5 days in New England, Cape Cod & Connecticut Itinerary

5 days in New England, Cape Cod & Connecticut Itinerary

Created using Inspirock United States trip itinerary maker

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Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
On the 16th (Fri), admire the masterpieces at Museum of Fine Arts, then take in nature's colorful creations at Boston Public Garden, and then stroll around Boston Common. Get ready for a full day of sightseeing on the 17th (Sat): get a sense of history and politics at Old State House, then get a taste of the local shopping with Faneuil Hall Marketplace, then wander the streets of North End, and finally appreciate the extensive heritage of Freedom Trail.

For where to stay, other places to visit, and other tourist information, read Boston trip planner.

Durham to Boston is an approximately 3.5-hour flight. You can also drive; or take a bus. When traveling from Durham in September, plan for a bit cooler days in Boston, with highs around 75°F, while nights are about the same with lows around 59°F. Finish your sightseeing early on the 17th (Sat) to allow enough time to drive to Hyannis.

Things to do in Boston

Museums · Parks · Historic Sites · Neighborhoods


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Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
On the 18th (Sun), take an in-depth tour of Sandwich Glass Museum, then examine the collection at Heritage Museums & Gardens, then steep yourself in history at Hoxie House, and finally don't miss a visit to Old King's Hwy.

To find where to stay, more things to do, traveler tips, and other tourist information, read our Hyannis trip builder website.

You can drive from Boston to Hyannis in 1.5 hours. Alternatively, you can take a bus; or fly. In September, plan for daily highs up to 73°F, and evening lows to 57°F. Wrap up your sightseeing on the 18th (Sun) early enough to drive to Newport.

Things to do in Hyannis

Museums · Childrens Museums · Historic Sites

Side Trip


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City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Start off your visit on the 19th (Mon): take a tour by water with Fish'n Tales Adventures, then see the interesting displays at The Breakers, and then get to know the fascinating history of Cliff Walk.

For ratings, other places to visit, traveler tips, and tourist information, use the Newport trip itinerary builder website.

Drive from Hyannis to Newport in 2 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 74°F, and evening lows to 58°F. Wrap up your sightseeing on the 19th (Mon) to allow time to drive to Mystic.

Things to do in Newport

Outdoors · Trails · Museums · Parks


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A historical leading seaport, Mystic has maintained a strong respect for the past.
Kick off your visit on the 20th (Tue): contemplate the long history of Olde Mistick Village and then meet the residents at Mystic Aquarium.

For traveler tips, other places to visit, and more tourist information, use the Mystic online holiday planner.

Traveling by car from Newport to Mystic takes 1.5 hours. Alternatively, you can do a combination of bus and train. September in Mystic sees daily highs of 75°F and lows of 58°F at night. Cap off your sightseeing on the 20th (Tue) early enough to catch the flight back home.

Things to do in Mystic

Zoos & Aquariums · Parks · Historic Sites

Cape Cod travel guide

Beaches · Dolphin & Whale Watching · Specialty Museums
Located on the southern shore of Massachusetts, Cape Cod contains some 15 towns and two islands. The arm-shaped peninsula is a popular holiday destination throughout the year because of its historical attractions, art galleries, award-winning restaurants, and a scenic coastline dotted by sandy beaches. Start your sightseeing in Provincetown, located at the very tip of the cape and famous for being the site of the first Pilgrims' landing in 1620. From there you can hit up all of the Cape's other small towns, renowned for their comfortable bed and breakfasts and distinctive cuisine of fresh fish and oyster dishes. This maritime community features more than a dozen lighthouses. Part of experiencing the Cape means a trip to its two islands--which showcase several lighthouses and numerous restaurants.

Connecticut travel guide

Aquariums · Theaters · Observatories
The Constitution State
Perhaps best known for its renowned private and public universities, Connecticut was once home to the country's first law school and still boasts one of the oldest secondary schools in America. More than just a small state packed with students, Connecticut offers visitors a chance to explore some of New England's finest tourist attractions while on vacation, including lighthouses, beaches, theaters, museums, galleries, and restaurants. Despite its small size, the state also boasts two large casino complexes, both located on Native American reservations. Rich in history and natural beauty, Connecticut draws newcomers from around the world, with large Polish, Chinese, and Hispanic communities.