Unique Ways to Experience the Bay, the Wildlife, and the Wild Ponies
Some of the best ways to visit Assateague Island have nothing to do with the Atlantic Ocean. Instead, they take you behind the island—into the flat, calm waters of Sinepuxent Bay—where wild ponies wander the shoreline, ospreys and bald eagles circle overhead, and the only waves you’ll feel are the gentle ripples from a passing boat.
Sail Alyosha offers four distinct Assateague Island tours, all departing from Olde Towne Marina in downtown Ocean City, Maryland. Every trip runs aboard Alyosha—our 50-foot sailing catamaran—and all of them take place on the calm, protected bay waters behind the island. Zero seasickness, zero uncertainty, and all the natural beauty of the Maryland coast from a completely different perspective.
Whether you’re looking for a peaceful boat ride with the family, a calm water cruise for date night, or a genuine sailing experience without open-ocean swells—there’s a trip here for you. The guide below will help you figure out which one fits.
Our Trips
A Guide to Pick the Best Trip for You
We have a great selection of trips that cover a wide range of interest. We also have Ocean adventures, and if you have a larger party or you don’t see what you want here – check out out Private Charter option!
Morning Assateague Tour on Alyosha
A Quiet Morning on the Water — Especially Great for Families
This is your classic Assateague bay boat tour—slow, scenic, and wonderfully calm. Two hours on the flat waters of Sinepuxent Bay aboard a 50-foot catamaran with two restrooms on board. No sails, no rushing. Just a gentle cruise along the island with your eyes on the shoreline, watching for wild ponies and shorebirds.
It’s especially great for families with small children. Spread out on the trampolines, settle into the cushioned seating, pack a breakfast—this is a trip that lets you just enjoy the morning.
Best for: Families with kids, early risers, anyone who wants a calm and beautiful start to their day.
Assateague Island Sunset Cruise
Watch the Sun Melt Into the Marsh
This is the trip for anyone who wants a gorgeous evening on the water with zero risk of rough seas. About 65–75 minutes on the flat, still waters of Sinepuxent Bay—no ocean, no Dramamine required. Alyosha glides along the channel as the sun sets over the western marsh, and you settle in on the trampolines or find your spot among the cushioned seating. On the way back, the Ocean City skyline lights up behind you. Bring your camera.
This has become one of our most popular leisure sailing experiences for birthdays and anniversaries. Let us know if you’re celebrating—we have flags for that.
Best for: Couples, date nights, birthdays, anniversaries, and anyone who wants a beautiful evening on the water with zero risk of rough seas.
Smooth Sailing Behind Assateague
All the Chill of Sailing, Without the Uncertainty of the Atlantic
This one is for people who love the idea of sailing but aren’t sure about open-ocean swells. When conditions are right, the tides and currents behind Assateague Island create some of the most pleasant bay sailing you’ll find anywhere on the East Coast—sails up, engine off, wind doing all the work.
You’ll head south with a running current, then come back on a long, flat spinnaker run with the wind behind you. Real sailing, calm water, and all the scenery of Assateague Island along the way. This is the perfect first sailing experience for the sail-curious.
Best for: Anyone who wants the full sailing experience—sails up, engine off—without the swells and chop of the Atlantic.
Anchored in Nature: Yoga on Alyosha
Breathe Deep, Float Easy — A Morning on the Water Like No Other
This is something completely different. A small group of up to 8 guests, a quiet anchorage in the bay, and a full hour of guided yoga on Alyosha’s spacious deck. No sails, no engine once we’re anchored—just open sky, fresh air, and the gentle sounds of the bay around you. The practice is suitable for all levels. We’ll close with time to unwind and socialize before heading back. It’s two hours that feel like a reset button.
A 6-person minimum is required for this trip to run (we have a yoga instructor onboard). Don’t let that stop you from booking—if we don’t hit the minimum, you’ll receive a full refund.
Best for: Yoga practitioners, wellness seekers, solo travelers, couples—anyone looking for a morning that’s more meaningful than the average vacation activity.
Ready To Book?
If you have a larger party or you are interested in something outside these trips please visit our Private Charter page.
What They All Have in Common
Every one of these Assateague Island tours takes place on the calm, protected waters of Sinepuxent Bay. Seasickness is not a realistic concern on any of them—if you’re comfortable on a dock, you’ll be comfortable here.
They all depart from Olde Towne Marina at 307 Dorchester Street in downtown Ocean City, Maryland. They’re all aboard Alyosha—a 50-foot catamaran with two restrooms, a roomy salon, cushioned seating, and trampolines built for lounging. Feel free to bring food and drinks (yes, including your own beverages). And keep your eyes on the shoreline. The ponies are usually out there.
