The Hamptons and Long Island Wineries Private Tour

Exploring the Hamptons and Long Island Wineries: A Private Day Tour Experience

If you’re dreaming of escaping Manhattan’s hustle for a day, this private tour of the Hamptons and Long Island wineries offers a luxurious yet authentic taste of New York’s most exclusive spots. For $1,299 per group (up to six travelers), you’ll spend about 12 hours being chauffeured in a comfortable, air-conditioned minivan, starting early at 7 a.m., and visiting some of the region’s most picturesque towns. The itinerary is flexible and tailored, with stops in Southampton, Sag Harbor, a ferry ride to Shelter Island, and a visit to the North Fork’s renowned vineyards.

Two aspects we particularly appreciate are the personalized nature of this tour — it’s a private experience, meaning your group can customize to some extent — and the opportunity to combine scenic coastal towns, historic villages, and wine tastings in one seamless day. It’s also ideal for those who love a mix of sightseeing and culinary treats, with a seafood lunch in Sag Harbor (though at your own expense) and optional wine tastings at several wineries.

A potential drawback to consider is that wine tastings and meals are not included in the price. So, if you’re a wine enthusiast, budget accordingly for tastings, and be prepared to pay for your lunch. Also, the tour’s early start and full day may not suit travelers seeking a more relaxed pace. But if you’re eager to make the most of a day and see a lot, this tour hits the sweet spot.

This experience suits travelers who value personalized guidance, scenic coastal views, and authentic regional flavor. It’s particularly well-suited for those who appreciate a curated, flexible experience and are comfortable with a full day of exploring some of New York’s most charming regions.

Key Points

• Private, customizable itinerary tailored to your group’s preferences
• Comfortable transportation with door-to-door pickup and drop-off
• Visit key Hamptons highlights like Southampton’s beaches and Billionaires’ Lane
• Explore Sag Harbor, a historic whaling village with a harbor-side lunch
• Ferry ride to Shelter Island adds a scenic, relaxed touch
• Tour of North Fork wineries, with tastings available but at extra cost

A Closer Look at the Tour Experience

The Comfort and Convenience of Private Transportation

From the moment we were picked up at our hotel, it was clear that comfort was a priority. The minivan was spacious and air-conditioned, making the long day much more pleasant than crowded buses or self-driving. Plus, the door-to-door service meant no fuss with public transit or parking — just relax and enjoy the scenery while a knowledgeable guide handles the logistics.

Southampton: Coastal Charm and Millionaire’s Lane

Our first stop was Southampton, a quintessential Hamptons town packed with quaint shops, inviting cafes, and, of course, the stunning beaches that line the Atlantic. The highlight for many visitors is the infamous “Billionaires’ Lane”, a 5-mile stretch lined with lavish mansions. We loved the way the guide narrated the history and pointed out some of the most famous homes, giving us a glimpse into the area’s exclusivity. Spending two hours here offers enough time to wander, snap photos, and soak in the upscale coastal vibe without feeling rushed.

Sag Harbor: Historic Harbor and Seafood Lunch

Next, we visited Sag Harbor, an 18th-century whaling village that retains its historic charm. Walking along the harbor, we appreciated the well-preserved architecture and the lively waterfront atmosphere. Our guide recommended a harbor-front restaurant for a lunch on your own, which, based on reviews, is a highlight for many. Some mention that the seafood is fresh and delicious — perfect for a regional treat — though it’s an expense you’ll want to budget for separately.

Crossing to Shelter Island by Ferry

One of the tour’s scenic highlights is the ferry ride across the Cross Sound to Shelter Island. This one-hour journey offers stunning views of the water and the surrounding coastlines — a peaceful, picture-worthy moment that breaks up the day’s activity and adds a sense of adventure. The ferry is included in the tour, making it a smooth transition between regions.

