In and Around the Big Apple
Days 1–3: New York City
For a small bite of the Big Apple, begin your first day at the Empire State Building, taking in the panoramic view of the city. Next head up to the Metropolitan Museum of Art. You could easily spend a whole day here, but you'll exhaust yourself if you do. Luckily, just behind the museum lies beautiful Central Park, where you can relax on a bench, rent a rowboat, or explore a meadow and watch the world go by. Exit the park's south end at 5th Avenue and work your way downtown, browsing the department stores and shops that abound. If you're there at dusk, walk instead south on 7th Avenue toward the bright lights of Times Square.
On Day 2 seek out some history via a ferry trip to the Statue of Liberty and Ellis Island. You can beat the crowds with any early start. Allow yourself about six hours if you plan to do a thorough visit with guided tours. If not, you can be back in Manhattan by lunchtime. After lunch, stroll through the Wall Street area, home of the colonial-era Fraunces Tavern, mid-19th-century Trinity Church, and St. Paul's Chapel, Manhattan's oldest surviving church building. Also here is the World Trade Center site, complete with time line and memorial. Just north are the neo-Gothic Woolworth Building (don't miss the splendid gilded lobby) and City Hall. Hop on the N or R Train to 8th Street, where you can stroll around Washington Square Park and Greenwich Village.
On your last day in town, do what many New Yorkers do on their days off—wander. Make your way to Chinatown for a dim sum breakfast or tapioca-filled soft drink. From here head north to SoHo and NoLita for galleries, chic boutiques, and restaurants. If you haven't eaten by now, hit a café a few blocks north in the happening East Village, home to yet more shops and vintage stores. From Union Square, walk up Broadway to the fashionable Flatiron District with its inimitable Flatiron Building. Take a break in Madison Square and soak up the surrounding skyline. Have dinner in one of the neighborhood's noted restaurants.
Days 4–6: The Hudson Valley
On Day 4, head up to Tarrytown to tour Kykuit or one of the other magnificent homes in the area. Or drive farther north and spend the day at Beacon, for its blend of cool art, old buildings, funky shops, and laid-back restaurants. Alternatively, Cold Spring is a nice day trip if you're traveling by train; if the shops and eateries don't interest you, take a hike—in Hudson Highlands State Park, that is.
On Day 5, head to Hyde Park and tour Franklin D. Roosevelt's home and/or the Vanderbilt Mansion. If you're here on a Friday or Saturday, have dinner at one of the Culinary Institute of America restaurants. If you're staying in Millbrook, check out a winery and one of the gardens.
On Day 6, visit Staatsburg, Annandale-on-Hudson, Tivoli, or Hudson. The stately beaux arts mansion at the Staatsburg State Historic Site; Bard's Frank Gehry-designed performing-arts center; the stunning gardens and classical revival-style mansion of Montgomery Place; and Frederic Church's Moorish-style home, Olana, are all highlights. Leave some time for strolling and shopping in any of the villages.
Days 7–8: The Catskills
Focus on either the northern or southern Catskills. Woodstock, which has a smattering of shops and restaurants, makes a good base in the northern Catskills. From here you can easily go hiking, canoeing, kayaking, tubing, or fishing, or go to see Kaaterskill Falls. The ski resorts are accessible from here as well: the Hunter Mountain ski area, for example, is 19 mi to the north and the Belleayre Mountain ski area is about 30 mi to the west. Or make quick jaunts into small villages in the area: Mount Tremper (which also makes a good base) and Phoenicia or, closer to Belleayre, Fleischmanns, Margaretville, and Arkville. Be sure to devote a few hours to exploring Woodstock.
In the southern Catskills the area around Monticello has a few good lodging choices, including a magnificent inn in Forestburgh and a golf-focused resort in Kiamesha Lake. If you head west, you can see the site of the famed 1969 Woodstock music festival on the outskirts of Bethel. The area is known for golf and fishing, so you may want to spend time on either or both of these activities.
Buffalo and Upstate
Days 1–3: Niagara Falls
Start in Niagara Falls, and spend two days taking in the sights, crossing to the Canadian side if you wish. On the afternoon of Day 2, head north of the falls to see the Castellani Art Museum or one of the state parks. On Day 3, head south to Buffalo, via Grand Island. If you have kids in tow, consider a visit to the Buffalo Zoological Gardens or the Buffalo Museum of Science. Otherwise, see the Albright-Knox Art Gallery or the Buffalo and Erie County Botanical Gardens. Frank Lloyd Wright lovers should head straight for the Darwin D. Martin Complex (just be sure to have made a tour reservation). In summer you might opt to center your trip on Chautauqua. Make quick trips around Chautauqua Lake and into Jamestown if you have time. Otherwise, take advantage of the Chautauqua Institution's rich cultural offerings.
Days 4–6: The Finger Lakes
Spend Day 4 in Ithaca, a perfect gateway into the region. On the morning of Day 5 take a quick trip to Taughannock Falls State Park in Trumansburg, where the falls are higher than Niagara Falls. In the afternoon, travel to Watkins Glen State Park. Walk the awesome gorge trail (note that the gorge trail is closed in winter) and check out a winery or two. On the morning of Day 6, swing down to Corning to see the Corning Museum of Glass, which is a must-see. Return to Ithaca for dinner and a good night's sleep.
Days 7–9: Cooperstown
Cooperstown deserves two full days, which will give you the chance to see the main sights and to walk about a bit. Classical music fans shouldn't miss the Glimmerglass Opera (July and August). Spend both nights in Cooperstown (many lodgings have a two-night minimum in season). On Day 9, head either north or east. If you're traveling with children, stop at the Petrified Creatures Museum in Richfield Springs on your way north before continuing on to Herkimer to dig for "diamonds" (really quartz crystals) or to take an Erie Canal cruise. Without kids, head straight to Herkimer for the cruise. Boats leave from the Gems Along the Mohawk retail complex, which has a restaurant. If you choose to head east instead, you can do some underground exploring in Howes Cave. A third option is to head northeast to Sharon Springs for lunch.