Chesapeake Beach’s private sailing cruise offers an unparalleled opportunity to take in the region’s natural beauty aboard a 42-foot yacht. For 2.5 hours, guests can expect to witness stunning cliffs, spot local wildlife, and even steer the boat under the guidance of the first mate. With a knowledgeable tour guide providing insights, participants can learn sailing techniques while enjoying complimentary refreshments. Whether you’re a seasoned sailor or a curious novice, this sailing adventure promises an unforgettable experience that may just leave you craving more of the Chesapeake’s enchanting charm.
This experience made our list of the 2 Best Cruises And Boat Tours In Chesapeake Beach Maryland.
Key Points

- A private sailing cruise on a 42-foot yacht that departs from Chesapeake Beach for 2.5 hours, starting from $686.00 per group (up to 1 person).
- Opportunity to steer the boat, learn sailing techniques, and observe historic instruments from WWII, along with spotting local wildlife like dolphins and ospreys.
- Onboard amenities include complimentary water and light snacks, a spacious and comfortable yacht, and a first mate for continuous assistance.
- Not suitable for individuals with mobility impairments due to the dynamic nature of sailing, the narrow hull design, and the steep steps with limited handrails.
- Guests will experience stunning views of the Cliffs of Calvert, navigate the waters of Chesapeake Bay, and gain insight into the region’s rich nautical heritage.
Activity Overview

The article highlights a private sailing cruise on a 42-foot yacht, departing from Chesapeake Beach and lasting 2.5 hours, with a cost starting from $686.00 per group (up to 1 person), and a live English-speaking tour guide.
Guests can enjoy the stunning views of the Cliffs of Calvert as they sail through the Chesapeake Bay.
The experience also includes the opportunity to steer the boat and learn sailing techniques, as well as the chance to spot local wildlife like dolphins and ospreys.
Plus, the cruise allows guests to observe historic instruments used to detect German U-boats during WWII and watch cruise ships and tankers navigate the bay.
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Experience Highlights

Sailing through the Chesapeake Bay offers guests stunning views of the Cliffs of Calvert, providing a picturesque backdrop to the experience. Participants can steer the boat themselves and learn various sailing techniques from the knowledgeable crew. Plus, they’ll have the opportunity to spot local wildlife, including dolphins and ospreys, as the yacht navigates the waters.
During the cruise, guests can also observe historic instruments used to detect German U-boats during World War II, gaining insight into the bay’s rich maritime history. As the yacht sails, participants can watch cruise ships and tankers navigate the waterways, adding to the immersive and educational nature of the excursion.
| Wildlife Spotting | Hands-on Sailing | Maritime History |
|---|---|---|
| Dolphins | Boat Steering | WWII U-boat Detection |
| Ospreys | Sailing Techniques | Cruise Ship Watching |
| – | – | Tanker Observation |
Onboard Amenities

Complimentary water and light snacks are always provided to guests throughout the cruise’s duration.
The spacious and comfortable yacht offers a relaxed experience, with a first mate available to assist passengers continuously.
Whether you’re taking in the stunning views of the Cliffs of Calvert or spotting local wildlife like dolphins and ospreys, you’ll have everything you need to enjoy the journey.
The yacht’s onboard amenities are designed to make your sailing adventure as comfortable and carefree as possible.
With the first mate’s expertise on hand, you can simply sit back, relax, and let the gentle breeze carry you through the tranquil waters of the Chesapeake Bay.
Meeting and Departure Information
Guests can find the departure point at the Rod N Reel Resort, located at dock X (Old Dock A), slip 15. Participants are encouraged to check availability for starting times, as the sailing cruise offers a range of departure options throughout the day.
Upon arrival, guests will be greeted by the friendly crew, who’ll guide them to the 42-foot yacht. The crew will provide a brief orientation and safety overview before setting sail.
Departures are punctual, so guests are advised to arrive a few minutes early to ensure a smooth start to their Chesapeake Bay adventure. With the flexibility of multiple departure times, guests can easily incorporate the sailing cruise into their Chesapeake Beach itinerary.
More Great Thing To Do NearbyRestrictions

