10 days in New York State Itinerary

10 days in New York State Itinerary

Created using Inspirock New York State trip planner
Make it your trip
Fly to Greater Rochester International Airport, Drive to Penn Yan
1
Penn Yan
— 2 nights
Drive
2
Cooperstown
— 2 nights
Drive
3
New York City
— 3 nights
Drive
4
Southold
— 1 night
Drive to John F Kennedy International Airport, Fly to Honolulu

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Penn Yan — 2 nights

Penn Yan is an incorporated village in Yates County, New York, United States. Kick off your visit on the 11th (Sat): do a tasting at Hunt Country Vineyards, learn about winemaking at Keuka Lake Wine Trail, then learn about winemaking at McGregor Vineyard, and finally admire the majestic nature at Watkins Glen State Park. On the next day, learn something new at Hands On Glass Studio, see the interesting displays at Corning Museum of Glass, and then learn about winemaking at Lime Berry Winery.

To see more things to do, traveler tips, other places to visit, and tourist information, you can read our Penn Yan trip planner.

Honolulu to Penn Yan is an approximately 14.5-hour combination of flight and car. You'll lose 5 hours traveling from Honolulu to Penn Yan due to the time zone difference. Traveling from Honolulu in September, you will find days in Penn Yan are a bit cooler (28°C), and nights are colder (14°C). Wrap up your sightseeing on the 13th (Mon) early enough to travel to Cooperstown.
Museums · Wineries · Nature · Parks
Side Trips

Cooperstown — 2 nights

Best known as the home of the National Baseball Hall of Fame and Museum, Cooperstown embraces Americana.
On the 13th (Mon), play a few rounds at Leatherstocking Golf Course and then see the interesting displays at The Farmers' Museum. Get ready for a full day of sightseeing on the 14th (Tue): see the interesting displays at National Baseball Hall of Fame and Museum, do a tasting at Rustic Ridge Winery, and then look for gifts at Beekman 1802 Kindness Shop.

Plan my Cooperstown trip by asking Inspirock to come up with tips and suggestions.

Traveling by car from Penn Yan to Cooperstown takes 3 hours. In September, daytime highs in Cooperstown are 27°C, while nighttime lows are 12°C. Finish your sightseeing early on the 15th (Wed) so you can drive to New York City.
Museums · Golf · Outdoors · Wineries
Side Trips

New York City — 3 nights

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
You'll explore and learn at 9/11 Memorial and Ellis Island. Explore hidden gems such as St. Patrick's Cathedral and Fifth Avenue. There's still lots to do: explore and take pictures at The Metropolitan Museum of Art, learn more about the world around you at American Museum of Natural History, see the interesting displays at New York Public Library, and go for a walk through Times Square.

To see ratings, reviews, other places to visit, and tourist information, use the New York City road trip planner.

Traveling by car from Cooperstown to New York City takes 4 hours. Alternatively, you can do a combination of taxi and train; or take a bus. Traveling from Cooperstown in September, expect New York City to be a bit warmer, temps between 31°C and 22°C. Wrap up your sightseeing on the 18th (Sat) early enough to travel to Southold.
Museums · Historic Sites · Neighborhoods · Shopping

Southold — 1 night

The Town of Southold is one of ten towns in Suffolk County, New York, United States. Kick off your visit on the 18th (Sat): learn about winemaking at Mattebella Vineyards and then stroll through Cooper's Beach. Get ready for a full day of sightseeing on the next day: admire all the interesting features of Pollock-Krasner House and Study Center and then kick back and relax at Orient Beach State Park.

To find traveler tips, other places to visit, where to stay, and more tourist information, you can read our Southold trip builder site.

Traveling by car from New York City to Southold takes 2 hours. Traveling from New York City in September, things will get slightly colder in Southold: highs are around 26°C and lows about 17°C. Finish your sightseeing early on the 19th (Sun) to allow enough time to travel back home.
Parks · Beaches · Outdoors · Nature
Side Trips

New York State travel guide

4.5
Scenic Walking Areas · Observation Decks · Historic Sites
The Empire State
Home to the country's most populous city, the state of New York is a major gateway for immigration into the United States, but also one of the nation's prime holiday destinations. Take a trip down the state's numerous wilderness trails and scenic roads to visit quaint small towns, sandy beaches, historical estates, and artist colonies. Though the majority of visitors head for the big-city restaurants, theaters, and museums, you can venture deeper into the rugged and remote mountain areas to discover a world of picturesque forests, rivers, mountains, and lakes. New York also boasts the nation's largest forest preserve, encompassing much of the northeastern lobe of the state.