Sample Itinerary
NEW ENGLAND
Journey Concept
Discover the magic of New England in fall, beginning in Boston’s storied city streets and ending in Vermont’s foliage-covered countryside. Here, culture meets nature, and autumn unfolds in a warm palette of gold, amber, and red — the perfect blend of history, comfort, and seasonal beauty.
8 Day Trip
Suggested Travel Months
September - November
DESTINATION #1
Days 1-4
Boston
Boston blends historic charm with modern sophistication, offering world-class museums, cobblestone neighborhoods, waterfront dining, and rich cultural heritage. With its walkable streets and iconic landmarks, the city invites exploration at every turn.
​
In October, temperatures are crisp and pleasant, with daytime highs around 60–65°F (15–18°C) and lows near 45°F (7°C) — ideal for fall foliage and city touring.
GETTING THERE
Sample flight plan is based on round-trip travel from Chicago.
Sample flight route: Chicago (MDW) → Boston (BOS)
Estimated total travel time: ~4 hours
Total travel time includes layovers and ground transport.
YOUR HOTEL
Four Seasons Hotel Boston
Overlooking Boston Public Garden, Four Seasons Hotel Boston blends timeless luxury with New England charm. Rooms and suites feature park views, marble bathrooms, and elegant residential styling in the heart of Back Bay.
Suggested inclusions during your stay:
​
Daily breakfast at Coterie or via in-room dining
-
Access to the indoor pool and fitness center
-
Concierge support for dining, cultural, and seasonal events
-
Walkable access to Newbury Street, Beacon Hill, and Back Bay
-
Easy transit for museums, theater, and waterfront excursions
Boston Experiences
Explore Boston’s rich cultural tapestry through historic sites, boutique shopping, waterfront strolls, museums, and exceptional dining — all enhanced by the crisp autumn air and vibrant seasonal foliage.​
​
Here are just a few of the many activities you can enjoy during your stay:
Stroll through Beacon Hill and Back Bay, where brick townhomes, tree-lined streets, and classic architecture shine in autumn.
Wander through Boston Common and the Public Garden as fall foliage transforms the city’s most beloved green spaces.
Walk Boston’s iconic Freedom Trail, tracing the city’s revolutionary history through historic streets and landmark sites.
Enjoy crisp fall views along the Charles River or Boston Harbor, taking in the city skyline from the water or scenic paths.
DESTINATION #2
Days 4-8
Vermont
Nestled in the heart of Vermont’s Green Mountains, Woodstock offers quintessential New England charm with covered bridges, rolling hills, and pastoral farmlands. October brings peak foliage season, transforming the landscape into a patchwork of amber, crimson, and gold.
In October, daytime highs average 55–60°F (13–16°C) with cooler evenings near 40°F (4°C) — perfect for cozy fires, scenic drives, and outdoor exploration.
GETTING THERE
Sample flight route: Boston → Woodstock, VT
Estimated total travel time: ~3 hours by private transfer
YOUR HOTEL
Woodstock Inn & Resort
A historic village resort surrounded by mountains and maple forests, The Woodstock Inn blends rustic charm with New England elegance. Rooms feature classic décor, warm textures, and a sense of country coziness ideal for fall.
Suggested inclusions during your stay:
-
Daily breakfast and seasonal dining venues
-
Spa and wellness services (à la carte)
-
Access to biking and hiking trails
-
Golf, tennis, and outdoor activities (seasonal)
-
Village shops, galleries, and cafés within walking distance
-
Concierge assistance for foliage drives and farm visits
Vermont Experiences
Experience autumn in Vermont through scenic foliage drives, farm visits, artisanal tastings, and outdoor activities like hiking, biking, and leaf peeping.​
​
​Here are just a few of the many activities you can enjoy during your stay:
Take in Vermont’s iconic autumn colors on scenic drives through rolling hills, forests, and countryside roads.
Stroll through charming village centers, discovering local shops, historic buildings, and classic New England character.
Visit local farms or orchards to experience Vermont’s agricultural traditions and seasonal harvests.
Explore peaceful hiking trails surrounded by vibrant fall foliage and fresh mountain air.
TRAVEL DAY
Vermont > Return Home
Day 8
Sample flight plan is based on round-trip travel from Chicago.
Sample flight route: Woodstock, VT → Boston (BOS) → Chicago (MDW)
Estimated total travel time: ~6 hours
Total travel time includes layovers and ground transport.