Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day

Long Island’s North Fork is a slice of New York that often gets overlooked in favor of Manhattan or The Hamptons, but for those craving a more relaxed, authentic experience with good wine, fresh seafood, and charming small towns, a private full-day tour like this one is hard to beat. Priced at $559 per person, the Long Island Wine Tour North Fork Sights, Bites & Flights offers roughly 7 to 8 hours of carefully curated visits, with expert guides, private transportation, all food and drinks included, and a flexible itinerary tailored to your interests.

What we love about this tour is how personalized it feels — your guide, Eric, and his team have explored and handpicked the best hidden spots, from secret speakeasies in Jamesport to oyster farms in New Suffolk. The emphasis on local expertise and authentic experiences really sets this apart from more generic group tours. Plus, the fact that everything — including gratuities, food, wine, and transportation — is covered in the all-inclusive price means no surprises or hidden costs.

A slight consideration is that this experience is quite full, with stops that include walking around towns and visiting farms, so it might not be ideal if you prefer a very leisurely or unstructured day. Also, the cost is on the higher side, but when you consider the private, all-inclusive nature and personalized approach, it offers good value for those wanting a comprehensive day in the North Fork.

This tour is best suited for travelers who love good food and wine, enjoy exploring small towns, and want a flexible, intimate experience without the hassle of planning. Whether you’re a first-time visitor or a longtime fan of Long Island, this trip offers enough variety to keep everyone engaged and satisfied.

Key Points

• Personalized Experience: Fully customizable to your interests, with expert guides who know the area inside out.
• All-Inclusive Pricing: Food, wine, gratuities, and transportation are included, making for a seamless day.
• Authentic Local Spots: Visit hidden gems, local farms, and charming towns that aren’t on the typical tourist map.
• Diverse Itinerary: From vineyards and oyster farms to street fairs and maritime museums, there’s variety packed into 8 hours.
• Expert Guides: Guides like Eric bring insider knowledge and stories that enrich the experience.
• Ideal for Food & Wine Lovers: The stops focus on quality local products, making it perfect for connoisseurs or curious travelers.

The North Fork of Long Island is a rewarding destination for anyone who appreciates good wine, fresh seafood, and a slow-paced, scenic vibe. This private day tour, offered by North Fork Sights Bites & Flights, is designed to give you just that — a day packed with authentic experiences, intimate visits, and a personalized touch.

At $559 per person, this experience might seem like a splurge, but when you factor in the guide’s expertise, all food and drinks, private transportation, and flexible itinerary, it offers notable value. It’s perfect for those who want to avoid the hassle of planning and prefer a seamless, curated day by knowledgeable locals.

How the Tour Works and What to Expect

Pick-up and Initial Impressions

Your day begins with a pick-up in a comfortable, air-conditioned vehicle, ready to whisk you away on a journey through some of Long Island’s most charming spots. From the outset, the emphasis is on personalization — the guide will tailor your stops based on your preferences, whether you want to focus on wine, seafood, shopping, or a mix of all.

Stop 1: Jamesport — Hidden Gems and Breakfast

The first stop takes you to Jamesport, a quaint village known for its historic charm and off-the-beaten-path spots. You might visit a speakeasy-style bar — a real hidden gem — and then enjoy breakfast or lunch at a local bakery or nook. This early stop sets a relaxed tone, allowing you to soak in the small-town atmosphere.

Reviewers love the way Eric, the guide, caters to specific interests. One remarked, “Thanks to Eric we had such a nice time exploring the North Fork wine country. Just beautiful!!!!” This first stop is perfect for those who appreciate authentic local venues rather than tourist traps.

Stop 2: Mattituck — Wineries, Beaches, and Gardens

Next, the tour shifts to Mattituck, a hub for top-quality vineyards and scenic spots. Depending on your tastes, you might visit wineries, explore apiaries, stroll beaches, or wander botanical gardens. The flexibility here means you won’t be stuck in a rigid schedule but instead enjoy the places that resonate most with your group.

One reviewer noted, “Eric definitely catered the day to our interests,” highlighting how well the tour adapts to individual preferences. Expect to learn about the wines and local agricultural practices directly from passionate owners and growers.

Stop 3: New Suffolk — Oyster Farms and Chocolates

In New Suffolk, the focus turns to seafood and sweet treats. You’ll tour an oyster farm — a highlight for seafood lovers — and visit a chocolatier for some delicious local confections. The two-hour stop is ideal for those craving a taste of the North Fork’s maritime bounty and artisan crafts.

This part of the tour synthesizes the area’s culinary richness with authentic farm visits, making it more than just a wine trip. The reviews mention how the guide “connected us with business owners and wine makers,” adding depth and personal stories to the experience.

Stop 4: Southold — Small Plates and Boutique Shopping

Southold offers a chance to indulge in local culinary favorites — small plates, perhaps featuring oysters or other regional specialties. Following this, enjoy browsing boutique shops or visiting an apothecary. Alternatively, if your group prefers, you can substitute this stop for another winery visit.

