Morning Assateague Tour on Alyosha
A Quiet Morning on the Water — Especially Great for Families
Are you interested in a quiet, scenic morning aboard the comfort of a 50-foot catamaran—with two restrooms? This 2-hour tour is not about sailing. It’s about enjoying the views on Sinepuxent Bay and Assateague Island from one of the most comfortable platforms on the water. And of course, we’ll be scouting the shorelines for ponies.
The flat, calm waters behind Assateague mean zero worries about seasickness—and they make this trip especially great for families with small children. Spread out on the trampolines, settle into the cushioned seating, and just enjoy the morning.
Who Is This Trip For?
Families with little ones. Couples looking for a peaceful morning. Anyone who wants to be on the water without any of the uncertainty that comes with the ocean. If you’ve got kids who would love to spot wild ponies from a boat, this is the trip. If you just want a calm, beautiful start to your day, this is also the trip.
If you are celebrating a special event like a birthday or anniversary let us know!
What to Expect
Two hours on the flat waters of Sinepuxent Bay, cruising along Assateague Island. This tour is offered only in the mornings and is especially nice during the shoulder seasons, when the migratory birds of Assateague make their appearance. Keep your eyes on the shoreline for ponies—they’re often grazing near the water.
There is plenty of room for everyone: trampolines built for lounging, cushioned seating for an additional 6 people, a roomy salon area, and cabins if you need them. Two restrooms aboard—which matters when you’ve got kids.
A Note on Motion Sickness
No worries about seasickness whatsoever. This trip stays in the calm, flat waters of the bay. Alyosha is a stable 50-foot catamaran, and in these waters, there’s virtually no rocking. If your kids (or anyone in your group) have been nervous about boats, start here.
Weather & Cancellation
This trip is weather dependent—if conditions aren’t right, you’ll receive a full refund. We need a minimum of 4 people for this trip to run. If we have fewer than the minimum, we’ll refund anyone who booked. Don’t let that discourage you though—book the trip, and if we don’t hit the minimum, we’ll find another time that works.
Here’s a bonus: if you’re a couple looking for a boat ride, this could—depending on other bookings—be your best chance at a private ride.
What to Bring
The flat, calm waters behind Assateague make it easy to enjoy any kind of spread you bring out. Pack breakfast, snacks, whatever you’d like—and feel free to bring any beverages, including alcohol. We know it’s a morning trip, but no judgement here—you’re on vacation.
Alyosha has plenty of bottled water onboard. For sun protection, we recommend sunscreen and sunglasses—the real action is outside on deck, and the morning sun on the bay can be strong.
Yes—this is one of the best trips we offer for families with little ones. The tour stays in the flat, calm waters of Sinepuxent Bay, so there’s virtually no rocking or motion to worry about. Alyosha has two restrooms onboard (which matters when you’ve got kids), plenty of space to spread out on trampolines and cushioned seating, and the whole experience is focused on wildlife spotting—especially the wild ponies along the shoreline. Most kids love it, and parents appreciate the zero seasickness risk.
We can’t guarantee pony sightings—they’re wild animals, after all—but we do see them frequently, especially during morning hours when they tend to graze near the water. The tour runs along the shoreline of Assateague Island for about two hours, giving you plenty of time to scan the beaches and marshes where the ponies roam. Bring binoculars or a camera with a good zoom if you want a closer look. Beyond ponies, you’ll likely spot ospreys, bald eagles, and other bay wildlife.
The tour runs throughout our season, but the shoulder seasons—late spring and early fall—offer something special. That’s when migratory birds make their appearance on Assateague, so you’ll see more wildlife variety beyond just the ponies. The temperatures are also more comfortable in the morning during those times of year. That said, summer mornings on the bay are beautiful too—just bring sunscreen and sunglasses because the morning sun on the water can be strong. Whenever you choose to go, the calm bay conditions and scenery stay consistent.
Getting to Our Ocean City Sailing Charters
Trips depart promptly at the scheduled time from Olde Towne Marina (307 Dorchester Street, Ocean City, MD 21842), right next to Oyster & Scales in downtown OC. Parking can be limited, so plan to arrive a few minutes early. You can’t miss Alyosha—we’re the only sailing vessel around. If you don’t see the boat, don’t worry—we’re probably off on another adventure and will return just before departure.