The Hamptons and Long Island Wineries Private Tour

This private tour of the Hamptons and Long Island wineries promises a full day of scenic beauty, exclusive sights, and tailored experiences—all in the comfort of a private vehicle with knowledgeable guides. Designed for up to six guests, it offers a chance to escape New York City’s hustle and bustle and dive into a more relaxed, upscale side of New York State.

One feature we particularly like is the flexibility of the itinerary, which allows your group to customize the day based on your interests. Whether it’s exploring quaint villages, enjoying fresh seafood, or sampling local wines, the tour’s private nature ensures you won’t be just another face in a crowd.

A potential consideration is that some activities—like wine tastings and meals—are at your own expense, so budgeting for those extras is wise. Also, this is a full 12-hour day, so it’s best suited for those who enjoy a leisurely, immersive experience rather than a hurried sightseeing dash.

This tour is ideal for travelers craving a personalized, high-end day out, especially those interested in combining scenic sightseeing with wine tasting and coastal charm. It’s perfect for couples, small groups, or anyone looking for a curated escape from NYC.

Key Points

• Private and customizable: Tailor your day to your group’s preferences for a more personalized experience.
• Scenic coastal stops: Enjoy the beauty of Southampton, Sag Harbor, and Shelter Island with minimal crowds.
• Wine and seafood focus: While tastings and lunch are at your own expense, the region offers fantastic options.
• Comfortable transportation: The use of a spacious, air-conditioned minivan ensures a smooth, relaxed journey.
• Expert guidance: Knowledgeable guides, like Scott, add insight and make the day more engaging.
• Door-to-door service: Pickup and drop-off from your NYC hotel makes it hassle-free.

Analyzing the Experience: What to Expect

Starting with Southampton

Your day begins early—around 7:00 am—with a pickup from your NYC hotel. The drive westward is part of the experience, offering a glimpse of the city waking up as you settle into a comfortable, air-conditioned minivan.

Arriving in Southampton, you’ll get a taste of the upscale vibe—think beachfront mansions on “Billionaires Lane,” cozy shops, and cafes. This area is about more than just wealth; it’s a snapshot of coastal leisure, with lovely beaches and scenic views. With a two-hour stop, you’ll have plenty of time to stroll, browse, or just soak in the ocean breeze. Reviewers like Jacquelon_S appreciated the guide’s extensive knowledge in explaining the area’s highlights, making it more than just a quick look.

Exploring Sag Harbor

Next up is Sag Harbor, an 18th-century whaling village that’s retained much of its historic charm. The harbor-side setting makes for a picturesque lunch spot, often praised for its delicious seafood options—though meals are at your own expense. Guests like Wesley_F loved how the day included plenty of photo-worthy moments and found the guide’s commentary engaging and informative.

For two hours, you can wander the quaint streets, admire the boats, and imagine the maritime past that built this charming town. It’s one of those spots where time seems to slow down, perfect for a relaxed meal or some quiet exploration.

Ferry to Shelter Island

After Sag Harbor, you’ll hop on a ferry—an included part of the experience—that takes you across the water from the Hamptons to Shelter Island. This hour-long ride is a highlight for many, offering stunning views of the water and coastline, with some guests mentioning how the ferry adds a touch of adventure to the day.

On Shelter Island, the scenery continues to impress, with quiet beaches and lush landscapes. Though not a scheduled stop, the ferry ride itself is often described as a peaceful, scenic break from road travel.

Sampling the North Fork’s Wineries

The final main segment takes you to the North Fork, renowned for its vineyards, farm stands, and small towns. With 29 wineries in the region, you’ll get a sense of Long Island’s burgeoning wine scene. While tastings are at your own cost, the reviews suggest that the quality of wine and the knowledge of guides like Scott make this part of the trip a real highlight.

We loved the way this segment balances scenic beauty with the chance to learn about local wines—perfect for wine enthusiasts or first-timers. The two-hour stop allows for multiple tastings if you choose to indulge, and the region’s lush vineyards provide excellent photo opportunities.

The Comfort and Convenience

Throughout the day, your group will be transported in a spacious, air-conditioned vehicle, which is a significant perk given the long hours involved. The door-to-door pickup from NYC adds convenience, especially after a full day of sightseeing.

Guides, like Scott, are noted for their patience, knowledge, and engaging commentary. As Wesley_F mentioned, Scott made the long day feel effortless and enjoyable, which is crucial when you’re on a tight schedule.

Is This Tour Worth the Investment?

At $1,299 for up to six people, the cost might seem steep at first glance. However, when you consider the private, bespoke nature of the experience, the door-to-door service, and the inclusion of ferry rides—plus the chance to see multiple regions in one day—it offers good value for a luxury group outing.

The cost of meals, wine tastings, and any additional activities are not included, so packing some extra cash for those expenses is wise. Still, the overall experience—combining scenic stops, cultural insights, and the comfort of private transport—makes it a worthwhile splurge for those seeking a tailored, memorable day.

Who Should Book This Tour?

This private tour is ideal for small groups or couples who want a personalized, relaxed experience without the crowds. Perfect for travelers who appreciate upscale coastal towns, wine, and good food, and prefer the convenience of door-to-door service.

If you’re a first-timer to Long Island or the Hamptons, this tour provides a rundown without the hassle of planning multiple stops. It’s also great for celebrating special occasions or simply indulging in a luxurious day out in New York State’s most exclusive regions.

Travelers looking for a guided experience that balances sightseeing with leisure will find this tour suits their needs perfectly.

FAQs

Is this tour suitable for children?
The minimum age is 21, as wine tastings and certain activities require government-issued ID. Children under 4 need a child safety seat, and those between 4-8 require a booster seat.

What is included in the price?
The private tour, licensed guide, NYC hotel pickup and drop-off, and transportation in a spacious, air-conditioned vehicle are included. Tasting fees, meals, and refreshments are not.

How far in advance should I book?
Most travelers tend to book about 58 days ahead, but booking early is recommended to secure your preferred date.

What is the duration of the tour?
The entire experience lasts about 12 hours, starting at 7:00 am and returning in the evening.

Is the tour customizable?
Yes, the itinerary is private and can be tailored to your group’s interests, making it flexible for specific preferences.

What about transportation?
You’ll be traveling in a comfortable, roomy minivan, which helps keep the long day relaxed and enjoyable.

Are meals included?
No, meals and wine tastings are at your own expense, giving you freedom to choose where and what to eat and drink.

Can I cancel if my plans change?
Yes, the tour offers free cancellation if you cancel at least 24 hours in advance.

What should I wear?
Smart casual attire is recommended, appropriate for both sightseeing and winery visits.

Are service animals allowed?
Yes, service animals are permitted on the tour.

Final Thoughts

The Hamptons and Long Island Wineries Private Tour offers a thoughtfully curated escape from the city, blending scenic coastal towns, historic villages, and vineyard visits into one seamless day. The private nature of the tour, combined with the attentive guides and comfortable transport, makes it a standout experience for small groups seeking personalized service.

While costs for tastings and meals aren’t included, the overall value lies in the flexibility and luxury of a bespoke day designed around your interests. For those craving an elegant, relaxed, and insightful look at one of New York’s most beautiful regions, this tour hits all the right notes—provided you’re ready for a full day of exploration.

Whether it’s your first visit or a return trip, this experience promises a memorable blend of scenic beauty, cultural richness, and the chance to enjoy some of Long Island’s best offerings—all with the comfort and exclusivity of a private guide.