Sailing Charters in Annapolis with Chronic Sailing
Difficulty
easy
Duration
2 hours to 5 days
Fitness Level
No advanced fitness needed; basic mobility is sufficient for onboard comfort and safety.
Overview
Chronic Sailing delivers private sailing charters in Annapolis with options ranging from sunset cruises to multiday adventures. Discover how their expert crew and luxurious boats turn the Chesapeake Bay into your personal playground.
Sailing Charters in Annapolis with Chronic Sailing
Adventure Tips
Book Early for Multiday Charters
Popular multiday trips fill quickly—reserve weeks in advance to secure your preferred dates.
Pack Layers for Evenings
Temperatures on the water can drop quickly after sunset, so bring a warm jacket or fleece.
Stay Hydrated and Use Sun Protection
Sun exposure is intense on open water. Apply waterproof sunscreen often and drink plenty of water.
Communicate Dietary Restrictions Early
Chronic Sailing’s crew accommodates special food and drink requests—mention them at booking.
Local Insights
Wildlife
- Ospreys soaring overhead
- Occasional schools of Atlantic menhaden below the boat
History
Annapolis is known as America's Sailing Capital with a maritime history dating back to the 17th century and hosts the prestigious United States Naval Academy.
Conservation
Efforts to reduce plastic use and avoid disturbing marine habitats are core to sustainable boating around the Chesapeake Bay.
Adventure Hotspots in Washington, DC
Frequently Asked Questions
Recommended Gear
Windbreaker or Waterproof Jacket
Protects against chilly breezes and occasional rain common in springtime Annapolis.
spring specific
Sunglasses with UV Protection
Reduces glare off the water and shields eyes during bright, sunny days.
summer specific
Non-Skid Deck Shoes
Ensures safe footing on wet or slippery boat decks across all seasons.
Reusable Water Bottle
Keeps you hydrated throughout your charter while minimizing single-use plastic waste.