Chesapeake Beach in Maryland offers more than just seaside views—it’s a top spot for memorable cruises and boat tours that showcase the natural beauty and maritime history of Chesapeake Bay. The town’s convenient location on the bay makes it easy to hop aboard a vessel for a close-up look at dolphins, ospreys, and historic landmarks like the Calvert Cliffs. Whether you’re craving a lively day sail with the chance to steer or a private yacht experience with personalized touches, Chesapeake Beach delivers authentic water-based adventures. Plus, many tours include unique features like fossil viewing or WWII relics, adding a layer of educational fun.
If you’re trying to decide how to spend your time on the water, this guide breaks down two standout options. One is a lively, guided day sail perfect for wildlife lovers and history buffs, while the other is a private yacht cruise suited for those seeking a more intimate experience. Both tours promise a chance to learn about Chesapeake Bay’s ecology and maritime significance — and perhaps even try your hand at steering the boat.
Quick Overview
This list covers two of the best cruises and boat tours in Chesapeake Beach Maryland. The first is the Chesapeake Beach: Beautiful Day Sailing the Chesapeake Bay, a 2.5-hour group day sail that offers wildlife sightings and historic insights. The second is the Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht, a more exclusive 2.5-hour experience for up to six people with personalized options.
1. Chesapeake Beach: Beautiful Day Sailing the Chesapeake Bay
At number one, this 5-star-rated cruise combines the joy of sailing with a chance to see dolphins and ospreys in their natural habitat. Departing from Chesapeake Beach, the 2.5-hour Beautiful Day Sailing is designed to give you a hands-on experience, with the opportunity to steer the boat if you wish. The tour includes views of the Calvert Cliffs, providing a spectacular backdrop and a unique waterside perspective on fossil-rich formations.
What sets this tour apart is the blend of wildlife viewing and historical storytelling. You’ll learn about Chesapeake Bay’s role in World War II, which many visitors find surprising and engaging. Watching large cruise ships and tankers pass through the bay’s strait adds an extra element of awe. The friendly, knowledgeable captain and crew ensure a safe, fun environment, and the reviews highlight the welcoming atmosphere and the “great conversations” shared onboard. The small-group setting makes it ideal for families, couples, or solo travelers wanting a relaxed yet informative outing.
Bottom Line: This cruise offers excellent value for the experience, wildlife encounters, and historical insights packed into a short, 2.5-hour sail. Perfect for first-timers or those craving an active, engaging day on the water.
2. Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht
If privacy and personalized service are your priority, the Private Sailing Cruise on a 42-Foot Yacht ranks highly with a 4.7-star rating. For around $654 per group (up to six people), this 2.5-hour tour offers a more intimate experience with plenty of opportunities to sail, relax, and take in the scenery.
The yacht is equipped with historic WWII instruments used to detect German U-boats, turning this into a mini maritime museum at sea. As you glide through Chesapeake Bay, you’ll get close-up views of the Cliffs of Calvert and watch massive cruise ships and tankers navigate the bay’s busy waterway. This tour is ideal if you want a more tailored experience, with options to steer the yacht or simply sit back with snacks and water onboard.
Most travelers appreciate that this cruise combines luxury, education, and sightseeing. The familiarity of the crew and the chance for close wildlife observation, such as dolphins and ospreys, make it perfect for couples, small groups, or anyone celebrating a special occasion. The trip’s premium quality and privacy come with a higher price tag, but for those seeking exclusivity, it’s an excellent choice.
Bottom Line: This private yacht tour is best suited for those wanting a customized, relaxed outing with the comfort of a small-group experience. It’s a bit pricier but offers a level of intimacy and luxury that many travelers find worth it.
How to Choose
When deciding between these two tours, consider your budget, group size, and what kind of experience you most enjoy. The group day sail offers a lively, social atmosphere perfect for wildlife and history lovers. Meanwhile, the private yacht appeals to those looking for a quieter, more personalized adventure.
If wildlife viewing and hands-on sailing are your priorities, the first tour provides excellent value and a fun, engaging experience. For a more exclusive, customizable outing with added comfort and privacy, the private yacht is a worthwhile splurge. Booking early is recommended, especially in peak season, to secure your preferred time.
Chesapeake Beach’s cruises and boat tours deliver a variety of ways to enjoy Chesapeake Bay—whether you want a lively group outing, a romantic private cruise, or an educational adventure. For a family outing, the day sail offers a perfect mix of wildlife and history, while couples seeking a special experience might prefer the quiet comfort of a private yacht. Both options guarantee a memorable day on the water—and a deeper appreciation for this scenic part of Maryland. If you’re ready to set sail, booking early will help you secure the best times and make the most of your Chesapeake Bay visit.