Ocean City: Sailing Catamaran Cruise with Crew

Imagine gliding across the Atlantic Ocean aboard a 50-foot catamaran, feeling the wind in your hair and spotting playful dolphins swirling around the boat. For just $110 per person, this nearly two-hour sailing trip offers a fantastic way to see Ocean City from a different perspective. Led by a certified crew, including Captain Steve Butz, known for his adventurous sailing tours, this experience strikes a good balance between relaxed sightseeing and engaging ocean activity.

What we love about this trip? First, the spacious deck with trampolines invites you to lounge comfortably while soaking up the sun and ocean air—perfect for a chill day or a lively thrill, depending on weather. Second, the chance to watch dolphins swim alongside the boat is truly special — a natural highlight that makes every trip memorable. The only potential downside? Because the trip is weather-dependent, rough seas or poor conditions might lead to cancellations or a less smooth ride, so flexibility is key.

This cruise suits anyone with a sense of adventure who appreciates natural beauty and appreciates safety. It’s especially ideal for families with children over age 4, seniors with fair mobility, or anyone looking for a relaxing yet active experience on the water. If you’re eager for a taste of open ocean sailing, with the possibility of dolphin sightings and stunning views, this tour will likely hit the right note.

Key Points

• Authentic Sailing Experience: The trip is centered on actual sailing, not just a boat ride, with the engines turned off to enjoy the wind.
• Natural Encounters: Dolphins often join the cruise, providing unforgettable moments for animal lovers.
• Spacious and Comfortable: Plenty of room on the deck, with trampolines and cushioned seating for relaxation.
• Expert Guidance: Captain Steve and crew make safety and comfort a priority, sharing stories of their sailing adventures.
• Weather-Dependent: The experience relies heavily on wind and sea conditions, which can affect the trip’s mood.
• Family Friendly: Suitable for most children above 4/5 and seniors with moderate mobility, with sheltered seating available.

You can check availability for your dates here:

Setting the Scene: Ocean Sailing in Ocean City

Picture yourself leaving the busy marina at Olde Towne Marina — a charming spot with a relaxed vibe, right near the water’s edge. The Alyosha, a sleek 50-foot catamaran, is your vessel for the next two hours. You’ll find the departure point near the Painted blue OC Bay Hopper Shed, with parking either free nearby or paid street options, making your arrival hassle-free if you plan ahead.

The experience begins with a quick, informal check-in—no fuss, just show up about five minutes early. Once onboard, you’re greeted by a spacious vessel built for comfort and fun. The deck offers lounging trampolines and cushioned seats, perfect for stretching out and enjoying the fresh sea air during the cruise.

What Makes This Sailing Trip Unique?

Unlike typical boat tours that just glide along, this one emphasizes true sailing. Once the engines cut out, the boat moves solely under sail, powered by the wind—a rare treat that brings an authentic touch to your adventure. The crew, led by Captain Steve, ensures everyone feels at ease, providing insight into the ship’s navigation and sharing tales of their world tours.

One highlight that keeps guests returning? The frequent dolphin sightings. Multiple reviews mention pods swimming right alongside the boat, making it a truly natural spectacle and a highlight for animal lovers and photographers alike. As one guest put it, “Pods of dolphins often playfully swim right off the bow of the boat, making a once-in-a-lifetime natural experience!”

The Itinerary: What You Can Expect

The trip’s route begins in the protected waters near Assateague Island, where the calmer bay offers a gentle start. As the boat moves out into the open Atlantic, the atmosphere shifts—there’s a sense of adventure with the wind and waves. The boat’s triangular sailing pattern is dictated by the wind, meaning no two trips are exactly alike, keeping the experience fresh.

The roughest part of the journey tends to be the OC Inlet, known for its sometimes choppy waters. Crew members skillfully navigate these conditions while explaining the nuances of ocean sailing, which makes the experience as educational as it is exhilarating. The cruise generally lasts about 1 hour and 50 minutes, giving plenty of time to relax, take photos, and enjoy the scenery.

Comfort and Practical Details

The Alyosha is designed with comfort and safety in mind. Besides the generous deck space, there are sheltered seats in the spacious cockpit, ideal if you prefer to stay out of the sun or need a break from the open deck. Restrooms, or “heads,” are aboard, although they are boat toilets—think gentle flushing and a different experience than land-based facilities, so plan accordingly.

