Our quest for independence was historic. Our struggle for freedom became legendary. From the site of the Boston Tea Party and the spot where the first shot was fired to the House of Seven Gables in Salem and the maritime culture of Portland, you’ll experience the glorious birth of a nation.

Detailed Itinerary

Day 1 - Boston

Arrive in Boston, Massachusetts, and check into your hotel. The rest of the day is free for you to relax or begin acquainting yourself with Boston. At an included dinner this evening, get to know your fellow travelers.
Included meals: dinner

Day 2 - Boston

An expert local guide leads this morning’s sightseeing tour of Boston, one of the first British settlements in America and one of the principal fronts in the Revolutionary War. Your tour begins on the Freedom Trail, where you’ll sweep through two and a half centuries of America’s most significant past as you follow the red brick line that connects the 16 most important historical sites in Boston.

Highlights include Old North Church, the Old South Meeting House, Paul Revere’s House, Faneuil Hall, the site of the Boston Massacre, the Old State House, King’s Chapel, the Granary Burial Ground, the Park Street Church, the Massachusetts State House, and Boston Common.

End the tour at Harvard Square, where you’ll have free time to explore the university’s campus and browse the surrounding shops. This afternoon, continue exploring the city on your own or opt to enjoy lunch, followed by a bird’s-eye view of the city from the Prudential Skywalk, one of the highest points in Boston.
Included meals: breakfast

$60 USD

Prudential Skywalk & Lunch The only observatory in New England, the Prudential Skywalk Observatory offers a 360-degree bird's-eye view of the city of Boston. Marvel at the city's sparkling vistas, and enjoy an included lunch. Please note: This optional requires advanced reservations.

Day 3 - Salem

Ever wonder where the British fired “the shot heard ‘round the world”? As you leave Boston for Lexington and Concord, you’ll tread the same ground where the first shots were fired, and where the Revolutionary War officially began. Here, a licensed local guide helps you discover how the Patriots foiled a secret plan by the British to destroy their stockpiles of ammunition and food, and how Minutemen forced the British to retreat back over the Old North Bridge, starting what would come to be known as the Seige of Boston.

Later this afternoon, you’ll venture to Salem, America’s Bewitching Seaport, known far and wide for its infamous witch trials. But did you also know that the name Salem means City of Peace (despite the many conflicts that soon followed), and that Salem was where local sea captains became America’s first millionaires?

As you visit the well-known House of Seven Gables, made famous by Nathaniel Hawthorne’s novel of the same name, you’ll step into the life of one such millionaire family—and even discover a secret staircase! Formally called the Turner-Ingersoll Mansion after its original owners, the house is the oldest surviving 17th century wooden mansion in New England, and is flanked by Hawthorne’s birth home as well as two enchanting seaside Colonial Revival gardens. Get a taste for Salem’s more supernatural side on tonight’s optional Haunted Footsteps tour.
Included meals: breakfast
Included entrances: The House of Seven Gables

$10 USD

Haunted Footsteps Tour Travel into the past on this Haunted Footsteps tour through Salem, where you'll follow your costumed guide by lantern light into some of the city's most haunting history and compelling lore and legends. (Seasonal)

Day 4 - Portland, Maine

This morning, leave Massachusetts behind as you travel north to Portsmouth, New Hampshire, the nation’s third-oldest city and one of its most beautiful. Spend some time exploring this picturesque seaport city, immersing yourself in the wonders of its downtown. Alternatively, you can join an optional harbor cruise to the Isles of Shoals, nine rocky islands six miles off the coast that were originally discovered by Captain John Smith—the same one from the Pocahontas tale. (During the fall months, an inland River & Fall Foliage Cruise will be offered instead.)

Next, catch a peak at the town where the first (and second) President Bush comes to get away from it all. One of Maine’s most loved resort towns, Kennebunkport is the perfect spot to kick back and relax. Thanks to its charming shops and cafés, its lovely beaches and its upscale residents, an afternoon spent here is always an afternoon well spent—whether you arrive during the summer or not. Later, transfer to Portland, Maine.
Included meals: breakfast

$40 USD

Portsmouth Cruise Discovered by the famous Captain John Smith—the same of Pocahontas fame—the Isles of Shoals are an archipelago of nine rocky islands six miles off the coast of New Hampshire and Maine with a rich and storied history.  Please note: In the fall months, an inland River & Fall Foliage Cruise will be offered instead.

Day 5 - Portland, Maine

After this morning's Tour Director-led sightseeing of Portland, spend time browsing the wonderful handicrafts and treasures found in Old Port, also known as downtown Portland. Enjoy a wealth of independent bookshops, from the exhaustive depth and breadth of Longfellow Books to the more offbeat selection at Casco Bay Booksellers.

The city boasts many delicious lunch offerings, from a pub meal and a microbrew at Gritty McDuff’s, the divine pies at Flatbreads and the delicious grilled and rotisseried meats and seafood at Fore Street to the ice cream at Maple’s Gelateria and the delectable desserts at Bar Lola (disclaimer: Go Ahead Tours does not maintain a professional relationship with any of the above-mentioned establishments; they just number among our staff’s many favorites).

Later, travel to one of Maine’s most breathtaking coastal gems—Boothbay Harbor. Jutting out into the Atlantic on a peninsula, Boothbay began as a fishing village and became a great vacation spot, somewhat off the beaten path. Explore the town’s many shops and galleries—and its unparalleled views on your own, or opt to join an excursion to the Boothbay Railway Village, where you can explore antique trains and railroads, autos and rural village history. Return later to Portland in time for tonight’s included Lobster Dinner.
Included meals: breakfast, dinner

$10 USD

Boothbay Railway Village At Boothbay Railway Village, you'll find over 50 antique cars to explore before riding on a coal-fired, narrow-gauge steam train that travels through a model of a century-old New England village.

Day 6 - Boston

Today, transfer back to Boston and spend the afternoon meandering the city streets and Boston Common. For a java delight or souvenir shopping, venture to one of the many cafes or shops along Boylston or Newbury Streets.
Included meals: breakfast

Day 7 - Boston

Begin your return journey home. Alternatively, stay on for two extra nights on beautiful Cape Cod.
Included meals: breakfast
(In the case of early morning departures, breakfast may not be provided.)