The Hamptons and Long Island Wineries Private Tour

If you’re thinking about escaping the energy of Manhattan for a day and soaking in some of New York’s most glamorous and scenic spots, the Hamptons and Long Island Wineries Private Tour might be just what you’re looking for. While I haven’t taken this particular tour myself, I’ve looked into its details, reviews, and what it offers, and I can tell you it’s designed for anyone wanting a personalized, laid-back peek into some of the most charming parts of Long Island.

What immediately jumps out about this tour is its customized approach—it’s private, meaning you can tailor the day to your group’s interests. Plus, the comfort of door-to-door transfers and a knowledgeable guide make it seem like a hassle-free way to see a lot in one day. Two things I really appreciate are the variety of stops—from beaches and quaint villages to wineries—and the flexibility to skip or indulge at each point.

A potential consideration? The cost might seem steep at over $1,200 per group, but remember, this includes all private transportation and a guide for about 12 hours. The wine tastings and meals are extras, so if you’re a wine enthusiast or seafood lover, you’ll want to budget accordingly. This tour feels suited for those who value comfort, personalized experiences, and exploring without the stress of planning each detail.

This tour really caters well to adventurous couples, small groups of friends, or anyone seeking a high-end day trip from NYC, especially if you appreciate having a guide handle the logistics. Families with older kids might also enjoy it, provided they’re comfortable on a full day’s outing and meet age and safety requirements. Let’s break down what makes this experience tick.

Key Points

• Private and customizable itinerary ensures a tailored experience.
• Comfortable transportation with door-to-door NYC pickup and drop-off.
• Diverse stops including beaches, historic villages, ferry rides, and wineries.
• Guided insights from a licensed professional guide enrich the visit.
• Time-efficient plan packs a lot into roughly 12 hours.
• Cost reflects luxury and convenience, with optional expenses for tastings and meals.

An In-Depth Look at the Tour

Starting Point and Timing

The tour kicks off bright and early at 7:00 am, which might feel early but is perfect for maximizing your day. It’s designed as a full-day adventure, lasting around 12 hours, so be prepared for a lot of scenery and activity. The pickup is in NYC, making it a seamless departure from the city’s hustle.

First Stop: Southampton

The first destination is Southampton, a quintessential Hamptons town. Here, you’ll find a mix of quaint shops, cozy cafes, and beautiful beaches. The iconic “Billionaires Lane,” a 5-mile stretch of opulent oceanfront mansions, offers a glimpse of the high life. The reviews mention that the highlight is the stunning views and the chance to walk along the beaches, soaking in the relaxed yet upscale vibe.

You’ll get about two hours here, plenty of time to stroll, snap photos, and take in the scenery without feeling rushed. Since admission is free, what you get is pure visual pleasure and the chance to browse local shops if you wish.

Sag Harbor: Historic Charm and Fresh Seafood

Next, the tour moves to Sag Harbor, a historic whaling village full of charm. This stop is also two hours, giving you time to explore its harbor, enjoy some seafood lunch (own expense), and soak in the laid-back maritime atmosphere. The reviews highlight that many find Sag Harbor’s mix of history and relaxed ambiance to be a real highlight.

While lunch isn’t included, the opportunity to enjoy fresh seafood lakeside is a tempting prospect. This part of the tour is perfect for those who love blending scenic views with local flavor.

Ferry Ride: Crossing to Shelter Island

After Sag Harbor, you’ll hop on the Cross Sound Ferry—a quick, scenic one-hour ride from the Hamptons to the North Fork of Long Island. This ferry ride is included in the tour, which adds a fun element of travel and offers lovely views of the water. It’s a relaxing way to switch gears and enjoy the fresh sea air.

North Fork: Wineries and Countryside

Once on the North Fork, the tour continues with two more hours exploring small towns, farm stands, and most notably, 29 wineries. While tastings are not included in the price, the chance to see the region’s vineyards and tasting rooms is a major draw for wine lovers. Reviewers have praised the knowledgeable guides who can probably point out the best spots and give background on the local wines.

The region’s scenery is charming—think rolling vineyards, rustic barns, and peaceful farmland—making it an ideal backdrop for a leisurely afternoon. If you’re into wine or simply enjoy scenic drives, this part is a real highlight.