What to bring? The crew provides bottled water, but you’re encouraged to bring your own food and drinks if you like. Sunscreen, sunglasses, and hats are essentials, especially since the focus is outside on deck—there’s little shade at times. The weather is a key factor: the trip is scheduled in the morning or evening when conditions tend to be milder. Good weather isn’t just a comfort; it’s a necessity for a safe and enjoyable sail. If storms or high seas cancel the trip, you’ll receive a full refund or the option to reschedule.

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The Crew and Safety

Captain Steve and his crew are frequently praised for their knowledgeable, friendly approach. They’re skilled at making everyone feel comfortable, whether you’re a seasoned sailor or a first-timer. As one guest said, “Captain Steve made sure my friends and I were comfortable, safe, and having fun!”

Safety is clearly a priority, with briefings on what to expect and guidance on seating and movement. The crew’s enthusiasm and professionalism shine through, enriching the experience with stories and insights into sailing life.

The Pricing and Value

At $110 per person, the trip offers good value for a nearly two-hour experience that combines adventure, relaxation, and wildlife encounters. The price covers the catamaran cruise, bottled water, professional crew, and lounging cushions. You’ll want to budget extra for parking or any snacks at the nearby restaurant, but in terms of pure experience, this cruise provides a memorable taste of ocean sailing at a reasonable cost.

Compared to other water-based activities in Ocean City, this tour stands out for its focus on authentic sailing rather than just sightseeing. Guests consistently mention it as “the best experience,” noting the skill of the crew and the natural beauty they get to witness.

Who Will Love This Trip?

This cruise is ideal for families with children over 4/5 who want a safe introduction to ocean sailing. It also appeals to adults seeking a relaxing escape, wildlife enthusiasts, and those eager to learn about sailing in a friendly environment. If you’re looking for a quiet, scenic way to experience Ocean City from the water, this tour ticks all those boxes.

The Ocean City Sailing Catamaran Cruise offers a genuine chance to see the Atlantic Ocean from a different perspective—on a well-equipped, spacious vessel with a crew that takes safety and guest enjoyment seriously. It’s not just a boat ride; it’s a sailing adventure where you can really feel the wind and see dolphins play.

If you value authentic experiences, friendly guides, and natural wildlife encounters, this tour delivers in spades. It’s especially suited for families, first-time sailors, or anyone who appreciates the simple pleasure of being on the water, under sail, and surrounded by nature.

While weather can influence the trip, when conditions are right, you’re in for a memorable cruise that combines education, relaxation, and the thrill of the open ocean. For a fair price, you gain access to an experience that will certainly be a highlight of your Ocean City visit.

How long is the cruise?
The cruise lasts about 1 hour and 50 minutes, nearly two hours of sailing fun.

What is included in the price?
Your fee covers the catamaran cruise, bottled water, professional captain and crew, cushions, and trampolines for lounging.

Do I need to bring anything?
Yes, bring sunscreen, sunglasses, and any food or drinks you’d like onboard. You might also want a hat for sun protection.

Is this activity suitable for children?
Yes, it’s appropriate for most children over age 4 or 5, especially since there are sheltered seats if they need a break.

What if the weather is bad?
The trip is weather-dependent. Poor weather may lead to cancellation, in which case you’ll get a full refund or the option to reschedule.

Where do we meet for the cruise?
Near the Painted blue OC Bay Hopper Shed at Olde Towne Marina, 307 Dorchester Street. Parking can be free nearby or paid street parking.

Is there restroom access onboard?
Yes, the Alyosha has restrooms (“heads”) available for guest use, though boat toilets are a bit different from land facilities.

Can I bring my own food?
Absolutely, you’re encouraged to bring your own food and drinks.

Is the trip suitable for seniors?
Yes, as long as they have fair mobility, since there’s sheltered seating and plenty of space.

Will I see dolphins?
Many guests report dolphins swimming alongside the boat, making it a natural highlight of the trip.

This sailing cruise in Ocean City promises a genuine taste of the ocean, blending adventure and relaxation in a way that appeals to a wide range of travelers. Whether you’re seeking a peaceful day on the water or a fun wildlife encounter, this tour offers a memorable, balanced experience.

You can check availability for your dates here: