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Dorchester Center, MA 02124
Experience nearly 2 hours of sailing on a spacious 50' catamaran in Ocean City, Maryland, with dolphins, stunning views, and a friendly crew.
Ocean City: Sailing Catamaran Cruise with Crew – An Authentic Ocean Adventure
If you’re dreaming of a day out on the water in Ocean City, Maryland, a sailing catamaran cruise with a knowledgeable crew might be just what you need. This nearly two-hour voyage promises a blend of relaxation, adventure, and scenic beauty—all atop a roomy 50-foot vessel equipped with trampolines for lounging and cushioned seats for comfort. From dolphin sightings to the thrill of sailing in open waters, this experience offers a unique way to enjoy the Atlantic coast.
What really draws us to this tour is the emphasis on actual sailing—not just a boat ride. The moment the engines cut and the sails catch the wind, you’re in for a natural, peaceful glide over the waves. Plus, the chance to watch dolphins play off the bow is a highlight that even seasoned travelers find memorable. On the flip side, some may find the open water adventure a bit weather-dependent, so it’s worth checking the forecast before booking.
This experience suits a wide range of travelers—from families with kids above five to seniors with moderate mobility—who are looking for an authentic, relaxed day on the water. Whether you’re a sailing novice or a seasoned sailor, the friendly and professional crew ensures you’ll feel confident and comfortable throughout. If you’re craving a blend of scenic beauty, wildlife encounters, and the thrill of being at sea, then this tour is likely a perfect fit.
This cruise delivers a true sailing adventure, which sets it apart from more typical harbor or sightseeing boat tours. Starting from a marina slip at Olde Towne Marina, the trip kicks off with a prompt departure—be sure to arrive about five minutes early to avoid missing the boat. Parking can be a bit tight, so arriving early and perhaps grabbing a drink at the nearby restaurant makes for a leisurely start.
Once aboard Alyosha, a 50-foot catamaran, you immediately notice the generous space—ample room for everyone to spread out and relax. The boat features trampolines at the front, perfect for lounging and soaking up the sun. Cushioned seats are also available for those wanting a bit more support, making the experience suitable for most ages, including seniors with fair mobility.
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The trip generally lasts about 1 hour and 50 minutes, but it’s the sailing part that truly makes this stand out. The journey begins in the protected waters of the bay off Assateague Island, heading out through the OC Inlet—the roughest part of the trip but also the most exhilarating. Once out in the Atlantic, the captain and crew let the wind dictate the course, typically following a triangular route that offers both open water sailing and scenic views.
During the sail, the engines are turned off, and the boat moves solely on wind power, creating an authentic seafaring atmosphere. The thrill of feeling the boat glide along the waves, combined with the scenic backdrop of the coastline, is a highlight for many. Interestingly, reviewers have pointed out that dolphins often swim close to the boat, making for spectacular wildlife viewing. One guest described the crew as “interacting” and “very helpful,” which adds to the relaxed, friendly vibe.
One of the most captivating aspects of this tour is the chance to see dolphins swimming playfully near the boat. We loved the way the crew shared stories about Captain Steve Butz’s sailing adventures—adding a layer of personal connection and expertise to the experience. The natural beauty of the Atlantic on a clear day, combined with the playful dolphins, creates a sense of wonder that’s hard to match.
The boat is well-equipped with restrooms (“heads”), making the trip comfortable for families and older travelers. However, keep in mind that it’s a sailboat, so the toilets are more sensitive than land-based ones, and a little planning might be needed. The crew provides plenty of bottled water, but guests are encouraged to bring their own food and drinks if they wish.
Protection from the elements is important. While Alyosha has a roomy salon and cabins, the main action happens outside on deck. Sunscreen, sunglasses, and hats are highly recommended, especially during peak summer months.
At $119 per person, the price seems reasonable considering the length, the quality of the boat, and the opportunity for wildlife and scenic encounters. When you think about the value of sailing in open water, feeling the wind, and potentially seeing dolphins, the cost includes a memorable experience with professional guidance in a relaxed setting.
The included amenities—bottled water, cushions, trampolines—add to the value, making it a comfortable and engaging outing. The crew’s expertise and friendly demeanor, as shared by reviews, make the experience even more enjoyable.
Reviewers consistently mention the crew’s expertise and friendliness. Katie described Captain Steve and his daughter as “sailing experts” who are “kind and helpful.” Others appreciated how the crew interacted with guests, making everyone feel relaxed and part of the adventure. The sense of personal touch and genuine passion for sailing shines through, making the trip more than just a boat ride.
One guest noted that the boat is “amazing and so comfortable,” and that the experience was “definitely the best excursion in OC.” The natural interaction with dolphins and the scenic views are what most visitors remember long after their trip ends.
This cruise appeals most to those looking for an authentic sailing experience rather than just a sightseeing tour. It’s ideal for families with children over five, given the safety and comfort features, and for older travelers who want a scenic, gentle ride with plenty of opportunities to relax and enjoy.
It’s suitable for those who enjoy wildlife watching and natural scenery, as well as anyone curious about sailing and wanting to learn the ropes from a friendly crew. The tour’s weather dependence means it’s best booked during good conditions—so keep an eye on the forecast.
In a nutshell, the Ocean City Sailing Catamaran Cruise offers a genuine taste of the open sea, combining scenic beauty, wildlife encounters, and the peaceful rhythm of sailing. The spacious boat, friendly crew, and natural dolphin sightings make this a memorable outing, especially for those who appreciate authentic sea adventures.
While it’s weather-dependent and a bit on the pricier side, the experience’s authenticity and comfort make it worth considering for your time in Ocean City. Whether you’re celebrating a special occasion or simply craving a relaxing day on the water, this tour delivers a good mix of fun, relaxation, and natural wonder.
If you’re seeking a laid-back, scenic escape with a touch of adventure, this cruise might just be your perfect oceanic day out.
How long is the cruise?
The cruise lasts about 1 hour and 50 minutes, with the total experience around two hours including boarding and safety briefings.
Where does the tour depart from?
It departs from a marina slip at Olde Towne Marina, specifically alongside Pier 23 restaurant and bar.
Is parking available?
Parking can be challenging, so arriving early is recommended. You might also want to enjoy a drink at the restaurant nearby before heading out.
What should I bring?
Bring passport or ID for identification, weather-appropriate clothing, sunscreen, sunglasses, and any snacks or drinks you prefer since food and drinks are not included.
Is the cruise suitable for children?
Yes, it’s appropriate for most children above age 4 or 5, especially those who can handle moderate movement and enjoy wildlife viewing.
Are there restroom facilities onboard?
Yes, Alyosha has restrooms (“heads”), but they are more sensitive than land-based toilets, so use them accordingly.
What if the weather is bad?
The tour is weather-dependent. If canceled, you’ll be offered a different date or a full refund.
Can I bring my own food and drinks?
Absolutely. You’re encouraged to bring your own food and beverages for the trip.
In summary, the Ocean City sailing cruise offers an authentic, relaxed, and scenic experience that’s well suited to nature lovers and sailing enthusiasts alike. With friendly guides, ample space, and the chance to see dolphins in their natural habitat, it’s a compelling way to spend a memorable day at sea.