Set sail with Kadima Host & Sailing Adventures aboard a beautifully restored 1987 Hylas 45 Sailing yacht (refit in 2025), departing from Arnold.
"Exceptional Experience Aboard the Vessel:
I recently had the pleasure of booking a trip through BoatBooker, and I couldn't be more pleased with the entire experience." — Robert,
Experience the beauty of Annapolis from the water aboard Endless Summer Charters MD, a beautifully restored 2002 Markley 35 Chesapeake Deadrise vessel that combines classic charm with modern comfort.
Climb aboard Burton Charters, Inc., a sleek and spacious 2000 Sea Ray 540 Cruiser, and experience the Chesapeake Bay in comfort and style.
"An amazing day that far exceeded all our expectations. We plan to be back yearly!" — Paula,
Annapolis Sailing Adventures, LLC is the premier crewed private charter operator in Annapolis - America's Sailing Capital! Let Captain Rick and first mate Annette take you and up to five of your family and friends on a sailing charter to remember abo
Kent Island is a Chesapeake Bay classic—an easy-launch gateway to wide-open water and a maze of protected creeks. Skippers come for the variety: slip through Kent Narrows to reach the Chester River and Eastern Bay in minutes, then set a course to quiet coves, sandy points, and working waterfronts steeped in watermen heritage.
Expect smooth cruising and plenty of sightseeing. Sparkplug lighthouses and sweeping bridge views frame routes where ospreys, herons, and dolphins make regular cameos. On breezy days, Eastern Bay rewards with postcard sailing; when it’s calm, the Narrows and backwaters offer relaxed exploration by runabout, pontoon, or center console. Dock-and-dine options abound around the Narrows, making it easy to tie up for fresh seafood before the next leg of your adventure.
Kent Island boating charters unlock seasonal highlights across the middle Bay. Spring brings clear mornings and lively shorelines; summer invites family sandbar trips and golden-hour cruises; fall delivers crisp air, glassy conditions, and stunning foliage along the Chester’s banks. With well-marked channels, full-service marinas, and short hops to destinations like historic waterfront towns, it’s a true captain-friendly hub for day trips and weekend itineraries.
Whether you’re chasing wildlife, lighthouse photo ops, or a leisurely hop between marinas and waterside restaurants, Kent Island packs big-Bay experiences into short, memorable runs. Launch, link the rivers and bays, and discover why so many boaters make this their go-to starting point on Maryland’s Eastern Shore.
