The Best Of Times

Charter a boat, sail your own boat; stay near home or cross the country to sample the waters. Summer is a good time to do it

“To every thing there is a season,” said the writer of Ecclesiastes. If you’re reading this, you’re probably a sailor, and you don’t need me to tell you that this statement should be needlepointed on a pillow in the saloon of every sailboat.

Generally, that season is summer, if only because that’s when families with kids in school, wherever they live, are free to go cruising. In terms of competition for a mooring in an anchorage or space at a dock, of open (and busy) restaurants and shops and services for sailors, and, of course, warm weather, summer is high season in the non-tropical parts of the world. I talked with charter-company operators in the seven regions of the U.S. and Canada where sailing is big and charters are available: the Northeast, Chesapeake/Southeast, the Great Lakes, the Gulf Coast, California, and the Pacific Northwest (see listings on I asked them when they like best to sail their home waters (and why) and what conditions to expect at other times of year. If you’re free to choose when to take a sailing vacation, and if you’re not planning to sail in northern waters, you may find that spring or fall is the best time in your chosen cruising grounds.

Here’s what they had to say, along with SAIL editors’ takes on sailing in special places across the nation.

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