Sample Six Curated Wines While Sailing Chesapeake Bay
2 hours
Up to 6 people
Six wines, mini-harbor tour, sail
Set sail from St. Michaels for a relaxed wine tasting experience on Chesapeake Bay. Sample curated wines as you take in waterfront views from a modern catamaran.
Per-person reservations: full refund up to 24 hours before departure. Private charters: full refund more than 7 days before, 50% refund 72 hours to 7 days before, and no refund within 72 hours. Full refund if the operator cancels due to weather or unforeseen circumstances. No-shows are charged full price.
Product ID: PY9QVZ
Arrive 15 minutes before departure at the dock behind the Harbor Inn & Marina.
Wear comfortable shoes that are easy to remove. Barefoot is welcome. Do not wear high heels.
Use the restrooms inside the hotel before boarding. There is also a head (toilet) onboard.
Dock behind Harbour Inn & Marina, 101 N Harbor Rd, St. Michaels, MD 21663
We had a great time out on the water with Rob (captain) and Steph. They not only sailed us around the Miles River, but also shared a general history of St. Michaels and the area. It was an enjoyable trip, and we would happily do it again!
Jason Lombard
September 1, 2026
We had a great time out on the water with Rob (captain) and Steph. They not only sailed us around the Miles River, but also shared a general history of St. Michaels and the area. It was an enjoyable trip, and we would happily do it again!
Jason Lombard
September 1, 2026
Sail a Historic 1935 Ketch on the Miles River
Pedal refuge and marsh roads with a bike, helmet, and map
Hear true local ghost stories on a nighttime walk through historic Cambridge
Choose your Gettysburg Licensed Battlefield Guide for a private 2–3 hour car tour
Discover Annapolis's Navy culture, history, and Chesapeake character
Cruise Chesapeake Bay waterways with fall views and complimentary warm apple cider