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Coastal New England

7 days
Get a glimpse of the events of the Revolution in Boston, then travel up the coast to explore the trading ports, cities and fishing villages that embody quintessential New England charm.

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

You should know: Check back in November for 2017 departure dates of this tour.

Let us handle the details

Expert Tour Director

      Local       cuisine

Handpicked hotels

Sightseeing with local guides

Private transportation

Personalized flight options

Your tour includes

  • 6 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, and Maine

Boston, Massachusetts 2 nights Hotel info

Day 1: Arrival in Boston

Included meals: Dinner

Travel to Boston, where you’ll meet your Tour Director and fellow travelers at a welcome dinner.

Day 2: Sightseeing tour of Boston

Included meals: Breakfast

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

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

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

• See Faneuil Hall and the Old State House 

• Enter the Old North Church

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.

Optional Excursion - Prudential Skywalk & Lunch $49*pp Details

Taste the fruits of the Atlantic at a seafood lunch, then continue on to New England's highest public observation deck, the Prudential Skywalk Observatory. High above Boston, you'll take in a 360-degree bird’s-eye view and an audio tour of the city’s landmarks, including Fenway Park, Hancock Tower, Boston Common and the Public Garden, the Esplanade, Faneuil Hall and Quincy Market, as well as MIT and Harvard across the Charles River. You’ll also have a chance to visit the Dreams of Freedom Immigration Museum.

Save $10 when you book this excursion up to 3 days before your tour departs. (On-tour price: $59)

Portsmouth, New Hampshire 1 night Hotel info

Day 3: Portsmouth via Lexington & Concord

Included meals: Breakfast

Stop in Lexington and Concord, where a local expert brings the history of the sites to life on a guided tour.

• Tread the same ground where the first shots of the Revolutionary War rang out

• Learn how Minutemen forced the British to retreat back over the Old North Bridge 

Continue on to the quaint 17th-century town of Portsmouth, where your Tour Director will help you get oriented. 

• Pass Market Square and Prescott Park

• See the outdoor Strawbery Banke Museum

Boothbay Harbor, Maine 2 nights Hotel info

Day 4: Boothbay Harbor via Kennebunkport & Portland

Included meals: Breakfast

Travel north to Kennebunkport, one of Maine’s best-known resort towns, and then Portland for a guided tour. Later, arrive in Boothbay Harbor.

• Pass the Portland Observatory and Fort Allen Park

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

Day 5: Free day in Boothbay Harbor

Included meals: Breakfast, Dinner

Spend the day exploring the old-time fishing village of Boothbay Harbor on your own or add an excursion.

In the evening, enjoy an included lobster dinner with your group.

Optional Excursion - Coastal Maine Whale Watching $65*pp Details

Hop aboard a boat at Boothbay Harbor for the chance to see local sea animals in their natural habitat. You’ll spend the morning cruising along the harbor and open waters of the Atlantic while keeping an eye out for whales, sharks, seals, puffins and more. Please note: If you take any medicine for seasickness, it is recommended that you bring it with you. Please note: This optional excursion is seasonal and runs from mid-May through August.

Save $10 when you book this excursion up to 3 days before your tour departs. (On-tour price: $75)

Boston, Massachusetts 1 night Hotel info

Day 6: Boston via Freeport

Included meals: Breakfast

Stop in Freeport, home to the world-famous L.L. Bean Factory Store, on your way back to Boston. Then, enjoy a farewell drink with your fellow travelers.

Day 7: Departure

Included meals: Breakfast (excluding early morning departures)

Begin your journey home, or continue on to Cape Cod.

Add Cape Cod $399 pp

A visit to coastal New England is not complete without a few days of oyster slurping and beach hopping on Cape Cod. Once the realm of fishermen, Cape Cod is now a destination for artists, writers and holidaymakers, who come for inspiration and relaxation. Take an excursion to Martha’s Vineyard, browse the art galleries or sit back and soak in the ocean beauty of the Cape.

Cape Cod, Massachusetts 2 nights Hotel info

Day 7: Cape Cod via Plymouth

Included meals: Breakfast

Make your way to Cape Cod. En route, stop in Plymouth, the first settlement in Massachusetts, to see the famed Plymouth Rock.

Day 8: Free day on Cape Cod

Included meals: Breakfast

Spend the day exploring the beach towns of Cape Cod on your own or add an excursion.

Optional Excursion - Martha's Vineyard $109*pp Details

Hop aboard a ferry for a day of exploration and discovery on the beautiful island of Martha’s Vineyard, known for its many-hued “gingerbread” Victorian homes, its sea-captain houses in Edgartown and its laid-back resort culture. After touring the island and enjoying a seafood lunch in Oak Bluffs, you’ll have free time to peruse the island’s charming shops and galleries. Don’t forget to stop by the famous Black Dog Cafe!

Save $10 when you book this excursion up to 3 days before your tour departs. (On-tour price: $119)

Day 9: Departure

Included meals: Breakfast (excluding early morning departures)

Transfer to the airport for your return flight home.

How's the weather?

  • Boston, Massachusetts, United States
  • Portsmouth, New Hampshire, United States
  • Boothbay Harbor, Maine, United States
  • Cape Cod, 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 dressier attire.


There are no major health risks associated with traveling to New England. 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.


One of the most enjoyable aspects of traveling is the delightful variety of local cuisine—even if you’re not traveling abroad. In New England, look out for especially delicious seafood specialties, such as lobster and clam chowder.


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

Time Zones

New England is 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: 8/8/2015

Number of Past Tours: 2

From: CA

Tour Director: 5 / 5

Tour Value: 4 / 5


Our Tour Director was tops. He stayed with us the entire tour and made optional activities available.