8 days in New England Itinerary

On the 24th (Tue), stroll through Castle Island, then contemplate in the serene atmosphere at Trinity Church, then wander the streets of Back Bay, and finally wander the streets of North End. Here are some ideas for day two: get to know the fascinating history of HarborWalk, then test your team's savvy at popular escape rooms, then admire the natural beauty at Arnold Arboretum, and finally explore the different monuments and memorials at Mount Auburn Cemetery.

To find out how to plan a trip to Boston, use our trip itinerary maker.

Madison to Boston is an approximately 5-hour flight. You can also drive; or take a bus. Traveling from Madison to Boston, you'll lose 1 hour due to the time zone difference. Prepare for somewhat warmer weather when traveling from Madison in January: high temperatures in Boston hover around 37°F and lows are around 23°F. Finish up your sightseeing early on the 26th (Thu) so you can go by car to Salem.

Kick off your visit on the 26th (Thu): explore the different monuments and memorials at Old Burial Hill, then enjoy the sand and surf at Singing Beach, then stop by Magika - Chapel of Archangel Michael, and finally examine the collection at Salem Toy Museum.

For maps, where to stay, other places to visit, and tourist information, use the Salem trip itinerary builder app.

Traveling by car from Boston to Salem takes an hour. Alternatively, you can take a train; or take a bus. In January in Salem, expect temperatures between 36°F during the day and 21°F at night. Finish your sightseeing early on the 27th (Fri) so you can drive to Exeter.

Start off your visit on the 27th (Fri): steep yourself in history at African Burying Ground Memorial, then contemplate the long history of Strawbery Banke Museum, then steep yourself in history at Portsmouth Historical Society, and finally do a tasting at LaBelle Winery. On the 28th (Sat), you'll have a packed day of sightseeing: see the interesting displays at Exeter Historical Society, then see the interesting displays at American Independence Museum, then explore the landscape on two wheels at Phillips Exeter Trail, and finally indulge your thirst for a good beer at Stoneface Brewing.

To find out how to plan a trip to Exeter, use our trip itinerary maker.

Traveling by car from Salem to Exeter takes an hour. Alternatively, you can drive. January in Exeter sees daily highs of 34°F and lows of 18°F at night. Finish your sightseeing early on the 28th (Sat) to allow enough time to drive to Boston.

You'll explore the less-touristy side of things at Room Escape Games and HarborWalk. Popular historic sites such as Castle Island and Old State House are in your itinerary. When in Boston, make a side trip to see Louisa May Alcott's Orchard House in Concord, approximately Concord away. Enjoy Boston some more: admire the masterpieces at Museum of Fine Arts, take a stroll through Back Bay, explore the different monuments and memorials at Mount Auburn Cemetery, and take in nature's colorful creations at Arnold Arboretum.

To find traveler tips, reviews, other places to visit, and other tourist information, read our Boston online itinerary builder.

You can drive from Exeter to Boston in an hour. Another option is to drive. Finish your sightseeing early on the 31st (Tue) to allow enough time to fly back home.