

Where To Eat:
Wauwinet is the home of Topper's, named the No. 1 overall restaurant on Nantucket by Zagat, so no need to leave the property for world-class cuisine. Or you can head into the heart of Nantucket’s historic district for a feast at Company of the Cauldron, though be forewarned; it’s so popular that locals start making reservations in April for summer dining. The menu changes weekly, so it’s a bit of a lottery what you will end up eating. For a more low-key meal, check out the new Lola Burger; we hear the tuna burger is the dish to try. 

Insider Tips:
The Nagler family of Rowayton makes the trek to Nantucket annually and suggests booking a surf lesson for your teens at Cisco Beach with the Nantucket Surf School. Tasha says to “book an 8 a.m. lesson to enjoy both an empty beach and gorgeous morning light for picture-perfect photos of your new surfer.”


Winvian | Litchfield hills, Connecticut

Why Go:
Winvian is a hidden, must-visit gem tucked in the hills of Litchfield, Connecticut. It is the only AAA Ten Diamond resort and spa in the state—five for the resort and five for the restaurant—and has been described as “whimsical luxury.” How whimsical? Inside one cottage is a Sikorsky helicopter furnished as a modern living room.

But don’t worry; the whimsy in no way usurps the luxury in the eighteen cottages spread around the 113-acre property. Plus each guesthouse has a unique architectural theme: from a double-decker tree house and a stable, to an artist’s studio and a greenhouse.

What To Do:
Can’t make it for an overnight stay? GQ calls Winvian, “The ultimate destinations spa.” You don’t need to be a guest to enjoy a day of pampering. Not looking to relax? Let the Winvian concierge help you satisfy your need for speed at the nearby Skip Barber Racing School. They offer one-and three-day racing programs, complete with photos to impress your friends.

Where To Eat:
The Winvian Restaurant is so fabulous there is no reason to leave the property. Chef Chris Eddy serves up true farm-to-table cuisine with ingredients from the nearly three acres of organic gardens he oversees. He also has his own apiary and guests enjoy fresh-from-the-hive honey.

Insider Tips:
Jayne and Christian Jepsen of Darien were married at the Winvian. They say it’s their “favorite escape for a quick romantic getaway, full of European elegance and charm with the comfort of being so close to home. We love to experience a different cottage each trip. Most recently we stayed in the cozy camping cottage in the middle of a snowstorm—simply lovely.”

Chatham Bars Inn | Cape Cod, Massachusetts

Why Go:
It was the first luxury resort on Cape Cod and still its toniest address. This idyllic resort recalls a time of summer’s simple pleasures: beachside lobster bakes, a walk into town for a visit to the penny candy store, or a ride on the local trolley.

What To Do:
Head out in the hotel’s top-notch fleet of boats for a day of big game sport fishing or a breezy sunset cruise, or take the Bar Tender shuttle to the nearby barrier reef, which is full of playful seals that delight children and grown-ups alike. During the right time of year, humpback and pilot whales can be spotted from the deck of the Starstruck yacht. On Wednesdays in July and August, the Coast Guard Station opens the lighthouse to the public; the view from the top can’t be beat. The ground seldom freezes on the Cape, so you can get in a round at the Chatham Seaside Links golf course, which is right next door.

Where To Eat:
Stay on property and enjoy five-star cuisine at Stars, or a signature cocktail at the Beach House. For a taste of a low-key New England life, head out to the Chatham Squire for live music, oysters and fried magic. Or try the Cape’s only five-diamond restaurant, Twenty-Eight Atlantic, at the nearby Wequassett Resort and Golf Club.

Insider Tips:
Martha and Peter Thompkins* of Stamford stayed at Chatham Bars for a weekend wedding. “The rooms are small but nicely appointed and decorated in soft pastel colors that are soothing and reflect the hotel’s site on the water,” says Martha. “It’s a lovely place for a wedding as there are many types of venues to hold a dinner and a ceremony.”
*not their real names


Samoset Resort on the Ocean | Penobscot Bay, Maine

Why Go:
The Samoset is the perfect marriage of two great vacations: the family escape and the golf getaway. It has been ranked among the best golf resorts in the U.S. by Condé Nast Traveler, and as one of the best family vacation destinations in the world by Travel + Leisure. This picturesque retreat sits on a jetty of land with an expansive view of Penobscot Bay.

What To Do:
Golf, golf and more golf. Each hole has an ocean view, challenging Mark Twain’s notion that the sport is a “good walk spoiled.” If you are looking to take your game to the next level, the resort offers private lessons with the Samoset Scoring School. Or just toss it all in and play disc golf in the resort’s “Ultimate Backyard.”

After your morning round, relax in the 200,000-gallon zero-edge pool set on the hillside, with sweeping views of Penobscot Bay, or visit the seaside spa for a day of pampering. Afterwards you can head into Rockland for a night at the Strand Theatre, a restored Art Deco theater that was written up in Architectural Digest and shows a mix of live theater, film and music.

Where To Eat:
Primo in Rockland has such elevated farm-to-table dining, even the animals are raised on the property. It also has a list of accolades that could fill their own article. Suffice it to say: Chef Melissa Kelly was named James Beard’s Best Chef in the Northeast in 2013.

Also, locals tell us they love Francine’s in nearby Camden, and recommend hitting Cappy’s for a world-class cup of “chowda.”

Insider Tips:
Nancy Ozizmir of Riverside spends part of every summer here, as her parents live nearby. She recommends renting the Flume Cottage. “It’s magnificently situated on its own jetty.” In fact, this two-bedroom retreat is perched over the ocean with views from every window.

