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New England Rail & Sail

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October 2 - October 8, 2026
7 Days / 6 Nights
Flight included
New England Rail & Sail tour

Tour Overview

Famous for its history, coastline, majestic mountains and glorious foliage, this unique tour of New England provides intimate views of the most dazzling fall color. Featuring three fantastic “rail” excursions and three “sail” experiences.

Tour Departs From
  • Wichita
  • Oklahoma City
  • Tulsa
Package Includes
  • 12 Included Meals
  • Narrated Pontoon Cruise
  • Winnipesaukee Scenic Railroad
  • Kancamagus Highway
  • Mountain Aerial Tram
  • Cafe Lafayette Dinner
  • M/S Mount Washington
  • Castle in the Clouds
  • Sightseeing Cruise
  • Nubble Lighthouse
  • City Tour of Portland
  • Portland Harbor Cruise
  • Old Port Exchange

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Activity Level 3: Active
Tour days tend to be longer and operate at a quicker pace. Expect to stand and walk for long periods of time, with short regular breaks and climb multiple flights of stairs. Some destinations may have changes in altitude and/ or temperature.

Price

    • 4159
    • Single
    • 3649
    • Double
    • 3559
    • Triple
    • 3459
    • Quad

Terms & Conditions

Cancellation Policy C
$300 Non-Refundable Deposit Per Person | Rates Per Person
Final Payment Due 120 days before departure
To review Village Travel's Cancellation Policies, Click Here

Travel Insurance
Optional Travel Protection Plan Available, for more information Click Here

Itinerary

Famous for its history, coastline, majestic mountains and glorious foliage, this unique tour of New England provides intimate views of the most dazzling fall color. Featuring three fantastic “rail” excursions and three “sail” experiences.

Day 1 // Gilford, NH

After a flight to colorful New England, travel to New Hampshire's scenic Lakes Region. Se

Day 2 // Gilford, NH

After breakfast, take a narrated pontoon cruise on peaceful Squam Lake. Hop aboard the Winnipesaukee Scenic Railroad for an old-fashioned train excursion along the former Boston-Concord-Montreal line. After lunch, visit the Canterbury Shaker Village for a special guided tour program at this historic site in a rural setting in central New Hampshire. Learn how the Shakers lived and worked on this site with a distinctive campus of 25 original and 4 reconstructed Shaker buildings, as well as nearly 700 acres of forests, open fields bordered by stone walls, well-tended gardens and picturesque mill ponds. Dinner is included this evening.

Day 3 // Gilford, NH

A local guide will join us on our White Mountain adventures today! Travel along one of the most scenic drives in America this morning—the Kancamagus Highway, which twists through the White Mountain National Forest blazing bright with hues of orange, red, and gold. We'll see waterfalls, rivers and stunning mountain vistas along the way. Enjoy leisure time in the charming village in North Conway. Next we take The White Mountain Express Gondola at Loon Mountain is a four-person high-speed lift that takes you to the 2,733-foot summit of Loon Peak. This evening, board the Cafe Lafayette Dinner Train and take a leisurely ride through the lush New England forest and magnificent landscape as a feast is served.

Day 4 // Portland, ME

Our day begins with a cruise on board replica steamship M/S Mount Washington. Soak in the scenery as the captain's entertaining narration offers insight into local legends and lore of the lake. Enjoy lunch aboard the vessel. The next stop is Wright Museum of WWII history. Travel to the seacoast town of Portland, Maine, where we'll stay the next three nights. You'll be delighted by dinner at a local favorite.

Day 5 // Portland, ME

Travel to Kennebunkport, the popular summer haven for artists, writers and U.S. presidents alike. A local guide shares the area's history and folklore as we take a scenic drive along Ocean Avenue with a pass by the Bush family summer home. Visit the Seashore Trolley Museum, then grab lunch on your own and explore the charming Dock Square area. Later, shop around in Perkins Cove, Ogunquit, a small fishing community with beautiful views. Board the Finestkind III for a leisurely sightseeing cruise along Maine's coastline to York Harbor, offering unparalleled views of elegant homes, rocky coastlines, and the picturesque Nubble Lighthouse. Tonight, indulge in a classic lobster dinner.

Day 6 // Portland, ME

This morning, a local guide will join us for a city tour of Portland. See views of sea captain houses and the elegant Victoria Mansion as we drive through historic neighborhoods. Pass through Calendar Islands of Casco Bay during a Portland Harbor Cruise. Keep your eyes peeled for harbor seals as we learn about the maritime history of Maine's biggest seaport. Explore the city's historic waterfront district, Old Port Exchange, which has been restored to its 19th century splendor with cobblestone streets and Victorian brick buildings. Land in Freeport, where you'll have time to visit the flagship LL Bean Store.

Day 7 // Home

Catch our return flight home today with many memories from an unforgettable New England adventure.

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