Coastal roads, charming towns, and iconic landmarks – explore the best of the USA’s East Coast.
This 10-night self-drive itinerary takes you on a scenic journey through the heart of New England. From the cobblestone streets of Boston to the tranquil lakes of New Hampshire and the timeless coastal beauty of Cape Cod, you’ll uncover historic towns, lush forests, and seaside charm along the way. With must-see highlights, driving distances, and hand-picked hotel stays, it’s the perfect blend of discovery and relaxation.
Nights: 2
Suggested hotel: Hilton Boston Park Plaza
Must-do things: Explore downtown Boston, stroll through Quincy Market, visit Harvard University, walk the Freedom Trail, climb the Bunker Hill Monument, catch a Red Sox game, enjoy the Boston Waterfront, shop along Newbury Street, and relax in Boston Common.
Drive to next stop: → Holderness 115 mi / 185 km ~ 2 hrs
Nights: 1
Suggested hotel: The Inn on Golden Pond.
Must-do things: Relax by Squam Lake, visit the Squam Lakes Natural Science Centre, kayak or canoe on the lake, enjoy local hiking trails, explore White Mountain National Forest, and roast complimentary s’mores by the fire at your inn.
Drive to next stop: → Woodstock 105 mi / 170 km ~ 2.5 hrs
Nights: 2
Suggested hotel: 506 On The River Inn
Must-do things: Unwind by the water, hike scenic trails, explore White Mountain National Forest, and enjoy cozy evenings with s’mores by the fire.
Drive to next stop: → Williamstown 115 mi / 185 km ~ 2.5 hrs
Nights: 1
Suggested hotel: The Williams Inn
Must-do things: Visit The Clark Art Institute or Williams College Museum of Art, explore the walking trails around Williamstown, and enjoy New American cuisine at your inn’s restaurant.
Drive to next stop: → Cape Cod (Chatham) 190 mi / 305 km ~ 4 hrs
Nights: 2
Suggested hotel: Queen Anne Inn (Chatham)
Must-do things: Explore Chatham Lighthouse Beach, browse downtown shops and cafés, visit the Cape Playhouse, take the ferry to Martha’s Vineyard or Nantucket, stop by the Woods Hole Oceanographic Institution, or tee off at one of 41 local golf courses.
Drive to next stop: → Boston 85 mi / 135 km ~ 2 hrs
Nights: 1
Hotels: Return to Boston airport area hotel (if overnight required)
Must-do things: Enjoy a morning bike ride along the Cape Cod Rail Trail, visit Monomoy National Wildlife Refuge, and make your way back to Boston for your flight home.
As your New England adventure comes to an end, take a moment to reflect on the region’s timeless charm — from Boston’s historic streets to the peaceful lakes of New Hampshire and the windswept shores of Cape Cod. Every stop offers a story, every view a new memory. With Virgin Atlantic Holidays, you’ll experience the very best of New England’s coastal beauty, small-town warmth, and classic Americana — all from behind the wheel of your own unforgettable journey.
Whether you’re craving a few extra stops, a scenic detour, or a little luxury along the way, our team’s here to help you map out your perfect road trip, simple, flexible, and full of unforgettable moments from start to finish.