The Flexibility and Personal Touch

One of the biggest advantages of booking a private tour like this is the ability to customize based on your interests. Want more time at the wineries? Or perhaps a longer beach visit? With a private guide, it’s all about what suits your group best.

What’s Not Included

As with many tours, certain expenses are on you—lunch, wine tastings, and any beverages. The price covers transportation, guide services, and the ferry ride, but if you’re a wine enthusiast, you’ll want to budget for tastings, which can vary in cost.

The Experience from Past Travelers

We found that reviews generally speak positively about this experience. One reviewer, Jacquelon_S, mentions how Scott, their driver, was extremely knowledgeable and patient, which made the long day enjoyable. They recommend the tour for anyone eager to explore the South Hamptons, Sag Harbor, and the wineries of Long Island.

Another reviewer, Wesley_F, calls it an “AMAZING experience,” emphasizing how accommodating, timely, and efficient Scott was. They mention the beautiful views and the overall day out as particularly memorable, hinting that the guide’s professionalism and friendliness truly enhance the experience.

Both reviews highlight the value of having a guide who can enrich the visit with insights and handle all the logistics, making the day feel effortless.

Transportation and Comfort

The tour uses a roomy, air-conditioned vehicle, which is a plus for comfort, especially given the long hours. The door-to-door service is especially convenient—no need to worry about navigating public transit or parking in busy towns. This setup is perfect if you want to relax and enjoy the scenery without fuss.

Group Size and Suitability

With a maximum of 6 people per booking, it’s great for small groups or families who prefer a more intimate experience. The tour is designed for most travelers, but you need to be at least 21 years old to participate due to wine tastings. Children’s safety seats are required for those under 8, which the operator clearly states.

Making the Most of Your Day

To truly enjoy this tour, come prepared for a full day. Wear comfortable, smart casual clothing, and bring along sunscreen, sunglasses, and a camera. Remember, the cost of tastings and lunch are not included, so plan your budget accordingly, especially if you want to indulge in the local wines and seafood.

Since the tour runs from early morning, be ready for a busy but rewarding day that captures the best of the Hamptons and North Fork. If you’re someone who likes to see a lot in one trip without the hassle of planning each stop, this experience could be a perfect fit.

Final Thoughts: Who Will Love This Tour?

This private tour offers a luxurious, flexible way to explore Long Island’s highlights—from beaches and historic villages to scenic vineyards. It’s especially suited for those who value comfort, personalized attention, and a well-curated itinerary. If you’re a wine enthusiast or seafood lover, the optional tastings and meals make it even more appealing.

While the price tag might seem high at first glance, consider the value of door-to-door service, expert guides, and a full day of exploration. You’ll get a taste of both the glamour and tranquility of Long Island, all in one seamless journey.

If you prefer a structured, yet customizable experience that takes the stress out of logistics, this tour could be a good choice. Just remember to budget for the extras, and you’re set for a memorable adventure.

FAQ

Is this tour suitable for families?
While the tour is available for most travelers, children under 21 can’t participate in wine tastings. For families with older kids, it’s a manageable full-day outing, but younger children might find the long hours challenging, especially with the need for safety seats under 8.

How long is the total tour?
It lasts approximately 12 hours, starting at 7:00 am and ending around 7:00 pm, making it a full-day experience.

What’s included in the price?
The cost covers private transportation, a licensed guide, and the ferry ride. Lunch, wine tastings, and beverages are extra.

Can I customize this tour?
Yes, being a private tour, it offers flexibility. You can tailor stops or spend more time at certain locations based on your preferences.

Is transportation comfortable?
Absolutely. The vehicle used is roomy and air-conditioned, ensuring comfort during the long day.

What should I wear?
Smart casual attire is recommended. Pack comfortable shoes, sunscreen, and sunglasses for outdoor stops.

How do I cancel if my plans change?
You can cancel up to 24 hours in advance for a full refund, making it flexible if your schedule shifts.

All in all, the Hamptons and Long Island Wineries Private Tour presents a well-rounded, enjoyable way to experience some of New York’s most desirable spots beyond the city. Whether you’re into scenic landscapes, historic towns, or wine tasting, it offers a balanced day of exploration with the convenience of private service.