Baltimore Wine Tour Charter — Eastern Shore & MD Winery Bus

Maryland actually has serious wineries

The Eastern Shore has 15+ commercial wineries, most of them small, family-owned, surprisingly good, and impossible to visit on a self-driving tour without designating someone to sober up by hour three. Charter is the answer.

Baltimore County + Northern Maryland adds another 8–10 wineries within an hour of downtown Baltimore. Between the two regions you can build a real wine day.

The classic Baltimore wine-tour day trip

Pick up at your spot in Baltimore around 10 AM. Cross the Bay Bridge into Eastern Shore wine country. Hit 3–4 wineries with tasting flights + lunch at one. Back in Baltimore by 6 PM. 8 hours total.

Favorite Eastern Shore stops

• St. Michaels Winery — historic waterfront town, small tasting room, easy walk to Chesapeake Bay Maritime Museum
• Costa Ventosa Vineyard — Chesapeake City, coastal breezes, outdoor tasting patio
• Bordeleau Vineyards — Eden, MD. Small family operation, red-forward tastings
• Layton's Chance Winery — Vienna, MD. Award-winning Maryland reds
• Crow Vineyard & Winery — Kennedyville, MD. Working farm, cabins on-site, cheese and charcuterie boards

Baltimore County + Northern Maryland

• Boordy Vineyards — Hydes, MD. Maryland's largest, tour + tasting + food pairing. Concert lawn most summer weekends.
• Basignani Winery — Sparks, MD. Family-owned, personal tasting-room experience
• Great Shoals Winery — cider-focused, worth the stop
• Old Westminster Winery — Westminster, MD. Natural wines, cult following
• Detour Winery — Keymar, MD. Historic barn tasting room

What we bring

• 20–30 passenger party bus for smaller crews — LED lighting, sound system, coolers if you want to keep some tasting-room bottles cold on the way home
• Executive minicoach for corporate wine outings — captain's chairs, wifi, restroom, tables for group tasting notes
• Professional CDL-P driver — knows the winery approach roads, calls ahead to reserve group parking
• Cooler + ice provided — for the bottles you buy along the way

Pricing

Full-day (8-hour) wine tour typically runs $1,400–$2,200 depending on vehicle size + season. Weekend Saturdays in peak wine season (September–October) book 4–6 weeks ahead.

Corporate + team-building wine tours

Wine tours are one of our most popular corporate offsite formats. We can pre-arrange group tastings at 2–3 partner wineries, coordinate lunch at Osteria 177 in Annapolis or the Point Crab House in Arnold, and provide a private driver who handles the itinerary logistics so your team can just show up. Talk to us about corporate wine tour packages.

Get a quote

Free quote in 60 seconds — tell us headcount, date, which wineries you're planning to hit, and we'll come back with a full itinerary + pricing.