Sailing Experiences For All on Alyosha

Sail Alyosha offers a full range of sailing experiences in Ocean City, from milestone celebrations to everyday adventures. You can book romantic date night sails, family-friendly bay cruises behind Assateague Island, ocean sailing trips for experienced sailors, private charters for weddings and proposals, corporate team-building events, and more. All trips depart from Olde Towne Marina in downtown Ocean City on Alyosha — a 50-foot sailing catamaran.

Yes. Alyosha hosts intimate wedding ceremonies on the water in Ocean City, Maryland. You can exchange vows with up to 12 guests aboard our 50-foot catamaran, either in the calm waters behind Assateague Island or under sail on the Atlantic Ocean. Bring your officiant, photographer, and champagne — we’ll handle the boat. Wedding dates book fast, especially during summer weekends, so contact us early to reserve your date.

The Assateague Island Sunset Cruise is our most popular date night experience. Capped at just 12 guests, it offers calm bay waters, a gorgeous sunset, and plenty of space for couples to relax together. For something more adventurous, try Ocean Sailing Advanced (3 hours on the Atlantic). When conditions align, our Moonlight Sailing trip — under the stars and a full moon — is the ultimate romantic experience.

Yes. Our Assateague Island trips are designed with families in mind. The Morning Assateague Tour and Assateague Island Sunset Cruise both feature flat, calm bay water (zero seasickness risk), two restrooms onboard, and plenty of space for kids to spread out on trampolines and cushioned seating. You can pack snacks, watch for wild ponies along the shoreline, and give your family a memorable morning or evening on the water.

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.

Absolutely. We’ve been part of many proposals on Alyosha and we’re very good at keeping secrets. You can book a private charter for an exclusive proposal experience, or choose the Moonlight Sailing trip (when available) or Assateague Island Sunset Cruise for a romantic backdrop. Let us know your plan when booking and we’ll make sure the moment is perfect — whether you want sunset behind Assateague, dolphins off the bow, or the Ocean City skyline lighting up.

Yes. We provide dignified burial at sea services off the coast of Ocean City, Maryland. Alyosha accommodates up to 12 family members and friends, offering a stable and respectful platform for your ceremony. We can take your group out on the Atlantic Ocean or into the calm waters behind Assateague Island, depending on your wishes and weather conditions. Captain Steve works directly with families to plan every detail, whether you want to scatter ashes, release flowers, or hold a ceremony on deck.

On a scheduled trip, you book individual seats (typically $99 per person) and may share the boat with other guests (up to 12 total). On a private charter, you reserve the entire boat for your group (up to 12 people) — it’s just you and your guests. Private charters are ideal for weddings, proposals, birthdays, anniversaries, bachelor/bachelorette parties, and corporate events. You can also book all 12 seats on any scheduled trip and receive a 10% discount, which effectively makes it a private charter.

Scheduled sailing trips with Sail Alyosha start at approximately $99 per person, with pricing varying by trip type, season, and availability. Private charters (entire boat for up to 12 guests) vary based on trip duration and customization. You can also book all 12 seats on a scheduled trip and receive a 10% discount. Visit our booking page for current pricing and to check availability.

Bring sunscreen, sunglasses, and comfortable clothing. Alyosha has plenty of bottled water onboard, but you’re welcome to bring your own food and drinks — including alcohol. For date nights and special occasions, champagne delivery to the boat is available when you book through Oyster & Scales restaurant. There are two restrooms (“heads”) aboard. A light jacket or layer is recommended for evening trips or early-season sails.

It depends on the trip. Our Assateague Island trips (Morning Tour, Sunset Cruise, Sailing Behind Assateague, Yoga on Alyosha) stay in flat, calm bay waters with virtually no motion — if you’re comfortable on a dock, you’ll be comfortable here. For ocean trips, Alyosha is a stable 50-foot catamaran that sails flat, but there can be motion depending on conditions. If you’re prone to seasickness on ocean trips, take preventative medicine (like Bonine or Dramamine) before leaving the dock.

Yes. Private charters on Alyosha are perfect for corporate outings, team-building activities, and client entertainment. You can bring up to 12 guests and tailor the trip to your group’s interests — choose ocean sailing for team bonding, Assateague Island cruises for relaxed client entertainment, or a custom itinerary designed around your event goals. It’s a unique alternative to the usual happy hour or conference room meeting.

Sail Alyosha is the only sailing charter business operating in Ocean City, Maryland. We offer authentic sailing experiences aboard Alyosha — a 50-foot St. Francis catamaran that’s crossed oceans and logged over 50,000 nautical miles with Captain Steve at the helm. Unlike powerboat tours, we offer real sailing under wind power on both the Atlantic Ocean and in the calm waters behind Assateague Island.

No sailing experience is necessary for most trips. On our Assateague Island cruises, Ocean Sailing, Ocean Sailing Advanced, and special events, you’re a passenger — just relax and enjoy the ride. The Hands On Sailing trip is designed for return guests who want to learn and actually crew the boat (helm, sails, navigation), but even on that trip, you can participate as much or as little as you want. The Big Blue is recommended for experienced Alyosha guests or adventurous sailors ready for a full-day offshore experience.

Alyosha is a 50-foot sailing catamaran — not a powerboat. We offer authentic sailing experiences under wind power, with the engines off and sails up. The boat has crossed the Pacific Ocean with Captain Steve (over 35 years of sailing experience, 50,000+ nautical miles logged). We’re also the only sailing charter business in Ocean City, and we specialize in both calm bay cruises behind Assateague Island and ocean sailing on the Atlantic. Whether you want romantic sunset sails, family adventures, hands-on sailing instruction, or milestone celebrations, Alyosha offers experiences you can’t get anywhere else in Ocean City.

All 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.

Alyosha can accommodate up to 12 guests on most trips. Some specialized experiences (like Hands On Sailing, The Big Blue, and Yoga on Alyosha) are limited to 6-8 guests to ensure everyone has meaningful space and attention. For private charters, you can bring up to 12 people for weddings, corporate events, birthdays, or any celebration.

A catamaran is a boat with two hulls instead of one (like a monohull sailboat). This design makes catamarans incredibly stable — they don’t heel (lean) like traditional sailboats, so they sail flat and level. Alyosha is a 50-foot St. Francis catamaran with trampolines at the bow for lounging, wide deck space, and a stable platform that doesn’t rock like smaller boats. If you’ve sailed on a catamaran before and loved it, or if you’re just curious what all the fuss is about, Alyosha delivers the full catamaran cruising experience.

Yes. You’re welcome to bring your own beverages, including alcohol, on all Sail Alyosha trips – no glass bottles please. For special occasions, we’ve partnered with Oyster & Scales restaurant (right next to the marina) to offer chilled champagne delivery to the boat — just order when you book your trip and it’ll be waiting for you onboard. Alyosha has plenty of bottled water for all guests.

All trips are weather-dependent. If the captain feels there’s any risk given the day’s conditions — including a forecast that doesn’t look promising — the trip will be cancelled and you’ll receive a full refund, no questions asked. For some trips (like The Big Blue), you may be offered the option to switch to a shorter sail closer to shore instead of a full refund. Captain Steve always makes the call with your safety and comfort in mind.

You can book scheduled trips directly through our online booking system at book.sailalyosha.com. For private charters, milestone celebrations (weddings, proposals, burials at sea), or custom experiences, we recommend reaching out directly so we can coordinate the details with you personally. You can also reserve all 12 seats on any scheduled trip (and receive a 10% discount) to make it a private experience.