Sail & Rail through New England

Train Rides & Cruises

9 Days

Starting At $CUSTOM
Climb aboard for a New England adventure with three scenic train rides and five different boat rides. Weave your way through the history of both the American Revolution and the Industrial Revolution as you circle from Boston to Portsmouth, Portland to Freeport, the Lakes of New Hampshire and Lake Champlain in Vermont. This grand adventure crosses both The Green Mountains of Vermont and The White Mountains of New Hampshire.

Sail & Rail through New England

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  • Three Train Rides
    • Maine Narrow Gauge Railroad
    • Winnipesaukee Scenic Railroad
    • Cape Cod Scenic Railroad
  • Five Boat Rides
    • Boston Swan Boat Ride
    • Isle of Shoals Narrated Cruise
    • Portland Harbor Cruise
    • Pontoon Boat on Squam Lake (On Golden Pond)
    • Lake Champlain Dinner Cruise
  • Boston Sightseeing, Freedom Train Tour
  • Portsmouth Trolley Tour
  • Shopping at L.L. Bean’s Store
  • Castle in the Clouds Estate
  • Vermont Maple Sugaring
  • Cape Cod Lighthouses
  • Eight Nights First Class Lodging
  • Eight Breakfasts
  • Two Lunches
  • Seven Dinners

Tour Options

If you need motorcoach transportation, check out our travel affiliate for the best prices.

Did You Know:   In the 1770s, British attempts to exert more-stringent control on America’s 13 colonies –primarily through taxation – led to the American Revolution. The Boston Massacre, the Boston Tea Party,  and several early battles—including Lexington and Concord, the Battle of Bunker Hill, and the Siege of Boston -occurred in or near the city.

Day 1 – This tour package begins in Boston where you visit the Quincy Marketplace and Faneuil Hall.   As alive today as it was in 1742 when the nation’s fathers proclaimed it “The Cradle of Liberty,” Faneuil Hall Marketplace combines the glories of Boston’s past with the urban sophistication of the city today.  Have lunch on our own in one of the many eateries and explore the shops and street vendors’ carts.

Next visit the Boston Common.  Established in 1634, this is America’s oldest public park and is abundant with an amazing variety of trees, shrubs and flowers.   Climb on board for a Swan Boat Ride.  For over 130 years, the Swan Boats have been a part of the Boston experience.  The boats grace the waters of the Boston Public Garden, the first botanical garden in the United States.

Your dinner this evening will be in Boston’s oldest Italian Restaurant.  With décor of old-world charm and style and aromas of home cooking, Mama Mia, that’s Italian!

Day 2 – Join a local guide for a 2-hour walking and windshield tour of the Freedom Trail.  Visits include the New and the Old State Houses, The Boston Tea Party, The Boston Massacre, Old Granary Burying Ground, Paul Revere’s House and Old North Church.  The tour also includes the USS Constitution (based on availability) and Bunker Hill.

Arrive about noontime in Portsmouth, New Hampshire, named “one of the most culturally rich destinations in the country.” Enjoy lunch on your own at one of the many shore side cafes or restaurants, walk along the streets and see the stimulating mix of historic buildings, art galleries and artisans’ boutiques.

After lunch, board the Victorian style M/V Thomas Laighton for a narrated cruise of the legendary Isles of Shoals. Located 9 miles off the coast, there are intriguing archipelagos of 9 islands steeped with history. As you glide through Portsmouth Harbor, you will see a unique working port with tugboats, tankers, the nation’s oldest and active naval yard, the closed castle-like prison, “the Alcatraz of the East”, the quaint Old Port waterfront, a famous grand resort hotel, 5 historic forts and 3 lighthouses proudly guiding mariners safely through the waters.

Next “jump” on the trolley for a seacoast tour of some of New Hampshire’s National Historic sites such as the magnificent Colonial, Georgian and Federal mansions, the legendary Wentworth Hotel and Portsmouth Naval Prison; a time warp spanning nearly four centuries.  Also travel by “Millionaire’s Row” and North Hampton’s beaches.

Arrive at your downtown Portland Hotel late afternoon.  Enjoy time to relax and refresh before dinner.  Dinner is a real treat this evening, as it is served on a “floating restaurant” where every seat affords ocean and harbor views.  Dine on some of the freshest seafood imaginable or Maine’s specialty, fresh steamed lobsters!  Of course, there are other selections for landlubbers.

Day 3 –  Travel back in time to experience, up close and personal, what it was like to ride, run and maintain Maine’s two-foot narrow gauge railroad.  Climb aboard an antique rail car pulled by steam or diesel locomotives and follow the 1846 right of way of the Atlantic and St. Lawrence Railroad that links Portland with Montreal.  Along the way, take in the magnificent views of Portland’s waterfront.

