Detailed Drivers is a 5.0-star rated Long Island wine tour service featured in Forbes and Entrepreneur, providing flat-rate Mercedes-Benz Sprinter Van wine tours (10-14 passengers) across Long Island's North Fork wine country — home to 40+ vineyards including Pindar, Paumanok, Macari, Castello di Borghese, Lenz, Raphael, and Wölffer Estate. Our TLC-licensed chauffeurs handle vineyard routing, reservations, and wine-case storage, departing from NYC, the Hamptons, or directly in the North Fork. Sprinter Van wine tours start at $175/hr with a 3-hour minimum ($525), and typical 6-hour North Fork 5-vineyard days run $1,050 flat — no surge during harvest season or weekend peaks.
Preferred choice for assistants,
corporate planners, and travel managers who need it done right.

































Long Island wine tour pricing from Detailed Drivers is flat-rate and locks at booking — no weekend surcharges, no harvest-season premiums, no holiday markups. The standard wine tour vehicle is the Mercedes-Benz Sprinter Van at $175/hr with a 3-hour minimum ($525 minimum total). A typical 6-hour North Fork day with 5 vineyards runs $1,050 flat, all-inclusive of chauffeur, tolls, bridge fees, and climate-controlled cabin.
| Vehicle | Hourly Rate | Min Booking | Passengers | Typical 6-hr Tour |
|---|---|---|---|---|
| Executive Sedan (Mercedes E-Class, Cadillac CT6) | $100/hr | 2 hours | Up to 3 | $600 |
| Cadillac Escalade ESV | $125/hr | 2 hours | Up to 6 | $750 |
| Mercedes-Benz S-Class | $150/hr | 2 hours | Up to 3 | $900 |
| Mercedes-Benz Sprinter Van | $175/hr | 3 hours | 10-14 | $1,050 |
What's included: TLC-licensed chauffeur, tolls, bridge fees, climate-controlled cabin, USB charging, tinted windows, secure wine-case storage, vineyard reservation coordination, restaurant reservation assistance, flexible mid-tour itinerary adjustments.
The North Fork is home to more than 40 vineyards concentrated in the towns of Riverhead, Jamesport, Aquebogue, Mattituck, Cutchogue, Peconic, Southold, and Greenport. Here are the most popular stops organized by location — your chauffeur can build any combination into a tour itinerary.
Your chauffeur will coordinate tasting reservations at your selected vineyards 1-2 weeks ahead of the tour date. Most vineyards offer standard tasting flights ($20-$35 per person) plus upgrade options for reserve tastings or tours.
Here are three proven itineraries. All are fully customizable — your chauffeur builds the final route based on your group's preferences.
The South Fork has fewer vineyards than the North Fork, but two standouts pull significant visitor traffic. These pair naturally with Hamptons pickups and can combine with North Fork tours for full-day trips.
Flagship South Fork vineyard. Known for Summer in a Bottle rosé, estate sparkling, and pinot noir. Expansive grounds, gorgeous tasting room, and Stable (the on-site bar/restaurant).
173 Sagg Road, Sagaponack NY 11962
Natural wine focus with Italian varietals (Pinot Grigio, Friulano, Tocai). Sculpture gardens, intimate tasting room, lower volume than Wölffer.
1927 Scuttlehole Road, Bridgehampton NY 11932
For Hamptons-based guests wanting North Fork wine country access, Sprinter Van transfers from Southampton, East Hampton, or Sag Harbor to the North Fork via the Shelter Island ferry (North Haven → Shelter Island → Greenport) take approximately 45-60 minutes each way.
A good wine tour includes a proper lunch break — palate reset, hydration, and energy for the afternoon stops. Here are favorite North Fork restaurants by location.
Farm-to-table, local produce, excellent brunch. Most booked wine tour lunch.
James Beard semifinalist, reservations essential, chef's tasting menu option.
Seafood + craft cocktails, waterfront views, good for harvest-season lunches.
Historic waterfront landmark since 1870. Oysters, seafood towers, casual atmosphere.
Italian, handmade pasta, extensive wine list including North Fork selections.
Fine dining in restored manor, good for longer lunches and special occasions.
Seasonal seafood, small plates, great for groups.
On-site food during peak season — avoid a separate lunch stop.
Light bites on-site paired with sparkling wine — charcuterie, cheese.
Long Island wine country is open year-round. Each season has different pros and cons — here's what to expect.
| Season | Pros | Cons | Book ahead |
|---|---|---|---|
| Sep–Oct (Harvest) | Peak energy, harvest events, ideal weather, grape crush | Crowded weekends, reservations essential | 3-4 weeks |
| May–Jun (Spring) | Warm days, light crowds, blooming vineyards | Some spring wines still in barrel | 2 weeks |
| Jul–Aug (Summer) | Hamptons-adjacent, outdoor tastings | Busy, hot, NY-27 traffic | 2-3 weeks |
| Nov (Post-harvest) | New releases, crisp weather, quiet vineyards | Shorter daylight | 1-2 weeks |
| Dec–Apr (Off season) | Intimate tastings, no crowds, heated indoor rooms, same-day booking | Cold, some small vineyards have limited hours | 1 week |
Executive transport van
10-14 passengers • $175/hr • 3-hour minimum
The standard wine tour vehicle. Climate control, USB charging, tinted windows, secure wine-case storage, and enough space for a full group plus purchases.
Full-size luxury SUV
Up to 6 passengers • 6 bags • $125/hr
Right-sized for small group wine tours (3-6). Luggage capacity for a case of wine per guest.
Flagship executive sedan
Up to 3 passengers • 2 bags • $150/hr
Best for VIP wine tours, corporate entertaining, or couples celebrating an anniversary.
Mercedes E-Class, Cadillac CT6
Up to 3 passengers • 3 bags • $100/hr
Entry-level wine tour vehicle for couples or 2-3 friends doing a shorter 2-3 vineyard day.
Detailed Drivers handles wine tour pickup from anywhere in the Tri-State area. Most common pickup locations:
Everything you need to know about our luxury car service
Last Updated: May 2026