Call to book1-877-929-7245
Tour Search
#Favorites

New England Autumn Rails & Sails

Save
4.4 stars(47 reviews)
Gallery

Admire how the historic towns and verdant forests meet the blue waters of the Atlantic on this rail and sail adventure through New England.

You are viewing the 2023 itinerary. Select your departure year
20232024
7 days From $2,895 per person
Travel among a group of like-minded travelers led by a professional tour manager

2023 Tour code: EC-NRSA-23

About the tour

The vibrant hues of autumn color the backdrop for this tour to some of New England's most historic and picturesque sites. This round-trip tour begins and ends in Boston, and in between, experience 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. Get a new perspective on the changing seasons on relaxing lake and harbor cruises. Dine on freshly caught lobster and be immersed in the unique history of the Eastern Seaboard all while touring through some of the most magnificent fall scenery the United States has to offer. 

Highlights

Activity level Natural Explorer

View details

You don’t mind spending the day on your feet. You enjoy sightseeing that includes walking, standing or stair climbing. You’re okay with longer days that are more active, such as multiple sightseeing stops, longer motorcoach journeys and getting on and off ships and trains.

What’s included

Itinerary

Day 1 - Boston

Arrive in Boston and transfer to your centrally located hotel on your own. After you are settled in your room, there is time to get acquainted with the city before joining your tour manager and fellow travelers at the hotel this evening for an introductory meeting. Overnight Boston, MA.

Day 2 - Kennebunkport

This morning board Amtrak's Downeaster at Boston's North Station for the journey to Wells, Maine. Upon arrival, we transfer by motorcoach to Kennebunkport, where you have time to explore the town's sites and have lunch before we set sail. This afternoon, get an up-close look at Maine's lobster industry on a scenic lobster cruise. Look at the colorful forests bordering the water's edge, pass the Bush family compound or have your picture taken with the day's catch. Following our cruise, we have some more time to explore Kennebunkport. Perhaps try another one of the local eateries, or simply enjoy the storybook views of rustic buildings against the deep blue waters and colorful foliage. Overnight Kennebunkport, ME.

Includes
  • Breakfast
Day 3 - Portland

From the beautiful waterline to the undeniable charm of the town's boutique shops and cobblestone streets, Portland has so much to offer. This morning we set out with a local guide to learn about the area's history, hear stories of the past and see some of the amazing sites in the area. Following the tour, you will have some free time to take in the essence of this coastal gem on your own. Begin with lunch at one of the eateries in town, perhaps warming your body and soul with a bowl of clam chowder. After, take some time to stroll through the streets, meander along the sandy and rocky beaches, see the region's lighthouses or explore the local arts scene. Later this evening, you will rejoin the group for a delicious lobster dinner. Overnight Kennebunkport, ME. 

Includes
  • Breakfast, Dinner
Day 4 - Lake Winnipesaukee Cruise

This morning we transfer from coastal Maine inland to Wolfeboro, New Hampshire. It is here that we board the MS Mount Washington for a scenic cruise across the beautiful waters of New Hampshire's largest lake, Lake Winnipesaukee. As we cruise, admire the fiery hues of autumn surround the lake. Later this evening, 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 upon the dramatic evening vistas. The experience is so special, it was even named on the Wall Street Journal's list of "Dinner Trains Around the World." Overnight Lincoln, NH. 

Includes
  • Breakfast, Dinner
Day 5 - Newport

This morning we drive to Newport, RI, 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 being a playground of the rich and famous, but it is just as special in the autumn. The most famous home in Newport is The Breakers, the Vanderbilt's summer home. We tour the 70-room mansion, now a National Historic Landmark, and its gardens and see how the elite lived during Newport's Gilded Age. The remainder of the day is at leisure to explore this coastal community. Overnight Newport, RI.

Includes
  • Breakfast
Day 6 - Newport

A day filled with adventure awaits! We start the day with an excursion aboard the Rum Runner II. This motor yacht is our guide back to the time of Prohibition. As we cruise through the waters of Newport Harbor and Narragansett Bay, we see sites of old speakeasies and learn about the rum smuggling routes outlaws took. During this cruise, beautiful seaside mansions, islands and marine life come into view and complete this sailing experience. The afternoon is free to explore Newport at your leisure. The evening concludes with a ride aboard the Newport & Narragansett Railroad for an elegant dinner train experience. Views of Aquidneck Island and Narragansett Bay are the backdrop of our trip as you dine on exquisite chef-prepared cuisine and are enraptured by the vintage Pullman-style experience the train offers. Overnight Newport, RI. 

Includes
  • Breakfast, Dinner
Day 7 - Tour Conclusion

This morning, your time on the East Coast comes to an end. A group transfer is available to Boston Logan Airport and South Street Station 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. If you’d like to discuss any particular vacation with us in this respect, then please don’t hesitate to call us.

Hotels

Boston Park Plaza

Boston Park Plaza

View hotel

The Colony Hotel, Kennebunkport

The Colony Hotel, Kennebunkport

View hotel

The Mountain Club on Loon, Lincoln

The Mountain Club on Loon, Lincoln

View hotel

Trains

Amtrak's Downeaster
Cafe Lafayette Dinner Train
Newport & Narragansett Bay Railroad

Enhance your holiday

Upgrades

Extend your stay

Reviews

4.4 stars4.4 / 5 · 47 reviews

  1. 5 stars
    (26)
  2. 4 stars
    (16)
  3. 3 stars
    (4)
  4. 2 stars
    (1)
  5. 1 star
    (0)

MARCIA STORMS

3 stars

Submitted 23 Oct 2022

It felt over scheduled, always rushing. There was very little time to explore the towns. We did have the opportunity to take the Lighthouse Lovers cruise in Portland on our own and really enjoyed it. The VBR planned dinner train was nice as was the Winnipesaukee Lake cruise. The weather wasn't conducive for the Scenic Lobster Cruise. Some of the group sat in the cold and rain on we benches. My opinion is it should have been canceled like the boat operator wanted.

Collected by Trustpilot

MARK ALBERS

5 stars

Submitted 23 Oct 2022

We thoroughly enjoyed our trip. Our tour director, Mary was excellent. She did a very good job of improvising when things didn't go according to planned.

Collected by Trustpilot

DOROTHY GLASGOW

5 stars

Submitted 19 Oct 2022

Enjoyed this tour, and the beautiful fall foliage and scenery.

Collected by Trustpilot

Jacque Tripp

5 stars

Submitted 19 Oct 2022

Our trip was more than what we expected. Our tour guide Mary, was very knowledgeable & prepared for alternate things to do when the unpredictable weather thwarted our plans. We would take another Vacation by Rails trip again.

Collected by Trustpilot

KENNETH RICHARD HILL

4 stars

Submitted 19 Oct 2022

Second day was was crammed with too much and did not get to hotel until 8:00 p.m.

Collected by Trustpilot

Hilary davies

5 stars

Submitted 19 Oct 2022

Fantastic scenery covering multiple locations in nice accommodation with a brilliant tour guide who kept the group entertained throughout the trip. Thoroughly recommend.

Collected by Trustpilot

Show 6 more reviews
Global Rail Adventures Brochure

Global Rail Adventures Brochure

The definitive guide to our 2023 Global Rail Adventures

Download brochure
Related inspiration from our journey blog