Awaken Travel Club | Fall 2027 Club Tour
New England by Train & Boat
Boston, the Maine Coast, the White Mountains & Mystic
Length
9 days, 8 nights
Starts
Boston, Massachusetts
Ends
Boston, Massachusetts
Hosted by
Cindi Sanden & Denise Karnes
This is the fall color trip, done the fun way. Over nine days we ride three different trains and take three boat rides, starting in Boston and heading up the Maine coast, across the White Mountains of New Hampshire and into Vermont, then down to the Connecticut shore.
Along the way there is Portland Head Light, a drive on the Kancamagus Highway when the leaves are at their best, a whole day at Mystic Seaport, two nights at Foxwoods, and a whale watch out of Plymouth before a farewell dinner together.
Day by Day
Day
1
Boston, Massachusetts
Arrive in Boston and check in to the hotel. At 6pm we meet our tour manager in the lobby and head out for a welcome dinner together.
Stay: Hilton Boston Park Plaza | Meals: Dinner
Day
2
Boston to Kennebunkport & Portland, Maine
A morning tour of Boston with a local guide, including the Freedom Trail and the Public Garden. Then we head up the coast to Kennebunkport, a pretty harbor town that has long been a summer favorite of well-known families, and on to Portland, Maine, with its lively waterfront of shops, galleries and restaurants.
Stay: Fairfield Inn, Scarborough, Maine | Meals: Breakfast, Dinner
Day
3
Portland & Casco Bay
Our first train of the trip: a short ride on Portland’s narrow-gauge railroad, whose rails are just two feet apart. Then our first boat ride, out on Casco Bay past the Victorian cottages of Little and Great Diamond Islands, watching for wildlife and fishing boats. We finish the day at Portland Head Light.
Stay: Fairfield Inn, Scarborough, Maine | Meals: Breakfast
Day
4
North Conway, New Hampshire
We leave the coast for the White Mountains. In North Conway, we board our second train, a scenic railroad that winds through the countryside of the Mount Washington Valley on one of the region’s historic rail lines.
Stay: Grand Summit Hotel at Attitash or Fairfield Inn, North Conway | Meals: Breakfast, Lunch
Day
5
Kancamagus Highway & Quechee Gorge, Vermont
This morning is the big fall color drive: the Kancamagus Highway, winding through the forests of the White Mountains. We cross into Vermont to see Quechee Gorge, then continue south to Springfield, Massachusetts for the night.
Stay: Sheraton Springfield Monarch Place | Meals: Breakfast, Dinner
Day
6
Mystic Seaport & Foxwoods, Connecticut
A day at Mystic Seaport, a living museum of a 19th-century seafaring village. Chat with costumed characters, watch boat builders and riggers at work in the shipyard, and visit the maritime art gallery. This evening we check in to Foxwoods Resort Casino for two nights.
Stay: Foxwoods Resort Casino, Mashantucket | Meals: Breakfast
Day
7
Essex steam train & the Connecticut River
All aboard our third train, a coal-fired steam train out of Essex, through forests, streams and small river towns. At Deep River Landing we switch to a riverboat for a relaxing cruise up the Connecticut River, then head back to Foxwoods.
Stay: Foxwoods Resort Casino, Mashantucket | Meals: Breakfast, Lunch
Day
8
Plymouth & a whale watch
Through Rhode Island to Plymouth, Massachusetts, for a whale watch with a naturalist out to Cape Cod Bay and Stellwagen Bank, a marine sanctuary where humpback, finback and minke whales come to feed. Then a visit to Plymouth Rock, and tonight a farewell dinner together.
Stay: Marriott Boston Quincy, Quincy | Meals: Breakfast, Dinner
Day
9
Boston
The tour wraps up after breakfast in Boston. Plan your trip home for the afternoon.
Meals: Breakfast
Included
- ✓Round-trip flights from any airport in the continental US, Chattanooga included, when you book by December 31, 2026
- ✓8 nights in hand-picked hotels, including 2 nights at Foxwoods Resort Casino
- ✓14 meals: 8 breakfasts, 2 lunches and 4 dinners, including a welcome dinner and a farewell dinner
- ✓A professional tour manager with the group the whole way
- ✓Motorcoach travel between every stop
- ✓Three train rides: the narrow-gauge railroad in Portland, the scenic railroad in North Conway and the Essex steam train
- ✓Three boat rides: Casco Bay, a riverboat on the Connecticut River and a whale watch out of Plymouth
- ✓Guided sightseeing: a Boston city tour with a local guide, Kennebunkport, Portland Head Light, the Kancamagus Highway, Quechee Gorge, a day at Mystic Seaport and Plymouth Rock
- ✓Round-trip airport transfers in Boston
Not included
- –Tips for your tour manager and motorcoach driver
- –Meals not listed in the day by day
- –Optional add-ons and anything on your free time
- –Travel insurance (optional)
- –Extra hotel nights in Boston before the tour (easy to add)
The pace
Moderate. Some days are long on the motorcoach and some are shorter. Expect walking tours, some stairs, uneven ground at the seaport and the lighthouse, and stepping on and off trains and boats.
Fall 2027 Date & Price
Per person, sharing a room. Round-trip flights from any airport in the continental US, Chattanooga included, are part of the price when you book by December 31, 2026. Traveling solo? $6,348 for a room to yourself. Want to share instead? Ask on the sign-up form by early April 2027 to be paired with another solo traveler through the Guaranteed Share program from Mayflower Cruises & Tours. It’s for non-smokers who don’t use a C-PAP machine. Your roommate will be the same gender and may be from outside our group.
Hotels listed are the current plan and can change to a similar hotel.
To save your spot: fill out the short form at awakentravels.com/NewEnglandSignUp or call us. Deposit $200 per person, due within five business days of reserving. Final payment is due 90 days before departure, in early July 2027.
Awaken Travel Club by Awaken Travels