Beyond the Familiar: Montreal, Boston & Ayer's Cliff

Montreal

Private Airport Transfer with Meet & Greet, Old Montreal Restaurants & Cafes - Dining Suggestions

Your private driver will be waiting to greet you upon arrival and escort you to your private vehicle for a seamless transfer to your hotel in downtown Montreal.. Old Montreal is a foodie’s paradise, blending centuries-old architecture with a vibrant culinary scene. For French-inspired fine dining in an intimate, stone-walled setting, Le Club Chasse et Pêche is a long-time favorite known for its elegant, locally sourced cuisine. Toqué! , a Montreal institution, and the stylish Monarque both offer refined Quebecois fare with seasonal ingredients and exceptional service—perfect for a special night out. For something more casual yet equally delicious, Dandy and Olive et Gourmando are go-to spots for gourmet brunches, fresh sandwiches, and excellent coffee, all served in bright, inviting spaces. And for a relaxed caffeine fix, pop into Tommy Café , a popular Old Montreal-born chain known for its great coffee, light bites, and lush, plant-filled interiors. Whether you're grabbing a quick lunch on the patio or indulging in an unforgettable dinner, Old Montreal has something to satisfy every craving. Please note, meals are not included. Speak to your Destination Expert for personalized recommendations, or to arrange a reservation, subject to availability.

Accommodation: Hotel William Gray (Deluxe King Balcony Room (Room Only)), Montreal

Montreal

Murals of Montreal: An Urban Canvas (2 hrs) - Private, Old Montreal at Leisure

Discover the artistic side of Montreal on a privately guided walking experience through the city’s vibrant streets. Make your own way to meet your expert guide, then set off on foot to explore neighborhoods alive with color and creativity. Admire large-scale murals that transform building walls into striking open-air galleries, many of which are created as part of Montreal’s celebrated mural festivals. Learn about the artists behind the works, the stories they tell, and the social or cultural messages woven into the designs. From bold abstract pieces to detailed portraits, each mural offers a unique glimpse into the city’s thriving urban art scene. Along the way, your guide will share insights into the evolution of street art in Montreal and how it has shaped the city’s creative identity.. Exploring Old Montréal at leisure is like stepping into a European postcard without ever leaving Canada. Cobblestone streets, centuries-old architecture, and grand public squares create an atmosphere of timeless charm, perfect for wandering without a set agenda. Start your stroll at Place Jacques-Cartier, where street performers and cafés spill into the square, then meander down Rue Saint-Paul, the city’s oldest street, lined with art galleries, boutiques, and cozy restaurants. Pause to admire landmarks like Notre-Dame Basilica, with its stunning Gothic Revival interior, or take in waterfront views from the Old Port, where you’ll find green spaces, museums, and ice cream stands perfect for a mid-afternoon treat. Pop into local artisan shops, linger over an espresso on a sun-drenched patio, or step into one of the area’s many museums, like Pointe-à-Callière or Château Ramezay, for a deeper look at Montréal’s layered history. Whether you're there to soak up the atmosphere, shop for something unique, or simply follow your curiosity down narrow alleyways and sunlit plazas, Old Montréal invites you to slow down and savor every moment.

Accommodation: Hotel William Gray (Deluxe King Balcony Room (Room Only)), Montreal

Montreal

Culinary Stroll Through Jewish Montreal (4 hrs) - Private

Trace the flavorful legacy of Jewish Montreal on a privately guided half-day walking tour through the city’s most iconic culinary landmarks. Make your way independently to meet your expert guide at the designated starting point, where your immersive journey begins through the cultural and historical threads woven into the delis, diners, and bagel shops that have shaped Montreal’s unique food identity. Over the course of the tour, visit eight notable establishments—each a touchstone of Jewish heritage in the city—where rich stories are paired with even richer bites. As you stroll through vibrant neighborhoods, your guide will share stories of migration, community, and culinary tradition, offering insights into how these eateries became symbols of cultural resilience and belonging. From the scent of freshly baked bagels to the legacy of famed smoked meat counters, the atmosphere alone evokes generations of history and hospitality. Whether you're drawn by the cultural narrative or the culinary backdrop, this experience offers a deeper understanding of the people, places, and traditions that continue to define Jewish life in Montreal.

