A wine day without Manhattan headaches. This Long Island wine and food trip takes you out of the city and into North Fork-style tastings with a private certified sommelier and two winery stops. You get structured time to taste, ask questions, and learn how the wines are made and why they taste the way they do.

What I like most is the pacing: 90+ minutes at each winery means you are not cramming samples between quick photo ops. The other big win is that you’re not driving, so you can focus on the glass and the conversation instead of traffic and parking.

One thing to consider: the lunch is included, but it can feel light if you love a big sit-down meal. Also, bus comfort can vary, and you’ll want to be ready for that long ride.

Key things worth knowing before you go

• Two winery tastings are the whole point: each stop includes 4 wines (often 4–5) with a sommelier-led format
• Your guide is a certified sommelier and the host energy matters a lot for first-timers
• The group is capped at 48, which is big enough to meet people, not so big that you vanish
• Lunch is a simple, local sandwich plate with chips and bottled water, not a full gourmet meal
• Expect a long day: start late morning from Manhattan, back in early evening
• Pellegrini can be a mixed bag for room comfort and facilities, depending on the day

Leaving Manhattan: the easy Long Island rhythm starts at 140 E 41st St

You meet at 140 E 41st St, New York, NY, with a 9:00 am start time. From there, the tour settles into a classic day-trip flow: drive out, taste slowly, eat what’s provided, then head back before dinner. It’s built for people who want wine country without the stress of planning and driving.

The ride is done in an air-conditioned vehicle, and the max group size is 48. In practice, that’s the sweet spot for social energy. Big enough that you can end up chatting with strangers, small enough that you usually still hear the guide and stay part of the group.

If you’re coming from Manhattan and you hate losing half the day to logistics, this kind of setup is a big deal. You get to show up, pay attention, taste, and actually enjoy the scenery and the stops.

Price and value: what $148 gets you (and what to expect)

At $148 per person, you’re paying for more than “entry into two wineries.” The included value here is:

• Tastings at 2 wineries (90+ minutes at each stop)
• 4 wines per location with the sommelier leading the experience
• A locally sourced sandwich lunch (plus chips and bottled water)
• A private certified sommelier and an organized day in a shared vehicle

If you were to DIY this from NYC, the costs pile up fast: transportation, winery reservations, tasting fees, and time. Here, the timing is handled for you and the tastings are built into the day.

That said, you should line up your expectations. This is a structured tasting day, not a food festival. If you’re the type who wants an enormous lunch with multiple courses, the included sandwiches may feel like a snack in between glasses.

The sommelier factor: Sam, Steve, and Rhonda make the learning stick

The tour is hosted by a private certified sommelier, and the guide’s personality really shows up in how fun and educational the day feels. In past departures, the experience has been led by Sam Kimball, and also by hosts including Steve and Rhonda. That matters because wine tastings can either feel like a script or feel like a real conversation.

You can expect the guide to walk you through what you’re tasting, not just pour and move on. One review noted that guests learned about grape types that used to drive winemaking in the region, which is exactly the kind of context that helps you remember what you liked and why.

If you’re new to wine, that guidance is gold. If you already know your stuff, you’ll still appreciate someone breaking down the glass in plain language—without making it feel like a classroom.

Pellegrini Vineyards: 4–5 wines, vineyard views, and a peek behind the scenes

Your first stop is Pellegrini Vineyards, where your sommelier runs a tasting of 4–5 wines (included). The tasting slot is about 1 hour 30 minutes, and you’re given time to taste and ask questions in a guided setup.

One of the best things here is how the property is designed for sight and story. A past guest said Pellegrini was their favorite because they got to see where the wine is processed and the storage containers. That kind of look makes the winemaking feel real, not abstract.

Facilities can be a mixed experience, though. There are mentions of a tasting room that can feel sterile for some tastes, and one note about restroom convenience (including that only one female restroom was available in that space). Pellegrini’s tasting-room choice also seems intentional—there’s an emphasis on being able to see the vineyard (including chardonnay plantings) from where you stand.

My practical takeaway: if restrooms are a priority for you, I’d treat this stop as the one where you should be proactive. Use the facility early if you can, and don’t wait until you’re right in the middle of your tasting.

RGNY tasting: different styles, strong ambiance, and a good comparison moment

Your second winery stop is RGNY, another 1 hour 30 minutes tasting window with 4–5 wines (included). The idea of two very different wineries is a smart move on a day trip—by the time you reach the second stop, your palate is awake and you can compare styles instead of starting fresh.

Guests have described RGNY’s tasting room and property as great, with a beautiful setting and a more enjoyable ambiance. One person called out that the two wineries produced very different styles, which is exactly what you want if you’re trying to understand what Long Island tastes like across wineries.

