New England is the birthplace of American maritime tradition, and yachting remains a favorite pastime today. A charter here immerses you in the local lifestyle, with everything from sandy beaches to clam bakes to whaling museums. Some of the architecture dates back centuries, and cobblestone streets still guide visitors to bistros and boutiques.

This eight-day itinerary combines days of relaxation with days of exploration, and includes stops at the world-famous islands of Nantucket and Martha’s Vineyard.

Day 1: Newport, Rhode Island

Local harbor tour
Cruising pace at your leisure
Arriving in Newport is like stepping into the heart of the yachting culture, and you will want a day to savor the experience. Walk along the waterfront promenade where countless yachts are berthed, explore the shops full of maritime goodies, and end your first day with a leisurely harbor cruise in view of the stunning, manicured mansions.

Day 2: Newport to Block Island

16 nautical miles
A little more than an hour and a half aboard a yacht that cruises at 10 knots
Less than three hours aboard a sailing yacht that cruises at 6 knots
Block Island combines New England style with a laid-back attitude. Victorian houses and quaint shops share the island with 17 miles of white, sandy beaches. Bicycle tours are a popular option here, with some roads running alongside beautiful stone walls that are hundreds of years old.

Day 3: Block Island to Cuttyhunk Island

30 nautical miles
Three hours aboard a yacht that cruises at 10 knots
Five hours aboard a sailing yacht that cruises at 6 knots
Cuttyhunk is south of Cape Cod, Massachusetts, and offers exceptional hiking with bird’s-eye views that make for fantastic keepsake photos. The island is best known as a quiet, remote place to simply relax and unwind, perhaps enjoying a long lunch on your charter yacht or a clam bake onshore before a refreshing nap in the gentle sea breezes.