Our quest for independence was historic. Our struggle for freedom became legendary. From the sight 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 a Welcome Dinner this evening, get to know your fellow travelers. (D)

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 a bird’s-eye view of the city from the Prudential Skywalk, one of the highest points in Boston, followed by lunch at Slapjack's. (B)

$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.

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 tred the same ground where the first shots were fired, and where the Revolutionary War officially began. Here, a lisensed 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, 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 mythic 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. (B)

$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 the rest of the day 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.) This evening,  transfer to the sublime city of Portland, Maine, and enjoy exploring its wealth of culinary delights. (B)

$40 USD

Isles of Shoals 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. (Seasonal)

Day 5 - Portland, Maine

Spend this free morning exploring the Old Port, also known as downtown Portland, and treat yourself to its many wonderful handicrafts and treasures. The town also boasts 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). This afternoon, catch a peak at the town where the first 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, well, get away from it all. 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. Tonight, return to Portland to sample even more of its great cuisine—and its eclectic mix of live music. Ask your Tour Director for more details. (B)

Day 6 - Portland, Maine

Travel to one of Maine’s most breathtaking coastal gems this morning—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. Spend the morning exploring 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. On your way back to Portland, stop in the outlet village of Freeport, home base for that great Maine purveyor of goods, L.L. Bean, as well as other well-known stores. Shop to your heart’s content before returning to Portland in time for tonight’s Farewell Lobster Dinner. (B, D)

$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 7 - Portland, Maine

Begin your return journey home. Alternatively, choose to stay on for two extra nights in Cape Cod. (B)