Accommodation: Hotel William Gray (Deluxe King Balcony Room (Room Only)), Montreal

Montreal, Stowe

Car Rental: SUV, Montreal to Stowe (2.5 hrs) - Self-Drive, Stowe at Leisure

Pick-up your rental car and prepare to hit the open road. An SUV will be reserved in your name. Please speak with your Destination Expert if you are interested in an upgrade option.. Driving from Montréal to Stowe is a scenic and easy journey that introduces you to some of Vermont’s most charming highlights along the way. As you cross into the U.S., opt to divert off the main road for beautiful views along Lake Champlain, with wide-open water, rolling hills, and mountain backdrops creating a picturesque start to your trip. Passing through Burlington, Pearl Street provides a lively slice of the city with cafés, shops, and a youthful college-town vibe that makes for a great stretch-your-legs stop. Families often enjoy breaking up the drive with classic Vermont attractions, including the Ben & Jerry’s Factory in Waterbury, famous for its fun tour and generous ice cream samples, or the Vermont Teddy Bear Factory in Shelburne, where kids can watch bears being made and pick out a cuddly souvenir. The final stretch into Stowe winds through quintessential countryside, covered bridges, and lush valleys, setting the tone for a relaxing mountain getaway. Today's drive time is approximately 2.5 hours, however the US-Canada border crossing and optional stops may increase this duration.. Spending time at leisure in Stowe invites you to slow down and soak in the charm of Vermont’s most iconic mountain town. Whether you’re wandering through the picture-perfect village with its boutique shops, cozy cafés, and local art galleries, or simply taking in the scenery from a porch, trail, or spa, the pace feels effortlessly relaxed. Outdoor enthusiasts can enjoy gentle walks or scenic bike paths, while those seeking quiet moments can unwind with a craft beer at a local brewery, savor farm-to-table cuisine, or explore scenic drives that reveal covered bridges and rolling Green Mountain views. From laid-back afternoons browsing local markets to peaceful evenings surrounded by mountain air, Stowe offers the perfect backdrop for unhurried, rejuvenating moments.

Accommodation: The Lodge at Spruce Peak (Studio), Montreal

Stowe, Boston

Stowe to Boston via Franconia Notch (4-5 hrs) - Self-Drive, Optional Activity: Evening Cruise in Boston Harbor

The drive from Stowe to Boston becomes especially scenic when routed through Franconia Notch, offering a beautiful transition from Vermont’s Green Mountains into the dramatic landscapes of New Hampshire’s White Mountains. As you travel through the notch, you may want to stop for a short walk or two - Flume Gorge is a popular choice, with its boardwalks winding between towering granite walls and rushing waterfalls, while other quick trails and lookouts provide easy ways to stretch your legs amid spectacular scenery. Opt to stop for lunch in one of the charming New Hampshire towns along the way North of notch in Littleton, or after you’ve worked up an appetite in nearby Lincoln, provide great options from casual cafés and classic diners to cozy spots serving hearty fare. Once back on the highway, the route becomes faster and more direct, eventually leading you into the vibrant energy of Boston. For additional routings, speak to your Destination Expert.. Opt to include an evening cruise on Boston Harbor, a relaxing way to see the city from the water as night falls. Glide past illuminated landmarks and waterfront neighborhoods while Boston’s skyline sparkles with city lights, creating a memorable and atmospheric close to the day. Please speak to your Destination Expert to pre-book a public cruise.

