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12-Day Long Island and New York Adventure Itinerary
Last updated: 2024 Jun 14Wine and Dine in Ronkonkoma
Morning
Start your day with a delightful breakfast at Maureen's Kitchen in Smithtown, known for its cozy atmosphere and delicious pancakes. After breakfast, head to the North Fork for a guided tour of the region's renowned wineries. Enjoy tastings at Pindar Vineyards and Macari Vineyards, and savor a gourmet lunch at Lieb Cellars.
Afternoon
After a leisurely lunch, explore the charming town of Greenport. Stroll along the waterfront, visit local boutiques, and enjoy the laid-back atmosphere. If you're up for more wine, stop by Sannino Vineyard for another tasting.
Evening
For dinner, indulge in fresh seafood at Cliff's Elbow Room in Jamesport. Try their famous lobster tails or the catch of the day. After dinner, relax with a nightcap at Long Ireland Beer Company and enjoy their selection of craft brews.
Bedtime
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Ronkonkoma North Fork Wineries Tour with Tastings and Lunch
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Ronkonkoma North Fork Wineries Tour with Tastings and Lunch
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Ronkonkoma North Fork Wineries Tour with Tastings and Lunch
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Ronkonkoma North Fork Wineries Tour with Tastings and Lunch
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Beach and Beer Loop
Morning
Enjoy a hearty breakfast at Mama Lisa Restaurant in Mastic Beach. Then, head to the Fire Island National Seashore for a fun Scavenger Hunt. Explore the beautiful beaches and hunt for clues along the way.
Afternoon
After the scavenger hunt, satisfy your hunger with a late lunch at That Meetball Place in Patchogue. Then, embark on the Holbrook Beer Loop. Visit local breweries such as Blue Point Brewing Company and Saint James Brewery, and sample a variety of craft beers.
Evening
For dinner, try the delicious Italian cuisine at Casa Rustica in Smithtown. End the day with a relaxing stroll along the Ronkonkoma Lake and enjoy the serene evening views.
Bedtime
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Fire Island Scavenger Hunt
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New York Holbrook Beer Loop
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New York Holbrook Beer Loop
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New York Holbrook Beer Loop
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Yacht Party and Long Island Wines
Morning
Start your day with a leisurely breakfast at Breakfast Club in Farmingdale. Then, get ready for a luxurious experience on the Great South Bay with a Yacht Charter. Enjoy the sun, sea, and good company as you cruise along the picturesque coastline.
Afternoon
After the yacht party, head to the North Fork for another round of wine tasting. Visit McCall Wines and Peconic Cellar Door for unique wine experiences. Enjoy a gourmet lunch at Lucharitos, known for its delicious Mexican cuisine.
Evening
For dinner, try the farm-to-table dishes at Jamesport Manor Inn in Jamesport. The historic setting and exquisite food make for a memorable dining experience. After dinner, unwind with a glass of wine at Sherwood House Vineyards and enjoy the peaceful surroundings.
Bedtime
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Long Island Yacht Charters, Party on the Great South Bay
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Ronkonkoma North Fork Long Island Wine Tasting and Lunch
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Ronkonkoma North Fork Long Island Wine Tasting and Lunch
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Ronkonkoma North Fork Long Island Wine Tasting and Lunch
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South Shore and Seaside Eateries
Morning
Enjoy a classic Long Island breakfast at Breakfast at Tiffany's in Miller Place. Then, embark on a South Shore Tour to explore the beautiful coastal towns. Visit the historic Montauk Point Lighthouse and take in the breathtaking ocean views.
Afternoon
For lunch, head to The Oar Steak & Seafood Grill in Patchogue. Indulge in fresh seafood and soak up the seaside ambiance. After lunch, take a relaxing walk along the beach or visit the Patchogue Theatre for the Performing Arts for a cultural experience.
Evening
End the day with a delightful dinner at Harbor Crab Co. in Patchogue. Try their famous crab dishes and enjoy the lively atmosphere. If you're in the mood for some entertainment, catch a live performance at The Paramount Huntington.
Bedtime
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New York West South Shore Tour
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New York West South Shore Tour
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New York West South Shore Tour
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New York West South Shore Tour
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Cultural Exploration and Gourmet Delights
Morning
Start your day with a visit to the Parrish Art Museum in Water Mill. Explore the impressive collection of American art and take a guided tour of the museum. Afterward, enjoy a light brunch at the museum cafe.
Afternoon
For lunch, head to Cowfish in Hampton Bays. Their creative menu and waterfront location make for a perfect midday meal. After lunch, visit the Pollock-Krasner House and Study Center in East Hampton for a glimpse into the lives of two iconic artists.
Evening
Indulge in a gourmet dinner at The 1770 House in East Hampton. The historic setting and exquisite cuisine create a memorable dining experience. After dinner, take a leisurely walk through the charming village and explore the local shops.
Bedtime
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New York West South Shore Tour
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New York West South Shore Tour
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Hamptons and Culinary Delights
Morning
Enjoy a leisurely breakfast at The Golden Pear Cafe in Southampton. Then, explore the picturesque village and visit the Southampton Arts Center for a dose of culture. If you're a fan of history, take a guided tour of the Sag Harbor Whaling Museum.
Afternoon
For lunch, head to Dockers Waterside Restaurant & Marina in East Quogue. Their waterfront location and fresh seafood make for a delightful dining experience. After lunch, take a scenic drive through the Hamptons and admire the beautiful estates and landscapes.
Evening
End the day with a gourmet dinner at The Plaza Cafe in Southampton. Their seasonal menu and elegant ambiance create a perfect setting for a memorable meal. After dinner, enjoy a live performance at the Bay Street Theater in Sag Harbor.