This flexibility is a big plus, especially for groups with varied interests. The review “light, fun and interesting” sums up this part of the day, emphasizing the casual yet engaging atmosphere.

Stop 5: Greenport — Walking Tour and Maritime Museum

The final stop takes you into Greenport, a lively seaside village. Here, you’ll enjoy a walking tour that touches on North Fork history, along with visits to the maritime museum and some local shops. You’ll get a good sense of the town’s character and maritime roots, which adds cultural context to your day.

The two-hour visit is a relaxed way to wind down, with reviews praising the “sense of North Fork history” and “spot shopping” that rounds out the experience.

Included and Optional Extras

The tour covers all food and drinks (including small plates at each stop), bottled water, soda, and gratuities. It also features private transportation in a comfortable, air-conditioned vehicle, which is crucial when hopping between multiple locations.

What’s particularly convenient is that everything — from admission fees to taxes — is included, freeing you from any hidden costs. It’s clear that the goal is to make this as seamless and stress-free as possible.

However, retail shopping isn’t included, so if you’re interested in purchasing local products, you should bring some extra cash or credit card.

The Experience Through the Eyes of Past Travelers

The reviews back up the experience as a hit — one guest simply said, “What a great day!” thanks to guides like Eric who “catered the day to our interests.” They appreciated the knowledgeable guides, beautiful views, and excellent wine selection, which made the day memorable.

Another reviewer, a longtime visitor to the North Fork, called the experience “spectacular,” highlighting that even those familiar with the area loved discovering new hidden spots. The fact that some guests had been visiting for over 30 years and still found fresh perspectives speaks volumes about the tour’s depth and local insight.

Practical Details and Tips

The tour runs Thursday and Friday from 3:00 PM to 10:00 PM, with availability from mid-August through early June. This timing makes it perfect for late afternoon to evening explorations, especially if you’re coming from New York City or elsewhere.

Since it’s a private tour, only your group participates, which allows for flexible customization and an intimate atmosphere. The tour is suitable for most travelers, but keep in mind the full day’s length and walking involved.

Rain or shine, the tour proceeds, so dress comfortably, and consider bringing layers if the weather shifts.

If you’re interested in combining this experience with airport transfers or other services, the provider offers additional options, though this specific tour focuses purely on the North Fork.

Who Is This Tour Best For?

This experience is ideal for wine lovers, seafood enthusiasts, and those who appreciate small-town charm. It’s perfect for travelers who want a private, tailored day without the hassle of planning logistics themselves. The flexible itinerary and knowledgeable guides make it especially attractive for curious visitors eager to learn about local producers and culture.

Couples, small groups, or even families will find the tour’s pace and content engaging. If you’re looking for a luxurious yet authentic taste of Long Island’s North Fork, this trip ticks all those boxes.

Final Thoughts

For anyone craving a relaxed, personalized day exploring Long Island’s North Fork, this tour delivers a well-rounded experience. From hidden taverns and boutique shops to seafood farms and scenic vineyards, it offers a genuine taste of what makes the area special.

The fully private setup, combined with all-inclusive convenience and expert guides, means you’ll spend your day savoring, learning, and enjoying without a worry. It’s a fantastic choice for those who want to combine luxury with authenticity — a true taste of North Fork’s laid-back charm and local treasures.

Whether you’re celebrating a special occasion, looking to indulge in regional specialties, or simply want a hassle-free way to see the area, this tour can be tailored to your tastes and leaves you with memorable moments and new favorites.

FAQ

How long is the tour?
The tour lasts approximately 7 to 8 hours, making it a full day of sightseeing, tasting, and exploring.

Is transportation included?
Yes, private transportation in an air-conditioned vehicle is part of the package, so you don’t have to worry about driving or parking.

What food is included?
All food, including breakfast/lunch at the start, small plates during the day, and dinner, is included in the price.

Are drinks included?
Yes, all alcohol, soda, and bottled water are covered, but you must be 21 or older to consume alcohol.

Can I customize the stops?
Absolutely. The tour is 100% customizable based on your preferences, so you can focus on wine, seafood, shopping, or a mix of everything.

What if it rains?
The tour goes ahead rain or shine, so bring appropriate clothing and be prepared for outdoor stops.

Can I book for a small group?
Since it’s a private tour, only your group will participate, making it ideal for intimate outings.

Is this suitable for families?
Most travelers can participate, but keep in mind the full-day length and walking involved. It’s best suited for those comfortable with a longer day.

How far in advance should I book?
Availability is typically open from August through June, so booking a few weeks ahead ensures you get your preferred date.

This comprehensive, tailored tour offers a genuine and relaxed way to experience Long Island’s North Fork — perfect for those who want an authentic, all-inclusive day with local guides who know their stuff.