Why is this sailing cruise not suitable for individuals with mobility impairments or motion sickness?
The boat’s design and the dynamic nature of sailing on the Chesapeake Bay may pose challenges for those with limited mobility or susceptibility to seasickness. Guests should consider their physical capabilities and tolerance for motion before booking this experience.
This private sailing cruise takes place on a 42-foot yacht, which features:
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A narrow, slender hull that can sway and rock with the waves
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Steep steps leading down to the cabin and up to the deck
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Limited handrails and secure seating for stability
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Potential for sudden movements and disorientation from wind and currents
Those with mobility issues or prone to motion sickness may find this cruise uncomfortable or inaccessible.
Guests are advised to assess their physical fitness before reserving this sailing adventure.
Sailing Through Chesapeake Bay
As the 42-foot yacht gently glides across the waters of Chesapeake Bay, guests are treated to stunning vistas of the Cliffs of Calvert, a natural geological wonder along the shoreline.
The sailboat’s sails billow in the wind, propelling the vessel forward as the crew points out local wildlife like dolphins and ospreys. Participants may even have the chance to steer the boat themselves, learning the basics of sailing under the guidance of the experienced first mate.
Throughout the cruise, guests can observe historic navigational instruments once used to detect German U-boats during World War II, and watch as massive cruise ships and tankers make their way across the bay.
Steering the Boat and Learning Techniques
The experienced first mate takes guests through a hands-on tutorial, demonstrating the proper techniques for steering the sailboat and adjusting the sails to harness the wind.
Guests learn to:
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Grip the wheel firmly and make small, controlled adjustments to keep the boat on course.
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Read the wind direction and position the sails accordingly to maximize speed and efficiency.
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Communicate with the crew to coordinate sail changes and maneuvers.
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Work together as a team to navigate the vessel through the tranquil waters of the Chesapeake Bay.
With the first mate’s guidance, everyone has the chance to take the helm and experience the thrill of sailing firsthand, developing a newfound appreciation for the art of yacht handling.
Spotting Local Wildlife and Observing Instruments
Along With navigating the yacht and learning sailing techniques, guests on the Chesapeake Beach sailing cruise can spot an array of local wildlife and observe historic instruments used during World War II.
Sailing through the tranquil Chesapeake Bay, visitors may catch glimpses of playful dolphins or majestic ospreys soaring overhead.
The cruise also offers the opportunity to view the historic instruments that were once used to detect German U-boats, providing a fascinating glimpse into the region’s wartime past.
As the yacht glides past cargo ships and cruise liners, guests can appreciate the breadth of maritime activity in the bay and gain a deeper understanding of the area’s rich nautical heritage.
Frequently Asked Questions
Can We Bring Our Own Food and Drinks on Board?
Yes, guests can bring their own food and drinks on board. The cruise provides complimentary water and light snacks, but guests are welcome to bring additional items to enjoy during the sailing experience.
What Is the Dress Code for the Sailing Cruise?
The dress code for the sailing cruise is casual and comfortable. Guests are encouraged to wear lightweight, breathable clothing that they don’t mind getting a bit wet. Closed-toe shoes are recommended for safety on the boat’s deck.
Are There Any Age Restrictions for the Passengers?
The sailing cruise does not have any age restrictions, as it’s suitable for passengers of all ages. Children are welcome to join the cruise, as long as they’re accompanied by an adult. The cruise’s flexible nature allows for a fun experience for the whole family.
Can We Disembark and Explore the Local Area During the Cruise?
No, passengers cannot disembark and explore the local area during the cruise. The 2.5-hour sailing experience is a private tour that does not allow passengers to leave the yacht. The cruise remains on the water throughout the duration.
Is There an Option to Extend the Duration of the Cruise?
Customers can inquire about extending the cruise duration during booking. The standard tour is 2.5 hours, but the company may offer longer options based on availability and customer preference for an additional fee.
Recap
The Chesapeake Beach private sailing cruise offers an unforgettable adventure on a 42-foot yacht.
Guests can marvel at the stunning Cliffs of Calvert, spot dolphins and ospreys, and even steer the boat under the guidance of the first mate.
With complimentary water, light snacks, and an English-speaking tour guide, this sailing experience provides a unique and relaxing way to explore the beauty of the Chesapeake Bay.
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