Discover the Magic of Chesapeake Bay with Shardana Sailing Charter
Nestled on Maryland’s Eastern Shore, Shardana Sailing Charter invites you to explore one of America’s most storied and picturesque waterways: the Chesapeake Bay. Whether you’re dreaming of a half-day escape, a full-day sail, or a weekend aboard a well-appointed cruising yacht, the Bay offers a perfect mix of scenic beauty, maritime history, charming waterfront towns, and local flavor. Below is your complete guide to what you might see and do — plus recommended itineraries and seasonal planning tips for Spring and Summer.
Half-Day Sail: A Relaxing Taste of Bay Life
A half-day charter with Shardana is the perfect introduction to the Bay’s beauty and atmosphere. In just a few hours, you can unwind, soak in the views, and explore the waterways around Rock Hall.
What You’ll Experience
Scenic cruising: Glide along calm waters lined with herons, ospreys, and salt marsh.
Iconic lighthouses: Sail past photogenic landmarks like Thomas Point Shoal Light, one of the last remaining screwpile lighthouses in the U.S.
Anchoring in a quiet cove: Enjoy a quick swim, sip your favorite drink, or relax with the Bay breeze.
Easy getaway: Perfect for families, couples, and small groups wanting a peaceful half-day on the water.
Spring & Summer Tips
Spring: Expect mild breezes and cooler water — ideal for long, comfortable sailing stretches. Ospreys return to their nesting platforms in March, making wildlife-watching especially rewarding.
Summer: Warm temperatures make mid-sail swims irresistible. Bring sunscreen, hats, and lightweight clothing for the best experience.
Suggested Half-Day Itinerary
- Depart Rock Hall
- Sail toward Swan Creek or the Chester River
- Anchor for a swim or wine break
- Optional shoreline sightseeing before returning to port
Full-Day Sail: Discover More of the Bay
A full-day charter gives you time to visit charming ports, anchor out for lunch, and immerse yourself in Chesapeake history and culture.
What You’ll Experience
Sailing + Shore Time: Visit beautiful destinations like St. Michaels or cruise by the Chesapeake Bay Maritime Museum.
Lunch on board or ashore: Enjoy a fresh seafood meal at Ava’s Pizzeria & Wine Bar, The Crab Claw, or Bistro St. Michaels.
Historic attractions: Pass lighthouses such as Cove Point and explore centuries-old maritime towns.
Wildlife encounters: Bald eagles, blue herons, and schools of small fish are common sights in the summer.
Spring & Summer Tips
Spring: Cooler days make full-day trips comfortable. The shore towns are lively but not crowded.
Summer: Dock-and-dine options are in full swing. Sunset on the return sail is breathtaking.
Suggested Full-Day Itinerary (Option 1: St. Michaels)
- Depart Rock Hall
- Morning sail across the Bay
- Dock in St. Michaels for lunch
- Visit the Chesapeake Bay Maritime Museum
- Afternoon sail back with anchor stop
Suggested Full-Day Itinerary (Option 2: Annapolis)
- Sail to “America’s Sailing Capital”
- Stroll historic downtown
- Explore the U.S. Naval Academy
- Dinner or happy hour on the waterfront
- Overnight anchoring in secluded rivers and creeks
- Visits to historic towns like St. Michaels, Solomons Island, and Annapolis
- Opportunities for wine tastings, museum visits, boutique shopping, and seafood feasts
- Sunset sails, stargazing, and morning coffee on the deck
- Sail south with breezy spring winds or calm summer seas
- Visit the Calvert Marine Museum
- Stop at waterfront favorites for fresh oysters or soft-shell crab
- Anchor out or stay at a marina for the night
- Leisurely sail up the Bay
- Explore the charming streets
- Visit Lyon Rum Distillery or St. Michaels Winery
- Enjoy dockside dining before a peaceful overnight anchorage
- Morning coffee on the water
- Swim in a quiet cove
- Enjoy a smooth final sail back to Rock Hall
- Chesapeake Bay Maritime Museum – Living history exhibits and lighthouse tours
- Thomas Point Shoal Lighthouse – A National Historic Landmark
- Cove Point Lighthouse – One of the oldest brick lighthouses on the Bay
- U.S. Naval Academy (Annapolis) – Campus tours with incredible maritime heritage
- Calvert Marine Museum – Home of the Drum Point Lighthouse
- Smith Island – Birthplace of Maryland’s famous multi-layer “Smith Island Cake”
- Bistro St. Michaels
- Ava’s Pizzeria & Wine Bar
- The Crab Claw
- Waterfront crab houses and Maryland’s famous crab cakes
- Dock-and-dine opportunities along Ego Alley
- Eastern Shore & Smith Island
- Dockside seafood
- Choose the length (half-day, full-day, sunset, weekend, or custom).
- Customize the itinerary with your captain.
- Pick your destinations based on history, food, swimming, or quiet coves.
- Pack lightly, with layers for spring and sun protection for summer.
- Use AI tools for weather, tide forecasting, and pre-trip planning — plus browse Shardana’s blog for route ideas.
Weekend Sail: A True Chesapeake Bay Getaway
A weekend charter with Shardana Sailing is the ultimate escape — a true, unhurried immersion into Chesapeake culture, food, and natural beauty. Spend sunrise on the water, explore multiple towns, dine at dockside restaurants, and anchor under the stars.
What You’ll Experience
Spring & Summer Tips
Spring: Perfect for quiet anchorages, cooler nights, and comfortable sleeping aboard. Wildlife is active and shore towns feel alive but not packed.Summer: Warm nights make for magical sunsets and after-dark stargazing. Expect vibrant nightlife in Annapolis and St. Michaels.
Weekend Itinerary (Sample for Planning)
Day 1: Rock Hall → Solomons IslandDay 2: Solomons Island → St. Michaels
Day 3: St. Michaels → Rock Hall
Must-See Historic & Cultural Attractions
Here are Chesapeake Bay “must-sees” to add to your trip:
Where to Eat Around the Bay
St. Michaels
Annapolis
Planning a Sail Trip with Shardana Sailing Charter
When planning a sail trip, Shardana makes it simple:
Sailing the Chesapeake Bay with Shardana Sailing Charter is more than a boat trip — it’s a journey through history, nature, and coastal culture. From lighthouse views to waterfront dining, from spring breezes to summer sunsets, the Bay’s magic is unforgettable.
