Long Island Wine Tour North Fork Sights Bites & Flights Half Day PM offers a thoughtfully curated adventure that blends wine, local delicacies, scenic views, and fascinating stories. Designed for those craving a flexible, personalized experience, this tour takes visitors off the beaten path to discover the area’s best-kept secrets—all in just about four to five hours. Whether you’re a wine lover, a foodie, or a history enthusiast, this tour promises a well-rounded taste of Long Island’s North Fork.
What we love most about this experience is its customizable nature—you pick the stops that excite your interest. The knowledgeable guides add a layer of authenticity and expertise, often sharing stories that you won’t find in guidebooks. The all-inclusive pricing covering food, drinks, transportation, and tips means no stress about extra costs or planning. A potential consideration is the limited time at each stop, which might feel brisk if you’re eager to linger longer. Still, this is ideal for those who want a taste of many spots without a full-day commitment. This tour is perfect for couples, small groups, or friends who want a relaxed yet engaging glimpse of Long Island’s North Fork with a personal touch.
Good To Know
- Personalized experience tailored to your preferences.
- Expert guides with insider knowledge and engaging stories.
- All-inclusive pricing covers food, wine, transportation, and gratuities.
- Flexible itinerary with options to customize stops.
- Optimal for short visits or those who prefer a half-day outing.
- Private transportation ensures comfort and convenience.
Why This Tour Stands Out

This tour’s greatest strength lies in its personalized approach. Unlike large, generic group tours, it is designed around your interests, whether that’s sampling wines, exploring beaches, or discovering local shops. The guides, like Eric from the reviews, are praised for their knowledge, flexibility, and professionalism. They don’t just chauffeur you around—they bring stories, insights, and a genuine passion for the area.
It’s a compact yet comprehensive experience that packs in a variety of sights, tastes, and stories, making it ideal for those with limited time but a desire for depth and authenticity. The flexible itinerary means if you’re more interested in visiting a winery or exploring the small shops in Southold, your guide can adapt the stops accordingly.
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The Itinerary Breakdown

Stop 1: Mattituck – A Taste of Local Charm
Your journey begins in Mattituck, a hub for vineyards, beaches, and botanical gardens. The tour offers options based on your interests—perhaps a stroll through a botanical garden, a visit to a local apiary, or a quick dip at a nearby beach. The free admission gives you a chance to soak in the scenery or explore on your own, setting a relaxed tone for the rest of the trip.
Reviewers appreciate this segment for its flexibility. One mentions, “We visited some really cool spots on the North Fork that we wouldn’t have known to check out,” highlighting the personalized touches guides can bring here. This stop usually lasts about an hour, giving you time to enjoy the natural beauty or snap some photos.
Stop 2: New Suffolk – Oysters and Chocolates
Next, a visit to an oyster farm offers a glimpse into the area’s seafood traditions. It’s a chance to learn how oysters are cultivated and enjoy fresh samples. Afterwards, a stop at a favored chocolatier lets you indulge in handcrafted treats—perfect for those with a sweet tooth.
This part of the tour is valued for its local authenticity. As a reviewer notes, “Eric took us to some really cool spots we wouldn’t have known about,” emphasizing the insider knowledge that makes these stops special. The oyster farm visit lasts about an hour, with free admission, giving you enough time to appreciate the setting and learn about sustainable farming practices.
Stop 3: Southold – Food and Shopping
Perhaps the most social part of the tour, Southold offers a chance to sample small plates at favorite local eateries. Expect delicious bites that showcase regional flavors, all included in the tour price. Afterward, you can browse boutique shops and an apothecary or opt for another winery visit if wine tasting is your main goal.
This segment, lasting around 1.5 hours, often receives praise for its casual, friendly vibe. One reviewer raved, “The food and drinks were both fantastic. We had a blast,” capturing the enjoyment of good company and good eats in a relaxed setting.
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Stop 4: Greenport – A Walking History and Shopping
Ending your afternoon, a walking tour of Greenport combines a bit of local history, maritime heritage, and boutique shopping. The Maritime Museum adds a cultural touch, and strolling the charming streets allows you to soak in the small-town atmosphere.
Guide-led stories about Greenport’s maritime roots are a highlight here. As one guest says, “The guides’ stories made the history come alive,” making this stop both educational and fun. You’ll have about 1.5 hours here, enough to explore at a leisurely pace.
What’s Included and What’s Not

