Welcome to Boston, the cradle of American history and home to a champion sports culture. This time is yours to do as you please! Settle in for the evening and relax at your hotel, or head out into the city and experience the city’s nightlife. Boston is celebrated for its innovative dining scene with historic oyster bars and modern food halls, so there are plenty of places to reset over an evening meal.

Optional Experiences:

• View Boston: If time allows, head to View Boston at the Prudential Center for panoramic views of the city’s skyline.
• Boston Historical Cruise: Take to the water on a Boston Harbour Cruise for a memorable introduction to the city and its rich history.

Hilton Boston Park Plaza, or similar

Rise and shine, the city calls. Dive into Boston’s rich revolutionary history, lively neighbourhoods, and proud sporting culture, from historic landmarks to the home of the Boston Red Sox at Fenway Park. Wander the city at your own pace, exploring The Freedom Trail and Boston Common, or discover each unique experience the city has to offer, from educational wildlife tours to haunted ghost trails.

Optional Experiences:

• Boston Whale Watching Tour: Travel onboard a high-speed catamaran, keeping an eye out for humpbacks, minke whales, finbacks, and white-sided dolphins while professional researchers from the Whale Centre of New England offer insight into everything whale
• Boston Ghosts & Gravestones: Guided by a 17th-century gravedigger, tour the spookiest Boston streets, hearing tales of murder, mayhem, ghosts, and ghouls.
• USS Constitution Cruise: Take to the water and discover the city from the sea on this narrated sightseeing tour around Boston Harbor, offering a clear and informative look at the city’s maritime history.
• Martha’s Vineyard Ferry: Escape the hustle and bustle of the city and board a ferry to the picturesque island, Martha’s Vineyard, for a chilled small-town adventure.
• Boston Old Town Trolley Tour: Hop aboard Boston’s old town trolley sightseeing tour, visiting 18 of the city’s top attractions while experts narrate tales of colonial rebellion, revolutionary fervour, and the birth of a nation.

Hilton Boston Park Plaza, or similar

This morning, pick up your rental car and journey west through Massachusetts. Visit local towns like Concord and Lexington before travelling the Mohawk Trail towards the Berkshires, passing Mount Greylock, Natural Bridge State Park, and MASS MoCA (contemporary art museum) along the way.

Home to museums, historic sites, and art venues, the Berkshires sits within the rolling hills of Western Massachusetts. Continue your journey through American history, or spend the day outdoors with activities such as golf, hiking, mountain biking, and fishing. Depending on the season and route, you can also add more adventurous experiences, including white-water rafting in the wider Western Massachusetts region.

Boston > The Berkshires (via the Mohawk Trail) | 182 miles

Holiday Inn & Suites Pittsfield-Berkshires, or similar

Leave the Berkshires and travel north into Vermont, following a scenic route through the Green Mountains and Green Mountain National Forest. This is a rewarding drive, with winding roads, covered bridges, mountain views, and classic New England countryside along the way. Continue towards the Mount Mansfield area, Vermont’s highest peak, where you can enjoy hiking trails and alpine views, or simply take time to explore the surrounding villages before settling in for your stay in the Green Mountains.

The Berkshires > Stowe | 192 miles

von Trapp Family Lodge & Resort, or similar

Spend the day exploring the colourful villages and rolling countryside of northern Vermont, sampling farm-to-table flavours, from Shelburne Farms and South Hero Island’s apple orchards to local cheeses, maple treats, craft breweries, and small-batch spirits. Stop in Shelburne for creative flavours at Sisters of Anarchy Ice Cream, or try a classic maple creemee at Mr. Creemee in Burlington. Later, head down to the Lake Champlain waterfront, where scenic cruises and sailing trips offer views across to the Adirondack Mountains.

von Trapp Family Lodge & Resort, or similar

Head east into New Hampshire and the White Mountains, one of New England’s great outdoor regions. Take in the views from the Bretton Woods Gondola, Mount Washington Auto Road, or Mount Washington Cog Railway, or choose a more active day of hiking, ziplining, or mountain biking. As evening falls, look for local wildlife on a moose tour around the Pemigewasset Valley or Gorham area, or enjoy a relaxed journey through the Pemi River Valley aboard the Café Lafayette Dinner Train.

Stowe > The White Mountains | 121 miles

North Conway Grand Hotel, or similar

Home to around 270 natural islands, Lake Winnipesaukee is a premier spot for water exploration. Tour the famous island channels via kayak or speedboat rental, or enjoy a scenic sunset dinner tour aboard the historic MS Mount Washington.

For another day of mountain adventures, head to Gunstock Mountain Resort, offering fun outdoor activities throughout the year. Through the winter enjoy skiing, snowboarding, and snow tubing, and in summer experience ziplining, aerial treetop challenges, a mountain coaster, and scenic chairlift rides.

