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Embrace the beauty of New England during this 8-Day guided tour. Behold Boston, one of the oldest cities in the U.S. and where much of the country was formed; here, you will traverse part of the red-brick Freedom Trail, where you will see the hall that housed the country’s first-ever town meeting and many more historic sites. Admire the bronzing leaves of Vermont’s lush trees as you travel to Stowe, where the real Von Trapp family of ‘The Sound of Music’ chose to live — and where you will stay. In Montpelier, visit a maple syrup farm where you can taste the sweet golden liquid tapped straight from the trees. Ride a gondola at Loon Mountain Resort into New Hampshire’s White Mountains and see as far as Canada. See Maine’s oldest lighthouse in Portland, then celebrate your trip with a decadent fresh lobster dinner.
Departures & Pricing
- 20 Sep 2026 - 27 Sep 2026
from $8,955 pp twin share * - 26 Sep 2026 - 03 Oct 2026
from $8,932.50 pp twin share * - 27 Sep 2026 - 04 Oct 2026
from $9,975 pp twin share * - 30 Sep 2026 - 07 Oct 2026
from $9,575 pp twin share * - 02 Oct 2026 - 09 Oct 2026
from $9,750 pp twin share * - 03 Oct 2026 - 10 Oct 2026
from $9,775 pp twin share * - 04 Oct 2026 - 11 Oct 2026
from $9,775 pp twin share * - 07 Oct 2026 - 14 Oct 2026
from $9,995 pp twin share * - 09 Oct 2026 - 16 Oct 2026
from $9,725 pp twin share * - 10 Oct 2026 - 17 Oct 2026
from $9,695 pp twin share * - 16 Oct 2026 - 23 Oct 2026
from $9,850 pp twin share * - 18 Oct 2026 - 25 Oct 2026
from $12,150 pp twin share * - 18 Sep 2027 - 25 Sep 2027
from $7,450 pp twin share * - 19 Sep 2027 - 26 Sep 2027
from $7,450 pp twin share * - 24 Sep 2027 - 01 Oct 2027
from $7,425 pp twin share * - 25 Sep 2027 - 02 Oct 2027
from $7,275 pp twin share * - 26 Sep 2027 - 03 Oct 2027
from $7,450 pp twin share * - 01 Oct 2027 - 08 Oct 2027
from $7,425 pp twin share * - 02 Oct 2027 - 09 Oct 2027
from $7,275 pp twin share * - 03 Oct 2027 - 10 Oct 2027
from $7,450 pp twin share * - 08 Oct 2027 - 15 Oct 2027
from $7,125 pp twin share * - 09 Oct 2027 - 16 Oct 2027
from $6,925 pp twin share * - 10 Oct 2027 - 17 Oct 2027
from $7,450 pp twin share * - 15 Oct 2027 - 22 Oct 2027
from $7,425 pp twin share * - 16 Oct 2027 - 23 Oct 2027
from $7,450 pp twin share * - 17 Oct 2027 - 24 Oct 2027
from $7,450 pp twin share * - 16 Sep 2028 - 23 Sep 2028
from $7,095 pp twin share * - 17 Sep 2028 - 24 Sep 2028
from $7,095 pp twin share * - 22 Sep 2028 - 29 Sep 2028
from $7,075 pp twin share * - 23 Sep 2028 - 30 Sep 2028
from $7,095 pp twin share *
* Prices and category availability are subject to change without notice.
Cabin grades, balcony upgrades and pre-cruise hotel options are quoted on enquiry — call 1300 414 198.
Itinerary
- 1
Welcome to Boston
Affectionately known as Beantown, this revolutionary city is one of the oldest in the United States. After settling in, perhaps take a stroll to Downtown Crossing or historic Faneuil Hall. For those looking to shop, Quincy Market offers big brands and local products, set indoors and surrounding the columns of a regal 19th-century building. Join your Travel Director for dinner and an opportunity to mingle with fellow guests at your hotel.
- 2
Beantown to Saratoga Springs
Today you’ll discover some of Boston’s most famous sights as you delve into the city’s transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. See Boston Common, Boston Public Garden, Trinity Church and Copley Square. This afternoon, explore Stockbridge with Insight Choice. Choose to visit the Norman Rockwell Museum, home to the largest and most significant collection of original Rockwell art. Alternatively, choose to take a guided tour of Chesterwood, the former summer home and studio of renowned 20th-century sculptor Daniel Chester French, famous for his work on the Lincoln Memorial. Travel on through the rolling hills of the Berkshires and onto your upstate New York hotel, situated within the Saratoga Spa State Park.
