Musings of a Little Girl in the Big City

Best Winery Tour in Long Island

You can find the Japanese version of this article here.

Can I be brutally honest? Summer in NYC is not that great! it’s just too hot and humid to enjoy any activity you might be doing. This being like my 5th summer in the city, I was kind of over it.

So I was on a mission this time around. I was going to spend as little time in the city as possible.

But not having a car when you’re trying to get away for the weekend can definitely be a challenge. Tak and I had already tried the bus route to Philly so I started researching places where I can get to by train to try something different.

This once lead me to a “weekend getaway package” on the LIRR website that included a train and cab ride to Freeport, NY’s “Nautical Mile.” Intrigued, I dragged my boyfriend with me, thinking, what do we have to lose?

A 1.5 hr train ride and short cab ride later, we were greeted with a very sad, desolate boardwalk.  I mean, the weather was beautiful and it was nice to be by the water get away from the city, but there just wasn’t much to see or enjoy. We stayed for lunch and promptly went back to the city.

So I talked to my coworkers about my failed attempt at a weekend getaway and one of the things that was suggested to me was a winery tour in Long Island by a tour company called H.I.S. H.I.S. is a Japanese tour company, and at that point, I was willing to try anything. I signed Tak and myself up as soon as the tour became available and also invited a fellow couple to go on the trip with us. The more, the merrier right?!

So this was my second attempt at getting away from the city, and I am happy to say it went much better this time around!

The best part was how easy and hassle-free it was. Even Tak who is not the biggest fan of guided tours agreed. Honestly, I thought it was perfect.

One Saturday Morning in Mid-July, at promptly 9 in the morning, a big coach bus took us from the meeting point at the Hilton Midtown to the North Fork area of Long Island, about a 2 hour ride from the city.

The first winery we went to was called Macari Vineyards:

Macari Vineyards Long Island ロングアイランドワイナリー
Macari Vineyards exterior
Macari Vineyards Long Island ロングアイランドワイナリー
Wine tasting at Macari Vineyards
Macari Vineyards Long Island ロングアイランドワイナリー
Wine tasting at Macari Vineyards
Macari Vineyards Long Island ロングアイランドワイナリー
Interior of Macari Vineyards
Macari Vineyards Long Island ロングアイランドワイナリー
at Macari Vineyards

From its farmhouse chic interior to the outdoor seating areas, I loved everything about Macari Wines!

We also had lunch and more wine at Lenz Winery before making our way to the last winery at Castello di Borghese.

I loved Castello di Borghese because they gave us eleven… yep, eleven generous and delicious tastings of various wines.

I actually couldn’t finish it all in part from being tired staying up late to make lunch for this day.  But we nonetheless had a great time here!

Castello di Borghese Long Island Winery ロングアイランドワイナリー
All the wine!

Castello di Borghese Long Island Winery ロングアイランドワイナリー

Castello di Borghese Long Island Winery ロングアイランドワイナリー
When there are four blue chairs and we have four in the group, you take a picture of course!

After being satisfied from all the wine tastings, the bus took us to the final stop, Wickham’s Fruit Farm for some PYO blueberries!

Tip: Their Apple Cider Donuts is a must! And this is coming from someone who doesn’t usually eat donuts!


Wickham's Fruit Farm
PYO blueberries at Wickham’s Fruit Farm

Wickham's Fruit Farm

chicken at Wikham's farm

Blueberries at Wickham's Farm
Blueberries at Wickham’s Farm
bleberry picking at Wickham's Farm
With my #1 (blueberry picker) 😉

Blueberry picking at Wickham's Farm


While the tour doesn’t include lunch, for wine tasting at 3 different places and blueberry picking, we thought it was well worth it for $89 a person! Plus you don’t have to worry about driving which is great.

And we had so much fun with our friends! Thank you H.I.S. Tours 🙂

Pin this post:

Day Trip Guide to North Fork Long Island


Have you been to the wineries in Long Island? Which ones are your favorite? Let me know in the comments below!

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