This tour’s all-inclusive approach is a major plus. For $339 per person, your package covers:
- Comfortable, air-conditioned vehicle transportation
- All food and drinks, including small plates and wine samples
- Gratuities and all fees and taxes
- Bottled water and soda
- Small-group, private experience
On the flip side, retail shopping is not included, so any purchases are on your own. The flexibility allows you to spend as much or as little time at shops as you like.
Transportation and Timing
The tour features private transportation, which means you won’t be stuck with strangers or waiting for slow groups. The vehicle is air-conditioned, ensuring comfort during the roughly four to five-hour experience. The tour departs in the late afternoon, from 3:00 PM, making it perfect for a relaxed, less rushed exploration.
Travelers praise the guides for their knowledge and friendliness, making the journey both informative and enjoyable. The tour is scheduled Thursday and Friday evenings from August through October, offering a great late-afternoon option.
Real Experiences from Guests

One reviewer shared, “Eric was our guide and took us to some really cool spots we wouldn’t have known,” emphasizing the value of insider tips. Another mentioned, “The guide was knowledgeable, flexible, and professional,” which speaks to the personal touches and expertise you’ll encounter.
Guests also appreciate the balance of wine tastings, local food, and scenic stops, making it a well-rounded snapshot of Long Island’s North Fork.
Pricing and Value

At $339 per person, this tour offers excellent value for a personalized, all-inclusive experience. Compared to booking separate winery visits, meals, and transportation, it simplifies planning and often works out more economical. The private nature means your group won’t be squeezed into a large bus, and the guides’ local insights add depth to the visit that DIY itineraries can’t match.
Who Is This Tour Best For?

This experience suits travelers seeking a relaxed, intimate day with flexibility and insider access. It’s ideal for couples, small groups of friends, or anyone wanting a curated taste of Long Island’s North Fork without the hassle of planning. If you love wine, good food, and local stories, this tour will hit all those marks while keeping things light and enjoyable.
The Sum Up

Opting for the Long Island Wine Tour North Fork Sights Bites & Flights Half Day PM means you’re in good hands with guides who are passionate and knowledgeable. The customizable stops cater to varied interests, whether that’s sampling wines, indulging in local bites, or exploring small-town history. The all-inclusive pricing and private transportation make for a seamless, stress-free experience that covers everything you need in just a few hours.
While it’s a brisk pace, the tour’s flexibility and insider tips mean you’ll leave feeling like you’ve uncovered some of the area’s best-kept secrets. It’s a fantastic choice for those wanting a memorable, authentic taste of Long Island’s North Fork without committing an entire day.
FAQ

Is this tour suitable for all ages?
While the tour is private and designed for adults, all food and drinks are served for travelers 21 and above. Non-drinkers or those under 21 can still enjoy the sights and bites, but alcoholic beverages are restricted to those 21+.
How long is the tour?
The tour lasts approximately four to five hours, making it a perfect half-day option for those with limited time or wanting a relaxed experience.
Are dietary restrictions accommodated?
Yes, the tour provider can accommodate dietary restrictions. It’s best to mention your needs when booking so they can tailor the stops accordingly.
What’s included in the price?
Your fee covers private transportation, all food and drinks, gratuities, fees, and taxes. Bottled water and soda are also provided throughout the tour.
Can I customize the stops?
Absolutely. The tour is 100% customizable based on your preferences, whether that’s more wine stops, local shopping, or scenic breaks.
Is transportation comfortable?
Yes, the vehicle is air-conditioned, ensuring a comfortable ride through the roughly five-hour experience.
What’s the cancellation policy?
You can cancel up to 24 hours in advance for a full refund. Cancellations less than 24 hours before the start are non-refundable.
This Long Island North Fork tour offers a well-balanced mix of sensory delights and stories, all with the benefit of a personalized touch. It’s perfect for those seeking an authentic, relaxed taste of the region, all wrapped up in a private, all-inclusive package that keeps things simple and enjoyable.
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