Luxury Holiday to New England

On this luxury holiday to New England you’ll meet Boston academics, Maine lobstermen, and brewers from Vermont, while staying in style at some of the region’s top hotels.


Day 1 & 2

Start your luxury holiday to New England in Boston, the Northeast’s historical and cultural capital. From your base overlooking the leafy Boston Common, you’ll be perfectly placed to explore this compact yet diverse city.

Spend your morning with a local historian as you stroll through the Beacon Hill, Downtown and North End Districts; the historic heart of the city and location of multiple pivotal moments for the first colonists and later revolutionaries. Then it’s time to don your thinking cap as you cross the Charles River to Cambridge, home to MIT and Harvard. From artificial intelligence and robotics to linguistics and economics, ideas that have changed the world have originated here.

The North Shore into Maine

Day 3

Leaving Boston, drive up the coast towards New Hampshire and ultimately into Maine. Known as the North Shore, you’ll pass salt marshes and tidal creeks, interspersed with rocky headlands and long beaches.  Along the way stop in the classic New England sea towns that hug the coast like Gloucester, Ipswich and Newburyport.

Enjoy lunch far away from the tourist crowds at a local’s favorite restaurant sitting on a quiet cove before continuing to Kennebunkport and your base for the next few days, the fantastic woodland getaway that is Hidden Pond.

The Kennebunks, Maine

Day 4 & 5

A relaxed day to explore the Kennebunks, the collective name for Kennebunk, Kennebunkport, Cape Porpoise, and Goose Rocks Beach. Wander the shops and galleries around Dock Square in Kennebunkport before taking a gentle oceanfront stroll out towards the Bush family estate on Walker’s Point, passing St Ann’s Church along the way. Take the pretty drive north along the coast to an idyllic lobster-fishing village and enjoy a low key lunch at one of the lobster huts or clam shacks that dot the shore

This afternoon, pick up a bottle of wine, before taking to waters of the Kennebunk River in a lobster boat, watching in anticipation as the crew haul their traps.  For a more adventurous outing,  kayak through the beautiful Cape Porpoise Harbor and its more than a dozen islands.

After dinner at Hidden Pond, sit under the stars while you roast s’mores around the campfire.

New Hampshire’s White Mountains

Day 6 & 7

Today you’ll head inland, taking the scenic back roads on your way to the stunning White Mountains, the highest range in the Northeast. Take a slight detour through Western Maine, passing through picture-perfect small towns before climbing into the White Mountains and your destination, the imposing Mount Washington Resort.

Take a full day to explore the surrounding White Mountains. Travel the dramatic Kancamagus Highway, one of New England’s great road trips, as it leads you through the heart of the mountains, your Journey Guide outlining the most spectacular viewpoints and hikes to hidden waterfalls  along the way or, for jaw-dropping views, take the fun cog railway or scenic auto road to the top of Mt Washington itself.

The Northern Green Mountains, Vermont

Day 8 & 9

This morning you have a true treat in store as you take a leisurely road trip through the rolling hills and small dairy farms of Vermont’s remote Northeast Kingdom. This isolated corner of the state is wonderfully undeveloped and blissfully crowd free. Along the way, follow your Journey Guide to find maple syrup farms, local cheese producers, and tiny Vermont villages with iconic white-steepled churches and picturesque covered bridges. End your day at one of New England’s great small luxury hotels, The Pitcher Inn.

The next day after breakfast, you are perfectly placed to venture out into the surrounding Green Mountains. On a hot summer’s day, head to secret river swimming holes or grab some bikes from the inn to ride up to a wooded lake for canoeing, swimming, and a picnic lunch. Alternatively, take a short road trip along the winding mountain roads to local cider farms and a cheese creameries to sample the local produce that Vermont is rightly famous for.

Mad River Valley & Route 100

Your journey continues as you travel south on Route 100, one of New England’s great road trips, as it follows the Mad River Valley. Don’t miss nearby Woodstock, an almost impossibly perfect village with its pristine village green surrounded by stately Victorian homes. A short drive from Woodstock, set in an old mill on the banks of the Ottauquechee River, is the flagship store of Simon Pearce, a famous pottery and glassware producer. Get a behind-the-scenes look at the glassblowers at work in the studio before lunch overlooking the river.

The Southern Green Mountains

Day 10 & 11

From your base in Townshend and the idyllic Windham Hill Inn, you’ll be perfectly place to head west into the Green Mountains, south to the town of Brattleboro, a mecca for painters and artisans, or east into a sleepy corner of New Hampshire, where the imposing Mt Monadnock, that inspired both Emerson and Thoreau, dominates the landscape.

In Weston, a picturesque village with houses and shops surrounding a village green, visit the Vermont Country Store, a vast collection of local, Vermont-made products. The nearby village of Grafton has been meticulously preserved by the Windham Foundation and for some of Vermont’s finest cheese, not to mentioned a chance to see the “cheddaring” process in action, a stop at the Grafton Village Cheese Company is a must.

Into Massachusetts and The Berkshires

Day 12 & 13

After breakfast at the inn, make your way south into Western Massachusetts and the stunning Berkshires. At the far western edge of Massachusetts, the bucolic Berkshires, are a world away from the hustle and bustle of Boston and in many ways live up to their storybook image of rural New England, with wooded hills, narrow winding roads, and historic villages. The area is renowned for its fall foliage with the hills turning a vibrant mix of oranges, reds and yellows.

After lunch at one of the Berkshire’s many great restaurants, continue through the hills, to the upscale town of Lenox. Enjoy your evening at the Stonover Farm, a luxury B&B and beautifully restored farmhouse on the outskirts of Lenox and a short walk across the fields to Tanglewood, the summer home of the Boston Symphony Orchestra.

Spend the last day of your New England holiday exploring the Berkshires before returning to Boston. As well as MASS MoCa, the area is a bastion of arts and culture with world class museums like the Clark, Williams College Museum of Art, and the Norman Rockwell Museum. Scattered throughout the rolling hills you’ll also find stately historic homes such as The Mount, Edith Wharton’s home, and Chesterwood, summer home of Daniel Clark French, the sculptor of the Lincoln Memorial.

From The Magazine


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