Private Sailing Adventure in Annapolis with Chronic Sailing
Difficulty
easy
Duration
2–4 hours
Fitness Level
Suitable for most fitness levels with no strenuous activity required
Overview
Experience the ultimate private sailing adventure on Chesapeake Bay with Chronic Sailing. Enjoy a personalized trip with expert captains in Annapolis, Maryland’s sailing capital.
Details
Annapolis, Maryland, known as the Sailing Capital of the United States, offers one of the most authentic sailing experiences you can find, and Chronic Sailing perfectly captures this spirit with their private charters on the Chesapeake Bay. Operating expertly on beautifully maintained catamarans and other vessels, Chronic Sailing provides an intimate, fun, and relaxing day on the water for all skill levels—from first-timers to seasoned sailors. The bay itself is prized for its calm waters, scenic bayside towns, and diverse wildlife, making it a standout location for water adventures.
Chronic Sailing’s private sailing trips are led by Captain Shawn Owen and his experienced crew, who bring both professionalism and a warm, welcoming energy. Guests repeatedly praise the spotless, spacious boats that offer multiple comfortable areas—from covered lounges protected from the breeze to open decks perfect for sun-soaking or spotting wildlife. The crew often enhances the trip with expert sailing instruction or tailored experiences, such as navigating the infamous Ego Alley in downtown Annapolis, where boats of all sizes parade, offering a unique and thrilling chance to show off your sailing prowess.
What makes Chronic Sailing truly special is their dedication to personalized service. Whether it’s a serene afternoon sailing, a lively bachelorette party cruise, or a hands-on sailing lesson, the crew’s attention to detail shines through, including thoughtful touches like coolers stocked with your favorite refreshments. Beyond the adventure, Annapolis’s rich maritime history and charming waterfront add an extra dimension to your day on the water.
The Chesapeake Bay also supports a diverse ecosystem, with opportunities to spot osprey, herons, and occasionally dolphins. The combination of beautiful natural surroundings and expert crewing makes Chronic Sailing a must-book experience for anyone visiting Annapolis who wants to create memorable, nautical moments in a stunning setting.
Adventure Tips
Book Early for Peak Times
Reserve your private charter ahead, especially for weekends and special occasions, to secure your preferred dates.
Bring Layers for Changing Weather
Even on sunny days, it can get breezy on the water—packing light layers will keep you comfortable.
Stay Hydrated and Use Sun Protection
Bring water and sunscreen to protect yourself during extended time on the open deck under the sun.
Communicate Dietary Preferences in Advance
If you plan to bring snacks or have special drink requests, inform the crew when booking to prepare accordingly.
Local Insights
Hidden Gems
- Quiet coves perfect for a swim or paddle beyond the main sailing routes
- Small historic waterfront parks that give insight into Annapolis' maritime past
Wildlife
- Osprey
- Blue Heron
History
Annapolis has been a key seaport and sailing hub since colonial times, with its rich maritime heritage showcased in its historic docks and shipbuilding traditions.
Conservation
Efforts on Chesapeake Bay focus on protecting water quality and restoring aquatic habitats to preserve its ecological balance and support sustainable sailing tourism.
Frequently Asked Questions
Photography Tips
Best Times
Best Viewpoints
- Ego Alley waterfront
- Onboard deck during sailing
- Historic Annapolis harborfront
What to Photograph
Recommended Gear
Comfortable non-slip shoes
Ensures safe footing on the boat deck during sailing maneuvers.
Layered clothing
Helps adapt to fluctuating temperatures throughout your trip.
spring specific
Waterproof jacket
Protects against wind and occasional rain while on the water.
fall specific
Sunscreen and hat
Essential for protecting skin from sun exposure during sunny sails.
summer specific