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Classic New England: Vermont to Massachusetts

8 days
From Vermont to Massachusetts, this tour offers a look at New England’s scenic landscapes, quaint towns and iconic cities. Stroll through bustling downtown areas, sample local cuisine and visit colonial-era sites as you travel toward the coast.

Let us handle the details

Expert Tour Director

      Local       cuisine

Handpicked hotels

Sightseeing with local guides

Private transportation

Personalized flight options

Maximum tour group size: 35 travelers

Tour Pace: You will walk for about 1.5 hours daily across mostly flat terrain, including paved roads and cobblestone streets, with few hills.

Let us handle the details

Expert Tour Director

      Local       cuisine

Handpicked hotels

Sightseeing with local guides

Private transportation

Personalized flight options

Your tour includes

  • 7 nights in handpicked hotels

  • Breakfast daily, 2 three-course dinners with beer or wine

  • Expert Tour Director

  • Private deluxe motor coach

  • Guided sightseeing and select entrance fees

Map of Tour of Massachusetts, New Hampshire, Maine, and Vermont

Montpelier Region 2 nights Hotel info

Day 1: Travel day & arrival in Montpelier Region

Welcome to Vermont! After arriving in Burlington, Vermont, make your way to the nearby Montpelier region.

Day 2: Sightseeing tour of Vermont

Included meals: Breakfast, Dinner

An all-day sightseeing tour introduces you to Vermont’s small towns and delicious local fare.

• Get a taste for local beverages with stops at Green Mountain Coffee and the Cold Hollow Cider Mill 

• Tour the Ben & Jerry’s Factory and enjoy samples of ice cream

• Visit a local vineyard for a guided tour and wine tasting 

End the day with your group at tonight’s welcome dinner.

North Conway, New Hampshire 2 nights Hotel info

Day 3: North Conway via Franconia Notch & Old Man of the Mountain Memorial Park

Included meals: Breakfast

Before leaving Vermont, learn about cheese making and sample award-winning cheddar at the Cabot Cheese Factory. Then, travel east to New Hampshire.

• As you pass through the White Mountains, stop at the state’s most iconic spots, including Franconia Notch and the Old Man of the Mountain Memorial Park 

• Drive through the landscapes of the state’s most famous scenic byway, the Kancamagus Highway

Day 4: Mount Washington

Included meals: Breakfast

Make your way to Mount Washington, located in the scenic White Mountains. Board the Mount Washington Cog Railway for a beautiful ride to the region’s highest summit. Then, take in the incredible vistas that the region is known for.

York Region, Maine 1 night Hotel info

Day 5: York via the Lakes District

Included meals: Breakfast

Transfer to York by way of Maine’s picturesque Lakes District and Kennebunkport. Stop in Portland along the way, where your Tour Director introduces you to the city’s most interesting sites.

• Pass the Portland Observatory and Fort Allen Park

• Visit the Old Port neighborhood, filled with independent bookshops and quaint local boutiques

Boston, Massachusetts 2 nights Hotel info

Day 6: Boston via Salem

Included meals: Breakfast

Stop in Salem, “Witch City,” to visit the famed House of Seven Gables. Later, arrive in Boston.

Day 7: Sightseeing tour of Boston

Included meals: Breakfast, Dinner

Set off on a guided tour of Boston, one of the oldest cities in America.

• Pass by Paul Revere’s House and the Boston Common

• View Faneuil Hall, the Old State House and King’s Chapel

• Enter the Old North Church

• Sweep through 250 years of American history on the Freedom Trail

End your tour in Harvard Square, where you’ll have free time to wander through the university’s campus. Later, enjoy a free afternoon or add an excursion.

Later this evening, say goodbye to your group at an included farewell dinner.

Optional Excursion - Boston Tea Party Museum & Lobster Lunch $75pp* Details

Head to the Fort Point Channel, where you’ll be transported back to 1773 at the Boston Tea Party Museum. During an interactive experience at this floating museum, you’ll discover what happened when colonists held this famous political protest against the British, which led to the Revolutionary War. Then continue on to a local seafood restaurant in Boston’s Seaport District to enjoy lobster, the most traditional New England fare, for lunch.