The Sagamore | Lake George, New York

Why go:
In 1791 Thomas Jefferson wrote to his daughter, “Lake George is without comparison, the most beautiful water I ever saw…” What became known as the “Queen of American Lakes” is still welcoming those seeking a cool respite from the hot and harried cities. At one time you needed to be a Rockefeller or a Vanderbilt to call Lake George your summer home. So many mansions, nicknamed “cottages,” were built in the early nineteenth century that a stretch of shore became known as Millionaire’s Row.

Those lacking a mansion of their own would tuck into The Sagamore, which was built in 1883 to serve the well-traveled set that arrived by rail. More than 130 years later this jewel of the lake is still welcoming guests. Recent and expansive renovations to the inn and the dining areas that stretch to the shores have brought this beauty back to her former glory.

What To Do:
Being at Lake George is, well, all about the water; people enjoy it all summer long on paddleboards, Jet Skis and rental boats, even parasailing from above. But don’t think this is an overcrowded tourist spot. The thirty-two-mile lake prides itself on the cleanliness of its deep water. Guests of The Sagamore can even enjoy a ride on The Morgan, a seventy-two-foot replica of a nineteenth century touring vessel.

Where To Eat:
We just learned about the brand new Chateau on the Lake, which opened at the end of last summer. This French addition to the dining scene in Bolton Landing is so popular, reservations are a must. It’s hard to find down the long winding driveway but the food, lake views and champagne make the trip worthwhile. 

Insider Tips:
Beth and Fran Sisca of Riverside have continued the family tradition that started in the 1960s of spending summers in Lake George. Fran says: “You have to get out on the lake; it’s spectacular, because it’s all about nature.” The Siscas recommend taking your boat for dinner at the Chateau, as the restaurant was a boathouse in a former life.


Greenwich Agenda

  • Harvest Fair and Gift Show

     @ Second Congregational Church

    Event Will Include Hay Mazes, Games, Crafts, Food, Holiday Shopping The community is invited to a Harvest Fair and Gift Show on Saturday, Nov....

  • New Fitness Class: SalsaTone

     @ Latin Moves Dance Studio

    Starting November 1st ~ Every Saturday morning 10 to 11 AM Instructor: Melissa Lopez Start your weekend off right with this exciting cardio...

  • Exhibit Ira BARKOFF

     @ Canfin Gallery

    “The beauty of the physical world becomes a metaphor for the capacity of the spirit to reveal itself". Ira Barkoff Evocation of...

  • Parties at the JCC Center

     @ Stamford JCC

    A place to celebrate birthdays and special occasions. Be a guest at your own party! The JCC offers a wonderful space for you and your guests to...

  • Flinn Gallery Art Opening

     @ Flinn Gallery 2nd floor

    FLINN GALLERY Opening Reception 'IN FOCUS' Thursday October 30, 6 - 8pm Seven artists share their visions - Carolyn Conrad,...


     @ Imagine Candy

    Imagine Candy located in Scarsdale Village- Winner of 2014 Best West of Westchester by Westchester Magazine- holds a Belgian Chocolate and Candy...

  • Flower Power

     @ SM Home Gallery

    SM Home Gallery show featuring two Greenwich based artists: Margaret Bragg and Penny Putnam. The art show runs thorough November 22nd....

  • Lynne Scalo Design Opening


    Please join Lynne Scalo, Greenwich Magazine and athome Magazine to celebrate the Greenwich showroom opening of Lynne Scalo Design Cocktails...

  • Breast Cancer Alliance Benefit Luncheon & Fashion Show

     @ Hyatt Regency Greenwich

    Breast Cancer Alliance to Host Branching Out, Coming Together, Aspiring to a Cure 19th Annual Benefit Luncheon & Fashion Show: November 6,...

  • Free Screening of Documentary ' Children of the Inquisition'

     @ Bush-Holley House

    Join filmmaker Joseph Lovett as he presents his documentary film and multi-platform project of personal exploration and...

  • P.A.L.S. 2nd Annual Soarin' Soiree~ November 7, 2014

     @ Greenwich Country Club

    You are invited to join our State Senator, L. Scott Frantz and our First Selectman, Peter J. Tesei, for an awe-inspiring evening to benefit Patient...

  • John Hardy Event

     @ Bloomingdale's

    John Hardy One of a kind. One at a time. Each by hand. Bloomingdale's is inviting YOU to meet the head designer Guy Bedarida as he presents...

  • Olivine Gabbro Opening


    Olivine Gabbro invites you to join them for their Opening Party! DJ | Cocktails | H'Orderves | Gift Bags Made to Measure Beautifully...

  • Meet Joshua Safran, Author of "Free Spirit: Growing Up On the Road and Off the Grid"

     @ YWCA Greenwich

    Meet the author of this powerful memoir. Joshua Safran is an author, attorney, occasional rabbi, and nationally recognized advocate for...

  • Markham Roberts: Decorating the Way I See It

     @ Belle Haven Club

    Join us as Interior Designer Markham Roberts shares coveted design insights, key to creating the perfect home. The program will include...


     @ Greenwich Water Club

    Like the Agapanthus flower, which starts as just a seed, we all have something to share with the world.  Sadly, we don't always nurture...

  • The Enchanted Forest

     @ Hyatt Regency Greenwich

    Junior League of Greenwich presents 2014 Enchanted Forest! Holiday Boutiques Gingerbeard Workshops Santa's Breakfast...

  • Junior League of Greenwich The Enchanted Forest

     @ Junior League of Greenwich

    The Junior League of Greenwich (JLG) will host its annual holiday fundraiser, The Enchanted Forest on Friday, November 21 through Sunday, November...

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