- 3
The Legends of the Fall and Stowe
Trace the roots of Vermont’s rural traditions as you travel from Saratoga Springs into the heart of New England. In Weston, step inside the Vermont Country Store, a family-run emporium preserving generations of heritage brands and household curiosities. Browse shelves filled with locally made maple syrup, nostalgic sweets and artisanal Vermont cheeses, each reflecting the state’s rich tradition of craftsmanship. Continue to Woodstock, a village renowned for its Federal-style architecture and artisanal spirit. At Billings Farm Museum, gain insight into sustainable dairy farming practices and how 19th-century life shaped the region’s agricultural legacy. Later, at Morse Farm Maple Sugarworks, learn how maple sap is turned into syrup and taste the seasonal delicacy ‘sugar on snow’.Your day concludes at the Von Trapp Family Lodge, home to the famed musical family who made Vermont their refuge after fleeing Austria. Enjoy a hearty three‑course dinner featuring Alpine flavours, thoughtfully paired with German‑style lagers brewed onsite at the Von Trapp Brewery.
- 4
A Taste of Vermont
Enjoy a Relaxed Start at the iconic Von Trapp Family Lodge, where Austrian heritage meets Vermont’s Green Mountains. Later, connect with the land at Bread Butter Farm during a guided tour, followed by a nourishing lunch by Blossom Whole Food Kitchen. This afternoon, take time to explore the picturesque town of Stowe, filled with artisan boutiques and local charm.
- 5
North Conway and the White Mountains
Journey to New Hampshire’s White Mountains and enter striking Franconia Notch. Take a scenic ride on the Gondola SkyRide at Loon Mountain Resort (seasonal). On a clear day, you'll have superb panoramic views of New Hampshire, Maine, Vermont, New York and Canada. Later, journey through the dazzling crimson and orange hues of the famed Kancamagus Scenic Byway to North Conway. This spectacular section of Route 112 is unspoiled by industry and boasts 34.5 miles of untouched natural beauty.
- 6
Sightseeing in the White Mountains
This morning's MAKE TRAVEL MATTER® Experience with naturalist guide Chris Lewey provides an up-close and personal insight into New England's wildlife and ecology. Then, more spectacular fall foliage awaits as you journey through Crawford Notch, an arresting pass through the White Mountains. Stop for pictures at the Silver Cascade Waterfall and Bretton Woods, which offers stunning views of Mount Washington, the tallest peak in the northeast at 6,288 feet (1,917 metres). Your Travel Director will guide you on a scenic hike to Diana's Baths, which features a series of small cascading waterfalls. Return to your hotel where you can enjoy an evening at leisure.
- 7
North Conway - Kennebunkport - Portland
Cross from New Hampshire into Maine this morning and travel to Kennebunkport, a year‑round coastal destination that is home to the rich and famous, and has even served as the summer retreat of former President George H. W. Bush. Travel along Ocean Drive, enjoying more stunning views of the Maine coastline, before arriving in Portland for an afternoon at leisure. In the evening, enjoy a delicious dinner featuring Maine lobster with your fellow travellers.
- 8
Portland - Boston
Head to Fort Williams Park, which is home to the iconic Portland Head Lighthouse that has been in operation since 1791 before driving along the jagged coast back to Boston. Guests departing Boston will arrive at Boston Logan International Airport. Those extending their stay will return to the Hyatt Regency Boston hotel.
Inclusions & exclusions
What’s included
- Enjoy the comfort of Insight's luxurious, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom.
- Our customized luxury coaches are sanitized before the start of your tour and are maintained to very high standards.
- Physical distancing measures have been implemented on our customized luxury coaches.
- Experience enhanced hygiene protocols to align with the latest guidance following COVID-19.
- All Travel Directors and Drivers have completed training in enhanced well-being and hygiene protocols.
- Hand sanitizer is freely available on board for you to use throughout the day.
Accommodation
- Hyatt Regency, Boston
- The Gideon Putnam, Saratoga Springs
- Trapp Family Lodge, Stowe
- Westin Portland Harborview, Portland
- White Mountain, North Conway
Common questions about this voyage
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Book this rail journey
Send us an enquiry and a consultant will be in touch, or call 1300 414 198 for personal help choosing a departure.
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