Accommodation: The Fairmont Copley Plaza (Deluxe King), Stowe

Boston

Discover Boston (4 hrs) - Private Tour, Dinner Reservations at Union Oyster House

Experience Boston like a local on a private guided tour offering a four-hour immersive journey into the heart of “Beantown.” After a seamless pick up from your hotel, set off on a personalized adventure inviting you to delve into Boston's rich history and vibrant culture. Your knowledgeable guide will share fascinating insights, transforming your exploration into an engaging narrative. Marvel at iconic landmarks, such as the renowned Old North Church, where Paul Revere's famous phrase "one if by land, two if by sea" echoed through history. Explore the site of the Boston Massacre, and wander through Faneuil Hall, a pivotal part of the bustling Faneuil Hall Marketplace. But it's not just about history – discover Boston's educational significance, at Harvard Square in Cambridge, where centuries of academic excellence unfold before you, and the historic Boston Latin School, the oldest public school in America. Moreover, with over sixty universities and colleges in the Boston Metro area, including renowned institutions like MIT and Boston University, you'll witness the city's thriving academic diversity. Conclude your tour with a transfer to your accommodation.. Step into history at Union Oyster House, America’s oldest continuously operating restaurant, serving guests since 1826. Located along Boston’s Freedom Trail, this iconic eatery offers a quintessential New England dining experience steeped in tradition. Dine in cozy, wood-paneled booths once frequented by Daniel Webster and enjoy fresh oysters shucked at the original raw bar. With its charming colonial ambiance and classic seafood dishes—like clam chowder and broiled Boston scrod—Union Oyster House is both a culinary landmark and a window into Boston’s storied past. Please note: Your meal is not included and will be paid for on location. Reservations are confirmed at the time of booking and are subject to availability.

Accommodation: The Fairmont Copley Plaza (Deluxe King), Boston

Boston

Freedom Trail Walking Tour (1.5 hrs) - Private Tour, Cucina Crawl in the North End (with Tastings, 4 hrs)

Meet your private guide and set off on a captivating private walking tour of the historic sites of the Freedom Trail, a journey through the heart of Boston's historic legacy. Immerse yourself in the rich tapestry of American history as you traverse this iconic trail, starting at Boston Common, the nation's oldest public park. As you venture along the red-brick path, witness the Massachusetts State House, a beacon of political history. Explore Park Street Church, where passionate orators like William Lloyd Garrison once rallied for social change. Stroll through Granary Burying Ground, the final resting place of influential figures like Paul Revere and John Hancock. Continue to King's Chapel, an architectural marvel and site of religious significance. Pause at the Benjamin Franklin statue and the Old South Meeting House, where revolutionary plans were hatched. Experience the profound resonance of the Boston Massacre Site and the Old State House. Your private guide will reveal the captivating stories behind each stop, making history come alive. Conclude your tour at Faneuil Hall, a marketplace with a rich past, where your understanding of Boston's pivotal role in shaping the nation's destiny will be forever enriched.. From a designated meeting point, set out with your private guide on a delightful gastronomic walking journey through Boston's historic North End, immersing yourself in the flavors that define one of the city's oldest neighborhoods. Steeped in colonial history with landmarks like the Paul Revere House and Old North Church, and enriched by the cultural legacy of Italian immigration, this off-the-beaten path area of Boston is perfect for discovering the authentic flavors that define this vibrant community. Your senses will come alive with the enticing aromas of pizzerias, restaurants, bakeries, pastry shops, and salumerias along the way. You will have the opportunity to tantalize your taste buds with a variety of Italian delights, such as pizza, pasta dishes, Italian meat and cheeses, cannoli, and coffee or Italian soda to top it all off.

Accommodation: The Fairmont Copley Plaza (Deluxe King), Boston

Boston, Kennebunkport

Boston to Kennebunkport (2 hrs) - Self-Drive, Kennebunkport at Leisure, Dining Reservation at White Barn Inn Restaurant

