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Ultimate New York City and Upstate New York Road Trip Itinerary
Last updated: 2024 Jun 14Iconic NYC Landmarks and Skyline Views
Morning
Start your day with a classic New York breakfast at Russ & Daughters Cafe, known for its bagels and lox. Afterward, head to the Empire State Building with your skip-the-line tickets for panoramic views of the city.
Afternoon
For lunch, enjoy a slice of authentic New York pizza at Joe's Pizza. Then, take a leisurely stroll across the Brooklyn Bridge for stunning views of the Manhattan skyline.
Evening
In the evening, savor a fine dining experience at Per Se, one of the city's top restaurants. Afterward, take a relaxing NYC Skyline and Statue of Liberty Night Cruise to see the city lights.
Bedtime
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Museum Day and Friends Experience
Morning
Enjoy a leisurely brunch at The Spotted Pig, a popular spot in the West Village. Then, immerse yourself in scientific wonders at the American Museum of Natural History.
Afternoon
For a fun and nostalgic experience, visit New York City The FRIENDS™ Experience in the afternoon. Grab a coffee at Stumptown Coffee Roasters nearby.
Evening
Dine at the iconic Carbone for a taste of old-school Italian-American cuisine. After dinner, take a stroll in Williamsburg to experience Brooklyn's hipster culture.
Bedtime
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Scenic Drive to Callicoon
Morning
Pick up a coffee and some pastries for breakfast at Toby's Estate Coffee. Then, start your road trip to Callicoon, enjoying the changing landscapes along the way.
Afternoon
Once you arrive in Callicoon, have a relaxed lunch at The Heron and take a walk around the charming town. Check-in to your accommodation and unwind.
Evening
For dinner, savor farm-to-table cuisine at Callicoon Brewing Company and enjoy a laid-back evening in this picturesque setting.
Bedtime
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Outdoor Adventures and Local Flavors
Morning
Start your day with a hearty breakfast at Peppino's Restaurant & Catering. Then, embark on a hiking or fishing excursion in the beautiful surroundings of Callicoon.
Afternoon
Enjoy a picnic lunch by the river or at Liberty State Park. In the afternoon, explore the local farms and maybe even participate in a farm-to-table cooking class.
Evening
For dinner, indulge in a fine dining experience at The Arnold House and sample the best of Catskills cuisine.
Bedtime
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Niagara Falls Excursion
Morning
Depart early for your day trip to Niagara Falls. Grab a quick breakfast at Peppino's Restaurant & Catering before hitting the road.
Afternoon
Spend the afternoon marveling at the natural wonder of Niagara Falls. Enjoy a leisurely lunch with a view at Top of the Falls Restaurant.
Evening
On your way back to Callicoon, stop for a relaxed dinner at The Silo Restaurant, known for its comfort food and charming atmosphere.
Bedtime
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Relaxation and Wellness Day
Morning
Take a slow morning and enjoy a leisurely breakfast at The Heron. Spend the morning pampering yourself with a spa treatment at a local wellness center.
Afternoon
Have a light and healthy lunch at The Laundrette and continue your relaxation with a yoga or meditation session.
Evening
For dinner, try the vegetarian and vegan options at The Arnold House and end your day with a peaceful evening in the countryside.
Bedtime
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Arts and Culture in the Catskills
Morning
Start your day with a delicious breakfast at Rolling River Cafe & Inn. Then, visit the Delaware Valley Arts Alliance to explore local art and cultural exhibits.
Afternoon
Enjoy a light lunch at The Heron and spend the afternoon browsing the unique shops and galleries in the area.
Evening
For dinner, try the seasonal and locally sourced menu at Nine River Road and perhaps catch a live music performance at a nearby venue.
Bedtime
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Outdoor Adventures and Culinary Delights
Morning
Embark on an outdoor adventure of your choice, whether it's hiking, kayaking, or horseback riding. Enjoy the fresh air and natural beauty of the Catskills.
Afternoon
Have a picnic lunch at a scenic spot or enjoy a casual meal at Peppino's Restaurant & Catering. In the afternoon, visit a local winery or brewery for a tasting.
Evening
For your final dinner in Callicoon, treat yourself to a special meal at The Heron and reminisce about your time in this idyllic setting.
Bedtime
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Farewell to Callicoon and Return to NYC
Morning
Enjoy a leisurely breakfast at The Heron and take one last walk around the town. Check out of your accommodation and begin your journey back to New York City.
Afternoon
Stop for a relaxed lunch at The Laundrette on your way back. Once you arrive in the city, check into your hotel and have some free time to explore.
Evening
For your final evening, choose a restaurant from your wishlist for a memorable farewell dinner in the city. Consider Eleven Madison Park for a truly special dining experience.
Bedtime
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Culinary Delights and Broadway Magic
Morning
Start your day with a delicious breakfast at Russ & Daughters Cafe. Then, take a Central Park Celebrity Homes & Film Spots Pedicab Tour for a unique perspective on the city.
Afternoon
Enjoy a leisurely lunch at The Spotted Pig in the West Village. In the afternoon, explore the vibrant neighborhood of Dyker Heights.
Evening
For dinner, savor the flavors of Japan at Ippudo NY. Afterward, attend a Broadway show for a night of theatrical magic.
Bedtime
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Art and Culture in the City
Morning
Begin your day with a visit to the Museum of Modern Art (MoMA) to explore its world-class collection. For a quick bite, grab a hot dog at Gray's Papaya.
Afternoon
Have a leisurely lunch at Shake Shack in Madison Square Park. Spend the afternoon wandering through the galleries of the Whitney Museum of American Art.
Evening
Dine at the iconic Katz's Delicatessen, known for its pastrami sandwiches. After dinner, take a walk through the vibrant streets of the Lower East Side.
Bedtime
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Final Day of Exploration and Farewell to NYC
Morning
Enjoy a classic New York breakfast at Peter Luger Steak House. Then, take a Hop-on Hop-off Sightseeing Tour by Open-top Bus to visit some of the city's top attractions.
Afternoon
For lunch, indulge in a burger at Minetta Tavern. Spend the afternoon shopping in SoHo and exploring the Intrepid Museum & Apollo Exhibit.
Evening
End your trip with a memorable dinner at Le Bernardin, one of the city's most acclaimed seafood restaurants. Take a final walk through the bustling streets of Times Square before heading to the airport.
Bedtime
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