Fall Foliage in New England by Train

September 24, 2023 thru September 30, 2023

The greens of New England are turning gold and red as we explore Massachusetts, Maine, New Hampshire and Vermont. We enjoy 4 different rail rides and a boat ride, through a variety of countryside and coastlines.  This is some of our country’s most beautiful and historic locations and the best time of year to see it all!


Air Transportation included


Train/lodging included


7 days, 6 nights

Activity Level Rating

3: Moderate



Meals Included

6 breakfasts, 3 lunches, 4 dinners


Roundtrip door to door transportation included


Tour director, driver & local guide tips included

Tour Highlights

  • Enjoy a day site-seeing in historical Boston before departing on our train ride
  • Indulge in a lobster dinner during our stay in Maine
  • Enjoy a boat ride around Lake Winnipesauke before headed to our historic resort in New Hamshire
  • Site-see while we ride the beautiful Conway Scenic Railway
  • Check out exciting historic locations as we cruise through Vermont
  • Your tour includes most meals, all lodging, and services of a Tour Director


  • Roundtrip air transportation Tucson to Boston (not including airline baggage & in-flight charges)
  • Transportation by air, train and deluxe motorcoach
  • Roundtrip door to door livery service
  • 6 nights lodging at excellent hotels
  • 6 breakfasts, 3 lunches, 4 dinners
  • Admission to all listed attractions
  • Your Professional Tour Director
  • All taxes and tips for included items (except for hotel housekeeping)

Day 1 - Tucson to Boston

We fly to Boston, Massachusetts’ capital and largest city, and check into our Boston area hotel.

Day 2 - Boston Day Tour

We start with a tour of the city of Boston. We’ll learn about the different districts of the city including the Back Bay where we find so many beautiful brownstones, each with its own unique architectural design. We will also see Beacon Hill and the gold domed state house, Boston Common, America’s first public park and the Public Garden. we see the Old Statehouse, once headquarters for English governors and later the site where the Declaration of Independence was read to the waiting citizens of Boston. We see the USS Constitution, the oldest commissioned warship afloat in the world!  After lunch we continue to the Boston Tea Party Museum and the JFK Library and Museum(B, L)

Day 3 - Train Ride to Maine

This morning, we board the Amtrak Downeaster train to Maine. Our local guide will meet us for a driving tour of the coastal village of Kennebunk and Kennebunkport.  This afternoon, we’ll enjoy free time in Perkins Cove, with its Marginal Way Shoreline Walking Path, benches to sit and watch the ocean roll in, boutiques and bobbing lobster boats. We check in to our hotel, then rejoin our group for a delicious lobster dinner. (B, L, D)

Day 4 - New Hampshire

Today we’ll explore New Hampshire. A boat ride on Lake Winnipesauke, one of the largest lakes enclosed in one state and a short coach jaunt brings us to Wolfeboro, the oldest summer resort in America. We enjoy free time for lunch and shopping in Wolfeboro, then tour the Wright Museum with its fascinating exhibits about military and home-life in World War II. In the late afternoon, we board the Winnipesaukee Railroad Turkey Dinner Train. We enjoy delicious hot roast turkey with all the trimmings during our two-hour trip along the lake. (B, D)

Day 5 - White Mountains of New Hampshire

We take the Kancamagus Highway through the beautiful White Mountains of New Hampshire.  Mid-morning, we arrive at the Conway Scenic Railway for boarding of our train. We’ll travel on what was once the Maine Central Railroad’s famed Mountain Division line, on tracks that were laid in the 1870s. Enjoy some of the most dramatic natural scenery in the East as we travel through spectacular Crawford Notch – past sheer bluffs, steep ravines, cascading brooks and streams, panoramic mountain vistas, across Frankenstein Trestle and Willey Brook Bridge en-route to Crawford Station. Tonight we escape the ordinary and relive the romance of dining on the rails as we ride a restored Pullman dining car while enjoying an elegant 5-course dinner on the Cafe Lafayette Dinner Train. (B, L, D)

Day 6 - Vermont

Today we travel by coach into the Berkshires via Vermont. After our included lunch at the Publik House, we enjoy a visit to the Vermont Country Store, Purveyors of the Practical and Hard-to-Find. In today’s global economy, merchants at the Vermont Country Store search throughout the nation and abroad to find goods that fill the needs of American and international customers alike.  We lunch at the Publyk House in Bennington, then travel on to Hemmings Automobilia, a filling station with memorabilia and an automotive museum with 27 vintage automobiles. Visit our Car Lover’s store, café and old-fashioned Sunoco Station. (B, L)

Day 7 - Flight Home

It’s almost time to head home, but first we enjoy a Fall Foliage Leaf-peeper tour along the Berkshires scenic back country roads before arriving in Stockbridge, a picture-postcard town, where Norman Rockwell lived and worked. We can explore the Rockwell Museum on our own, stop in the Red Lion Inn to view its extraordinary teapot collection, shop in Stockbridge’s many quaint shops and lunch before we head to the airport for our flight home filled with memories of the fabulous fall colors and wonderful New England. (B)

Itinerary subject to change.

