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New England Tours & Itineraries

Suggested itineraries for guided or self-guided tours of Boston, Cape Cod & the Islands, Northern and Southern New England, from 4 to 10 days.

View from Cadillac Mountain, Acadia National Park, Maine
View from Cadillac Mountain, Acadia National Park, Maine

New England is compact. You can drive between any two points in the region in a day; but to drive from the Connecticut shoreline to northern Maine (550 miles/885 km, 9+ hours) would be a long day.

Never mind! You won't be spending long days driving. Usually, you'll drive only an hour or two from one destination to the next.

Suffice it to say that you can see a lot of New England in a week's travel. Ten days is better, of course, and two weeks gives you time to go into some depth of the cultural offerings of Boston or the Berkshires, spend some time hiking and camping in the White Mountains, spend a few days sailing the Maine coast in a windjammer, or get into serious beach mode on Cape Cod.

Guided Tours

If you'd rather have someone else do the planning, logistics and reservations for you, take a guided tour. Many tour companies operate guided tours that explore New England. The most popular tours are, of course, fall foliage tours. Every major tour operator seems to have at least one.

Fall foliage in New England USA

Active Travels

Active Travels, a Boston-area travel agency for those who want personally-planned, innovative travel itineraries, is the brainchild of acclaimed travel writer and guidebook author Steve Jermanok and travel agent Lisa Leavitt.

Steve Jermanok & Lisa Leavitt, Active Travels, Boston MA
Lisa Leavitt & Steve Jermanok on an active vacation hiking in New Hampshire's White Mountains.

In 1995, Steve put more than 20,000 miles on his car as he researched and wrote Outside Magazine’s Adventure Guide to New England. It would be the first of 11 books he would write on New England, working with Lonely Planet (with co-author Tom Brosnahan), Frommer’s, Discovery Channel, and other world-class travel publishers.

Steve’s latest book, New England Seacoast Adventures, describes the best walks, bike rides, and paddling spots along the northeastern coast.

Steve is also a prolific travel writer for periodicals, writing more than 1500 magazine, newspaper and web articles in the past 20 years. He’s been a columnist at The Boston Globe, Men’s Journal, National Geographic Adventure, and a contributing editor at Budget Travel.

More than 500 of his articles were on the region he knows and loves best, his home: New England.

Steve and travel agent Lisa Leavitt, Steve launched their boutique travel agency, ActiveTravels, in May 2012, at 89 Roundwood Road, Newton MA 02464 (Tel: +1 (617) 614 9877).

Their specialty is the Dream Day Itinerary. Ideally suited for the independent traveler, these detailed itineraries include lodgings, activities, restaurants, and off-the-beaten-path special stops, incorporating lots of local flavor. Top guides take you to sites based on your particular love of art, architecture, the outdoors, and/or history. In fact, many of the suggested activities, hotels, and restaurants on the Dream Day Itinerary were painstakingly researched by Steve for his travel articles.

Steve and Lisa have welcomed travelers from across America and around the globe, and introduced them to New England, including clients from New Zealand, the UK, and Switzerland. They will book you in their favorite country inns on backcountry roads aglow in fall foliage color that only a local would know. They can arrange a day-tour by bike to five lighthouses near Portland, Maine; hire a private sailboat for a cruise out of Newport, Rhode Island; and arrange an inn-to-inn walking trip in Vermont.

If you'd like a travel agency to help you plan and book your trip to New England, check out Active Travels, fill out the short website questionnaire so Steve and Lisa can know your travel preferences and budget, then consult with them to create your perfect New England adventure.

Mention that you're coming from for special consideration.

Highlights of New England

Here are the high points. Pick and choose what interests you, then plan your trip.


4-Day Boston & Vicinity

Charles River Esplanade & Boston
Charles River Esplanade & Boston

You can see a surprising amount of New England in four days from a base in Boston by spending some time in the city and taking excursions by car, bus or train into the hinterland. More...

4- or 5-Day Cape Cod & the Islands

Provincetown, Cape Cod MA.
View of Provincetown, at the tip of Cape Cod, from the Pilgrim Monument tower.

Cape Cod's got it all: charming towns, long sandy beaches, great dining—especially seafood, shopping for antiques. And then there are the historic islands of Nantucket and Martha's Vineyard and if you have that extra day, a detour to experience the sumptuous Gilded Age mansions of Newport RI. More...

6- to 10-Day Northern New England

Mount Washington, New Hampshire

This itinerary through Maine, New Hampshire and Vermont is particularly well suited for outdoor activities, but is also fine just for scenic drives. The tour can be split into two mini-tours: a 4-day trip along the Maine coast to Bar Habor, and a 6-day trip through the White Mountains of New Hampshire and the Green Mountains of Vermont. More...

7- to 10-Day Southern New England

Cliff Walk & The Breakers mansion, Newport RI
Cliff Walk & The Breakers mansion, Newport RI

Start this tour in Boston, New York City, or indeed anywhere along its route to get a good introduction to the Pioneer Valley, the Berkshire Hills, northwestern Connecticut, the Connecticut shoreline, Newport and Providence, Rhode Island, and the South Shore of Massachusetts Bay. More...