chesapeake bay
Crossing the Chesapeake Bay in a kayak can be an adventure that’s perfect for a break from competitive fishing, and great for cooler fall weather when fewer boaters are around and the wildlife of the Bay is active. Crossing the Bay is not something to be undertaken lightly. It is recommended only for intermediate to advanced kayakers.

There are a number of factors that can make this trip hazardous, so be sure to plan adequately to get the most out of it, and above all be safe!

Plan Your Route

The first thing to figure out is your likely route. If you can, you should try to go with the tide, instead of against it, and have the wind at your back. Before you even think about undertaking a crossing, you should consider several different variables.

Check the Tides

As mentioned previously, tide is a key consideration because if the current is flowing the wrong way, it’s possible to be swept out to sea. Even if the tide is coming into the Bay, it can still be an issue because the cross-currents are powerful. Therefore, you should look at the tide times and consider crossing in the upper part of the Bay, rather than close to the mouth. Waves can be large, so be sure you have experience in handling a kayak in surf-like conditions.

Check the Wind

The wind is the second most important factor, and anything over 15-20 knots in the wrong direction should probably serve as a deal killer; ideally, you want a tailwind that will help you along, rather than a headwind that will fight your progress, so be sure to consult local weather information a day in advance to know if the wind and other conditions will favor you. Even if you feel confident about the weather, know that it can change rapidly, so you should be prepared for fluctuations from the forecast.

Other Craft

Something else to be aware of is that there may be other watercraft plying the Bay, not all of them helmed by sober sailors, so choosing a day that’s slightly cooler and a kayak that’s highly visible is a good idea. A radar reflector is good to have rigged, to make sure your small craft shows up on the radar of larger powered boats. Try to make sure you stay out of known shipping lanes as much as possible.

Visiting Islands

If you’re going to attempt this crossing, you should take care planning your route. Fortunately, there are several islands and land masses in the upper part of the Bay that make navigation and exploration a little easier and more rewarding if you want to stop at or start your crossing from any of them.

The Southern Bay islands of Smith Island and Tangier Island offer the sight of great blue herons from the Martin National Wildlife Refuge, as well as sea creatures such as oysters, herring, rockfish, bay anchovies and rare blue crabs.

On the small masses of land to the north of the Southern Bay islands, explorers have been known to find antique bottles, arrowheads and other Indian treasures from 400 years of fishing by the local Algonquin tribes and 17th-century colonial fishermen. Cherrystone and littleneck clams found there can make a delicious meal that requires little preparation. The larger islands in this region are privately owned, so if you want to camp on one of them, you’ll need to go with an approved outfitter (see this link for more information).

Start Early and Bring Emergency Supplies

Depending on your route, you may have to paddle more than 17 miles. It’s best to start early in the morning when less watercraft will be on the Bay.

It’s a good idea to bring some key supplies along for the trip. A waterproof VHF radio is a good thing to have, as you’ll likely get out of cellphone range, as are flares, a mirror, a personal flotation device (PFD) and a float plan you can leave with someone on land. If you can, try to have a friend with a powered boat on standby for potential emergencies.

DVDs to Watch

A good to DVD to watch if you’re planning this trip is “Kayak Kevin’s Chesapeake Bay Tour,” a documentary of Kevin Whitley’s trip across the Bay and along the surrounding coastline. Other kayakers who have documented the trip (you can Google them) include Josh Tart, Galen “Tug” Owen and Lee Williams.