Washington DC Sailing Charters | Private Chesapeake Bay Trips | Shardana Sailing
→ ~100 mi from Washington, D.C. · Rock Hall, MD

Private sailing charters, a couple hours from D.C.

Far enough to feel like a true getaway, close enough for a long weekend — a private, captained day on the Chesapeake Bay.

Why Washington, D.C.

A true escape from the pace of the District

D.C. is one of our most common departure points for guests, from couples marking anniversaries to families planning reunions and companies rewarding their teams.

Every charter is fully customized, so your day — or weekend — on the water reflects exactly what you came for.

  • Capacity Private yacht for up to six guests
  • Crew Dedicated professional captain
  • Route Fully customizable — coves, towns, wineries
  • Distance ~100 miles, roughly two hours to Rock Hall
Charter options

Choose your trip

From $450

Half-day sail

Ideal for a Saturday getaway from D.C.

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Full day

Full-day sail

Worth the drive — cruising, swimming, and Bay towns.

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Evening

Sunset sail

Skip the Potomac for a Chesapeake Bay sunset instead.

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Multi-day

Overnight charter

Turn the trip into a full weekend escape.

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~2 hoursDrive from Washington, D.C.
US-50 EastVia the Chesapeake Bay Bridge

Getting here

We depart from Osprey Point Marina, 20786 Rock Hall Avenue, Rock Hall, MD 21661. From D.C., most guests take US-50 East across the Chesapeake Bay Bridge onto Maryland's Eastern Shore, arriving in roughly two hours depending on traffic.

Ready to set sail from near Washington, D.C.?

Leave the District behind for a private day on the Chesapeake Bay.

Shardana Sailing Charters · 20786 Rock Hall Avenue, Rock Hall, MD 21661 · 215-238-1635 · info@shardanasailing.com