Get Out on the Chesapeake Bay This Summer

The Chesapeake Bay is one of the most significant features of the Eastern Seaboard and certainly a prime reason to visit the Eastern Shore of Maryland. It is the largest marine estuary in the country, and as such, this stunning ecosystem is a true natural wonder. Though there are various ways to enjoy this body of water, Chesapeake Bay boat tours do, of course, reign supreme.

Aside from simply being a beautiful way to spend an afternoon, Chesapeake Bay boat tours offer a unique opportunity to fully immerse and connect with the bay’s enchanting waters in a way you can’t do on land. Whether you’re inclined towards a leisurely sightseeing sail around the bay or a hands-on fishing expedition, there are plenty of Chesapeake Bay boat tours.

These boat tours offer an excellent way to observe the bay’s wildlife and diverse habitats while also gaining an understanding of the marine estuary dynamics. One cruise around the bay, and we think you’ll come away with a new perspective on the importance and value of this stunning ecosystem. Moreover, these Chesapeake Bay boat tours offer an ideal way to disconnect from the hustle and bustle of daily life.

If finding solace away from the harried every day is at least part of your goal when visiting the Eastern Shore, then you’ll find the perfect home away from home at our Rock Hall, MD Bed and Breakfast. Here, the day’s adventures on the bay transition seamlessly into evenings of relaxation and reflection, surrounded by the comfort and hospitality that Maryland’s Eastern Shore is renowned for. It’s a perfect way to deepen your connection with this remarkable region, ensuring that the memories of your time on the Chesapeake Bay linger long after your boat has docked. Book your stay at our top-rated Bed and Breakfast today!

The Best Chesapeake Bay Boat Tours

Nothing compares to being out on the water while the fresh air blows through your hair. If you want to explore the Chesapeake Bay during your time on the Eastern Shore, consider taking a sailing excursion or other boating experience. Whether you’re a seasoned sailor or new to boating, you’ll love the experience of being out on the water, enjoying the serene natural beauty, and getting to know the rich cultural history of these waters.

Rock Hall’s history is deeply intertwined with The Chesapeake Bay. Established in the 18th century, Rock Hall grew as a vital port town. Its strategic location on the bay made it an essential point for shipping, but it was a particularly crucial port to industries like fishing, crabbing, and oystering, which have been the lifeblood of the community for centuries. These industries not only shaped the local economy but also influenced the culture and traditions of Rock Hall. As they are locally known, these watermen have passed down their knowledge and skills through generations, maintaining a deep connection with the bay’s waters.

Whether you’re looking for a leisurely day sail, a romantic sunset cruise, or a more exhilarating fishing experience, the Chesapeake Bay has something for every maritime enthusiast. Many top-rated boat tours leave from right here in Rock Hall, too, making this an easy afternoon excursion for guests at our Inn. We’ve listed our favorite boat tours on the Chesapeake Bay below.

Blue Crab Charters is our top choice for Chesapeake Bay boat tours. They offer a range of cruises aboard their fleet of sailboats, including day sails, sunset cruises, and private events. They’ve served the area for over 25 years, making them a staple in Rock Hall’s maritime community. This is the tour operator included with our Adventure Getaway Package, which includes a 90-minute sail, a picnic lunch basket to take with you, and a dinner for two at a local restaurant.
Another local tour operator is Shardana Sailing Charters. They offer a luxury private sailing experience with a range of options, including half and full-day adventures, sunset sails, and more.
For a variety of Chesapeake Bay boat tours, including full-day, sunset, and even overnight adventures, look to Experience Sail in Rock Hall.
If you’re interested in fishing, we recommend Wayne Gatling Guide Services, a local guide service that has been leading fishing excursions on The Bay for 50 years!

Where to Kayak on the Eastern Shore

Of course, these aren’t the only Chesapeake Bay boat tours you can take while in town. If you’re looking for something a little more relaxed and at your own pace, consider a kayaking adventure. The stunning Chesapeake Bay and its many inlets and backwaters are a kayaker’s dream.

There are more than 20 designated Chesapeake Bay Water Trails to paddle, giving you a fantastic guide to the different ecosystems and areas worthy of your time. You can design your own adventure, too – and you can launch it from right here at our Rock Hall, MD Bed and Breakfast!

Just a quarter-mile stroll from our Bed and Breakfast to our dock grants access to complimentary kayaks, inviting beginners to explore the tranquil waters of our inlet. It’s a great place to start your Chesapeake Bay kayaking journey, but it’s also the perfect place for those new to the sport to try a safe and easy paddle. It won’t matter too much where you go, as you’ll find Chesapeake Bay teeming with diverse bird species, other wildlife, and beautiful scenery everywhere you turn.

Beyond our calm little inlet, one of our favorite places to enjoy kayaking on the Chesapeake Bay is the Blackwater National Wildlife Refuge Paddling Trails. This spot is often called the “Everglades of the North,” thanks to the diverse habitats you’ll find here. There are over 50 acres of forests, fields, and marshes, and the water teems with wildlife. For more Chesapeake Bay kayaking, head to the Eastern Neck Island Water Trail (#12 on this list).

Local guides can also take you on a Chesapeake Bay kayaking adventure. We love to team up with our friends at Chester River Kayak Adventures. They provide expert-led tours, including half-day and sunset expeditions. They also offer kayak rentals, allowing you to craft your own journey or enjoy a week-long water adventure. However you choose to interact with The Chesapeake Bay, we look forward to treating you to a comfortable and peaceful retreat on the Eastern Shore of Maryland. Book your room with us today!