Must be booked 20 days before departure

Day 8: Departure

Included meals: Breakfast (excluding early morning departures)

Begin your journey home, or extend your stay to continue exploring Boston.

Add Boston $449 pp

From picturesque shopping streets to the Public Garden, take a few days to enjoy the many charms of Boston.

Boston, Massachusetts 2 nights Hotel info

Day 8: Free day in Boston

Included meals: Breakfast

Spend the day exploring Boston on your own or add an excursion.

Optional Excursion - Revolutionary New England: Lexington & Concord $79pp* Details

Gain insight into early American history during your time in Lexington and Concord, hubs of the American Revolution. In Lexington, the site of the first shot of the Revolution, you’ll visit battlefields, war monuments and colonial buildings. In Concord, drive by the homes of famous early American authors, such as Nathaniel Hawthorne and Louisa May Alcott, as you take in the historic backdrop of this quaint New England town.

Must be booked 20 days before departure

Day 9: Free day in Boston

Included meals: Breakfast

Spend one last day exploring Boston on your own.

Day 10: Departure

Included meals: Breakfast (excluding early morning departures)

Transfer to the airport for your return flight home.

How's the weather?

  • Burlington, Vermont
  • North Conway, New Hampshire, United States
  • Boston, Massachusetts, United States
Temperature Precipitation
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Passport & Visa Requirements

Valid government-issued identification is required for air travel within the United States. If you’re not a U.S. citizen, please be sure to have your required identification with you as well.

Baggage Allowance

Airlines have varying weight restrictions on luggage. Be advised that most domestic airlines impose additional charges if you choose to check any baggage, and that you are responsible for any such costs. Contact your airline for detailed information regarding luggage size and weight restrictions for your flight, but please note that Go Ahead travelers are restricted to one checked bag per person due to storage limitations on motor coaches and other internal transfers, which may include train connections or flights. One carry-on bag is also permitted, provided that it does not exceed 45 total inches (length + width + height). Make sure you label your baggage and carry valuables, medication and documents in your carry-on bag.

Clothing & Packing Tips

We recommend packing lightweight, loose-fitting clothing that can be easily layered. For sightseeing, we suggest bringing a sturdy pair of walking shoes or sneakers, as well as a lightweight jacket or rainwear. If you’re planning a visit to a high-end restaurant or performance, you may also want to bring dressier attire. Also, please be respectful and avoid showing bare legs or shoulders when visiting churches or other religious sites (entrance may be denied on this basis).


There are no major health risks associated with traveling to this region. During the summer months, take care for sun exposure and heat. Be sure to check with your doctor or healthcare provider for the latest updates and personal travel requirements.


The United States contains some of the most varied food in the world. Most of the cuisine on this tour is well-known to Americans, but look out for delicious seafood specialties—such as lobster and clam chowder—in Portland and Boston.


Round-trip flights arrive in Burlington, Vermont, and depart from Boston, Massachusetts. All included transportation on this tour is by private motor coach. Boston is a walkable city, but the city’s metro system—known to locals as the T—is affordable and easily accessible. That said, Boston’s streets are not laid out in a grid pattern; asking your Tour Director for directions is advised. 

Time Zones

Your tour will fall on Eastern Standard Time (EST).


At the conclusion of your tour, it’s customary to offer your Tour Director and driver a gratuity. We recommend tipping $3USD/CAD per person per day for your driver and $6USD/CAD to $9USD/CAD per person per day for your Tour Director. If applicable, we also recommend $2USD/CAD per local guide. Tips can only be paid in cash.

See what our travelers say about this tour—all reviews are authentic and unedited.

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4 / 5

4 / 5

Traveled On: 9/19/2015

Number of Past Tours: 4

From: AB

Tour Director: 5 / 5

Tour Value: 4 / 5

Great 8 Days

My first GoAhead Tour, I went by myself and enjoyed it very much! The weather and the people on the tour were great. The tour director did his very best to make sure everyone's trip was enjoyable.