North Conway Grand Hotel, or similar

Cross state lines, leaving New Hampshire for Maine, the Pine Tree State, known for its vast forests, rugged Atlantic coastline, and historic lighthouses. Follow the Rangeley Lakes and High Peaks scenic byways through wilderness landscapes, pausing in Rangeley or Carrabassett Valley. Alternatively, take the coastal route via Portland and Portland Head Light before continuing to Bangor/Orono; an ideal base for Moosehead Lake, Acadia National Park, and Katahdin Woods & Waters International Dark Sky Sanctuary.

North Conway > Bangor/Orono (via Portland) | 195 miles

Hotel Ursa, or similar

Spend the day at New England Outdoor Center near Millinocket, ideal for exploring Maine’s forests, lakes, and mountain landscapes. Activities vary by season, with white-water rafting and evening wildlife tours available during the summer; snowmobile tours and cross-country skiing during winter; and biking, fishing, and guided hikes throughout the year. Speak to your travel expert about activities available during your holiday and the best ones for you.

Hotel Ursa, or similar

Cross the international border into Quebec and continue into the Eastern Townships, a scenic region of rolling hills, forests, lakes and French-speaking communities. Your first Canadian overnight stop is Lac-Mégantic, a relaxed lakeside town where guests can walk along the shores of Lake Mégantic, explore the town centre, browse local cafés and shops, or visit nearby Parc ational du Mont-Mégantic, home to the ASTROLab and Observatory and set within one of the world’s great Dark Sky Reserve regions.

Bangor > Lac-Mégantic | 165 miles

Estello Suites & Spa, or similar

Travel west through the Eastern Townships, following a scenic route of farmland, wooded hills, lakes, and small villages. Pause in North Hatley, one of the region’s most attractive lakeside villages, with historic homes, cafés, boutiques, and views across Lake Massawippi, before continuing towards Vignoble Le Cep d’Argent for a taste of Quebec’s sparkling wine. Arrive in Magog later in the day, a lively town beside Lake Memphremagog with a walkable centre, lakeshore promenade, restaurants, and mountain views.

Lac-Mégantic > Magog | 75 miles

Hotel Cheribourg, or similar

Spend the day exploring the Magog and Orford area. Mont-Orford National Park offers hiking trails, forest scenery, lake views, and seasonal activities including kayaking, cycling, snowshoeing, and cross-country skiing, while nearby Le Marais de la Rivière-aux-Cerises provides an easier wetland walk on boardwalks and interpretive trails close to Magog.

Depending on the season and pace of the day, you may also visit Bleu Lavande for its lavender fields and local products, or Saint-Benoît-du-Lac Abbey, a peaceful lakeside abbey known for Gregorian chants, cheese, cider, and scenic grounds.

Hotel Cheribourg, or similar

Leave the Eastern Townships and travel towards Centre-du-Québec, where the landscape gradually shifts from wooded hills and lakes to broader agricultural plains influenced by the St Lawrence River. Stop in Sherbrooke to follow part of the Murals of Sherbrooke Trail, an open-air route through the downtown area that tells the city’s history through large-scale public art, before continuing to Odanak where you can visit the Abenaki Museum for an introduction to Abenaki heritage, traditions and contemporary life. End the day in Trois-Rivières, a quiet riverside community well placed for a relaxed overnight stay.

Magog > Trois-Rivières | 106 miles

Auberge du Lac St Pierre or similar

Follow the St Lawrence River valley from Trois-Rivières, with time to pause at the Quai de Sainte-Angèle for views across the river before continuing through farmland and riverside communities into the Montérégie region. En route, guests may visit Kahnawàke, a Kanien’keháka community on the south shore of the St. Lawrence, to learn more about Indigenous history, culture and contemporary life, before continuing to Rigaud for Sucrerie de la Montagne, a traditional Quebec sugar shack set in woodland and known for maple syrup heritage, rustic buildings, and regional food. Continue into Montreal for the evening and settle in for a two-night stay.

Trois-Rivières > Montreal | 79 miles

Le Saint Sulpice, or similar

Fill your final day with Montreal’s rich mix of historic architecture, markets, museums, restaurants, and cultural districts, or take a relaxed self drive excursion west of the city. Hudson, set beside the Ottawa River, makes an attractive half-day trip, with historic homes, independent shops, cafés, galleries, and peaceful waterfront views, while nearby Vaudreuil-Dorion offers heritage buildings, churches, parks, and riverside scenery.

Optional Experiences:

• Notre-Dame Basilica of Montreal: Walk through the neo-Gothic church, The Basilica of Our Lady of Montreal, admiring the stunning architecture and discovering its history.
• La Grande Roue de Montréal: Ride Canada’s tallest observation wheel with sweeping 360 views of Montreal’s city skyline
• Mont Tremblant & The Laurentians Day Tour: Discover one of Canada’s most beautiful and unique ecosystems on a guided tour through the Laurentian Mountains and cruise along the Lac des Sables.

Le Saint Sulpice, or similar

This morning make your way to Montréal-Pierre Elliott Trudeau International Airport, where your cross-border adventure comes to an end. Check-in in time for your onwards connection to continue your journey, or return flight home.