The Trips At a Glance
| Morning Tour | Sunset Cruise | Sailing Behind Assateague | Yoga on Alyosha | |
| Duration | ~2 hours | ~65–75 min | ~2 hours | ~2 hours |
| Time of Day | Morning | Evening | Varies | Morning |
| Sails Used? | No | Possibly | Yes | No |
| Max Guests | Up to 12 | Up to 12 | Up to 12 | 8 |
| Best For | Families & early risers | Couples & celebrations | Sailing lovers | Wellness seekers |
| Seasickness Risk | None | None | None | None |
| Min. to Run | 4 guests | 4 guests | 4 guests | 6 guests |
Pricing
Trips average $99 per person, with pricing subject to availability and seasonality. Visit our booking page for current rates and availability.
Celebrating Something Special?
Being such a unique trip Alyosha has become a popular backdrop for birthdays, anniversaries, and other milestones. Let us know what you’re celebrating when you book—we have anniversary and birthday flags, complete with a nautical number set, that you’re welcome to raise during your trip. Whether it’s a milestone birthday on the Sunset Cruise or a quiet anniversary morning on the bay, there’s something about being out on the water that makes the moment feel bigger. We’ve even had a proposal or two.
Frequently Asked Questions
Common questions about Assateague Island tours and sailing trips from Ocean City, MD
Sail Alyosha offers four guided Assateague Island boat tours from Ocean City, Maryland: the Morning Assateague Tour (great for families), the Assateague Island Sunset Cruise (best for couples and celebrations), Sailing Behind Assateague (for those who want a real sailing experience on calm water), and Yoga on Alyosha (a guided yoga session at anchor in the bay). All four tours take place on the flat, protected waters of Sinepuxent Bay behind Assateague Island.
Yes—the wild ponies of Assateague frequently graze near the water’s edge on the bay side of the island. On any of the Sinepuxent Bay tours, you’ll cruise or sail along the shoreline of Assateague Island with clear views of the beach and marshes. Pony sightings are common, especially in the mornings. The Morning Assateague Tour is particularly popular with families hoping to spot the ponies.
Yes. All four Assateague tours stay in Sinepuxent Bay, the flat, protected waterway on the west side of Assateague Island. There is no Atlantic Ocean exposure on any of these trips. Alyosha is a 50-foot catamaran—she’s an incredibly stable platform even in bay conditions—and in these waters, there’s virtually no boat motion to speak of. If seasickness has been keeping you off the water, these are the trips that will change that.
No experience is necessary. On the Morning Tour, Sunset Cruise, and Yoga trip, you’re a passenger the whole time—just sit back and enjoy the ride. On Sailing Behind Assateague, you’re still a passenger while Captain Steve handles the boat, though he’s happy to explain what’s happening with the sails if you’re curious. Sail Alyosha also offers hands-on sailing experiences for those who want to learn.
The Morning Assateague Tour is our top pick for families. It’s offered in the mornings when conditions are calmest, stays on flat bay water, and has the most deck space to spread out. Alyosha has two restrooms on board—which matters when you’ve got little ones. Pack breakfast, bring the kids, and keep everyone’s eyes on the shoreline for ponies. If the morning doesn’t work then the Assateague sailing trip is another good option.
The Assateague Island Sunset Cruise is our most popular date night experience. About 65–75 minutes on the calm waters of Sinepuxent Bay, watching the sun set over the western marsh before turning back to see the Ocean City skyline light up. It’s also become a favorite for birthdays and anniversaries—let us know if you’re celebrating and we’ll have a flag ready to raise.
All Sail Alyosha trips depart from Olde Towne Marina at 307 Dorchester Street in downtown Ocean City, Maryland. Alyosha is docked at the end of the pier—you can’t miss her, she’s the only sailing catamaran around. Parking can be limited at the marina, so plan to arrive a few minutes early. If the boat isn’t at the dock when you arrive, she’s likely out on another trip and will return just before your scheduled departure time.
Assateague Island tours with Sail Alyosha start at approximately $99 per person, with pricing varying by trip type, season, and availability. Visit our booking page for current pricing and to check open dates.
Bay sailing—like the tours offered behind Assateague Island—takes place on the flat, calm, protected waters of Sinepuxent Bay. There’s minimal boat motion, no ocean swells, and virtually no seasickness risk. Ocean sailing departs through the OC Inlet and onto the open Atlantic, where conditions can range from gentle rolling swells to a more exhilarating ride depending on the day. Sail Alyosha offers both: the Assateague bay tours for those who want a calm water cruise, and ocean sailing trips for those ready to head offshore.
You’re welcome to bring any food or drinks you’d like on board—including alcohol. Alyosha has bottled water for all guests. Sunscreen and sunglasses are a must (the real action is outside on deck), and a light layer is a good idea for morning trips or breezy days. There are two restrooms aboard. Comfortable, casual clothing is all you need—no sailing gear required.
All four of our Assateague trips take place on the flat, calm waters of Sinepuxent Bay—not the open ocean. There are no swells, no chop, and virtually no boat movement to speak of. A good rule of thumb: if you’re comfortable walking on a boat dock, you’ll be comfortable on Alyosha out here.
That said, if you do start feeling off, Captain Steve and the crew have seen it before and will take good care of you. They’ll get you to a comfortable spot, keep you in fresh air, and offer some practical suggestions to help settle things down.