Arrive in Gloucester to board the Yorktown. Settle in to your cabin and familiarize yourself with the ship and her crew.

Travel to Bar Harbor, one of the loveliest towns on Maine’s coast, locates on Mount Desert Island. Surrounded by Acadia National Park, this quaint fishing village on Mount Desert Island was a fashionable resort town in the late 1800s and the summer home of influential families, including the Astors and Rockefellers. Tour Acadia National Park to discover the Wild Gardens of Acadia, showcasing over 300 native plant species. Also visit the Abbe Museum’s collections chronicling Maine’s 10,000 years of Native American culture and history.

Call at Bath, located on the banks of the Kennbec River and known for its well-preserved, 19th century architecture. Visit the Maine Maritime Museum to see displays on shipbuilding, lobstering, and boats that once cruised the Grand Banks off of Newfoundland in search of cod.

Nantucket is one of the premier destinations along the eastern seaboard, where seaside cottages and old-fashioned lamps still illuminate the streets. Named a National Historic District, the island has retained much of its 17th-century architecture and today nearly 40 percent of the island is protected conservation land. During your full day in Nantucket you may wish to visit the impressive whaling museum, with its skeleton of a 43-foot finback whale; Hadwen House, a grand 19th-century Greek Revival home; or the Greater Light house. Enjoy the historic ambiance of this quintessential New England town.

Sail into the yacht-filled harbor of Newport, the one-time summer playground of New York’s wealthiest families. Many of the grand "cottages" they built are now cared for by The Preservation Society of Newport County and are open to the public. See The Breakers, the 70-room Italian Renaissance mansion of Cornelius Vanderbilt II. Also explore the historic center of Newport with its fine architecture and enjoy time at leisure.

Sail down the East River - with the Manhattan skyline in view - and continue up the Hudson River, whose leafy hillsides are resplendent in fall colors this time of year. From Yonkers, drive to Pocantico Hills for an excursion to Kykuit, home to four generations of Rockefellers, whose mansion and surrounding grounds is a National Trust for Historic Preservation site. Explore the impressive sculpture garden, with works by David Smith and Henry Moore, and the six-story stone mansion which houses many works of art, including beautiful tapestries by Picasso. Later visit the Union Church, unassuming and charming upon first glance, but a closer look reveals a gem for art enthusiasts. As requested by the Rockefeller siblings following their mother’s death, Henri Matisse, who was a close friend of Abby Aldrich Rockefeller, agreed to create the beautiful stained glass Rose Window as a memorial to the matriarch. The siblings later commissioned Marc Chagall to create a memorial window for their father upon his death. Chagall went on to create eight additional windows for the church, all of which are beautifully displayed today.

Visit the Franklin D. Roosevelt Presidential Library and Museum, conceived by FDR to house the many historical papers, books, and memorabilia throughout his life. After privately raising funds to build the site, he donated it to the National Archives to ensure that the public would have access to such important historical documents. Also visit Eleanor Roosevelt’s Val-Kill, a National Historic Site. Wander the bucolic grounds and visit the cottage where Eleanor lived until her death. Continue to the Vanderbilt Mansion National Historic Site. Purchased by Frederick Vanderbilt in 1895, the mansion was home the socially distinguished for nearly two centuries, and is an exceptional monument of the Gilded Age. Explore the mansion and its lovely grounds, which offer stunning views of the Hudson River. Alternateively, visit the Dia Art Foundation in Beacon, whose works include art from the 1960s to the present.

Following breakfast on board, disembark in New York City and transfer to the airport for return flights.