Next, visit the oldest lighthouse and most sought after destination in Maine, The Portland Head on Cape Elizabeth.  Portland Head has long protected Portland and the adjacent area. Cape Elizabeth residents were deeply committed to American independence from British rule. In 1776, the new Town of Cape Elizabeth posted a guard of eight soldiers at Portland Head to warn citizens of coming British attacks.  The original tower measured 72’ from base to lantern deck and was lit with 16 whale oil lamps. It was first lit on January 10, 1791.

Your next stop is Freeport, home of Maine’s most famous retailer, LL Bean.  There will be time on your own for lunch and to explore the famous Outlet Stores and LL Bean’s flagship store.   On your way out of Freeport, stop at the Big Freeport Indian for a photo op.  The Freeport Indian is 50’ tall and in the interests of political correctness is now called MBNA, Maine’s Big Native American.

After lunch, enjoy a 90-minute narrated scenic cruise around Portland’s busy harbor and innermost islands to witness lighthouses, forts, lobster boats, seals and seabirds. Four lighthouses may be seen up close, with as many as seven in view during the cruise.

Arrive back at your downtown Portland hotel for dinner on your own this evening and time at leisure in Portland’s Olde Port District, one of the most successful revitalized warehouse districts in the country.  Just steps from the water, one can stroll down the cobblestone streets and experience the quaint charm of the district. The boutique shopping and one-of-a-kind stores are unparallel to any other New England City.

Day 4 – On your way out of Maine, visit Len Libby Candies, home of decadent made-in- Maine confections. While you are there, witness the world’s only life-sized chocolate moose.

Arrive mid-afternoon in Meredith, New Hampshire and climb aboard the Winnipesaukee Scenic Railroad. Travel on vintage, restored coaches and journey along the shores of Lake Winnipesaukee. Travel between Meredith and Lakeport always within view of the lake. The railroad line was built in 1849, well before any development occurred on the then remote lake. Journey through the front yards of many of the fine resort homes. This line was once a part of the Boston & Maine Railroad that brought tourists to the lake for summer vacations from the late 1890’s to the 1950’s. Weirs Beach was a busy summer resort with many fine “Grand Style Hotels” lining the shore of the lake. Enjoy the specially packed “Hobo Lunch” during the ride.

Travel a short way to Moultonborough and arrive at Castle in the Clouds.  Formerly known as “Lucknow,” this is a sixteen-room mountaintop mansion built in 1913-1914 by shoe industrialist, Thomas Plant.  You approach “Lucknow” aboard a trolley that winds up the mountainside to the home’s spectacular setting.  The tour begins with a ten-minute orientation, after which the visit is self-guided.

On your way to your Lakeside Hotel in Laconia, NH stop in Meredith, NH for some shopping.  Make sure to visit the world-renown, Annalee’s Doll Shop.

Close your eyes and imagine yourself on the water’s edge of a beautiful lake surrounded by a landscape of soaring pines and deep blue skies mirrored by pristine waters. Now open your eyes…to your Lakeside Hotel on Lake Winnipesauke!

Relax over a delicious dinner served in the hotel.

Day 5 –  Board your luxury motor coach and travel to “Squam Lake.” Covering 6,791 acres, Squam is the second-largest lake located entirely in New Hampshire and is where the 1981 film On Golden Pond was filmed.  Board a canopied pontoon boat and sail off on a fascinating and picturesque 50-minute cruise and learn about the natural forces that created these lakes, the wildlife that makes them so special and the people who have enjoyed these lakes for over 5,000 years.

After your cruise, begin your travels into Vermont, The Green Mountain State, which by this time of year should be covered with the orange and gold tones of autumn.

This afternoon you visit one of the nation’s oldest (built in 1859) and best-preserved state capitols still in use.  In the country’s smallest State House, embark on a guided tour and marvel at the fossil embedded marble floors, the original representative’s desk still used in the chambers today, a beautiful collection of artwork and original lighting fixtures. Enjoy lunch on your own, at the State House Café, prior to your tour.

Watch how real maple sugar is made, from the trees to the finished product, on a traditional Vermont maple sugar farm. You will tour the sugarhouse, sample fresh-made maple syrup and visit the largest and most unique maple, crafts and mail order shop in the area.  Your tour ends with a sugar-on-snow party!

Continue on through the Green Mountains and into Burlington, Vermont’s largest city. Check into your hotel and enjoy time to relax and refresh before dinner this evening.

Dinner this evening will be served aboard a 424-passenger cruise ship sailing on Lake Champlain. Savor the majestic beauty that surrounds the lake and watch the sun set over the Adirondack Mountains. Enjoy dinner and live entertainment as you sing along to “Moonlight in Vermont.”

