WASHINGTON, D.C. Embrace your inner politico. The first stop is the newly renovated National Portrait Gallery. Come evening, the dining room at Citronelle (202/625-2150; dinner for two $190) fills with senators and K-Street lobbyists (not at the same table). Stay at the historic Willard InterContinental (202/628-9100; www.intercontinental.com; doubles from $269). Washington, D.C., to Philadelphia: 140 miles
PHILADELPHIA The National Constitution Center on Independence Mall is worth an afternoon, although foodies may want to head straight to Reading Terminal Market for a hot Amish pretzel. Don't miss the post-Impressionist paintings at the Barnes Foundation, a private gallery in the suburb of Merion. Philadelphia to New York City: 100 miles
NEW YORK CITY Check into the Ritz-Carlton New York, Battery Park (212/344-0800; www.ritzcarlton.com; doubles from $425), which has Statue of Liberty views and valet parking. Stroll up the renovated Hudson River Park before hitting the galleries in Chelsea. Forget Fifth Avenue—Bleecker Street has all the shopping you need. And dinner?Sant Ambroeus (212/604-9254; dinner for two $130) serves up Milanese risotti in the West Village. New York City to Lenox, Massachusetts: 160 miles
THE BERKSHIRES Your base for the mountains: the Wheatleigh (413/637-0610; www.wheatleigh.com; doubles from $525), in Lenox, Massachusetts, an Italianate country house with one of New England's best restaurants. Save time for antiquing in Sheffield and Stockbridge. Lenox to Boston: 130 miles
BOSTON Watch rowers ply the Charles River and check into the XV Beacon (877/982-3226; www.xvbeacon.com; doubles from $475). Then get your claws on a lobster roll at B&G Oysters, in the South End (617/423-0550; dinner for two $90). Boston to Portland: 110 miles
SOUTHERN MAINE COAST Book a waterfront cottage at the White Barn Inn & Spa (207/967-2321; www.whitebarninn.com; doubles from $350), in Kennebunkport. Portland's Fore Street (207/775-2717; dinner for two $72) sticks to local ingredients, so you can enjoy a fresh catch at the end of your long haul.