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.
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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
A Long Island wine tour from Detailed Drivers costs $175/hr for a Mercedes-Benz Sprinter Van (10-14 passengers) with a 3-hour minimum ($525 minimum booking). A typical 6-hour North Fork 5-vineyard day runs $1,050 flat, all-inclusive. For smaller groups (up to 6), the Cadillac Escalade ESV at $125/hr ($375 minimum) works for 3-4 vineyards in a day. Flat rate includes TLC-licensed chauffeur, tolls, climate control, and luggage storage for wine purchases. No surge during peak wine season (September–October) or harvest festivals. Call (888) 420-0177.
Long Island wine country is concentrated on the North Fork — a peninsula stretching roughly from Riverhead east to Greenport, approximately 85 miles east of Midtown Manhattan via the Long Island Expressway (I-495) and NY-25. The North Fork is home to more than 40 vineyards including Pindar Vineyards, Paumanok, Macari, Lenz Winery, Castello di Borghese, Raphael, Osprey's Dominion, Duck Walk Vineyards North, and Palmer Vineyards. The South Fork (Hamptons) has fewer vineyards but includes Wölffer Estate in Sagaponack and Channing Daughters in Bridgehampton.
The North Fork's western edge (Riverhead) is 80 miles from Midtown Manhattan via the Long Island Expressway — about 95–120 minutes off-peak, 150–200 minutes during Friday afternoon traffic. The center of wine country (Cutchogue, Mattituck, Peconic) is 90 miles from Manhattan, and the eastern tip (Greenport) is 95 miles. South Fork vineyards in Sagaponack and Bridgehampton are 85–95 miles from Manhattan via Sunrise Highway (NY-27).
The Mercedes-Benz Sprinter Van ($175/hr, 10-14 passengers) is the standard wine tour vehicle — large enough for a full group, climate-controlled, with USB charging, tinted windows, and secure storage for wine cases. For parties of 4-6, the Cadillac Escalade ESV ($125/hr) works for shorter 3-4 vineyard days. For couples or small groups, the Executive Sedan ($100/hr, up to 3) is sufficient for a 2-3 vineyard day. All Detailed Drivers wine tour vehicles include a TLC-licensed chauffeur familiar with North Fork routing.
Popular North Fork vineyards include Pindar Vineyards (Peconic, the North Fork's largest), Paumanok (Aquebogue, award-winning Chenin Blanc), Macari Vineyards (Mattituck, biodynamic farming), Castello di Borghese (Cutchogue, Long Island's original vineyard), Lenz Winery (Peconic, sparkling and Merlot), Raphael (Peconic, Italian varietals), Osprey's Dominion (Peconic, 30+ wines), Duck Walk North (Southold, Riesling focus), Palmer Vineyards (Riverhead, coastal Cabernet Franc), and Pellegrini Vineyards (Cutchogue). South Fork: Wölffer Estate (Sagaponack, sparkling rosé) and Channing Daughters (Bridgehampton, natural wines).
A typical North Fork wine tour day covers 4-6 vineyards over 6-8 hours, with a 45-60 minute stop at each vineyard for tastings and a 75-90 minute lunch break. Most groups prefer 5 stops plus lunch. Shorter 3-vineyard half-day tours run about 4 hours. Long-day tours of 6+ vineyards are possible for committed groups but often produce diminishing returns as palate fatigue sets in. Your chauffeur can adjust the itinerary mid-tour based on group energy and interest.
Yes — most wine tour itineraries include a 75-90 minute lunch break. Popular options: Love Lane Kitchen (Mattituck, local farm-to-table), The North Fork Table & Inn (Southold, James Beard semifinalist), Scrimshaw (Greenport, seafood and cocktails), Claudio's (Greenport, historic waterfront), Caci North Fork (Southold, Italian), and Jamesport Manor Inn (Jamesport, fine dining). Your chauffeur handles reservations if requested at booking. Some vineyards (Macari, Sparkling Pointe, Lieb Cellars) also have on-site food service if you prefer to eat at the vineyard.
Yes — most North Fork vineyards require reservations for tastings on weekends (Friday-Sunday) during peak season (May-November). Detailed Drivers can coordinate vineyard reservations as part of your booking — provide your preferred vineyards and we'll confirm your tasting appointments with 1-2 weeks notice. Weekday tours are more flexible, but advance booking is still recommended for guaranteed seating at popular vineyards like Wölffer, Paumanok, and Macari.
Peak Long Island wine tour season is September through October during grape harvest — weekend crowds are significant but vineyards run special harvest events, tastings, and crush experiences. May through June offers excellent weather with lighter crowds. July-August is busy with summer Hamptons traffic spilling into North Fork. November-April is low season — fewer events but easy same-day bookings and more intimate tasting experiences. Winter tours are available — many vineyards have heated indoor tasting rooms.
Call (888) 420-0177 or visit detaileddrivers.com/reservations. Provide date, pickup location, group size, and preferred vineyards (or ask us to build the itinerary). Booking 2-3 weeks ahead is recommended for weekends, 1 week for weekdays. Confirmation with chauffeur contact and vineyard reservation confirmations sent 24-48 hours before your tour date. For corporate wine tours or groups of 15+, we coordinate multiple Sprinter Vans.
Last Updated: May 2026