Nantucket & Martha's Vineyard

The islands of Nantucket and Martha's Vineyard are as distinct as two neighboring islands can be. This tour lets you explore both of them in a week. You'll see the highlights of both islands -- the beaches and historic sites of Nantucket and the scenic landscapes and quaint towns on the Vineyard.

Day 1: Arrive on Nantucket

Explore the cobbled streets of historic Nantucket, which has some of the best shopping in the region. Walk, bike, taxi, or take a shuttle bus down to Jetties Beach, a beautiful expanse of sand that has the added benefit of numerous amenities, including tennis courts, volleyball nets, a playground, and a skate park. After the beach, bike or drive out to Madaket Beach on the west side of the island to watch the sunset.

Day 2: Biking the Island

Spend your second day on the island taking a bike tour. From town take the Milestone Road path out to 'Sconset, where you can marvel at the tiny rose-covered cottages in this picturesque summer community. Bike back to town on the Polpis Road bike path, passing the red-striped Sankaty Head Lighthouse along the way. On the Polpis path, you can take a side trip to Wauwinet, where it's possible to hike or four-wheel-drive out to Great Point Lighthouse.

Day 3: Beaching & Boating

In the morning, bike to Surfside Beach, just 3 miles south of town. In the afternoon, take a cruise around Nantucket Harbor, checking out the multimillion-dollar yachts and the workaday fishing boats.

Day 4: Arrive on Martha's Vineyard

Take the seasonal ferry from Nantucket to Oak Bluffs, the most boisterous town on Martha's Vineyard. Wander through the camp meeting grounds to see the elaborate 19th-century "gingerbread cottages," in the island's first summer community. Ride the Flying Horses Carousel and duck into Mad Martha's Ice Cream Parlor to buy a cone, which you can eat while watching the world go by on Circuit Avenue. At night, head to Vineyard Haven to see a play at the Vineyard Playhouse, or go out to the airport to hear live music at the island's top club, Outerland.

Day 5: Edgartown

Bike or drive to Edgartown, where you can wander past white picket fences in front of grand sea captains' houses. Numerous gift shops, clothing stores, and art galleries are in the center of town. Take a bike ride to Katama, also called South Beach, which fronts the Atlantic Ocean.

Day 6: Aquinnah

Drive, bike, or take the shuttle bus out to Aquinnah, the homeland of the Vineyard's Native American community. Walk out to the viewing spot where you can see both the majestic red-clay Gay Head Cliffs and the picturesque red brick Gay Head Lighthouse. A long path leads down to the beach itself, a pristine beauty.

Day 7: An Arboretum & a Fishing Village

Visit Chilmark's Polly Hill Arboretum in the morning. It's a delight to wander past stone walls, through the dogwood alley and the "tunnel of love," an arbor of bleached hornbeam. Spend the afternoon in the tiny fishing village of Menemsha, part of the town of Chilmark. It's fun to wander down the dock, watching the fishing boats unloading the catch of the day, which will be served in the island's restaurants that night. The waters of Menemsha Beach in Vineyard Sound are surprisingly warm in the summer. Watching the sunset over a picnic dinner in Menemsha is a Vineyard tradition.