Chesapeake Beach, Maryland, is a standout spot for those who want to combine scenic views with authentic local experiences. Its proximity to the Chesapeake Bay makes it an ideal place for sailing adventures, and the variety of tours available caters to all interests—whether you’re after a relaxing day on the water or a walk through historical sites. We’re particularly fond of the Beautiful Day Sailing the Chesapeake Bay because of its chance to see dolphins and ospreys in their natural habitat, along with the unique opportunity to learn about the Bay’s WWII role. Plus, steering the boat yourself adds an extra layer of fun.
For those interested in history and stunning vistas, the Guided Walking Tour to The Cliffs offers a relaxed stroll with wonderful views, historical insights, and visits to the Chesapeake Beach Railway Museum. And if you want a private experience, the Private Sailing Cruise on a 42-Foot Yacht promises luxury, quiet waters, and the chance to steer or spot wildlife in a more intimate setting. Below, you’ll find detailed descriptions of these top Chesapeake Beach tours, helping you choose the perfect experience.
1. Chesapeake Beach: Beautiful Day Sailing the Chesapeake Bay
At number one on our list is the Beautiful Day Sailing the Chesapeake Bay. For $102 per person, you get a 2.5-hour sailing trip that departs from Chesapeake Beach. What sets this tour apart is its focus on wildlife viewing, including dolphins and ospreys, which are common sights on the trip. The captain will take you past the striking Calvert Cliffs and share stories about the Bay’s lesser-known WWII history, such as maritime defenses and submarine tracking stations—topics that add depth to the scenery.
This tour is ideal for travelers looking for an active, engaging experience. You’ll have the chance to steer the boat, which is rare on most sailing tours, making it perfect for those who want to feel like a true sailor. Watch cruise ships and tankers making their way through the bay—an impressive sight that highlights the Bay’s importance as a shipping route. The fossils along the Cliffs of Calvert are also visible from the water, giving a unique perspective that land-based tours can’t match.
Bottom Line: This tour offers a balanced mix of wildlife, history, and hands-on sailing in a friendly, small-group setting. It’s especially suitable for those who love being on the water and want a memorable, interactive experience.
2. Chesapeake Beach: Guided Walking Tour to The Cliffs
The Guided Walking Tour to The Cliffs is a 1.5-hour stroll that combines scenic views with local history for just $41 per person. This tour is perfect for visitors who prefer a relaxed pace but still want to learn about Chesapeake Beach’s fascinating past and natural features. The guide shares insights into the town’s development and the significance of the Cliffs of Calvert, which have drawn visitors for generations.
You’ll walk down to the shoreline to admire the spectacular elevated views of Chesapeake Bay, which are particularly striking at sunrise or sunset. The tour also visits historic homes perched along the cliffs, showcasing architectural styles and stories from past residents. Included is a visit to the Chesapeake Beach Railway Museum, where you can learn how the railway transformed this quiet seaside town into a bustling vacation spot.
This tour appeals to history buffs and nature lovers alike, offering an easy way to combine educational content with scenic beauty. The walk is accessible, making it suitable for many fitness levels, and the intimate group size enhances the experience.
Bottom Line: A great choice for those who want a slow-paced, informative experience that combines history, architecture, and breathtaking views without leaving the town.
$41 per person
3. Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht
For those seeking privacy and luxury, the Private Sailing Cruise on a 42-Foot Yacht is the way to go. Priced at $654 for up to six people, this 2.5-hour experience is perfect for celebrating a special occasion or simply enjoying a peaceful escape. The yacht offers plenty of space for relaxing while cruising through the calm waters of Chesapeake Bay.
During the trip, you’ll see the Cliffs of Calvert from a different perspective and spot passing cruise ships and tankers—an impressive display of the bay’s busy maritime traffic. The tour provides historical insights into WWII, including the historic instruments used to detect German U-boats, adding an educational twist. Wildlife viewing is also a highlight—dolphins and ospreys are common sights, and there’s an opportunity to steer the boat, making this a personalized adventure.
Snacks and water are included to keep you comfortable as you soak in the breathtaking scenery. This cruise is ideal for groups seeking exclusivity, comfort, and a tailored experience on the water.
Bottom Line: This private yacht tour offers a luxurious, customizable experience, perfect for those celebrating a special event or simply wanting a relaxing, upscale day on the bay.
$654 per group up to 6
How to Choose
Choosing between these Chesapeake Beach tours depends on your interests and budget. If wildlife, hands-on sailing, and history are your main priorities, the Beautiful Day Sailing is an excellent pick for active travelers. For a more laid-back, educational experience, the Guided Walking Tour offers scenic views and local stories at a budget-friendly price. Finally, if you value privacy and comfort, the Private Yacht Cruise provides an upscale, intimate setting suitable for special occasions or a quiet day with family or friends.
Think about how much time you have—most tours are under three hours—and what kind of experience appeals most: active adventure, historical exploration, or luxurious leisure. Booking early is recommended, especially for private cruises, as they fill quickly during peak seasons.
Final thoughts
Chesapeake Beach offers a variety of tours that showcase the natural beauty and maritime history of the Chesapeake Bay. Whether you want to sail on a shared boat, take a leisurely walk with scenic views, or enjoy a private yacht experience, there’s something to match your travel style. For an active day on the water, the Beautiful Day Sailing stands out. If history and scenery are more your speed, the Guided Walking Tour is a bargain and offers plenty of photo opportunities. And for special occasions or ultimate comfort, the Private Yacht Cruise delivers a memorable, personalized adventure.
No matter which option you choose, booking in advance ensures you get the best time slot. Chesapeake Beach truly offers a friendly, scenic escape filled with opportunities to experience the water and history up close. We recommend choosing a tour that fits your interests and making it part of your Maryland getaway—these experiences will leave you with stories to tell and memories to cherish.