Day 6 –  Start your day with a tour of the birthplace of some of America’s most lovable bears, The Vermont Teddy Bear Factory.  Shop in the Bear Shop, make your own bear and grab a snack at the Teddy Bear Pantry.

Next visit a National Historic Landmark on the shores of Lake Champlain. Shelburne Farms was created in 1886 by Dr. William Seward and Lila Vanderbilt Webb as a model agricultural estate.  The 400-acre estate is home to a herd of 125 purebred, registered Brown Swiss cows, the Inn and Restaurant, originally the 19th century home of Seward and Webb, a cheese making facility, bake shop, gift shop and educational center.  Your visit includes a guided tour and time to sample their award-winning cheeses.

Discover treasures from America’s past at the Shelburne Museum, described as one of the world’s great museums of American folk art, artifacts and architecture. The Museum’s founder, Electra Havemeyer Webb, was a pioneer collector of Americana and American folk art.  Explore 37 exhibit buildings, stroll through 45 scenic acres, and discover 80,000 pieces of Americana including the most important collection of wildfowl decoys in the world, an outstanding collection of quilts, coverlets, and hooked rugs and over 200 horse drawn vehicles. See the 220-foot side-wheel steamboat, the Ticonderoga that is a National Historic Landmark.  Enjoy lunch on own at the museum’s café.

Stop in the quaint Village of Shelburne and visit the Shelburne Country Store, an original 1859 Vermont country store where you will find all your favorites. Discover the world’s best melt-in-your-mouth fudge, all kinds of penny candy and chocolates, toys for children of all ages, books, handy kitchen items, bath and beauty products, Vermont crafts and more!

Welcome to Church Street Marketplace! The Marketplace is located in an historic district and is considered an outdoor pedestrian mall with shops, street vendors, boutiques and restaurants. Enjoy time on own to shop or sit back and sip a beverage served at a sidewalk café.

Enjoy dinner served in a beautiful Victorian home built by Lemuel S. Drew in the mid – 1800’s. The menu offers cuisine for everyone, including house favorites and creative inspirations, which are sure to please even the most discriminating guests.

Day 7 –  Along the way visit Canterbury Shaker Village an internationally known museum founded in 1969 to preserve the heritage of the Canterbury Shakers. Designated as a National Historic Landmark for its architectural integrity and significance, the Village has 25 restored original Shaker buildings, 4 reconstructed Shaker buildings, and 694 acres of forests, fields, gardens, nature trails and mill ponds. Have lunch on your own at one of the concessions on property.

Arrive in Boston mid-afternoon and visit the John F. Kennedy Presidential Library and Museum that is dedicated to the memory of our nation’s thirty-fifth president.  Located in a ten-acre park, overlooking the sea that Kennedy loved and the city that launched him to greatness, the Library stands as a vibrant tribute to the life and times of John F. Kennedy.

Enjoy the remainder of the afternoon at your leisure in Boston. Visit historic sites, shop in the galleries and boutiques or stroll along the cobblestone streets.

Arrive at your Boston hotel to relax and refresh before dinner.

Tonight enjoy dinner at the famous Cheers Restaurant, “Where everyone knows your name.”

Day 8 – Experience the revolution of glass blowing with a visit at the Sandwich Glass Museum located in Sandwich, the oldest town on Cape Cod. The Museum’s galleries display in chronological order the various types of glassware produced in Sandwich from 1825 until the company’s closing on January 1, 1888.  Visit the gift shop that offers hundreds of glass items featuring the works of Cape Cod and national glass artisans.  In addition to contemporary glass, the Museum Shop features Sandwich Glass reproductions, using the same techniques made famous by the Boston and Sandwich Glass Company. (All pieces are carefully crafted and finished by hand, giving each an individual quality.)

Climb aboard the Cape Cod Central Railroad and feel the rhythm of the train and spirit of the crew as you are whisked away on an exhilarating rail journey while enjoying a delicious gourmet luncheon.  You’ll pass beautiful cranberry bogs, natural woodlands, lush marshes and beautiful sand dunes as you make your way to the Cape Cod Canal.

Next embark on a driving tour of the Nauset Lighthouses, also known as the “Three Sisters of Nauset.”  These 3 lighthouses were built in 1837 to help the vessels find their way into Nauset Beach. To distinguish the location from the single light in North Truro and the double lights at Chatham, it was determined that there would be three lighthouses at Nauset Beach.

Before heading back to Boston stop for a tour and sample unique wines at a local winery in Cape Cod, then travel back to Boston for your farewell dinner.

Enjoy a farewell dinner and toast your traveling companions at the oldest restaurant in Boston and the oldest restaurant in continuous service in the U.S. – the doors have been open to diners since 1826.

Day 9:  Your tour ends and you depart for home.

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