The drive from Boston to Kennebunkport offers a relaxing journey along New England’s scenic coast and charming towns. Heading north, you pass through coastal Massachusetts and southern New Hampshire, where rolling hills, farmland, and quaint villages create a quintessential New England backdrop. The most direct route follows I-95 and takes approximately 2 hours, however you may wish to detour along Route 1. This route opens onto the scenic Atlantic shoreline, with opportunities to spot sandy beaches, rocky coves, and small harbors along the way. The final stretch into Kennebunkport winds through picturesque streets lined with historic homes, boutique shops, and local eateries, setting the stage for a leisurely seaside escape filled with charm, coastal views, and classic Maine hospitality.. Charming and quintessentially New England, Kennebunkport invites visitors to explore its scenic coastline, quaint streets, and lively village atmosphere. The town’s sandy beaches, including Goose Rocks Beach and Kennebunk Beach, offer sun-soaked relaxation, gentle waves, and stunning views of the Atlantic, perfect for a leisurely day by the water. Strolling through the village, you’ll discover an array of boutique shops, art galleries, and local craft stores, each brimming with unique finds and coastal charm. Dining is equally delightful, with a mix of casual seafood shacks, waterfront bistros, and upscale restaurants serving fresh, locally sourced fare. From scenic walks along the harbor to sampling lobster rolls, indulging in artisanal treats, or simply soaking in the picturesque architecture and seaside ambiance, exploring Kennebunkport is a harmonious blend of relaxation, shopping, and culinary enjoyment.. Enjoy a reservation at White Barn Inn Restaurant, housed within a beautifully restored 19th-century barn on the grounds of White Barn Inn. The dining room, with its post-and-beam architecture, soft candlelight, and white-linen–covered tables, exudes an atmosphere that is both elegant and inviting. The seasonally driven menu showcases the region’s rich bounty, featuring dishes such as butter-poached Kennebunkport lobster, grass-fed beef tenderloin with Perigueux sauce, and wild-mushroom risotto with black truffle, all prepared with classic technique and a focus on local ingredients. An extensive, sommelier-curated wine list complements the cuisine, offering vintages from around the world, while attentive and polished service ensures each meal is seamless and memorable. Accolades including AAA Five Diamond and Forbes Five Star reflect the restaurant’s dedication to excellence.

Accommodation: White Barn Inn (Junior Suite with Fireplace), Boston

Kennebunkport, Bar Harbor

Kennebunkport to Bar Harbour via Route 1 (4.5 hrs) - Self-Drive, Dining Options in Bar Harbor

The drive from Kennebunkport to Bar Harbor is a scenic journey through coastal Maine, showcasing charming seaside towns, forested stretches, and panoramic ocean views. Traveling north, you pass through towns like Camden and Rockland, where boutique shops, art galleries, and cozy cafés make perfect stops for a leisurely lunch or a coffee break. Winding along Route 1, the route offers glimpses of lighthouses, harbors filled with fishing boats, and rugged coastline, all quintessential Maine scenery. As you approach Bar Harbor and Acadia National Park, the landscape opens to dramatic ocean vistas, rocky shores, and mountain views, providing a memorable and picturesque drive that combines small-town charm with the natural beauty of Maine’s midcoast.. Bar Harbor offers a vibrant dining scene that perfectly complements its coastal charm, with options ranging from casual seafood shacks to refined, waterfront restaurants. Fresh lobster, clams, and other Maine seafood are stars on many menus, often paired with locally sourced produce and creative farm-to-table dishes. The town’s streets are lined with cozy cafés, bakeries, and ice cream shops, ideal for a relaxed breakfast, a midday snack, or a casual coffee break while exploring. For a more upscale experience, several waterfront and historic inns host restaurants with scenic views and carefully curated menus, providing a memorable backdrop for dinner. Whether you’re craving a lobster roll by the harbor, a gourmet tasting menu, or a slice of classic Maine pie, Bar Harbor offers a delightful mix of flavors that capture the spirit of coastal Maine. Please speak to your Destination Expert for personalized recommendations, or to arrange a reservation.