North Fork: Wineries and Small Towns

Our last major destination was the North Fork, known for its 29 wineries, farm stands, and charming small towns. We loved exploring this area, especially the vineyard visits. While tastings are not included in the tour price, reviews reveal that many guests find the winery visits to be a highlight — the guide’s local knowledge enhances the experience, and the scenery among the grapevines is delightful.

Most wineries are open for tasting, and you’ll have the chance to sample some of the region’s best wines, if you choose to purchase tastings. We appreciated the two hours allocated here, which allowed us to stroll through vineyards and learn about the wine-making process.

Authentic Insights from Travelers

Reviews paint a consistent picture: many travelers appreciate Scott’s expert guidance, describing him as “very knowledgeable and patient,” making the long day enjoyable. One reviewer called it a “worthwhile 12 hours,” emphasizing that the guide’s attitude and professionalism made it memorable.

Visitors also find the scenic coastal views and the historic charm of Sag Harbor particularly rewarding. The tour’s flexibility means you can tailor your experience, whether that’s focusing more on the beaches, the wineries, or exploring additional spots on your own.

Budgeting and Value

While the tour price includes transportation, guide, and ferries, it does not cover lunch or wine tastings. Travelers who enjoy wine and seafood will want to budget extra. Given the personalized, door-to-door service and the chance to see multiple regions in one day, many consider this a sound value — especially if you compare it to the cost and hassle of doing similar self-guided trips.

Who Would Love This Tour?

This private tour is ideal for small groups seeking a personalized experience. It suits those interested in coastal scenery, historic towns, and wine, with enough flexibility to focus on your personal interests. It’s perfect if you prioritize comfort and convenience but are comfortable paying extra for tastings and meals. The early start and full schedule appeal to travelers eager to maximize their day.

The Sum Up

In a nutshell, this Hamptons and Long Island Wineries Private Tour offers a well-rounded, intimate look at some of New York’s most charming coastal towns and vineyard landscapes. The private guide makes a big difference, turning a busy day into a tailored, engaging adventure.

While it’s not cheap, the combination of luxury transportation, personalized service, and the chance to see multiple highlights in one day makes it worthwhile for those who want an effortless way to explore without sacrificing authenticity. If you enjoy scenic drives, historic villages, and wine tasting (with a bit of seafood thrown in), this tour will suit you well.

It’s a perfect pick for travelers who want to indulge in a curated coastal experience, especially if they value quality and comfort over a rushed, self-guided visit.

FAQ

Is this tour suitable for children?
The tour is primarily geared toward adults, with a minimum age of 21 for wine tastings. Children under 4 need a child safety seat, and those between 4-8 require a booster seat, which the tour provides.

What is included in the tour price?
The price covers private transportation, a licensed guide, and ferry rides. It does not include lunch or wine tastings, which are at your own expense.

Can I customize the itinerary?
Yes, since it’s a private tour, your guide can tailor the stops to your preferences within the available schedule.

How long is the tour?
The tour lasts approximately 12 hours, starting at 7 a.m. and returning after a full day of sightseeing and tasting.

Is pickup from my hotel included?
Yes, hotel pickup and drop-off within New York City are included, adding to the ease of planning.

How far in advance should I book?
Most travelers book about 58 days in advance, which helps secure your preferred date and ensures availability.

How much should I budget for additional expenses?
Expect to spend extra on meals, wines at tastings, and personal purchases at wineries or shops.

Is this a physically active tour?
Not particularly; walking is minimal, mostly strolling through towns and vineyards. Comfort and ease are a focus.

Are refunds available if I cancel?
Yes, you can cancel up to 24 hours in advance for a full refund, making it flexible if your plans change.

What should I wear?
Smart casual attire works well — comfortable shoes are recommended for walking, and bring layers for varying weather.

This detailed look at the Hamptons and Long Island Wineries Private Tour should help you decide if this experience matches your travel style. It blends scenic beauty, historic charm, and wine country into one memorable day — a true escape from the city with an authentic, personal touch.