Sag Harbor to Newport
Day 1: Sag Harbor
On the South Fork's north coast, Sag Harbor has a strong maritime flavor that largely stems from its history as a whaling port. The centuries-old Main Street, lined with boutiques, galleries, and restaurants, leads to the wharf where tall ships from around the world would arrive.
Thanks to careful preservation, much of Sag Harbor's 18th- and 19th-century architecture remains intact, including Greek-revival houses once owned by whaling captains. Also abundant are early-colonists' homes as well as Victorian houses built for wealthy industrialists.
Nick & Toni’s – 136 N Main St. East Hampton
Tutto il Giorno – 5 Bay St, Sag Harbor
The Golden Pear (breakfast) – 111 Main Street, Sag Harbor
Day 2: Block Island (45 nm)
Explore by bike and find miles of pristine beaches, a varied terrain of hills, freshwater ponds, 2,000 miles of stone walls and a unique variety of flora and fauna.
“Unpretentious Block Island is a barefoot and bicycle kind of place, with rolling green hills, hundreds of freshwater ponds, and dramatic 250-foot bluffs that remind many of Ireland. So bewitching is it that The Nature Conservancy was inspired to call the island ‘one of the last great places in the western hemisphere.’” — 1,000 Places to See Before You Die
Day 3: Cuttyhunk (46nm)
Depart for Cuttyhunk and enjoy lunch on the aft deck before hiking to its highest point. Here is a spectacular view of the eastward-running archipelago. To the southeast are the distinguishing cliffs of Martha’s Vineyard. Spend the rest of the day swimming or relax with cocktails as the sun sets.
Days 4 & 5: Nantucket (46nm)
It is a quick cruise to neighboring Nantucket. Once a quiet whaling community, Nantucket is now home to trendy scene-seekers. Outside of the town, however the island’s windblown dunes and moors feel as remote as they must have ages ago. After lunch on board, take a tour of the whaling museum and the cranberry bogs. Shop for lightship baskets along the cobbled streets in town and stop in at the Whaling Museum for a fascinating immersion in island history. That evening, savor fresh seafood specialties at the Brant Point Grill, overlooking the harbor lights.
Day 6: Edgartown, Martha’s Vineyard (27nm)
Depart this morning for the chic port of Edgartown, Martha’s Vineyard. Meander through the cobblestone streets or stroll the beaches of famous Chappaquiddick Point. There’s so much to do during your stop in Martha’s Vineyard. From golf, fishing, nightclubs, biking, horseback riding, museums and nature walks, your yacht charter will be bustling with exciting activities.
Martha’s Vineyard is a special place. It has been said that “Martha’s Vineyard develops a fever in the hearts of those who come here from which they never recover; and they keep right on spending their vacations here – rain or shine – winter, spring, summer or fall – year after year.”
Have lunch onboard or ashore at a dockside restaurant for some fresh seafood and then head back to the yacht for some water sport fun.
Day 7: Newport (49nm)
Next, go to Newport to shop, dine, and unwind. Newport’s mansions, most notably The Breakers, the Vanderbilt family’s opulent Beaux-Arts “cottage,” are a must-see. It’s clear from the forest of masts rising above Newport’s harbor that this is one of the world’s foremost sailing centers.
Enjoy the view of the historic waterfront dominated by the white spire of 310-year-old Trinity Church. Take an evening stroll around Bannister’s Wharf and stay on to dance at the Boom Boom Room or check out IYRS and view the restoration of the Coronet in progress.
Tallulah on Thames – 464 Thames Street, Newport, RI
Castle Hill (sunset cocktails on the lawn)
Sag Harbor to Newport
Yachts for charter in the area