Cruising the Chesapeake Bay on a Leopard 42


Sailing in the tropics is no revelation to me. From the Bahamas to the Dry Tortugas, I've sailed in the golden warm sunlight plenty of times. This fall, I was given the opportunity to take out the popular Leopard 42 to sail somewhere I’d never been before: The Chesapeake Bay. This quick 3-day journey was nothing short of extraordinary, and we made pit stops at a few tourist hotspots, like the Maritime Museum in the quaint town of St Michaels. If you’re ready for a change of scenery and weather to get you excited for the holiday season, sailing the Chesapeake Bay in the fall is the perfect change of pace. Before you keep reading, check out the video from our long weekend here.


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Open Waters 

We started our journey from Port Annapolis Marina and made our quest to the Maritime Museum. The voyage was about 25 nautical miles and winds were fairly light. We spent some of the journey under sail but decided to motor sail the last half of the way for the sake of time. The temperature was somewhere in the 50's, which was such a breath of fresh air from the normal scorching summer days I'm used to. The air was crisp and the light gray clouds filled the sky with tiny beams of light peaking through. It was most certainly a brisk autumn day. The Chesapeake Bay Bridge Tunnel was an extravagant sight to see. It is the longest fixed water crossing in Maryland with a length of about 4.35 miles. Spending the day on the open waters all bundled up with a cup of coffee was both a cozy and thrilling experience. 


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Maritime Museum 

When we finally arrived at the Maritime Museum, we were astonished by the historic lighthouse.  Our slip had been reserved ahead of time, so it was a breeze docking the Leopard 42 and connecting to shore power. We had a favorable spot right in front of the 1879 Hooper Strait Lighthouse and the Maritime Museum. The lighthouse is accessible for free to anyone who visits the museum. 


The Chesapeake Bay Maritime Museum opened in 1965 and was formerly a complex of seafood packing houses, workboats, and docks. It is an 18-acre waterfront campus that explores and preserves the environment, culture, and history of the Chesapeake Bay region. Since it opened, its vision has been to tell the stories of the people who once inhabited the region. The museum is full of physical visualizations and hands-on accessories. It is also very kid-friendly while being a very informative and fascinating experience. 


The Hooper Strait Lighthouse was built in 1879 to light the way for boats navigating the shallow shoals of Hooper Strait. The lighthouse illustrates how the 19th-century lighthouse keepers tended to their station. It is a very hands-on exhibit, and visitors can climb the sea hatch, tend the giant lens, or stand watch on the lookout for ships. If you step out onto the highest-floor balcony, you can see the breathtaking Chesapeake Bay from all sides. The lighthouse was my personal favorite, and I spent a good hour reading about all of the ways lighthouse keepers lived. 


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Not only were these places of interest enthralling - but the employees and staff were absolutely astounding.  They were welcoming, helpful, and accommodating during every bit of our stay. Both the museum and lighthouse were great attractions for school field trips, families, or tourists eager to learn the history of Chesapeake Bay. 


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Exploring the Town

On the second day of our expedition, we decided to explore the charming town of St Michaels. It was a very calm town with plenty of Federal, Gothic Revival, and Italianate architecturally structured houses. We took it upon ourselves to rent bikes to look about. Exploring the beautiful neighborhood homes was especially intriguing, mainly because I am used to Florida architecture. Most of the homes were decorated with fun Halloween and fall-themed knick-knacks. The houses of St Michaels resembled the striking northern homes you see in Hallmark movies. The leaves on the trees were starting to change colors, and some had even fallen to the ground, radiating a homely fall feeling. The sun was shining, but there was a cool, fresh wind. The weather on this day of exploration couldn't have been more ideal. 


There were a few popular restaurants, cafes, and small shops along the main streets. Plenty of the people wandered the town, leisurely meandering from one place to the next. Throughout the trip, I was able to try a few different places, and I was delightfully impressed with both the food and service. We ended the day with ice cream cones from a local parlor and took in the enchantment St Michaels had to offer. 


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Inn At Perry Cabin 

If you're looking for a captivating place that encapsulates the elegance of St Michaels, the Inn at Perry Cabin is a perfect depiction. When the sun goes down, the glowing lights along the water reflect beautifully off of the Chesapeake Bay. This resort on the Eastern Shore is both cozy and luxurious with waterfront views. The crew of the Leopard 42 took the opportunity to enjoy a romantic night right outside of the inn. It was a candlelit evening on the flybridge of the Leopard 42, with champagne and plenty of ambiance. If romance is in the air, the Inn At Perry is an ideal destination for a perfect date night.


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Unforgettable Memories 

Sailing the Leopard 42 through the Chesapeake Bay was an exceptional experience. Navigating those waters in the fall is uniquely different from the tropics, but it adds an unexpected charm to the adventure. The trip was nothing short of remarkable and if the opportunity arose, I would eagerly visit St Michaels again. It served as a compelling reminder to step out of one's comfort zone and savor the diverse facets of sailing, proving that the other side of the nautical spectrum has its own beauty and allure.


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Topics: Leopard 42

Cristina Strait

Cristina is a Senior Yacht Sales Marketing Coordinator and Event Planner specializing in the growth of the sailing and boating industry.


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