There’s also a value signal here: some people found RGNY more satisfying than Pellegrini, while others liked Pellegrini more for the behind-the-scenes look. Translation: the best plan is to keep an open mind and treat each stop as its own experience, not a competition.

If you like to buy a bottle, this is often where that happens. Your sommelier will have a good sense of what you enjoyed, and that makes choosing easier when you’re standing in the tasting room with a lot of options.

Lunch reality check: Macari mini sandwiches, chips, and when you might want more

Lunch is included and it’s sandwich-based, not buffet style. You get two mini sandwiches to choose from:

• The Macari mini sandwich: roasted turkey breast, creamy brie, sliced apple, fig jam, and arugula
• The Michelina mini sandwich (vegetarian): fresh mozzarella, tomato, and basil pesto

Plus there are local potato chips and bottled water. That combo is practical for a wine day: it keeps you fueled without sending you into a food coma.

Still, there’s a clear theme in the feedback: some people wished there was more food. So here’s my advice. If you’re hungry in a normal day, plan to treat lunch as a solid snack, not as your full meal plan. And if you want extra bites, be ready to pick up something on your own at a later stop.

Also, at the second winery, at least one guest noted that more food could be ordered if needed (at your own expense). So if you find yourself still peckish after lunch, you might have an option once you’re back in the winery world.

Timing and pacing: how the 9 hours usually feel

This tour runs for about 9 hours. You start at 9:00 am and return to the meeting point by early evening. Reviews have mentioned arrival back around 5:30 to 6:30 pm, so you should plan for a full day away from the city.

The winery pacing is the core structure: roughly 90 minutes at each winery. That’s what makes it feel less rushed than the typical “taste in 30 minutes and run” format. It also helps with decision-making. You can actually figure out which wine you want to buy rather than grabbing whatever is most vivid in the first minutes.

For your personal comfort, I suggest:

• Wear layers. Winery rooms can swing from cool tasting spaces to warmer outdoor areas.
• Bring a phone charger or power bank. You’ll take photos and your battery will drain faster than you expect.
• Have your questions ready. Your sommelier can answer faster when you don’t have to think on the spot.

Bus comfort, restrooms, and seat belts: plan like you mean it

This is a shared vehicle day, so comfort matters. You’ll get an organized ride in an air-conditioned vehicle, and some guests have said the bus was comfortable and had a restroom.

But I’d be honest: other feedback mentioned a bus restroom that didn’t meet expectations and one note about seat belts not working properly. That doesn’t mean the whole trip is bad, but it does mean you shouldn’t ignore the basics.

Do this:

• Pick a seat near the restroom if that matters to you.
• Check your seat belt fit and function when you board.
• Use restroom breaks early. Waiting until you’re squeezed between tastings is how a relaxed day becomes a stressful one.

Who this tour suits best (and who might prefer a different plan)

This is designed for adults 21+. No children are allowed, and that alone helps keep the tone focused on tasting and conversation instead of managing a mixed-age group.

It’s also a great fit if:

• You’re in your first wine routine and want structure
• You want a social day without planning every stop
• You want a sommelier to translate the “why” behind the wine
• You don’t want to drive from Manhattan

If you’re a hardcore food person, you might want to pair the lunch with an additional snack plan of your own. And if you strongly prefer boutique, intimate tastings with heavy attention to details like restroom setup, you might find that a guided group day has trade-offs.

Should you book this Long Island wine day trip from NYC?

I’d book it if your goal is a smooth, organized Long Island wine experience with a certified sommelier and enough time to taste at two wineries without racing all day. The value is strongest if you care about learning and tasting more than you care about a huge meal.

Skip it or adjust your expectations if:

• You need a bigger lunch than sandwiches and chips
• Restrooms are a top priority and you’re the type who hates delays
• You want the most flexible, DIY-style control over timing and pace

If you want a clean way to get out of Manhattan, taste real wine, and come back with a better sense of what you like, this day trip is a solid pick. Just go in with a plan for the lighter lunch and a practical mindset about the long ride.

FAQ

How many wineries are included?

You stop at 2 wineries, and each winery includes a guided tasting of 4 wines.

What’s the total time for the tour?

The tour runs for about 9 hours.

Is lunch included, and what is it?

Yes. Lunch includes sandwiches (Macari mini sandwich with turkey and brie, or Michelina mini sandwich vegetarian), plus local potato chips and bottled water.

Do I need to be 21 or older?

Yes. The minimum age is 21, and no children are allowed.

Is there a sommelier on the tour?

Yes. The tour includes a private certified sommelier.

Where do I meet, and what time does it start?

You meet at 140 E 41st St, New York, NY 10017, and the start time is 9:00 am.

What group size should I expect?

The tour has a maximum of 48 travelers.

Is the tour offered in English?

Yes, it’s offered in English.