Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht

If you’ve ever dreamed of gliding over calm waters while taking in stunning bay views, this private sailing cruise in Chesapeake Beach might be just what you’re looking for. While I haven’t personally taken this exact trip, I’ve gathered enough details to give you a clear picture of what to expect. It’s a cozy, personalized way to enjoy the Chesapeake Bay, perfect for those who appreciate a mix of relaxation and a touch of adventure.

What stands out immediately is the intimate setting, with just your group on a spacious 42-foot yacht, and the chance to see wildlife like dolphins and ospreys—something many travelers find memorable. I also love that it offers a bit of hands-on fun, like steering the boat or pulling the sails if you’re into that. On the flip side, some might find it less ideal if they’re not comfortable on the water or looking for a more active or family-focused experience. Still, this tour is best suited for those who want a peaceful, scenic cruise with a sprinkle of sailing skills thrown in.

If you’re into scenic views, calming waters, and a chance to witness the bay’s passing ships and historic instruments, this cruise could be a highlight of your trip. Just keep in mind it’s a private experience, so you won’t be part of a large group, adding to the personal touch. It’s a little pricier than some other water activities, but the exclusivity and the views tend to justify the cost.

Key Points

• Private & intimate experience with a maximum of 6 guests, perfect for personalized service.
• Scenic views of the Chesapeake Bay, Cliffs of Calvert, and passing ships provide plenty of photo opportunities.
• Wildlife sightings like dolphins and ospreys add a special touch (though not guaranteed).
• Hands-on sailing opportunities available for those interested in steering or pulling sails.
• Water and snacks are complimentary, making the cruise comfortable without extra fuss.
• The cruise lasts around 2.5 hours, making it manageable but enough time to unwind and enjoy the surroundings.

You can check availability for your dates here:

Setting Sail in Chesapeake Beach

This cruise begins at the Rod N Reel Resort, a well-known spot that’s easy to find and offers convenient parking. The boat itself is a spacious 42-foot yacht, well-suited for a small private group. We liked that the experience is flexible—you can sit back and enjoy the views or get involved with sailing if you’re curious.

The primary draw is the chance to see stunning vistas of the Chesapeake Bay. As you cruise, you’ll pass the cliffs of Calvert, which are especially beautiful at sunset or on a clear day. The quiet waters make wildlife spotting more likely, and many reviews mention seeing dolphins or ospreys. While sightings aren’t guaranteed, the possibility adds an element of surprise and excitement.

The Itinerary and Highlights

The tour generally lasts about 2.5 hours, making it a manageable escape without feeling rushed. The skipper and first mate steer the boat, so you can relax and soak in the scenery. If you’re interested in sailing, the crew offers a private tutorial — teaching you how to steer or pull the sails. This isn’t a full sailing lesson, but it’s enough to get a feel for how the boat works.

An interesting aspect of this cruise is the display of historic instruments used in WWII to detect German U-boats. It’s a small but fascinating reminder of the bay’s past, and it’s likely to appeal to history buffs or those curious about the region’s wartime stories.

Throughout the cruise, you’ll see huge cruise ships and tankers traveling up and down the bay. Watching these giants move across the horizon adds to the sense of scale and activity on Chesapeake Bay. It’s also an opportunity to appreciate the busy, working nature of the waterway, contrasting with the peaceful cruise experience.

What’s Included and What to Consider

Included in your booking are the boat tour, water, snacks, and a first mate. The fact that water and snacks are provided makes the cruise feel more comfortable, especially on warm days. The private group setting ensures a quiet, personalized experience—no crowded boats here.

However, it’s worth noting that hotel pickup and drop-off aren’t included, so you’ll need to arrive at the meeting point—Dock X at the Rod N Reel Resort. Parking is free, which is a plus.

Some rules include no high-heeled shoes, pets, smoking, vaping, fishing, or red wine onboard. Also, the tour isn’t suitable for those with mobility impairments or motion sickness, so keep that in mind.

The Experience: What It Feels Like

Picture yourself on a comfortable yacht, feeling the gentle sway of the water, with the breeze cooling your skin. The captain and crew are friendly, sharing tidbits of local history and pointing out interesting sights like passing ships or historic instruments. You might get lucky and catch a glimpse of dolphins leaping nearby, adding a magical touch to the trip.

For those wanting some hands-on action, the opportunity to steer or pull sails is a highlight. It’s a fun chance to learn a bit about sailing without any pressure—perfect if you’re curious but not looking for a full-fledged sailing lesson.

Most travelers seem to appreciate the beautiful views of the cliffs and bay, which are especially stunning in good weather. The relaxed pace allows you to unwind, take photos, chat with your crew, or simply enjoy the scenery.

More Great Tours Nearby

The Cost and Value

At $654 for a group of up to six people, this cruise isn’t the cheapest activity around. That said, you’re paying for an exclusive, private experience with personalized attention and stunning scenery. If you’re traveling with friends, family, or a small group, it can feel like a good deal for a memorable, tailored outing.

Some reviews note that the experience provides a relaxing escape with enough time to enjoy the views, wildlife, and sailing. It’s not a high-energy activity, but if you’re after a peaceful, scenic journey with a touch of adventure, many find the price worthwhile.

Who Is This Tour Best For?

This cruise is ideal for couples, small groups of friends, or anyone seeking a tranquil bay experience. It’s particularly suitable if you enjoy scenic water views, wildlife spotting, or learning a bit about sailing. However, it’s not suited for those with mobility issues or seasickness, as the boat isn’t equipped for mobility aids, and the waters are calm but still moving.

If you’re looking for a family-friendly adventure with kids, it might work, but keep in mind the rules about pets and the fact that it’s not specifically designed for children. It’s more about quiet, scenic enjoyment than active or educational programs.

Final Thoughts

All in all, this private sailing cruise offers a quiet, personalized way to see the Chesapeake Bay. The views of the cliffs, passing ships, and wildlife make it a memorable experience, especially if you value tranquility and scenic beauty over high-energy activities. The opportunity to participate in sailing adds a fun dimension, whether you’re a seasoned sailor or a complete beginner.

The cost reflects the exclusivity and comfort of a private boat, making it a worthwhile splurge for those wanting a special day on the water. It’s best suited for those who enjoy peaceful waterways, scenic vistas, and a touch of maritime history.

If you’re after a relaxing, scenic escape that offers a great mix of views, wildlife, and hands-on sailing, this cruise probably deserves a spot on your Chesapeake Bay itinerary.

FAQ

Q: Is food included in the cruise?
A: No, food isn’t included, but you can buy some from the restaurant at the resort before or after your trip.

Q: Can I see wildlife during the cruise?
A: Wildlife sightings like dolphins and ospreys are possible, but they’re not guaranteed. It’s a bonus if you’re lucky.

Q: Do I need sailing experience to enjoy this tour?
A: No experience is necessary. The crew offers a private tutorial if you want to learn how to steer or pull the sails.

Q: How long is the cruise?
A: The cruise lasts about 2.5 hours, which is enough time to relax and enjoy the scenery without feeling rushed.

Q: Is parking available at the meeting point?
A: Yes, free parking is available at the Rod N Reel Resort.

Q: Is this tour suitable for children?
A: It’s not specifically designed for kids, and there are rules against pets and smoking. It’s best for adults or older children comfortable on the water.

If you’re craving a peaceful, scenic boat ride with a touch of sailing fun in Chesapeake Beach, this private yacht experience could be just what you’re looking for. It’s an intimate way to enjoy the bay’s beauty, with plenty of opportunities for wildlife viewing and relaxation.

You can check availability for your dates here: