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New England Autumn Rails & Sails

 
4.4 stars(118 reviews)
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Duration
7 days
From per person
$3,799
Tour code
RAS27
Mobility Rating 2
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Travel among a group of like-minded travelers led by a professional tour manager
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Admire historic towns, beautiful fall foliage and the blue waters of the Atlantic on this autumnal rail and sail journey along the Eastern Seaboard

Embark on an autumnal tour of coastal New England at the most picturesque time of the year. From Boston, explore popular East Coast locations like coastal Kennebunkport and Portland in Maine, Lake Winnipesaukee in New Hampshire, and Newport in Rhode Island.

Delight in excursions aboard two of America's unique dinner trains and gain a new perspective on the changing seasons on lake and harbor cruises.

Each stop on this memorable tour provides a new chance to be immersed in the unique history of the Eastern Seaboard.

Unforgettable Experiences

Viewing fall foliage on two scenic rail journeys
Viewing fall foliage on two scenic rail journeys
Savor delicious cuisine and breathtaking routes through fall's best scenes while riding aboard the Café Lafayette Dinner Train and the Newport & Narragansett Railroad's Dinner Train.
Getting a seaside perspective on Maine’s lobster industry
Getting a seaside perspective on Maine’s lobster industry
Step aboard one of the largest sightseeing ships in New England for a scenic cruise that reveals beautiful coastal scenery and the ins and outs of the lobster industry.
Marveling at fall scenery on a lake cruise
Marveling at fall scenery on a lake cruise
Relax while cruising across the calm waters of New Hampshire's largest lake, Lake Winnipesaukee, to the town of Weirs Beach aboard the historic MS Mount Washington.
Touring the Vanderbilts’ summer home
Touring the Vanderbilts’ summer home
Find yourself in awe of Italian Renaissance architecture, seaside views and Gilded Age grandeur while wandering the many rooms of Newport's most famous mansion, The Breakers.
Uncovering Prohibition history in Newport Harbor
Uncovering Prohibition history in Newport Harbor
Step aboard the Rum Runner II for a cruise back to the times of Prohibition, gliding through the waters of Newport Harbor and Narragansett Bay on a motor yacht constructed nearly 100 years ago.

What’s included on the tour?

Itinerary

DAY1Arrival in Boston

Your autumnal explorations begin today as you arrive in Boston and transfer independently to our hotel, conveniently located in a premier Back Bay location. After checking in and getting settled, take some time to get acquainted with your historic surroundings.

Tales of the American Revolution and the country's infancy await around every corner, allowing you to get to know America's past however you see fit. If time allows, you might like to take an Old Town Trolley tour (payable locally) to get acquainted with the city and see its most impressive sights, or you could explore on foot, wandering amongst the sites of the Freedom Trail.

Returning to the hotel this evening, meet the Tour Manager and your travel group for a brief introductory meeting, and then you are free to find dinner locally. With its coastal location, Boston is renowned for its seafood, and a hearty bowl of clam chowder is the ideal way to warm up on a chilly autumn evening. Overnight Boston, MA.

DAY2To charming coastal Maine aboard Amtrak

An early morning transfer takes us to Boston's North Station, where we board Amtrak's Downeaster for the journey deeper into New England to Wells, Maine. We arrive later this morning and join our motorcoach to continue the day's travels to Kennebunkport.

There is some free time to find lunch and admire the seaside ambiance of this fascinating town before we head to the harbor, where we step aboard the 65-foot Kylie's Chance for a sightseeing cruise. Look out over the water as we cruise past colorful forests bordering the water's edge, the Bush family compound, and Bumpkin Island, often occupied by seals. A highlight of the cruise, though, is getting to know Maine's lobster industry. Learn how fishermen trap these beloved crustaceans and maybe even get your picture with the day's catch!

Following our cruise, we head to our hotel in the laid-back town of Ogunquit. With the remainder of your day at leisure, you might like to seek out some seafood for dinner. Overnight Ogunquit, ME.

Includes
  • Breakfast
DAY3Exploring coastal Portland

From the beautiful waterline to the undeniable charm of the town's boutique shops and cobblestone streets, Portland has so much to offer, and we uncover it this morning. We board our motorcoach after breakfast and travel to this coastal gem, where a local guide steps aboard to unveil the area's history, stories and amazing sites. Admire historic buildings and lighthouses with beautiful water views and fire-hued foliage forming the backdrop.

Following the tour, enjoy free time to take in the essence of Portland at your own pace. You might like to find lunch in a local eatery before meandering the cobbled streets or wandering the sandy and rocky beaches. This is an incredibly artistic city with galleries and cultural shops dotted throughout downtown.

Returning to Ogunquit, you can relax in the hotel's peaceful setting, just steps from the water, ahead of a group dinner this evening. Overnight Ogunquit, ME.

Includes
  • Breakfast, Dinner
DAY4Fall foliage vistas by cruise and scenic train

Departing Maine after breakfast, we travel into the heart of fall foliage country in Wolfeboro, New Hampshire. It is here that we board the historic MS Mount Washington for a scenic cruise across the beautiful waters of New Hampshire's largest lake, Lake Winnipesaukee.

As we cruise, admire the gold, copper and crimson hues of autumn surrounding the lake and relax as the onboard narration reveals regional stories and historic tidbits. Our cruise takes us across the lake to Weirs Beach, where you have free time for lunch.

Later in the afternoon, our route continues into the White Mountains to Woodstock, New Hampshire, where we board the Café Lafayette Dinner Train for a 20-mile journey through the Pemigewasset River Valley. Savor a chef-prepared five-course dinner in a fully restored dining car as you gaze at the dramatic evening vistas, including multi-hued foliage illuminated by the sinking sun. We continue to our hotel for the night in Lincoln, savoring a free evening with mountain views. Overnight Lincoln, NH.

Includes
  • Breakfast, Dinner
DAY5Exploring Newport and The Breakers

Today's travels take us back to the coast to Newport, Rhode Island, the yachting capital of the world. This seaside town is nicknamed "New England's summer resort" and is known for its summer "cottages," as well as for being a playground of the rich and famous. But it is not just summer scenery that attracts visitors; Newport is breathtaking in the fall.

Our motorcoach arrives in Newport early this afternoon, and there is free time to wander the colorful downtown district. You could find lunch or shop on Thames Street or stroll along the bustling waterfront with distant foliage views.

Later in the afternoon, we head to the most famous home in Newport: The Breakers, the Vanderbilts' summer home. We tour the 70-room mansion, now a National Historic Landmark, and see how the elite lived during Newport's Gilded Age. Afterward, we check into our hotel with the remainder of the day at leisure to explore this coastal community. Overnight Newport, RI.

Includes
  • Breakfast
DAY6Breathtaking views of Newport Harbor and Narragansett Bay

Following breakfast at our hotel, we start the day with a cruise aboard the Rum Runner II, a motor yacht constructed during the height of Prohibition. Settle into your seat for a cruise through Newport Harbor and into Narragansett Bay, surrounded by scenes of lighthouses, Newport mansions, former speakeasies and small islands adorned in autumn's spectral hues. As we cruise, we learn about the rum-smuggling routes outlaws took and how this ship played a role in their operations.

The afternoon is free to explore Newport at your leisure, and then this evening, our coach transfers us to Grand Bellevue Train Station to board the Newport & Narragansett Railroad for an elegant dinner train experience.

Views of Aquidneck Island and Narragansett Bay form the backdrop of our route as we dine on chef-prepared cuisine and soak up the vintage Pullman-style experience the train offers. This experience is a truly scenic way to conclude our fall foliage explorations. Overnight Newport, RI.

Includes
  • Breakfast, Dinner
DAY7Traveling home

Few places compare to New England during the fall months, and this trip dove headfirst into its most colorful and charming locations. From the historic city of Boston, we traveled to coastal Maine, admiring lighthouses and the scenic shorelines while learning about the lobster industry and sightseeing on a cruise. From here, our route took us inland to Lake Winnipesaukee and into the colorful White Mountains, before heading back to the coast in Newport, Rhode Island. Complete with multiple cruise experiences, two memorable dinner train journeys and endless autumn scenery, this was a vacation to treasure.

This morning, your time on the East Coast comes to an end. After breakfast, a group transfer to Boston Logan Airport and South Street Station is available for planes and trains departing after 1:00 p.m.

