Boston, New England & New York Road Trip

Itinerary

3 Nights – Boston
1 Night – Ptown
1 Night – Hyannis
1 Night – Providence
1 Night – Mystic
2 Nights – New Haven
3 Nights- New York

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✈️ UK to Boston (3 nights): Boston is a fantastic place to kick off your New England adventure. This bustling city is packed with history, having played a key role in the American Revolution. A great place to start exploring is by heading to the Boston Tea Party Ships and Museum, where you can step aboard 18th-century ships and relive the famous tea party. Take a stroll along the Freedom Trail, a 2 ½ -mile route through Boston’s North End, to check out landmarks such as the Old North Church and Paul Revere’s House. For sports fans, Fenway Park is a must-see. Even if you’re not able to watch a baseball game, you can take a tour of this iconic stadium. And don’t leave without trying Boston’s signature dish, Boston baked beans, made with molasses, brown sugar, and salt pork. After exploring the city, there are plenty of pubs, bars, and breweries to try, including TV’s famous Cheers bar, where everyone knows your name! On the final day in Boston, you’ll pick up your rental car.

🚗🚢 Boston to Provincetown (1 night): Leaving the city of Boston, you’ll catch a scenic ferry across the water to Provincetown, or ‘Ptown,’ as it’s affectionately called, located at the very tip of Cape Cod. This lively and artsy town is famous for its stunning beaches, eclectic shops, and vibrant LGBTQ+ scene. Take your time wandering around the colourful streets and art galleries and explore the beautiful coastline. Ptown has some fantastic restaurants and cafés, from fresh seafood shacks to more stylish restaurants. And when night falls you’ll find a great choice of cabarets and nightclubs to dance the night away. With a car at your disposal, you could also take the opportunity to explore further, including the nearby towns of Wellfleet, known for its fresh oysters and lovely beaches, and Truro, where you can enjoy a quieter, more relaxed atmosphere.

🚗 Provincetown to Hyannis (1 night): The drive from Provincetown to Hyannis takes around an hour, although you’ll probably want to take your time stopping for photos and taking short detours to explore the small towns along the way, such as Orleans and Brewster. Hyannis, with its laid-back vibe and charming waterfront, is the perfect base for heading to the island of Martha’s Vineyard, which is just a short ferry ride away.  Martha’s Vineyard is quintessentially ‘New England’, famous for its pretty villages, rolling hills, pristine beaches, and lighthouses. Some of the must-see towns to visit include Edgartown, with its beautiful 19th-century buildings and peaceful harbour, and Vineyard Haven, a bustling port town filled with galleries, shops, and restaurants. Oak Bluffs is another hugely popular spot with its colourful ‘Gingerbread’ cottages and lively atmosphere.

🚗 Hyannis to Providence (1 night): After exploring Hyannis, you’ll head west towards Providence in Rhode Island. The drive will take around 1½ –2 hours, offering plenty of time to relax and enjoy the scenic views en route. Providence is Rhode Island’s capital city and is known for its colourful arts scene due to being home to the prestigious Rhode Island School of Design (RISD). Visit the RISD Museum, wander through the artistic streets, and enjoy the public art installations dotted around the city. The Rhode Island State House, with its grand marble dome, is another must-see, as is Benefit Street, home to beautifully preserved Colonial-era homes. For a peaceful walk, head to RiverWalk for lovely views along the water.

🚗 Providence to Mystic (1 night): In under an hour, you’ll take the drive southwest from Providence to the charming town of Mystic where you’ll feel like you’ve stepped back in time, with its cobbled streets and 19th century ships. Located along the Mystic River, it’s known for its maritime heritage and picturesque setting on the coast.  The Mystic Seaport Museum is a highlight, offering insights into the area’s seafaring past with historic ships and a recreated 19th-century village. The Mystic Aquarium is another fantastic spot, where you can get up close with marine life. While you’re here, wander through the old streets of Downtown Mystic, pop into local shops and cafés, and enjoy views of the Mystic River. The Mystic River Bascule Bridge still opens for passing boats, adding an extra bit of nostalgic charm to the town.

🚗 Mystic to New Haven (2 nights): From Mystic, it’s about a 1-hour drive to the historic city of New Haven, during which you’ll pass the Long Island Sound coastline, taking in views of Hammonasset Beach State Park and Guilford Harbor along the way.  New Haven is most famous for being home to Yale University, one of the country’s most prestigious universities. The campus is a beauty to explore, with a mix of stunning architecture, from Collegiate Gothic to modern designs. Don’t miss the Yale University Art Gallery or the Beinecke Rare Book & Manuscript Library.  New Haven also offers plenty for museum lovers, including the Peabody Museum of Natural History. For one of the best views in the city, head to East Rock Park. And if you’re hungry, you have to try New Haven’s famous apizza – a delicious crispy, coal-fired pizza.

🚗 New Haven to New York (3 nights):  The grand finale of your road trip will bring you to New York City, the ‘Big Apple’. Everything here is ‘big’: from big buildings, big landmarks, big culture, big flavours, and big energy… all packed into one legendary city. You’ll want to squeeze in as many iconic sights as possible into your 3-night stay. Start with the top attractions such as Times Square, the Empire State Building, and the views from Top of the Rock. Also don’t miss Brooklyn Bridge or or Grand Central Terminal. Take a stroll through Central Park or explore world-famous museums including the American Museum of Natural History, the Guggenheim, the 9/11 Memorial & Museum, and the Met. If your feet need a break, hop on a ferry to Staten Island for a different perspective of the Manhattan skyline and a close-up view of the Statue of Liberty. When night falls, New York really comes alive, after all, this is the city that never sleeps. Catch a Broadway show, enjoy drinks at a rooftop bar, or explore the nightlife of the Lower East Side and beyond.

✈️ New York to UK: Finishing your trip on a high from the sights and sounds of New York, you’ll head back to the UK.