Planning Your 2024 Cruising Season

Often the most memorable cruising plans start with the words “next year, we should go…” Well, sailors, next year is here.

It’s time to start planning your cruising season to maximize your precious time on the water. Here are some tips to help get you started. 

cruising boats
Maximize your precious time on the water by planning your 2024 cruising season now. Photo of Eagle Cove by Susan Theuns

  1. Go somewhere new. It seems obvious to say it, yet we know sailors who go to the same old gunkholes every weekend summer after summer. We don’t blame them, as once you get to know an anchorage, its channel markers, its anchor-holding quality, and its prevailing breeze, it’s easy to go back. Break out of your comfort zone in 2024 and find a new place to go, if even for one night. You may just find a new favorite. 
  2. Event hop. This comes naturally to the extroverted cruisers among us. Memorial Day at the Chestertown Tea Party, Fourth of July fireworks, the blossoming of the American Lotus Flowers (July into August on the Sassafras River), the Rock Hall Pirates and Wenches Fantasy Weekend in August, the Eastport Oyster Boys’ ShoreRivers concert on the Wye River in September: the waterfront schedule is packed with events worth traveling to. Add an Orioles or Nationals game to your cruising schedule, and you’ll be busy all summer long. 
  3. Choose your friends wisely. Introverted cruisers may opt for sailing solo or doublehanded or only with one other couple or a select group of friends. Such are the cruisers who seek out the quiet and secret anchorages. They’re the ones who never want to tell SpinSheet where they anchor. To these peaceful sailing friends, we see and appreciate you and promise not to tell, as long as you send us sunset photos (wink). 
  4. Join the club. If you want to find themed raftup and cruise planning experts, join an active cruising club such as the Hunter Sailing Association #1, Corinthians, Back Creek Yacht Club, or the Sailing Club of the Chesapeake (see page 46 for more). When you’re a member of a cruising club, you can join the planning committee or let someone else plan the cruises and just show up with snacks and a smile. 
  5. Escape the jellies. Sailors on the Middle or Southern Chesapeake Bay may not even know that they can avoid jellyfish by sailing north in July and August. The Northern Bay has more freshwater and lower salinity, which makes for fewer or no jellyfish or nettles. That’s a very good reason for planning your northbound trips in mid-summer into the dog days.  
  6. Hole up. Find where the best hurricane holes are near you so that you can overnight there on the windiest weekends of the sailing season. A friend had a gas dock attendant recommend one (up the eastern branch of the Corrotoman River), and it ended up being a beautiful hidey hole on a breezy night and highlight of the summer cruise. 
  7. Follow your stars. Plan a cruise between August 11-13 somewhere far from a city to see the Perseids Meteor Shower, always one of the best of the year. We recommend the Wye or Choptank Rivers on the Eastern Shore or the Rappahannock or Piankatank Rivers or even farther south on Mobjack Bay.  
  8. Go where the wind blows you. If you plan on sailing south, yet an 18-knot southerly has blown in, this is a good reminder that sailing plans are set in sand, not stone. Be flexible and choose a smarter route wherever possible (see #6).  
  9. Throw a dart. If you can’t make up your mind where to go, why not throw a dart, or close your eyes and point somewhere on a Chesapeake Bay chart, to see where it lands?  
  10. Go where you know. As much as we love to discover new anchorages and destinations, sometimes it’s that place you know like an old friend that speaks to you. Go ahead and enjoy whatever part of the Bay that feels like home, because paradise is in our own backyard.

Find more great cruising articles here.

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