12-Day Eastern Americas Undiscovered Gems: Canada, USA & Bermuda in October
This 12-day journey redefines the classic Eastern Americas route by pairing the peak autumn foliage of the north with the exclusive, sun-drenched sophistication of the mid-Atlantic. Starting in the historic, cobblestoned heart of Quebec City, you will wind through the undiscovered mountain passes of Vermont and the rugged Maine coastline before flying to the secluded luxury of Bermuda.
Embrace the 'shoulder season' magic of October, where the crowds dissipate, and the landscapes transform. Expect world-class gastronomy in Montreal, private estate tours in New England, and five-star resort living in Hamilton, all while utilizing premium transit options including luxury rail and private chauffeured crossings.
Day 1: Quebec City, Canada - Arrival & Old World Luxury
Private Transfer to Old Quebec
Arrive at Jean Lesage International Airport (YQB) and meet your private chauffeur for a transfer to the historic heart of the city.
Check-in at Auberge Saint-Antoine
Settle into your suite at this Relais & Châteaux property, which blends museum-grade artifacts with contemporary luxury.
Private Walking Tour of Petit Champlain
Discover the hidden alleys of North America's oldest shopping district with a local historian.
Gastronomic Dinner at Chez Muffy
Enjoy a farm-to-table feast inside a historic stone warehouse overlooking the St. Lawrence River.
Day 2: Quebec City, Canada - The Charlevoix Escape
Train de Charlevoix Departure
Board the luxury scenic train for a journey between the mountains and the river, viewing the spectacular autumn foliage.
Baie-Saint-Paul Exploration
Wander through this artist colony, visiting independent galleries and artisan cheese shops.
Le Massif Viewpoint
Take a private shuttle to the summit of Le Massif for a panoramic view of the fall colors reflecting in the estuary.
Return to Quebec City
Relax in the lounge car with local cider as the sun sets over the Laurentian Mountains.
Day 3: Quebec City to Montreal, Canada - The Gastronomy Corridor
VIA Rail Business Plus to Montreal
Enjoy executive class service on Canada’s premier rail line, featuring complimentary meals and drinks.
Arrival in Montreal & Luxury Check-in
Check into the Ritz-Carlton Montreal, the 'Grande Dame' of Sherbrooke Street.
Private Mural & Art Tour
Explore Montreal's vibrant Plateau district, known for its creative spirit and hidden street art gems.
Dinner at Toqué!
Experience the pinnacle of Quebecois cuisine at this world-renowned institution.
Day 4: Montreal, Canada to Burlington, USA - Cross-Border Mountains
Private Chauffeured Crossing
Cross the border into Vermont via a private car service, navigating the scenic rural roads of the Eastern Townships.
Shelburne Farms Elite Tour
Visit this 1,400-acre working farm and forest, a National Historic Landmark on Lake Champlain.
Burlington Waterfront Lunch
Dine at Hen of the Wood, featuring the finest seasonal ingredients Vermont has to offer.
Sunset Sail on Lake Champlain
Charter a private sailboat to watch the October sun dip behind the Adirondack Mountains.
Day 5: Stowe, USA - Foliage & Fireplaces
Hot Air Balloon Ride
Soar over the Green Mountains for a bird's-eye view of the world-famous Vermont fall foliage.
Smugglers' Notch Scenic Drive
Drive the winding pass through towering cliffs and vibrant maple forests.
Trapp Family Lodge Tea
Visit the historic home of the Von Trapp family (of Sound of Music fame) for Austrian-inspired refreshments.
Spa Evening at Lodge at Spruce Peak
Unwind with a mountain-inspired massage at Vermont’s premier luxury resort.
Day 6: Stowe to Portland, USA - The White Mountains Route
Kancamagus Highway Drive
Travel through New Hampshire's most scenic route, stopping at hidden waterfalls and covered bridges.
Luxury Picnic in North Conway
Enjoy a curated gourmet picnic with views of Mount Washington, the highest peak in the Northeast.
Arrival in Portland, Maine
Check into The Press Hotel, located in the historic Portland Press Herald building.
Old Port Culinary Tour
Explore the cobblestone streets and taste the finest oysters and lobster in the country.