Includes
  • Breakfast

Additional information

Departure times

Departure times vary based on selected rail vacation. This information will be provided in your final documents. For more information please speak with your rail specialist.

Mobility information

Due to the nature of our tours, they are generally unsuitable for those with restricted mobility. Please reference our Mobility Ratings Information, and if you’d like to discuss any particular vacation with us in this respect, then please don’t hesitate to call us at 1-877-929-7245.

Hotels

Hilton Boston Park Plaza
Hilton Boston Park Plaza
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Hampton Inn Lincoln White Mountains, Lincoln
Hampton Inn Lincoln White Mountains, Lincoln
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Wyndham Newport Hotel, Middletown
Wyndham Newport Hotel, Middletown
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Gorges Grand Hotel, Ogunquit
Gorges Grand Hotel, Ogunquit
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Trains

See more details about this tours trains.

Amtrak's Downeaster

Colonial cities, stunning beaches, and breathtaking scenes of the Eastern Seaboard abound on Amtrak's Downeasterroute. Ideal for commuters and vacationers alike, this comfortable train offers unbeatable views of towns in Maine, New Hampshire, and Massachusetts. Five daily trains run between Boston, MA, and Portland, ME, with select trains venturing even further north to Brunswick, ME. Passengers can complete the route in its entirety in approximately 3 1/2 hours or travel from city to city, breaking the 145-mile route into shorter connections throughout New England.

Cafe Lafayette Dinner Train

Passing through the colorful Pemigewasset River Valley and the deep forests of the White Mountains in New Hampshire, the Cafe Lafayette Dinner Train offers guests a gourmet dining experience and superb scenery in one  excursion. The train departs from North Woodstock, NH, and follows a 20-mile roundtrip route over two hours. During its passage, guests are treated to a dining experience reminiscent of those enjoyed by rail travelers many decades ago. Five courses of incredible, locally sourced dishes are presented throughout the evening, each prepared to order by an award-winning chef.   

Newport & Narragansett Bay Railroad

Surround yourself in the romance of yesteryear aboard Rhode Island's  Newport & Narragansett Bay Railroad. The seaside beauty of Aquidneck Island is on full display as the train navigates its 12 1/2-mile course along  Narragansett Bay. Travelers are seated in fully restored Pullman coaches, with large windows framing the carriages and offering glorious views of the changing scenery. Each trip begins and ends at Portsmouth Station and follows tracks laid in the 1870s along the island's western shores. Guests may select from daytime rides, elegant dinner train experiences, and specialty trains for their nostalgic  voyage.   

Enhance your trip

Extend your stay

Many of our guests choose to spend additional nights before or after their tripGreat Rail Journeys would be happy to make hotel arrangements for you.

Reviews

4.4 stars4.4 / 5 · 118 reviews

  1. 5 stars
    (69)
  2. 4 stars
    (34)
  3. 3 stars
    (9)
  4. 2 stars
    (4)
  5. 1 star
    (2)

S. Clayton

5 stars

Submitted 14 Oct 2025

The train and boat rides were very nice. The towns we visited were beautiful!

Collected by Trustpilot

Stephen Snow

5 stars

Submitted 14 Oct 2025

Excellent trip!

Collected by Trustpilot

Lee Leppo

5 stars

Submitted 13 Oct 2025

Fitz our tour guide was great. Antonio our bus driver was geat.

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SUSAN ANDERSON

5 stars

Submitted 12 Oct 2025

This was our second trip using Vacations by Rail and again totally enjoyed our experience. We love the planned itinerary and how smoothly checking into hotels and transfers go. Our travel manager was fantastic and we traveled with a great group of people we got to know and shared a lot of laughs. Great way to see New England during the Fall!

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Debra Lucas Greiner

5 stars

Submitted 11 Oct 2025

We really enjoyed our trip. The timing of all events was great. The variety was good. All included food exceeded our expectations. The rails and the sails were fun. Our guide, Mary, was knowledgeable and very capable.

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Lita Buck

5 stars

Submitted 10 Oct 2025

Unfortunately the fall colors were not there because of a drought. Towns we visited were nice. The food was okay when provided

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