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New England's Rails & Sails featuring Newport

Boston Lobster Boats On Kennebunkport Harbor Portland Maine Cafe Lafayette Dinner Train Lake Winnpesaukee The Breakers Newport Lighthouse

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

8 days    $3,095

About the Tour

From the lush green of summer to the fiery hues of fall, the vibrant East Coast scenery is 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 places like Kennebunkport and Portland in Maine, Weirs Beach in New Hampshire and Newport in Rhode Island. Dine on freshly caught lobster, be immersed in the unique history of the Eastern Seaboard and enjoy looks at some of the most magnificent scenery the United States has to offer. 


  • Rail travel on Amtrak
  • Two scenic rail excursions: Café Lafayette Dinner Train and Newport & Narragansett Railroad Dinner Train
  • Hotel accommodations for 7 nights
  • 10 meals, including a lobster dinner
  • Boston City Tour, including the Freedom Trail
  • Scenic Lobster Cruise
  • Portland sightseeing tour
  • Mt. Washington Cruise on Lake Winnipesaukee
  • Cruise aboard the Rum Runner II
  • Newport Craft Brewing & Distilling Tour
  • Transportation aboard a deluxe motorcoach
  • Services of a professional Tour Manager
  • Baggage handling
View Dates & Pricing

Call to Book 1-877-929-7245

Activity Level       View Details


  • 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 - Boston

    Start the day with a guided tour of Boston. Learn about Boston's history and see landmarks pivotal to the birth of a nation. Our tour ends at Quincy Market, where you can enjoy lunch at leisure in one of the restaurants or food stalls within this historic market. The remainder of the afternoon is free to sightsee at your leisure. Perhaps take a tour through the Boston Tea Party Ship and Museum. Of course, the views of the observation deck at Prudential Center are wonderful, and you can always have a seat at the harbor and watch the boats pass by. Your tour manager can help you plan your day. This evening, you will rejoin your group for dinner. Overnight Boston, MA. (B, D)

  • Day 3 - 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.

  • Day 4 - 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. (B, D)

  • Day 5 - Lake Winnipesaukee Cruise

    This morning we transfer from coastal Maine inland to Meredith, New Hampshire. It is here that we board the Mount Washington for a scenic cruise across the beautiful waters of New Hampshire’s largest lake, Lake Winnipesaukee. As we cruise, see other boats moving across the waters, beautiful lakeside houses and lush patches of colorful forest. This one-way cruise takes us to Weir’s Beach, New Hampshire, where you have time to explore the resort town’s most beloved sites. 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. (B, D)

  • Day 6 - 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. The most famous home 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. (B)

  • Day 7 - 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. After lunch on your own in Newport, we meet at Newport Craft Brewing and Distilling Co. for a tour of their beer- and spirit-making facilities. Sample some of the most popular offerings, such as Rhoderage and the 1639 Pale Ale, as well as its spirits, such as White Squall Coastal Moonshine and seasonal beers. 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. (B, D)

  • Day 8 - 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. (B)


Included hotels are the Boston Park Plaza (Boston)*; The Colony (Kennebunkport); Mountain Club on Loon (Lincoln) *; and Newport Marriott (Mystic)*.

*The 09/8/2020 departure will stay at the DoubleTree (Boston) and the Indian Head Resort (Lincoln)

*The 09/12/2020 departure will stay at the DoubleTree (Boston), Indian Head Resort (Lincoln),and Wyndham Newport (Newport)

*The 10/3/2020 departure will stay at the Indian Head Resort (Lincoln) and the Wyndham Newport (Newport)


It is your responsibility to check and fulfill the passport, visa, health and immigration requirements applicable to your itinerary. We do not accept any responsibility if you cannot travel, or incur any other loss because you have not complied with any passport, visa, immigration requirements or health formalities. You agree to reimburse us in relation to any fines or other losses which we incur as a result of your failure to comply with any passport, visa, immigration requirements or health formalities.


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Prices are land-only, per person based on double occupancy. Prices are correct at the time of this web page going live; however are subject to confirmation at time of booking. Hotels & Accommodations are subject to change based on availability.
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