Day 7: Portland, USA - Coastal Elegance
Private Lobster Boat Charter
Head out into Casco Bay with a local lobsterman to learn the trade and enjoy a fresh-caught lunch on deck.
Portland Head Light Visit
Visit the most photographed lighthouse in America during the golden afternoon light of October.
L.L. Bean Flagship Visit
Take a private car to nearby Freeport for a luxury shopping experience at this American icon.
Dinner at Fore Street
Savor wood-fired cuisine in one of the most acclaimed restaurants in the Eastern United States.
Day 8: Portland to Hamilton, Bermuda - To the Atlantic Isle
Chauffeur to Boston Logan (BOS)
Enjoy a smooth 2-hour drive south to Boston for your direct flight to the Atlantic.
First Class Flight to Bermuda
Transition from the crisp fall air to the sub-tropical warmth of Bermuda.
Arrival at Hamilton Princess
Check into the 'Pink Palace', Bermuda’s legendary luxury hotel overlooking the harbor.
Sunset Cocktails at 1609
Sip a Dark ‘n Stormy as the yachts return to the marina under a purple October sky.
Day 9: Hamilton, Bermuda - Craters & Crystals
Crystal & Fantasy Caves Tour
Explore these breathtaking underground formations and azure subterranean lakes.
Lunch in Flatt’s Village
Dine at Village Pantry, a hidden gem favored by locals for its fresh, sustainable seafood.
Bermuda Aquarium & Zoo
A boutique, high-end experience focusing on the unique biodiversity of the Mid-Atlantic ridge.
Harbor Front Fine Dining
Enjoy a sophisticated Italian-Bermudian fusion dinner at Harry’s at the Waterfront.
Day 10: St. George’s, Bermuda - UNESCO Heritage
Private Guide through St. George’s
Discover the 400-year-old history of this UNESCO World Heritage town and its colonial architecture.
Fort St. Catherine Exploration
Visit the island's most formidable fortress with stunning views of the Atlantic.
Beach Club Relaxation
Spend the afternoon at a private beach club on the secluded North Shore.
Dinner at Wahoo’s Bistro
Sample the award-winning fish chowder in a relaxed, high-end waterfront setting.
Day 11: South Shore, Bermuda - Pink Sands & Hidden Coves
Private Catamaran Charter
Sail along the South Shore to see the famous pink sand beaches from the water, stopping for snorkeling.
Jobson’s Cove Picnic
Enjoy a luxury catered lunch at this tiny, naturally enclosed cove with crystal clear water.
Spa at The Loren
Visit the island’s newest luxury boutique hotel for a cliffside wellness treatment.
Farewell Dinner at Marcus’
Celebrate your journey with world-class soul food and art at the Hamilton Princess.
Day 12: Hamilton, Bermuda - Final Reflections
Morning Walk on Front Street
Do some last-minute duty-free shopping for luxury watches and high-end island apparel.
Leisurely Brunch
Enjoy a final Bermudian brunch with fresh local fruit and pastries overlooking the harbor.
Private Transfer to L.F. Wade International
Relax in a premium vehicle for the short drive to the airport for your flight home.
Departure
Board your flight, carrying the memories of autumn forests and turquoise waters.
Best Time to Visit Americas
For this specific route, October is the absolute 'Sweet Spot'. In Quebec and New England, it marks the peak of the autumn foliage, with crisp air and brilliant colors. In Bermuda, October offers the perfect shoulder season weather—warm enough for swimming but past the peak humidity of summer and the height of hurricane season. It is the ideal time for those seeking luxury without the mid-summer crowds.
Visas & Border Crossings
Traveling between Canada, the USA, and Bermuda requires a valid passport. For most European, Australian, and British citizens, an eTA is required for Canada and an ESTA for the USA. Bermuda requires an arrival authorization form. Crossing the Canada-USA land border via private car is typically efficient in the Vermont region, but always allow 45-60 minutes for processing during peak travel times.
Getting Around Americas
This itinerary utilizes a sophisticated mix of transport. We recommend Business Class on VIA Rail for the Quebec-Montreal corridor for its comfort and efficiency. For the cross-border segment into the US, a private chauffeured car offers the most flexibility for foliage viewing. Between the US mainland and Bermuda, several major airlines offer short, high-frequency flights (approx. 2 hours) from hubs like Boston or New York.
