14 days tailor made from $6,690 pp
From $6,690 pp
At a glance
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Don't forget that all of our itineraries are totally customized and so this is just an idea of what we can build for you.
Embark on a captivating Massachusetts adventure, starting in the historic city of Boston. Spend a couple of days exploring Boston’s rich history, particularly its pivotal role in the American Revolution.
Walk the famous Freedom Trail, visit the historic Faneuil Hall Marketplace, and stroll along the Boston Harbor. After soaking in Boston’s historical ambiance, head to Provincetown at the tip of Cape Cod. Known as a gay-friendly destination, Provincetown offers a contrasting, laid-back seaside escape with beautiful beaches, vibrant art galleries, and a bustling nightlife centered around Commercial Street.
Choose between a scenic ferry ride or a leisurely car drive to travel from Boston to Provincetown. The ferry offers stunning coastal views, while the drive allows you to explore quaint towns and picturesque landscapes at your own pace. In Boston, delve into the city’s revolutionary past by visiting landmarks like the Paul Revere House and the Old North Church.
In Provincetown, immerse yourself in the local arts scene and welcoming LGBTQ+ culture. Visit the Provincetown Art Association and Museum, and enjoy the lively entertainment, including cabarets and nightclubs. Don’t miss the town’s beautiful beaches like Race Point Beach and the nearby Cape Cod National Seashore for a tranquil seaside experience. This combination of Boston’s historical depth and Provincetown’s artistic charm and natural beauty makes for a diverse and enriching Massachusetts journey.
In detail
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Don't forget that most of our itineraries can be totally customized. Our expert team will be able to talk you through all the options.
About Boston
Boston, the capital of Massachusetts, stands as one of the oldest cities in the United States, rich in history and cultural significance. Renowned for its central role in the American Revolution, the city is a living museum of American history, with its streets and landmarks narrating the nation’s founding story.
Today, Boston has transformed into a vibrant, quirky city that effortlessly blends its historical heritage with modern innovation and charm. As you wander through its diverse neighborhoods, you’ll encounter a plethora of attractions, from historical sites and prestigious universities to cutting-edge restaurants and lively cultural scenes. The city’s unique blend of the past and the present makes it a fascinating destination, offering an array of experiences for history buffs, culture enthusiasts, and urban explorers alike.
Things To Do In Boston
The Freedom Trail: A 2.5-mile walking route marked by a red line on the pavement, connecting 16 historic sites tied to the American Revolution, from the gold-domed State House to Paul Revere’s house in the North End.
Boston Common: The oldest public park in the United States, Boston Common has been a gathering place since 1634 and sits at the natural starting point of the Freedom Trail.
Museum of Science: Spanning dinosaurs to artificial intelligence across 700-plus exhibits on the Charles River, this is a strong option for a rainy afternoon or anyone travelling with younger guests.
Faneuil Hall: A Boston landmark since 1743, serving as both market and public meeting hall. It forms part of the Freedom Trail, with the adjacent Quincy Market a reliable lunch stop.
USS Constitution: The oldest commissioned warship still afloat, docked at the Charlestown Navy Yard and free to board. Active-duty Navy crew guide visitors through the decks. Photo ID required for those 18 and over.
About Provincetown
Provincetown, often referred to as P-town, is a picturesque town located at the northern tip of Cape Cod in Massachusetts, easily accessible by a short ferry ride or a scenic car drive from Boston. This charming seaside town is celebrated for its warm and welcoming atmosphere, making it a favored destination, particularly within the LGBTQ+ community.
Provincetown’s inclusive and vibrant ambiance has earned it a reputation as a place where visitors from all walks of life can feel at home. With its stunning beaches, lively arts scene, and an array of entertainment options, Provincetown beckons travelers to embrace its unique blend of natural beauty and a spirited, open-hearted community. Whether you seek relaxation on pristine beaches or the excitement of a lively arts and cultural scene, Provincetown promises a memorable and welcoming experience for all who visit.
Things To Do In Provincetown
The Pilgrim Monument: This 252-foot granite tower marks the Mayflower Pilgrims’ first landfall in 1620, a full five weeks before they reached Plymouth. The views across Cape Cod Bay from the top are worth the climb alone.
Race Point Beach: One of the most spectacular stretches of coastline on the East Coast, Race Point sits within the Cape Cod National Seashore and draws swimmers, sunbathers, and seal-spotters in equal measure.
Dolphin and Whale Watching: Provincetown sits in some of the most whale-rich waters on the Atlantic seaboard. Humpback whales are a common sighting on cruises out of MacMillan Pier, running April through October.
Province Lands Bike Trail: This six-mile loop threads through the dunes of the Cape Cod National Seashore, with sweeping ocean views and access to both Race Point and Herring Cove beaches.
Bars and Nightlife: Atlantic House, known locally as the A-House, is one of the oldest gay bars in America and still the anchor of Provincetown’s nightlife. Three distinct spaces cover all bases: the cozy Little Bar, the Macho Bar, and the Big Room dance club. The Crown & Anchor’s Paramount is the largest waterfront venue in town.
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