With its sandy North Shore beaches, rocky outcrops, green parks, hemlock woods and wild estuaries full of shorebirds, it is no wonder that Gloucester has attracted such a rich and diverse artists' community. Fitz Hugh Lane, Winslow Homer and John Sloan are just some of the artists who have taken inspiration from Gloucester's beautiful surrounds. Still boasting dozens of galleries and boutiques, as well as museums, theaters and an artists' colony, the city's art scene clearly continues to thrive.

It's no wonder that the Pilgrims fell in love with America when they landed at gorgeous Plymouth, set in the calm waters of Plymouth Harbor along Cape Cod Bay. It was here that the first English colonists made war and then peace with the Natives, celebrating their newfound cooperation with the first Thanksgiving dinner. Visit the landmarks that honor this piece of American history, from Plymouth Rock to Mayflower II to Burial Hill. Or just enjoy the sandy beaches and calm sea breeze.

Visit Provincetown and have a blast enjoying some of Cape Cod’s best beaches (Race Point Beach and Herring Cove Beach are favorites of TripAdvisor travelers). Plenty of cool boutiques, restaurants and art galleries give this town a fun and funky vibe. It’s an exceptionally LGBT-friendly destination as well. One tip: if it’s high season, take the ferry or a quick flight from Boston (unless you enjoy spending hours sitting in traffic).

From quaint town shops and quiet beaches, to honky tonk arcades and carousels, the York area is guaranteed to entertain the whole family. Old York, run by the local historical society, contains nine different restored buildings, including "The Old Gaol," the oldest jail in America. The beautiful coastline provides cliff walks with views of an authentic Maine lighthouse. Head to nearby York Beach and visit York's Wild Kingdom, an amusement park and zoo that is home to Rewa, a White Bengal tiger.

Yes, getting there is a bit of a project. But vacationers have been braving the ferry for years, and this tiny island off Cape Cod remains one of the most popular and picturesque destinations in New England. Among the island's towns, you're sure to find the Vineyard that's right for you. With stately Greek revival houses dating back to the whaling era of the early 19th century, Edgartown is a seaside village of boutique shopping and pristine harbour views. For more of a "beach town" feel, Oak Bluffs has the Flying Horses carousel, an arcade and an easy walk to the beach, plus the history and charm of the "gingerbread" houses in the Methodist campgrounds. Vineyard Haven offers visitors a blend of both. For a real retreat, Chilmark/Aquinnah is the place to get away from it all. In the off-season, the island is quieter and far less crowded, but the shore is always beautiful. Whenever you visit, leave your car behind! Cabs are plentiful and greet the incoming ferries to help you reach your destination. Most visitors prefer to explore the island on a bicycle, scooter or tourist-friendly public buses.

This pleasant, walkable town right at the elbow of Cape Cod is a classic New England vacation spot. Bringing kids? Check out calm beaches like Cockle Cove Beach and Harding’s Beach. If you’re looking for stunning scenery, however, try Chatham Lighthouse Beach. Its tides can be strong (heed the posted warnings), but it’s one of the most beautiful beaches on the Cape.