Two excellent boat tours await in Chesapeake Beach, Maryland. The practical 2.5-hour Chesapeake Bay Cruise is perfect for sightseeing and includes light snacks – a good value for families and nature enthusiasts. For a more intimate experience, we love the Private Sailing Cruise aboard a 42-foot yacht, which offers close-up views of the magnificent Calvert Cliffs and hands-on sailing lessons. The smaller group sizes on both tours mean better wildlife viewing and personal attention from guides. While these aren’t suitable for travelers prone to seasickness or those with limited mobility, they’re the best way to experience the bay’s natural splendor. Let’s look at our recommended tours.
Key Points
- Chesapeake Bay Cruises offer scenic 2.5-hour guided tours aboard a 42-foot yacht, providing a relaxing and highly-rated water activity.
- The private sailing cruise experience on the 42-foot yacht allows visitors to enjoy stunning views, spot wildlife, and learn sailing techniques.
- Pricing for the Chesapeake Bay Cruise and private sailing cruise are competitive, with group sizes kept small for a personalized experience.
- Accessibility and mobility limitations exist, but the cruises offer a flexible cancellation policy and a reserve now, pay later option.
- Highlights of the cruises include breathtaking Chesapeake Bay scenery, learning about the local environment, and engaging with knowledgeable guides.
Chesapeake Beach: Chesapeake Bay Cruise With Snacks

The Chesapeake Beach: Chesapeake Bay Cruise With Snacks offers visitors a chance to explore the scenic waterways of the Chesapeake Bay. This guided tour lasts 2.5 hours and accommodates a private group. Guests will sail aboard a 42-foot yacht, taking in the picturesque views of the bay and its surrounding landscapes.
During the cruise, snacks will be provided, allowing travelers to relax and enjoy the experience. The small group size ensures an intimate and personalized outing, with the opportunity to ask questions and learn more about the local environment from the knowledgeable guide.
Priced at €649.15 per group (up to 1 person), this private sailing excursion ranks highly among the water activities available in Chesapeake Beach.
Factors such as popularity, diversity, availability, customer ratings, and performance over time contribute to its strong positioning. For those seeking a unique and memorable way to experience the Chesapeake Bay, this cruise is an excellent choice.
Read our full review: Chesapeake Beach: Chesapeake Bay Cruise With Snacks Review
Book now: Check availability
Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht

For those seeking a unique and memorable way to experience the Chesapeake Bay, the Private Sailing Cruise on a 42-Foot Yacht offers an exceptional opportunity.
This 2.5-hour private sailing adventure takes guests on a stunning journey along the Cliffs of Calvert, providing breathtaking views and the chance to spot dolphins and ospreys.
Priced from $686.00 per group (up to 6 people), the cruise allows participants to steer the boat and learn sailing techniques from the knowledgeable first mate. Guests can also observe historic instruments used to detect German U-boats during World War II and watch as cruise ships and tankers navigate the bay.
Complimentary water and light snacks are provided, and free parking is available at the meeting point.
While the cruise isn’t suitable for those with motion sickness or mobility issues, it promises an unforgettable experience for those who can participate.
With a flexible cancellation policy and a reserve now, pay later option, this private sailing cruise is a must-try for anyone exploring the beauty of the Chesapeake Bay.
Read our full review: Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht Review
Book now: Check availability
Frequently Asked Questions
What Are the Safety Protocols on the Cruises?
The cruises have safety protocols in place to protect passengers. They’ve got life jackets, emergency procedures, and well-trained staff to ensure everyone’s safety throughout the voyage. These measures aim to provide a secure and enjoyable experience for all travelers.
Can I Bring My Own Food and Drinks?
Passengers are generally allowed to bring their own food and drinks on most cruises and boat tours. However, it’s important to check the specific policies of the cruise line or tour operator before setting sail.
What Are the Wheelchair Accessibility Options?
The cruise lines generally provide wheelchair-accessible areas and offer assistance to passengers with mobility needs. Many offer ramps for boarding and designated seating areas. Passengers should inquire about specific accessibility accommodations when booking their cruise.
How Long Are the Typical Cruises and Tours?
The typical cruises and tours in the area last from 1 to 2 hours. Many offer options for longer excursions as well, ranging from half-day to full-day trips. The length varies depending on the specific cruise or tour selected.
Do the Cruises Offer Any Educational or Interpretive Programs?
Many cruises and tours offer educational or interpretive programs to enhance the experience. They may feature naturalist guides who share information about the local wildlife, ecosystems, and history of the area during the excursion.
Recap
Chesapeake Beach offers a variety of cruises and boat tours for visitors. From scenic Chesapeake Bay cruises with snacks to private sailing trips on a luxurious yacht, there’s something to suit every taste. With stunning waterfront views and the opportunity to explore the region’s rich maritime heritage, these boat tours provide a delightful way to experience the charm of Chesapeake Beach.
