If you’re interesting in charting a sailboat on the Chesapeake Bay or beyond, click through the buttons on this page for sailing resources, such as destination and how-to articles, tips for sailors on provisioning and planning, and charter company ideas.


Chartering isn’t hard, and there are so many tools to help plan your sailing vacation along the way. ~By Zuzana Prochazka
Chartering in New Zealand, sleeping under the night stars of the Southern Cross was a nightly occurrence (for a week or two) for Singles on Sailboats club members.
How a group of DC sailors formed an eight-boat flotilla for a charter sailing vacation in Phuket, Thailand, for seven days in late February.
A low-cost charter shared among friends makes for an awesome sailing vacation in the British Virgin Islands. 
Anticipating stunning natural beauty and great sailing conditions, nine sailors from Baltimore's Peninsula Sailors embarked on a seven-day bareboat charter through NSS...
An Annapolis family celebrates a big milestone with a sailing charter vacation in French Polynesia.
Sailors from the Chesapeake on a mid-February charter in the US and Spanish Virgin Islands.
Here are ideas for eight great winter sailing charter vacation destinations to take the chill off
The Whitsundays Islands, Australia, continue to be a popular spot for sailing charters, snorkeling, diving, and other outdoor activities, making them a must-visit destination for...

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