New England Rails and Sails

Featuring Four Rail Excursions and Three Scenic Cruises

September 25 - October 3, 2021


Itinerary       Pricing       Inclusions



September 25: Arrive Boston

Arrive in Boston, Massachusetts with an included transfer to your hotel. Meet your Tour Manager in the hotel lobby at 6:00 p.m. for a welcome dinner.

Meals: D

September 26: Boston and Kennebunkport, Maine

Begin the day with a sightseeing tour of historic Boston including the Freedom Trail and the Public Garden. Then, travel up the coast and stop at Kennebunkport, one of Maine’s coastal jewels and the summer home to many of America’s rich and famous, before continuing to the seaside town of Portland, Maine. Rich in history and culture, Portland boasts a vibrant waterfront with one-of-a-kind shops, galleries and restaurants.

Meals: B

September 27: Maine Narrow Gauge Railroad and Casco Bay Cruise

Begin the day at the Maine Narrow Gauge Railroad and Museum. The museum is dedicated to preserving Maine’s history with the two foot narrow gauge railroad system. See the extensive collection of rail cars and take a short 1.5 mile long ride along the Eastern Promenade of Casco Bay. Later, Maine’s rocky shoreline and wooded islands come into view on a scenic cruise in Casco Bay. Sail past lovely Victorian cottages dotted along Little and Great Diamond Islands as you watch for lobstermen, local fishing fleets and the abundant sea birds, seals and other wildlife.

Meals: B, D

September 28: New Hampshire's White Mountains and North Conway Scenic Railroad

Leaving the coast today, travel west into New Hampshire’s White Mountains. Experience towering peaks, stunning scenery, quaint towns and villages before boarding the North Conway Scenic Railroad to enjoy the Mt. Washington Valley countryside. Relive part of railroad history when the first train traveled through this region over 135 years ago. Later enjoy time for shopping at some of the many outlet stores or browse the local shops in North Conway.

Meals: B, L

September 29: The Kancamagus Scenic Byway and Green Mountain Railroad

This morning, travel the Kancamagus Scenic Byway as it follows a beautiful path through the White Mountains. It is one of the world’s most spectacular fall-foliage trips and meanders through vast forests, old logging roads and Indian hunting paths. Cross into Vermont and stop at Quechee Gorge to view the spectacular scenery of the area before arriving in Chester to board the Green Mountain Railroad. Enjoy the ride while taking in views of covered bridges, the Connecticut River and the Brockway Mill Gorge.

Meals: B, D

September 30: Norman Rockwell Museum and Mohegan Sun

Leaving Vermont this morning, travel to the town of Stockbridge in Massachusetts’ culturally rich Berkshires region. At the Norman Rockwell Museum see the world’s largest collection of the artist’s original artwork. See his beloved paintings from The Saturday Evening Post and the Four Freedoms to the best in the field of American Illustration. You’ll spend some free time in the quaint Berkshire town of Stockbridge before continuing to the incredible Mohegan Sun Resort, your home for the next two nights.

Meals: B

October 1: The Essex Steam Train and Riverboat Becky Thatcher

The Valley Railroad Company operates the coal-fired locomotives of the Essex Steam Train. Be swept away by the hiss of the steam and the blast of the whistle as you pass through some of the most beautiful country in the state. See forests and streams, beautiful vistas and nostalgic towns. At Deep River Landing, you board the Riverboat Becky Thatcher for a relaxing trip up the Connecticut River, before returning to Mohegan Sun.

Meals: B, L

October 2: Plymouth Rock and Whale Watching Cruise

Today pass through the state of Rhode Island, famous for its maritime history. In Plymouth, Massachusetts climb aboard your sea going vessel for a whale watching excursion. This naturalist guide-led cruise sails out to Cape Cod Bay and Stellwagen Bank, a marine sanctuary and primary feeding ground for Humpback, Finback, Minke and the endangered Right Whales. Pay a visit to Plymouth Rock where our forefathers first settled on American soil. Tonight, gather for a farewell dinner hosted by your Tour Manager.

Meals: B, D

October 3: Travel Home

This morning, take the group transfer to Boston’s Logan Airport for flights out after 12:00 p.m.

Meal: B




Tour Rates

Based on Double Occupancy:

From $3,349 pp

Single Supplement: +$1,429


FREE airfare when booked by January 31, 2021!


Tour Activity Level

Easy 1 2 3 4 5 Active



• 14 Meals: 8 breakfasts, 2 lunches and 4 dinners
• Round trip airport transfers
• Experience Four New England Trains:
  ❖ Maine Narrow Gauge Railroad
  ❖ Conway Scenic Railroad
  ❖ Green Mountain Railroad
  ❖ Essex Steam Train
• And Three New England Cruises:
  ❖ Cruise Portland’s Casco Bay
  ❖ Becky Thatcher Riverboat Cruise
  ❖ Captain John Whale Watching Cruise
• Panoramic city tour of Boston with a local guide including the Freedom Trail
• Visit Kennebunkport, one of Maine’s coastal jewels
• Spend one night in the mountain town of North Conway
• Travel the Kancamagus Scenic Byway through the White Mountains on a spectacular fall-foliage trip
• See Quechee Gorge State Park, Vermont’s “Little Grand Canyon”
• Visit the Norman Rockwell Museum
• Spend two nights at the incredible Mohegan Sun Resort and Casino
• $45 in Mayflower Money


Hotel Accommodations
Day 1 – Boston Park Plaza, Boston, Massachusetts
Days 2 and 3 – Best Western Merry Manor Inn, Portland, Maine
Day 4 – Residence Inn, North Conway, New Hampshire
Day 5 – Fairfield Inn, Williamstown, Massachusetts
Days 6 and 7 – Mohegan Sun Resort Casino, Uncasville, Connecticut
Day 8 – Marriott Boston Quincy, Quincy, Massachusetts


Rooms for the night before the tour are available. Cost for a room in Boston is $499, tax included.

*All pricing and inclusions subject to change and based on availability. Airfare not included in above pricing.

**Air itineraries may not be available until documents are received. Air seats are assigned by the airline for the entire group. Seat changes can only be attempted upon receipt of tickets and documents at which time availability may be limited. If specific seat assignments are vital to your reservation, we recommend individual air reservations rather than booking air with the group.

***Must have 16 passengers booked through Roseborough Travel Agency to guarantee a Roseborough Escort.


Travelers Protection Plan (TPP) – $150 per person land only

This nonrefundable fee waives all cancellation fees when we are notified of cancellation one day before the tour departs. If you must leave the tour early due to personal illness, illness or death of a member of your immediate family, TPP guarantees full refund for any unused services after the departure of the tour. Other benefits include medical expenses for illness and injury, emergency transportation, 24 hour hot line, and lost or stolen baggage assistance. Return air transportation is included ONLY if your air tickets were provided by Mayflower Cruises & Tours. If you purchase the optional Travelers Protection Plan (TPP), you will be refunded all payments, including deposit amount, less the TPP premium amount.

Cancellation Charges Without Traveler’s Protection Plan (TPP)
• 61 days and more – deposit amount
• 60 – 31 days – 20% of the tour cost
• 30 – 15 days – 30% of the tour cost
• 14 – 1 day prior – 40% of the tour cost
• Day of departure or early departure from tour – 100% of the tour cost
No refund on unused portion

Exclusions: Mayflower Cruises & Tours reserves the right to alter its refund and cancellation policy when a substantial amount of cancellation or postponement of travel is attributable to: conditions resulting from an act of God, natural or man-made disaster, fire, government action, civil disorder, war, hostilities between nations, or unavailability of transportation through no fault of Mayflower Cruises & Tours.




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