Chesapeake Bay Charters Itineraries

Half, Full or Multiple Day Boat Rentals

Sailboat Charters / Rentals Half Day

  • Cruise the South River
  • Cruise to Thomas Point Lighthouse

Sailboat Charters / Rentals Full Day

  • Cruise the South River, swim in Harness Creek and lunch at Mike’s Crab House
  • Cruise the West River and lunch at Pirates Cove or Big Mary’s Dock Bar
  • Cruise to Thomas Pt Lighthouse then under the bridges to Sandy Pt Lighthouse and then to Bloody Pt Lighthouse

Powerboat Charters / Rentals Half Day

  • Tubing or skiing on Broad Creek on the South River
  • Cruise the South River and stop at Harness Creek and go for a swim & picnic
  • Cruise to Thomas Pt Lighthouse and the Bay Bridges
  • Fishing in the Bay or on South, West or Rhodes River

Powerboat Charters / Rentals Full Day

Cruise to any one of these destinations:

  • Annapolis Harbor
  • Baltimore Inner Harbor
  • Kent Island
  • Tilghman Island/Knapps Narrows
  • Rockhall
  • Oxford
  • St Michaels

Two Day Sailing Adventure

Choose a destination that is no more than 25 to 30 miles from South River. The following are some suggested destinations:

    • Annapolis Harbor
    • Whitehall Bay
    • Herrington Harbor
    • Knapps Narrows/Tilghman Island
    • Baltimore Inner Harbor
    • Magothy River
    • St Michaels
    • Rockhall
    • Kent Island
    • Kent Narrows
    • North Beach

Three Day Sailing Adventure

Although you have three days, you need to plan to be no further away than 25-30 miles from South River at the end of your second day. Here are a few suggested routes for days one and two:

      • St Michaels & Annapolis Harbor
      • Chesapeake Beach & Herrington Harbor
      • Magothy River & Baltimore Inner Harbor
      • Rockhall & Kent Narrows
      • Tilghman Island & Solomons Island
      • St Michaels

Four Day Sailing Adventure

In four days you can venture further away. Plan your trip for three destinations so that you can arrive back to South River by 6PM on day four. Here are a few sample itineraries:

      • Oxford, Cambridge, Tilghman Island
      • Rockhall, Chestertown, Kent Island
      • St Michaels, Oxford, Chesapeake Beach
      • Herrington Harbor, Solomons Island, Chesapeake Beach
      • Baltimore Inner Harbor, Rockhall, Annapolis



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