Getting Started
Your First Chesapeake Bay Sailing Charter: What to Expect
A plain-language walkthrough of a first charter out of Norfolk — from the inquiry call to docking back at the slip.
June 18, 2026 · 6 min read
Guides
Chesapeake Sailing Guides
Straightforward advice from our team on planning a charter, choosing a vessel, reading the seasons, and making the most of your time on the Bay.
Planning
Captained vs. Bareboat: Which Charter Is Right for You?
The practical differences between hiring a captain and skippering yourself — certifications, capacity, cost, and comfort.
June 25, 2026 · 5 min read
Destinations
The Best Time of Year to Sail the Chesapeake Bay
Season-by-season conditions on the Southern Chesapeake — wind, water temperature, crowds, and what each month is good for.
July 9, 2026 · 5 min read