Nantucket Island
Overview
Located 30 miles off the coast of Massachusetts, Nantucket is home to some of the most pristine beaches on the planet. Worlds away from the mini-golf and crowds on Cape Cod, Nantucket's inaccessibility adds to its sense of exclusivity and charm. Visitors can access the island by slow ferry (2 hours and 15 minutes from Hyannis), fast ferry (1 hour from the same), or plane (45 minutes from Boston). If you want to take your car, the fare will be an extra $650 round trip. Your best bet is to rent a bike and use the numerous bike paths, hop on the the island shuttle, or rent a car. If you want to drive oversand, rent a Jeep with an oversand permit attached.
Fondly nicknamed "The Grey Lady," the island is sometimes shrouded in fog, which often burns off by the afternoon. Grey cedar-shake homes dominate the landscape, which creates a sense of harmony and aesthetic continuity.
The Bluff Walk
The Bluff Walk is a public way located in Siasconset (nicknamed "'Sconset") at the far eastern end of the island. Take a left on Front Street and follow the paths marked "Public Way."
Dining
Nantucket caters to a clientele that is used to quality--and its restaurants reflect that. Be prepared for prices to match, but if you can get beyond the sticker shock, you will definitely be able to find more restaurants than you will be able to sample in a weekend. Some high-end favorites include the romantic Oran Mor, the creative and eclectic Proprietor's Table, and stylish, seaside Cru. Mid-range options include The Brotherhood of Thieves (don't miss their nachos), The Downyflake (coconut donuts are the best), and Pi Pizzeria (for authentic coal-fired pies).
The Grand Tasting
The most popular event of the weekend, The Grand Tasting takes place on both Saturday and Sunday. It's held at the magnificently ornate Marble House, home of the storied Vanderbilt family and one of Newport's crown jewels. VIP tickets get you in an hour early, so you can make your way through the tent at your leisure and have first pick of the multitudes of samples on offer. Not to worry if you miss out on VIP tickets, though, because the regularly priced tickets get you the same benefits, and the food and wine simply don't run out. Whatever events you choose to attend, if you are a lover of food and wine, you are sure to be delighted.