Awaken Travel Club | Fall 2027 Club Tour
New England by Train & Boat
Three trains, three boats and New England in its fall colors.
Boston, the Maine Coast, the White Mountains & Mystic | Hosted by Cindi & Denise
Solo-friendlyComing on your own? Welcome! The solo price is right on this page, or tell us you’d like to share and we’ll try to find you a roommate.
Sign-ups are open | Oct 2 - Oct 10, 2027
$4,549 per person, sharing a room
✈️ Round-trip flights included when you book by December 31, 2026
The trip
Why we love this one
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.
The highlights
What we'll do together
Three train rides
A short narrow-gauge ride in Portland, a vintage train through the Mount Washington Valley in North Conway, and a coal-fired steam train through the Connecticut countryside.
Three boat rides
A ferry ride past the islands of Casco Bay, a riverboat trip up the Connecticut River, and a whale watch out of Plymouth with a naturalist on board.
Peak fall color
The Kancamagus Highway through the forests of the White Mountains, one of the prettiest fall drives anywhere, then a stop at Quechee Gorge in Vermont.
The Maine coast
A stop in the harbor town of Kennebunkport, two nights by Portland and its busy waterfront, and a visit to Portland Head Light on the rocky shore.
The route
Where the road takes us
- 1BostonDays 1, 2, 8 & 9
- 2KennebunkportDay 2
- 3Portland & Casco BayDays 2 & 3
- 4North ConwayDay 4
- 5Kancamagus HighwayDay 5
- 6Quechee GorgeDay 5
- 7SpringfieldDay 5, overnight
- 8Mystic & FoxwoodsDays 6 & 7
- 9EssexDay 7
- 10PlymouthDay 8
Dotted lines are the boat rides: Casco Bay, the Connecticut River riverboat and the whale watch.
Day by day
Your itinerary
- 1
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 PlazaMeals: Dinner - 2
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, MaineMeals: Breakfast, Dinner - 3
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, MaineMeals: Breakfast - 4
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 ConwayMeals: Breakfast, Lunch - 5
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 PlaceMeals: Breakfast, Dinner - 6
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, MashantucketMeals: Breakfast - 7
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, MashantucketMeals: Breakfast, Lunch - 8
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, QuincyMeals: Breakfast, Dinner - 9
Day 9: Boston
The tour wraps up after breakfast in Boston. Plan your trip home for the afternoon.
Meals: Breakfast
Hotels listed are the current plan and can change to a similar hotel.
The details
What's included
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 departure
Date & price
Oct 2 - Oct 10, 2027
$4,549per person$6,348 solo
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? Tell us on the sign-up form and we’ll do our best to match you with another member. We can’t promise a match, so the solo price applies unless we find you a roommate.
Early October is usually a great time for fall color in the White Mountains.
Sign-ups are open
How to save your spot
The club has 32 seats on this departure. Round-trip flights are included when you book by December 31, 2026, so the sooner the better.
- 1
Fill out the short form
Tell us who is coming, how you’d like to room and where you’d like to fly from. It takes about two minutes.
- 2
We reach out to you
Cindi or Denise will be in touch to go over your details and reserve your spot in the club’s group.
- 3
Pay your deposit
$200 per person, due within five business days of reserving. That makes your spot official.
Deposit
$200 per person, due within five business days of reserving. You can pay by check or by Visa, Mastercard or Discover.
Final payment
Due 90 days before departure, in early July 2027.
If you need to cancel
Without the tour company's Travelers Protection Plan, these cancellation charges apply per person:
- 91 days or more before departure
- Your deposit
- 90 to 31 days before
- 20% of the tour cost
- 30 to 15 days before
- 30% of the tour cost
- 14 to 1 day before
- 40% of the tour cost
- Day of departure, or leaving the tour early
- 100% of the tour cost
There is no refund for any part of the tour you don't use.
Travel insurance
Travel insurance is optional and is not included in your tour price. If you'd like to look at coverage, you can see Faye's plans or compare plans from other companies on Squaremouth. Their licensed teams can answer any questions about what a plan covers.
Mayflower Cruises & Tours also offers its own Travelers Protection Plan. It can only be added within 24 hours of your deposit, and with it your deposit is $599 per person with the group flights, or $499 if you book your own flights.
Questions first? Call (423) 401-9997 or email [email protected].
Good to know
Questions members ask
Are flights really included?
Yes. When you book by December 31, 2026, round-trip group flights from any airport in the continental US, Chattanooga included, are part of the $4,549 price, and so are your airport transfers in Boston. Just tell us your airport on the sign-up form.
What if I sign up after December 31?
You can still come if there is room. The tour price stays the same, and round-trip flights from Chattanooga add $900 per person. We’re happy to price other airports for you.
Can I book my own flights?
Yes. While the free flights offer is on, you get $400 per person off your trip price instead. Your airport transfers are still included as long as your flights fit the tour’s arrival and departure times (we’ll give you those) and we have your flight times at least 60 days before the trip.
Can I pick my seat on the plane?
The airline assigns seats for the whole group, and they may not show until you check in at the airport. If a certain seat really matters to you, booking your own flights may be the better choice.
I’m traveling solo. What does that cost?
$6,348 per person for a room to yourself.
Can you find me a roommate?
We’ll try. Tell us on the sign-up form that you’d like a roommate, and we’ll do our best to match you with another member traveling solo. We can’t guarantee a match, so if we don’t find one, the solo price applies.
Do I need a passport?
No, the whole trip is in the US. You’ll fly with a REAL ID or your passport, and the name on your reservation has to match that ID exactly, so please give us your name just as it appears on it.
How active is this trip?
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.
Who runs the tour?
Mayflower Cruises & Tours runs the tour, with a professional tour manager with the group the whole way. Cindi and Denise are your hosts, and you book through us.
What about travel insurance?
Travel insurance is optional and is not included in your tour price. If you'd like to look at coverage, you can see Faye's plans or compare plans from other companies on Squaremouth. Their licensed teams can answer any questions about what a plan covers.
Mayflower Cruises & Tours also offers its own Travelers Protection Plan. It can only be added within 24 hours of your deposit, and with it your deposit is $599 per person with the group flights, or $499 if you book your own flights.
Fall 2027 club tour
Ready to come along?
This is the club's big tour for fall 2027, and we'd love to have you with us. Fill out the short form to save your spot, or give us a call if you have questions first.
Hear all about it at our online club meeting
Thursday, Nov 19 at 2:00 PM Eastern
A guest from our tour company walks us through this trip and answers your questions. It’s online, so you can join from home.
Add your nameTraveling with you
Your hosts
Cindi Sanden
Denise Karnes
Cindi and Denise started the Awaken Travel Club because travel is better with people who get it. We handle the planning, the questions and the details, so all you have to do is pack and come along.