New England Rails and Sails

2025 Boston > Boston | Price from $3999

9 DAYS • 14 MEALS Tour New England by rail and sail during autumn’s splendor by taking three exciting rail excursions and three fun-filled New England cruises. Also, travel the beautiful Kancamagus Highway through the White Mountains and spend two nights at Foxwoods Resort and Casino.

Tour Itinerary

Day 1: Arrive in 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. Meal: D

Day 2: 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, D

Day 3: Maine Narrow Gauge Railroad and Casco Bay Voyage

Begin the day at the Maine Narrow Gauge Railroad for a short 1.5 mile-long ride. Dedicated to Maine’s history, the two-foot wide narrow gauge railroad system was essential in navigating the state’s hills and forests. Later, Maine’s rocky shoreline and wooded islands come into view on a scenic voyage on Inner Casco Bay. Sail past lovely Victorian cottages dotted along Little and Great Diamond Islands as you watch for wildlife and local fishing fleets on Portland’s iconic ferry service. Later, make a stop at the historic Portland Head Light. Meal: B

Day 4: New Hampshire’s White Mountains and North Conway Scenic Railroad

Leave the coast today and travel west into New Hampshire’s White Mountains. In North Conway, board the North Conway Scenic Railroad. You will enjoy the Mt. Washington Valley countryside and relive part of railroad history when the first train traveled through this region over 135 years ago. Meals: B, L

Day 5: Kancamagus Scenic Byway and Quechee Gorge

Begin the day by traveling 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 at your hotel for the night. Meals: B, D

Day 6: Mystic Seaport and Foxwoods Resort Casino

Spend the day at Mystic Seaport “The Museum of America and the Sea.” Here, history comes alive as you walk the bustling street of a 19th-century seafaring village and talk with the many costumed characters. Watch boat-builders, riggers and lumbermen hard at work in the preservation shipyard and visit the nation’s leading maritime art gallery. Later, come to the incredible Foxwoods Resort Casino, your home for the next two nights. Meal: B

Day 7: The Essex Steam Train and Riverboat Becky Thatcher

The Valley Railroad Company operates the coalfired 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 Foxwoods. Meals: B, L

Day 8: 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

Day 9: Travel Home

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

Itinerary is subject to change.

Tour Highlights

  • 14 Meals: 8 breakfasts, 2 lunches and 4 dinners
  • Round trip airport transfers
  • Experience Three New England Trains: Maine Narrow Gauge Railroad, Conway Scenic 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 Mystic Seaport, “The Museum of America and the Sea”
  • Spend two nights at the incredible Foxwoods Resort Casino

Hotel Accommodations

Day 1 Hilton Boston Park Plaza, Boston, Massachusetts
Days 2 and 3 – Fairfield Inn, Scarborough, Maine
Day 4 – Residence Inn, North Conway, New Hampshire
Day 5 – Sheridan Monarch Place, Springfield, Massachusetts
Days 6 and 7 – Foxwoods Resort Casino, Mashantucket, Connecticut
Day 8 – Marriott Boston Quincy, Quincy, Massachusetts

DATES & AVAILABILITY

September 21, 2024 | $3,799

Per Person Twin

$3,799

Single Room Add

+$1,499

$399 AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $589, tax and breakfast included.

September 25, 2024 | $3,799

Per Person Twin

$3,799

Single Room Add

+$1,499

$399 AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $589, tax and breakfast included.

September 27, 2024 | $3,799

Per Person Twin

$3,799

Single Room Add

+$1,499

$399 AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $589, tax and breakfast included.

September 28, 2024 | $3,799

Per Person Twin

$3,799

Single Room Add

+$1,499

$399 AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $589, tax and breakfast included.

October 2, 2024 | $3,799

Per Person Twin

$3,799

Single Room Add

+$1,499

$399 AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $589, tax and breakfast included.

October 4, 2024 | $3,799

Per Person Twin

$3,799

Single Room Add

+$1,499

$399 AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $589, tax and breakfast included.

September 27, 2025 | $3,999

Per Person Twin

$3,999

Single Room Add

+$1,399

FREE AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $599, tax and breakfast included.

October 1, 2025 | $3,999

Per Person Twin

$3,999

Single Room Add

+$1,399

FREE AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $599, tax and breakfast included.

October 3, 2025 | $3,999

Per Person Twin

$3,999

Single Room Add

+$1,399

FREE AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $599, tax and breakfast included.

October 4, 2025 | $3,999

Per Person Twin

$3,999

Single Room Add

+$1,399

FREE AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $599, tax and breakfast included.

October 4, 2025 | $3,999

Per Person Twin

$3,999

Single Room Add

+$1,399

FREE AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $599, tax and breakfast included.

October 8, 2025 | $3,999

Per Person Twin

$3,999

Single Room Add

+$1,399

FREE AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $599, tax and breakfast included.

October 10, 2025 | $3,999

Per Person Twin

$3,999

Single Room Add

+$1,399

FREE AIRFARE from major U.S. cities. Call for details.

Rooms for the night before the tour are available. Cost for a room in Boston is $599, tax and breakfast included.