Package Pricing

$3,875 per peerson

Double Occupancy

Deposit: $200

$4,475 per person

Single Occupancy

Deposit: $200

Final Payment Due:

June 22, 2023

Deposit: n/a

Price Includes

• Roundtrip air transportation Tucson to Boston (not including airline baggage & in-flight charges)
• Transportation by air, train and deluxe motorcoach
• Roundtrip door to door livery service
• 6 nights lodging at excellent hotels
• 6 breakfasts, 3 lunches, 4 dinners
• Admission to all listed attractions
• Your Professional Tour Director
• All taxes and tips for included items (except for hotel housekeeping)

Booking Policy


  • None through June 22, 2023
  • $200 – June 23 – July 12, 2023
  • $2200 – July 13 – August 23, 2023
  • 100% After August 23, 2023

Travel Insurance

In today’s changing travel environment, it’s important to protect your travel investment so you can relax and enjoy your trip. Unforeseen events such as flight delays, baggage loss or even a sudden sickness or injury could impact your travel plans. For your convenience, we offer the following Travelex Insurance Services protection plan for this tour:


360° Adult Group Choice Flyer – Provides an overview of benefits and coverage limits

360° Adult Group Choice Policy – Provides the full coverage term details, including exclusions and limitations

$248 covers trip costs up to $4,000 or $313 covers trip costs up to $5,000. Cost may be more or less depending on your total trip cost. If you do not wish to purchase at booking, the plan can be purchased any time prior to final payment. Contact us to purchase. For questions regarding benefits or coverages, please contact Travelex Insurance Services at 888-574-7026 and reference plan number GCB-0521.

The product descriptions provided here are only brief summaries. The full coverage terms and details, including limitations and exclusions, are contained in the insurance policy. Travelex Insurance Services, Inc. CA Agency License #0D10209. Travel Insurance is underwritten by Berkshire Hathaway Specialty Insurance Company; NAIC #22276. X41


Level 3: Moderate

Expectations: Expect a moderate amount of walking. There will be time to rest on the coach and between attractions. To enjoy this tour, you should be prepared to walk slightly longer distances, climb stairs and tolerate periods of standing, for example on city walks, sightseeing stops or ship excursions. The daily pace and timing can fluctuate significantly between longer and shorter travel days, with additional activities possibly occurring in the early morning or evening. There may be some changes in altitude or temperatures.

Visit our Activity Level Ratings page under Plan Your Tour for full information on the ratings system.


For your reference, we send to you a detailed itinerary approximately 3-4 weeks prior to the scheduled tour departure. This has day-by-day times and events, hotel information where you can be reached in case of an emergency, and airline information.

The times listed on the itinerary are all approximate. We cannot be held responsible for schedule changes due to unforeseen circumstances with the weather, transportation agents, highway conditions, hotels or contracting agents.


It is always a good idea to carry on your person a list of medications that you are taking and an emergency contact phone number while you are traveling. And we suggest making a copy of the itinerary and provide it to a friend or family member.


All hotel baggage handling fees are included. We also include basic gratuities for the Tour Director, Coach Driver, Livery Drivers and local Tour Guides. If someone has truly gone above and beyond additional tipping is permitted, but never required.


For your convenience, we have a (round-tour) door-to-door pickup service with each multi-day tour. (This service is not available to all clients depending on your location.) Approximately 2 to 3 days prior to the departure date you will receive a call from our office and we will tell you your assigned pickup time. (These times can vary up to 15 minutes depending on traffic.)


With passenger health in mind, we are not currently offering daily seat rotation. You will have an assigned seat and boarding order to allow for social distancing among passengers. At booking let us know if you prefer Front, Middle or Back of motorcoach. Each section comprises 4 to 5 rows. We will try to accommodate all requests. If we are unable to honor all requests, preference will be given based on date of your tour deposit.


If you would like to request special accommodations at the hotel(s) where we are lodging, please call us as soon as possible and we will forward these requests for you. The phone numbers of the hotel(s) where we are staying are listed on the itinerary.

Many hotels around the country have instituted a "reconditioning fee" of $300 or more that is levied upon a guest that smokes in a non-smoking room. If this occurs during our tour you will be responsible for paying this fee to the hotel prior to check-out.


We pay close attention to your requests but please realize that these are merely requests and cannot be guaranteed.


Pleasurebent Tours acts solely as an agent in arranging hotels, transportation, sightseeing, baggage-handling, and other services and does not assume any liability for injury, damage, loss or delay due to any act or default of any company or person. We, along with our subcontractors, reserve the right to make changes to an itinerary if it is necessary for the proper handling of a tour.

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