New York City · HAMPTONS & LONG ISLAND TOURS
This is the shortlist you would send a friend: 15 hamptons & long island tours worth the money, each with its price, its traveller verdict and the one thing to know before you commit.
Escape NYC for Southampton, Cooper’s Beach, Sag Harbor, wine tasting, and Tanger Outlets on a long but well-filled Hamptons day trip.
“Viewing the yachts and boats on the return. At the harbor was great. The main interpreter was also great”
Escape New York for Southampton, Sag Harbor, a wine tasting, and Tanger Outlets on a full-day Hamptons tour with transport.
Escape Manhattan for two Long Island wineries, guided tastings, a local sandwich lunch, and a relaxed ride with a certified sommelier.
“Very professional guide and driver. All the wineries were amazing. Great experience! We’ll repeat it when we come back to NY”
Review of a private Hamptons day trip from NYC, with Southampton, Sag Harbor, Montauk, winery options, pricing, timing, and practical tips.
“Long day 12+ hours. Ronald was professional, very informative, and accommodating for seeing various sights that we were interested in.”
Spend nine hours tasting Long Island wines, meeting winemakers, exploring vineyards, and sampling farm treats with a sommelier guide.
“Thank you so much for your feedback. It was a pleasure hosting you on Day Trip To Wine Country™!”
Review of Montauk’s private beach fire at Kirk Park Beach, with attended flames, luxury chairs, s’mores, practical tips, and honest drawbacks.
“This was such a fun event! The team setup a bonfire for 60 of us to enjoy the evening after a surprise engagement. They handled everything and took care of all the guests. I cannot recommend them enough.”
Cruise Sag Harbor, Montauk, and the Hamptons on a private yacht with a captain, water toys, and room for up to 10 people.
“This trip was amazing. Our captain Carter and our steward Sydney made it really special for our whole family. Sydney really got our little ones included in the fun which made the trip. It was so nice we booked another charter later in the week.”
Sail Manhasset Bay and Long Island Sound with Captain Steve, spotting Gatsby-era mansions, lighthouses, City Island, and the NYC skyline.
“This was a five star experience all around. From the beautiful boat to the amazing views of Kings Point, City Island, Hart Island, New Rochelle and NYC. From the second we stepped on the boat Captain Steve greeted us with a warm welcome that made us feel instantly comfortable. He was so attentive throughout the entire trip and had both of my nieces involved with the sailing. He is one of the most friendly, chatty and chill guys I've ever met which definitely made our sailing experience so much fun and relaxed. The weather was perfect, a sunny afternoon on a beautiful boat with the friendliest captain in the world...…”
Spend 12 hours exploring Southampton, Sag Harbor, the North Fork, and Long Island wineries with private transport from New York City.
“Scott was a great host! Very accommodating, timely, extremely knowledgeable, efficient and patient. Our group spent an amazing day out in Southampton, Sag Harbor and the North Fork. I will definitely book this trip again next summer.”
Review of Long Island Winery Tour with private pickup, tastings, live music, winery stops, pricing, timing, and booking advice.
“The wineries were nice, spending time with friends was great but it was way too expensive for the number of wineries and the number of tastings. For instance Osprey offered 3 tastings for $10 and 5 for $15. Considering the price of the tour, I think it would have been appropriate for Winston to purchase the 5 tastings. Keith, the driver, was great!”
Explore Long Island’s North Fork with Eric on a private half-day tour of wineries, oysters, chocolates, local food, and Greenport.
“Working with Eric was seamless from start to finish. He’s professional, friendly, and truly looks out for his guests. Eric meticulously planned an incredible oyster farm tour where we learned the process firsthand and enjoyed the freshest farm-to-table oysters. It was the highlight that set the tone for a perfect day. He made my friend’s bachelorette weekend an absolute hit, made me look like a fabulous hero, and even helped capture great group photos throughout the day. As a passionate local and true North Fork insider, Eric curated the best of the region with beautiful wineries, hidden gems, local bites, and special surprises like Bobby Flay’s world-famous meatballs. From flowers…”
Review of a private Long Island wine tour to Pindar, Raphael, and Lenz, with private transport, six tastings, practical tips, and value advice.
“Our trip was absolutely refreshing and unforgettable. From the moment we set off, everything was perfectly organized smooth transport, warm hospitality, and a well-planned itinerary that balanced relaxation with adventure.”
Review of Yacht Hampton’s private four-hour boat rental from Sag Harbor, with flexible routes, luxury vessels, SeaBobs, and clear costs.
“Our boat rental experience was absolutely phenomenal. The yacht was a masterpiece of luxury and comfort, offering us a day of pure relaxation. The crew was attentive and friendly, ensuring every moment was enjoyable. Sailing along the Hampton coastline, we were treaRead more”
Explore Montauk through a playful two-hour scavenger hunt with a remote host, local clues, oddball challenges, and stops around town.
“We had a great time even though we (just my husband and I) weren't really sure what we were getting ourselves into. This is not your typical hunt, and we went in thinking we were going to hit all the historical highlights of Montauk. If that's what you're looking for this may not be the best experience. On the other hand, it was super fun, and we did enjoy getting out of our comfort zone. We also learned a lot about Montauk history and its fun facts. This experience was in the off-season which was both good and bad. Good in that it wasn't crowded when walking around but having…”
Book a private JFK or LaGuardia transfer to Long Island with a chauffeur, flat pricing, flexible vehicles, and door-to-door service.
“WINSTON AIRPORT TRANSPORTATION was AWESOME. They bailed me out. They we're able to pick me up in 15 minutes from me calling them. The dispatcher on the phone was sooo helpful The driver was great!”
Pick a deck, a pier, a borough or a table.
