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New England Rails and Sails - 8-day escorted holiday through six New England states to enjoy the annual fall foliage by way of scenic rail and cruise excursions.

New England Rails and Sails

This seasonal 8-day holiday takes travellers throughout New England, showcasing the region’s vibrant fall foliage. The only thing more brilliant than the fall colours is the unique excursions by rail and sea. Book early for Fall and ensure you see this amazing annual sight!

New England Rails and Sails
Cape Cod Central Railway

Tour Inclusions & Scenic Highlights

  • Services of a professional tour manager
  • Transportation by deluxe motorcoach
  • Hotel accommodations for 7 nights
  • 11 meals
  • Boston city sightseeing
  • Excursions aboard the North Conway Railroad, Essex Steam Train and Cape Cod Central Railroad
  • Scenic cruising along Portland’s Casco Bay to Diamond Island, Becky Thatcher riverboat cruise, and Hyannis Harbor Cruise
  • Roundtrip airport transfers
  • Taxes and services charges
Scenic highlights of your trip include:
  • Freedom Trail
  • Paul Revere’s House
  • Boston Common
  • White Mountains
  • Mystic Seaport
  • Gillette Castle
  • Cape Cod Canal

Tour Map

New England Rails and Sails Map
New England Rails and Sails Map


Day 1 – Boston
Arrive in Boston and transfer to your centrally-located hotel. The remainder of the day is at your leisure to explore the city. Join your tour manager at 18:00 this evening to meet your fellow travellers and receive local dining suggestions. Overnight Doubletree Hotel.

Day 2 – Boston Sightseeing / Travel to Maine
Today’s sightseeing tour takes you to some of Boston’s most important landmarks. Follow the Freedom Trail along the winding streets of this 17th century city. Visit Paul Revere’s House, the Old and new State Houses, and Boston Common, America’s oldest park.

After your city tour, continue by motorcoach north to Portland, Maine. Check into your hotel and prepare for a group dinner this evening at one of Portland’s bayside restaurants. Overnight Holiday Inn by the Bay. (D)

Day 3 – Casco Bay Cruise
Board an island ferry at Casco Bay this morning for a cruise along the rocky shores of Maine. Keep an eye out for seals, wooded islands, and Victorian cottages. After your cruise, travel by coach through the White Mountains of New Hampshire to North Conway, where the remainder of the day is at your leisure. Overnight Holiday Inn Express or Green Granite Inn. (B, D)

Day 4 - Conway Scenic Railroad and Kancamagus Scenic Byway
After breakfast at your hotel board the Conway Scenic Railroad for the colourful journey through New Hampshire’s White Mountains. Relive the railroad’s 130-year history while travelling through the colourful meadowlands, thick forests and rushing rivers. This afternoon travel the Kancamagus Scenic Byway through the White Mountains for one of the most scenic fall foliage excursions. Overnight Holiday Inn Express or Green Granite Inn. (B, L)

Day 5 - Quechee Gorge / En Route to Mystic
Today’s journey takes you along New Hampshire’s scenic country roads as you travel south to Mystic, Connecticut. Along the way, stop at Quechee Gorge, Vermont’s “Little Grand Canyon,” to see the 50-metre deep chasm wedged between the White and Green Mountains. Upon arrival in Mystic, make time to explore this seaport village. Overnight Hampton Inn. (B, D)

Day 6 - Essex Steam Train and Riverboat excursions
Today brings a full day of rails and sails. After breakfast, transfer to the historic Essex Station where you’ll board vintage rail cars pulled by an authentic coal-fired locomotive through the countryside to Deep River Landing. From here, board the Becky Thatcher riverboat for a relaxing cruise along the Connecticut River. In addition to stunning landscapes, you’ll get a firsthand look at some amazing local landmarks including Gillette Castle and Goodspeed Opera House. After your cruise, pick up the Essex Steam Train for your return trip. Your travels continue to Hyannis, Massachusetts. Overnight Resort and Conference Center or Holiday Inn. (B)

Day 7 - Hyannis Harbour Cruise and Cape Cod Scenic Rail
Enjoy another full day of scenic rail and cruising! After breakfast embark on a cruise along Hyannis Harbour in a replica of a Maine coastal steamer. After your harbour cruise, board the Cape Cod Central Railroad for a scenic rail excursion along the Cape’s cranberry bogs, salt marshes, and sand dunes. This evening’s farewell dinner with the group is a traditional Cape Cod lobster dinner. Enjoy recounting your favourite moments of the trips with your fellow travellers and swapping email addresses to keep in touch with your new friends. Overnight Resort and Conference Center or Holiday Inn. (B, D)

Day 8 - Transfer to Boston
After breakfast, there is a bit of time to explore Hyannis before transferring to Boston’s Logan Airport for your return flight home this afternoon. You may wish to extend your stay in Boston to enjoy the last of the fall colours in this historic city. (B)

  1. Dates & Pricing
  2. Trains & Transportation
  3. Accommodations

Dates & Pricing

Dates and prices are unavailable. Please review our selection of Fall Colour Train Holidays in America.


The Conway Scenic Railroad travels two scenic routes to multiple destinations throughout New Hampshire.

The Cape Code Central Railroad skirts the Cape’s cranberry bogs, woodlands, salt marshes, sand dunes, and ocean vistas to make a truly memorable journey to the Cape Cod Canal.

The Essex Steam Train pulls vintage rail cars through the Connecticut countryside to Deep River Landing.

The Casco Bay cruise is an island ferry that cruises along the rocky shores of Maine with fishing fleets and yachts that travels to Diamond Island and return.

The Becky Thatcher riverboat cruises the Connecticut River, past riverfront houses, woodlands, and the historic Gillette castle.

The Hyannis Harbour cruise sails the harbour of the tony resort town of Hyannis in a replica of a Maine coastal steamer.


Boston Park Plaza Hotel: Located in Boston’s historic Back Bay, this 941-room hotel is one of the city’s most recognized landmarks. Close to Boston Common, Newbury Street, Faneuil Marketplace, and the Theatre and Financial Districts, the hotel has many amenities including a fitness centre, business centre, 9 restaurants and lounges, and complimentary wireless Internet in Pairings Restaurant.

Holiday Inn Express: This 78-room hotel is conveniently located close to Mt. Washington Valley attractions and offer breathtaking views of the White Mountains. Hotel amenities include a glass-domed heated pool, hot tub, business centre, free high-speed wireless Internet and on-site guest laundry.

Green Granite Inn: Located in the White Mountains of New Hampshire, the inn offers beautiful views and comfortable hotel amenities including an indoor pool and hot tub, seasonal outdoor pool, and fitness centre.

Hilton Hotel: Located less than a kilometre from Mystic Seaport, across the street from the Mystic Aquarium and Olde Mystic Village, and close to area casinos, this 182-room hotel offers high-speed Internet access in all guest rooms, a heated indoor swimming pool and outside pool deck, fitness centre, restaurant and fireside lounge.

Hampton Inn: Conveniently located near popular Mystic attractions, guests enjoy amenities including complimentary high-speed Internet access, 24-hour coffee/tea in the lobby, fitness centre, indoor heated saltwater pool, and business centre.

Cape Cod Resort: This relaxing resort and spa offers unique hotel amenities including a wave pool, fitness centre, nightly bonfires and movies (in-season) and a variety of spa services. The hotel has a wine bar, restaurant and lodge on the premises.

Contact Holidays By Rail online or call a rail specialist at 0800 033 7960

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British Travel Awards Winner 2013 Best Small Holidays By Train Tour Operator
British Travel Awards Winner 2012 Best Small Holidays By Train Tour Operator
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