Accommodation: Harborside Hotel (Oceanfront King Room), Kennebunkport

Bar Harbor

Best of Acadia National Park (4 hrs) - Small Group, Bar Harbor & Acadia at Leisure

Discover the very best of Acadia National Park on this exhilarating small-group adventure from Bar Harbor. With a maximum of seven guests, your local guide will lead a fully narrated tour highlighting iconic sights including Sieur de Monts Spring, Thunder Hole, and Otter Cliff, with plenty of photo stops along the way. Take in the crystal-clear waters of Jordan Pond and enjoy a delectable, locally sourced lobster roll before ascending to the breathtaking vistas of Cadillac Mountain. This immersive driving tour blends natural beauty, local flavors, and expert storytelling, offering an unforgettable journey through Acadia National Park and the charming town of Bar Harbor.. Spending time at leisure in and around Bar Harbor offers a delightful mix of coastal charm, natural beauty, and New England character. The town’s streets are lined with an array of boutiques, specialty shops, and artisanal stores where visitors can find everything from handmade jewelry and local crafts to nautical décor and unique souvenirs. Art lovers will appreciate the numerous galleries showcasing works by Maine artists, including paintings, photography, sculpture, and glasswork, perfect for finding a one-of-a-kind piece to take home. Between shopping and gallery-hopping, you can relax at a café or ice cream parlor along the waterfront, take a gentle stroll along the Shore Path, or simply watch the boats drift in Frenchman’s Bay, making for a leisurely day that combines culture, charm, and the quintessential Bar Harbor seaside experience. Please note, a National Park Pass is required if venturing into the Park.

Accommodation: Harborside Hotel (Oceanfront King Room), Bar Harbor

Bar Harbor, Ayer's Cliff

Bar Harbor to Ayer's Cliff (5 hrs) - Self-Drive, Optional: Dining at Ripplecove Hotel & Spa

The drive from Bar Harbor to Ayer’s Cliff, Quebec, is a scenic cross-border journey that blends coastal views, forested countryside, and charming New England towns before transitioning into the rolling landscapes of rural Quebec. Leaving Mount Desert Island, you’ll pass through quiet Maine communities and wooded stretches that feel peaceful and unhurried, with opportunities to stop for coffee, lunch, or a stroll in towns like Bangor or Lincoln. As you continue north toward the border, the scenery opens into farm fields, lakes, and gentle hills, offering a relaxed and picturesque route. Crossing into Quebec, the drive becomes even more pastoral, with winding country roads leading through small villages and open countryside on the way to Ayer’s Cliff. The final approach brings you to the serene shores of Lake Massawippi, setting the stage for a tranquil arrival in one of the Eastern Townships’ most charming communities.. Savor the flavors of the Eastern Townships with a dining experience at Ripplecove Hotel & Spa. Le Riverain Restaurant offers refined, seasonal cuisine in a warm, elegant lakeside setting, showcasing the region’s finest local ingredients. For a more relaxed atmosphere, Le Cove Bistro pairs panoramic views with a creative bistro menu, while the Sloop Bar serves casual weekend fare poolside, from slushes and ice cream to ready-to-enjoy drinks. Wine lovers can explore Le Cellier, the hotel’s award-winning cellar, home to over 4,000 bottles and curated by an expert sommelier. Please speak with your Destination Expert should you wish to secure any dining reservations in advance of your stay.

Accommodation: Ripplecove Hotel & Spa (Superior Suite, Lake Pavilion (Room Only)), Bar Harbor

Ayer's Cliff

Optional Activities at Ripplecove

Embrace lakeside leisure with a wide range of summer activities at Ripplecove Hotel & Spa. Paddle the serene waters of Lake Massawippi by kayak, canoe, or paddleboard, or cast off from the private dock for a peaceful fishing session. Back on land, explore surrounding trails on foot or by bike, challenge friends to a tennis match, or unwind with a game of petanque. Guests can also relax poolside or take advantage of boat excursions and curated nature experiences. Speak with your Destination Expert to pre-book, or consult the Concierge upon arrival.

Accommodation: Ripplecove Hotel & Spa (Superior Suite, Lake Pavilion (Room Only)), Ayer's Cliff

Ayer's Cliff, Montreal

Ayer's Cliff to Montreal (2 hrs) - Self-Drive, Rental Car Drop Off - Rental Car

Enjoy a direct drive to Montreal. Drive time is approximately 2 hours.. After packing up make your way to the rental car drop off centre and return your vehicle.