DAY 1: EXPLORING THE MAJOR TOWNS

If you arrive in Vineyard Haven, the main port-of-call for the island, you can get into the Vineyard state of mind by having breakfast or lunch at the world famous Black Dog Tavern where you'll have a great view of the VH harbor from the rustic dining room.

Vineyard Haven (VH) is known for its eclectic mix of shops from Carly Simon's Midnight Farm - a boutique and funky home goods store - to the country classics of Bramhall and Dunn. You might want to come back to VH for a little shopping therapy later on but for now...

Head over to Oak Bluffs (OB), a ten-minute drive from Vineyard Haven along a lovely harbor view road. The most colorful town (both literally and figuratively,) Oak Bluffs is home to the celebrated Gingerbread Cottages. A stroll through the Oak Bluffs Campground is a journey into a fantasy world of intricately carved miniature houses in candy-colored pastels. Oak Bluffs also has many other Victorian era homes scattered throughout its small downtown area and the famous Flying Horses - the oldest operating platform carousel in the US.

The next stop on your Island tour is Edgartown, and you get there via State Beach - a two-mile stretch of calm waters and smooth shores which is popular with families. If you're looking for a little surf, continue on to Edgartown and check out the waves of South Beach, probably the most popular destination for younger beachgoers.

Edgartown proper is a picturesque whaling town. The colonial homes and historic buildings are all painted white, and picket fences and manicured flower gardens are de rigeur. Many charming B&Bs line the town's old-fashioned Main Street. Edgartown is also known for upscale shops and fine dining establishments.

Stop for a takeout lunch at the Quarterdeck where you'll find the best fried clams on island. Enjoy your snack on the upper deck of the Edgartown Wharf where you'll have a great view of the Edgartown Harbor and Chappaquiddick while watching the On Time ferry make its two-minute trip back and forth from tiny Chappy.

Edgartown and Oak Bluffs are the only two towns where liquor is sold on island. The bars of Edgartown range from fun and local to the classic elegance of the Harbor View Hotel & Resort's Bar and Atria's Brick Cellar Bar.