Bedtime
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New York West South Shore Tour
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New York West South Shore Tour
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New York West South Shore Tour
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Vineyards and Waterfront Dining
Morning
Start your day with a delicious breakfast at Plattduetsche Park Restaurant in Franklin Square. Then, head to the North Fork for a day of wine tasting. Visit Bedell Cellars and Castello di Borghese Vineyard for unique wine experiences.
Afternoon
For lunch, enjoy a picnic at McCall Wines or visit Elbow East in Southold for a casual waterfront meal. After lunch, explore the charming town of Greenport and visit the East End Seaport Museum for a glimpse into the region's maritime history.
Evening
End the day with a gourmet dinner at Noah's in Greenport. Their farm-to-table menu and waterfront location create a perfect dining experience. After dinner, take a sunset cruise on the Peconic Bay and enjoy the stunning views.
Bedtime
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Ronkonkoma North Fork Wineries Tour with Tastings and Lunch
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Ronkonkoma North Fork Wineries Tour with Tastings and Lunch
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Ronkonkoma North Fork Wineries Tour with Tastings and Lunch
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Ronkonkoma North Fork Wineries Tour with Tastings and Lunch
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Lighthouses and Local Flavors
Morning
Enjoy a hearty breakfast at Modern Snack Bar in Aquebogue. Then, embark on a lighthouse tour of Long Island. Visit iconic landmarks such as the Montauk Point Lighthouse and the Fire Island Lighthouse.
Afternoon
For lunch, head to CJ's American Grill in Mattituck. Their diverse menu and relaxed atmosphere make for a perfect midday meal. After lunch, visit the Long Island Aquarium in Riverhead for a fun and educational experience.
Evening
End the day with a delicious dinner at Tweeds Restaurant & Buffalo Bar in Riverhead. Their unique menu and historic setting create a memorable dining experience. After dinner, take a stroll along the riverfront and enjoy the evening views.
Bedtime
Find amazing hotels in Long Island, New York.
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New York West South Shore Tour
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Fire Island Scavenger Hunt
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New York West South Shore Tour
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Historic Sites and Local Brews
Morning
Start your day with a visit to the Vanderbilt Museum in Centerport. Explore the beautiful estate and take a guided tour of the museum. Afterward, enjoy a light brunch at the museum cafe.
Afternoon
For lunch, head to The Whale's Tale in Northport. Their seafood dishes and waterfront location make for a delightful dining experience. After lunch, visit the Heckscher Museum of Art in Huntington for a dose of culture.
Evening
End the day with a visit to Oyster Bay Brewing Company in Oyster Bay. Take a tour of the brewery and sample their unique beers. Afterward, enjoy a casual dinner at Canterbury's Oyster Bar & Grill in Oyster Bay and try their fresh seafood dishes.
Bedtime
Find amazing hotels in Long Island, New York.
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New York West South Shore Tour
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New York West South Shore Tour
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Nature and Culinary Delights
Morning
Enjoy a leisurely breakfast at The Shed Restaurant in Huntington. Then, spend the morning exploring the beautiful Caumsett State Park in Lloyd Harbor. Take a guided nature walk and enjoy the peaceful surroundings.
Afternoon
For lunch, head to Prime: An American Kitchen & Bar in Huntington. Their waterfront location and diverse menu make for a perfect midday meal. After lunch, visit the Cold Spring Harbor Fish Hatchery & Aquarium for a fun and educational experience.
Evening
End the day with a gourmet dinner at Blackstone Steakhouse in Melville. Their prime steaks and elegant ambiance create a perfect setting for a memorable meal. After dinner, enjoy a live performance at the The Paramount Huntington.
Bedtime
Find amazing hotels in Long Island, New York.
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New York West South Shore Tour
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New York West South Shore Tour
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New York West South Shore Tour
click to access prices
Cultural Exploration and Waterfront Dining
Morning
Start your day with a visit to the Parrish Art Museum in Water Mill. Explore the impressive collection of American art and take a guided tour of the museum. Afterward, enjoy a light brunch at the museum cafe.
Afternoon
For lunch, head to Cowfish in Hampton Bays. Their creative menu and waterfront location make for a perfect midday meal. After lunch, visit the Pollock-Krasner House and Study Center in East Hampton for a glimpse into the lives of two iconic artists.
Evening
Indulge in a gourmet dinner at The 1770 House in East Hampton. The historic setting and exquisite cuisine create a memorable dining experience. After dinner, take a leisurely walk through the charming village and explore the local shops.
Bedtime
Find amazing hotels in Long Island, New York.
Popular
New York West South Shore Tour
click to access prices
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Beaches and Landmarks
Morning
Spend the morning at Santa Monica (Beach and Pier). Make sure to grab a quick breakfast at Freddys Red Tacos before taking a leisurely walk along the sandy shore, enjoy the ocean breeze, and maybe even dip your toes in the water. Don't miss the iconic Ferris wheel and the lively atmosphere of the pier.
Afternoon
Visit the famous Rodeo Drive in Beverly Hills for a luxurious shopping experience. If you're looking for lunch checkout Honor Bar for an insanely delicious Fried Chicken Sandwich. Then you can keep exploring the high-end boutiques and soak in the glamorous ambiance of this renowned street.
Evening
Take a scenic drive along Mulholland Drive and enjoy breathtaking views of the city lights. Make a reservation beforehand if you're looking for dinner, we recommend checking out Yamashiro for its amazing views and delicious japanese cuisine. End the day with a visit to the Viper Room, a historic nightclub known for its live music performances.
Bedtime
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