Boston & Cape Cod Trip

Sample Itinerary of Boston & Cape Cod Trip

As with all our holidays they are tailor made to suit your requirements and durations, below is just one of the many suggestions we have for Boston and Cape Cod Twin Centre, we can however include another destination if that's what your looking for. This Boston and Cape Cod holiday allows you to enjoy all the fun of the Sail250 as art of the America 20th Anniversary Celebrations! Sail250 in Boston will run from July 11 to July 16, 2026 and will feature a stunning fleet of international ships in Boston Harbor!

Boston - 4 nights

Hotel - Harborside Inn of Boston

Fly direct to Boston with one of our airline partners like Virgin Atlantic / Delta Airlines. On arrival into Boston, collect your vehicle and make your way to the Harborside Inn of Boston, located centrally near popular attractions like Faneuil Hall and Quincy Market. Harborside Inn of Boston is ideally for those wanting to walk around the city as iconic landmarks like the Freedom Trail, Boston Tea Party Ships & Museum and HarborWalk are within half a mile's walk!

Boston is a charming city rich in historic sights which are best discovered by walking the Freedom Trail. This is a 2 and a half mile route taking you through downtown Boston and Charlestown past 16 historic sites including churches, museums and burial grounds. Or perhaps you would prefer a Boston Duck Tour; board a renovated World War 2 landing vessel as you journey around the attractions on land such as Boston Common and the famous Cheers Bar, before you head to the water to cruise down the St Charles River, a fantastic way to explore the highlights of Boston.

Whilst in Boston you will be able to enjoy Sail250 Boston and spot all kinds of stunning ships in the harbour. Why not also enjoy a Boston Harbor sightseeing cruise to see all the fantastic historical landmarks within the city.

Things to Do in Boston

• Experience Sail250 Boston (11–16 July 2026): Watch spectacular tall ships from around the world fill Boston Harbor, with waterfront festivals, ship tours, and anniversary celebrations.
• Walk the Freedom Trail: Discover key sites of America’s founding, including Boston Common, Faneuil Hall, Paul Revere’s House, and the Old North Church.
• Harbor Cruise & Waterfront Dining: Take a scenic Boston Harbor cruise and enjoy fresh seafood along the historic waterfront and Seaport District.
• Explore Historic Neighbourhoods: Visit Beacon Hill, Back Bay, and the North End for classic architecture, shopping, and authentic Italian dining.

Cape Cod - 4 nights

Hotel - Hyannis Harbor Hotel

After enjoying Boston, you'll drive down to Hyannis Cape Cod, approximately a 1 and a half hour journey. Here you will be staying in the Hyannis Harbor Hotel located directly on Hyannis Harbor! The Hyannis Harbor Hotel is a quaint boutique hotel with coastal charm and authentic Cape Cod charm. Hyannis Harbor Hotel is ideal for families and couples alike and offers fantastic views of Hyannis Harbor.

The waterfront location is just steps from the Ferry to ferry to Nantucket and Martha's Vineyard, and just a short walk to the streets of the Harborfront Village or nearby Ocean Street where you can enjoy shops, restaurants and more. Plus, Cape Cod's popular beaches and parks, including Kalmus Beach, are within walking distance.

Things to Do in Hyannis & Cape Cod

• Relax on Cape Cod’s Beaches: Unwind on beautiful sandy beaches such as Kalmus Beach and Craigville Beach, ideal for classic New England coastal relaxation.
• Visit the Kennedy Legacy Sites: Explore the John F. Kennedy Hyannis Museum and walk near the Kennedy Compound for a glimpse into presidential history.
• Take a Cape Cod & Islands Ferry: Enjoy a day trip by ferry to Martha’s Vineyard or Nantucket, two of New England’s most charming islands.
• Scenic Coastal Drives & Lighthouses: Discover iconic Cape Cod lighthouses, seaside villages, and coastal routes perfect for leisurely sightseeing.

After your time in Cape Cod, begin your journey back to Boston ready for your return flight home to the UK.

All our holidays are tailor-made and can be adapted by changing hotels durations and destinations to suit the individuals tastes and requirements – please do get in touch so we can start planning.