Stephanie Cunningham

Cape Cod has been a reoccurring destination for many New Englanders over the decades and rightly so, it has all the components of a beach vacation that caters to all walks of life with plenty to do. Personally, Cape Cod has been a place for childhood (and adult) memories for as long as I can remember, and its impact has been profound on my connectedness to the water that surrounds it. One town that I particularly feel privileged to call my home away from home is Chatham. An area that if you look at a map is referred to as the ‘elbow’ of ‘the Cape’. Billed as a luxury seaside town, its shops & restaurants, beautiful resorts and rugged sandy beaches live up to its reputation and should be your primary destination if you are planning a weekend in Cape Cod.

Crete is a contradiction in terms. On one hand, you have its gorgeous mountain range running the length of the island—plunging into the Mediterranean Sea, dotted by traditional seaside villages. On the other, you have a soft, unhurried, laid-back approach that feels deeply authentic. It's unforgettable long after you leave.

Visiting Spain always gets me giddy! After my first visit to Madrid in my 20s, I continue to come back again and again, finding new ways to enjoy this deeply traditional yet modern city. Madrid is a city that lives boldly and beautifully, where centuries of royal history blend seamlessly with a modern, magnetic energy. It’s a city defined by passion, artistry, and warmth, where every moment feels both timeless and alive, and where visitors quickly discover that Madrid isn’t just a destination—it’s a feeling. I agree!

One may not think of going to Arizona for the holidays—with the lack of snow, cold, and gray skies that are typical of the season (at least here in the Northeast!), it seems counterintuitive. But—Scottsdale is one of the few exceptions. The golden-hour sunsets combined with a pop of holiday lights, a fire pit, and a hot toddy warms the soul and really brings the meaning of this time of year to heart. I have had the pleasure of spending a few holidays in this area and it has always been fantastic!

Bermuda is one of those islands that most people forget about. Not in the Caribbean chain, this amazingly close, friendly, and beautiful island is a real joy to experience. Elevated and luxurious, yet subtle and charming, it really does have something for everyone! It is also an easy acclimation—there are no unique plugs needed, the dollar is accepted everywhere, and everyone speaks English. Bermuda has no shortage of things to do: golf, biking, watersports, and boating. With all of this, you will want to return again and again and again.

In July 2023, I did a site inspection of the Hotel Aigua Blava located in Begur, one of the most beautiful coastal towns in Costa Brava. This property is situated in one of the many coves within the area of Badia de Aiguablava, a Catalonian privileged area. This property is cozy - perfect for a couple getaway or a family with small children. The sales contact welcomed me like family, in spite of it being the height of the busy season.

Welcome to Boston! Home of the lobster role, the World Champion Red Sox and Patriots and the best place to call home! A city steeped in history and vibrant culture, where every cobblestone street tells a tale of Paul Revere's ride and beyond. Boutique hotels in Boston's neighborhoods offer a diverse range of experiences for every traveler. Immerse yourself in the rich tapestry and diversity of this city, where you can explore world-class museums, indulge in culinary delights, enjoy the world-famous sports teams or stroll along the scenic waterfront all in one place.

Martha’s Vineyard, one of the many gems of New England, is nestled off the coast of Massachusetts. “The Vineyard” is an idyllic island known for its pristine beaches, charming towns and rich history. This “haven” has been a retreat for luminaries, presidents and artists alike, drawing visitors with its natural beauty and serene ambiance.

Welcome to Newport, Rhode Island! Where history, charm and coastal beauty converge to create an unforgettable destination. Only two hours from Boston, Newport is easy to get to and is nestled along the stunning shores of Narragansett Bay. Newport beckons travelers with its rich maritime heritage, Gilded Age mansions, and picturesque landscapes. Whether you're strolling down the cobblestone streets of downtown, exploring the opulent estates of the ever-prominent gilded age, or sailing the crystalline waters, Newport offers a perfect blend of culinary excellence, relaxation and/or adventure.

The Adirondacks hold a special place in my heart and visiting Lake Placid brought back a flood of wonderful memories. My grandparents owned a "camp" on Lake George, part of the broader Lakes Region, which includes Saranac Lake, Mirror Lake, Lake Placid and Lake Champlain, among others. Every summer, my family would load up the station wagon - kids, dogs, cats, bikes, coolers and anything else that could fit and head up for the summer from Boston. The town of Lake Placid is nestled in the Adirondack Mountains, surrounded by breathtaking landscapes of lakes, mountains and forests. Renowned for its natural beauty, it's a magnet for outdoor enthusiasts. Having hosted two Olympic Games in 1932 and 1980, the Village of Lake Placid also offers a charming array of shops and restaurants.

As a New Englander and snowboarder, I feel fortunate to have the opportunity to be within a few hours’ drive to some of the best snow-capped peaks and slopes in the world. The variation of each of the mountains, lodges and enchanting landscapes in the east, await even the most discerning skier or snowboarder. This best ski resorts east coast guide gives you a peek into the some of the biggest and most popular of these alpine retreats.