Ocean City Sunset Cruise on Alyosha
The Only Sailing Catamaran Sunset Cruise in Ocean City, Maryland
Ocean City sunsets are legendary, and being on the water to see them is a perfect cap to a great day. Take it up a notch by jumping aboard our spacious and tranquil 50-foot sailing catamaran with room to actually breathe. Alyosha holds up to 12 guests—which means you get trampolines to lounge on, cushioned seating to claim, and space to enjoy the sunset cruise without fighting for a spot at the rail or listening to noisy engines ruin a peaceful moment.
And here’s what makes this sunset cruise different: every evening, Alyosha’s Captain makes the call based on conditions—ocean or bay. (We will try to take into account your preference!) Some nights, Alyosha heads out through the inlet for a sunset over Ocean City’s skyline with a chance of spotting dolphins along the way. Other nights, we cruise behind Assateague Island on the flat, calm waters of Sinepuxent Bay, where the sun melts into the marsh and the birds put on a show. Both are stunning. Both are completely different experiences. And both are designed with your comfort in mind—we never take Alyosha into rough conditions on a sunset cruise.
Bring your camera. Bring someone you like. This is the best sunset cruise Ocean City has to offer.
The Best Sunset Cruise Ocean City Has to Offer
Here’s what most people don’t realize until they’re already on the water: powerboats are loud. The engine runs the entire time, and you’re yelling over the noise to have a conversation during what’s supposed to be a peaceful sunset cruise. Alyosha is different. Once we’re cruising along the channel, the diesel engines are either at idle or off completely—especially if we get the sails up. It’s quiet. Peaceful. The way a sunset cruise should be. And because Alyosha is a 50-foot catamaran—not a narrow tour boat—there’s actual space. Trampolines built for lounging at the bow. Cushioned seating on deck for groups. A roomy salon and two restrooms if you need them. You’re not crammed shoulder-to-shoulder with strangers on this sunset cruise. You can spread out, claim your spot, and actually enjoy the ride.
Real Sailing Vessel:
Alyosha is a 50-foot St. Francis catamaran that's crossed oceans and logged over 50,000 nautical miles with Captain Steve at the helm. She's the real deal—not a tour boat pretending to be a sailboat.
Small Group Experience:
Capped at 12 guests (not 30+), which means you actually have room to spread out and enjoy the sunset cruise without feeling crowded.
Quiet Cruising:
Sailboats don't need loud engines running constantly. When the sails are up, it's just wind and water—the way a sunset cruise should sound.
Two Possible Routes, Both Beautiful:
On ocean evenings, you'll watch the sunset over Ocean City's skyline with a chance of dolphins. On bay evenings, the sun sets over the Assateague marshes surrounded by birds and wildlife. The captain picks the best option each night based on conditions.
Comfort-First Approach:
We know sunset cruises are about the experience—the photos, the conversation, the moment. That's why we never take Alyosha out when conditions would make the ride uncomfortable. If the ocean is rough, we head to the calm waters behind Assateague. Either way, you win.
Who Is This Sunset Cruise For?
Couples, friends, families—this sunset cruise works for everyone. Alyosha provides a remarkably stable platform, so if you’ve got little ones or anyone in your group who’s nervous about boats, this is a safe bet. Spread out on the trampolines, settle into the cushioned seating, or claim a spot in the cockpit. There’s plenty of room and no wrong place to sit.
This sunset cruise Ocean City has also quietly become one of our most popular experiences for date nights and celebrations. The combination of a peaceful evening, a gorgeous sunset, and the space to actually enjoy it together makes it ideal for couples and special occasions. If you are looking for other options check out our other smooth sailing trips.
Perfect For:
- Couples & Date Nights: Looking for a romantic Ocean City sunset cruise that isn’t crowded or noisy
- Celebrations: Birthdays, anniversaries, proposals, or just marking a special occasion
- Families: Kids love the trampolines, and parents love the two restrooms and calm water
- Friends: Groups who want a beautiful evening on the water without the party boat atmosphere
- First-Time Sailors: This sunset cruise is the perfect introduction to sailing—calm, comfortable, and unforgettable
What to Expect on Your Sunset Cruise
About 65–75 minutes on the water—long enough to fully unwind and soak in the scenery, short enough that nobody gets restless. Each evening, the captain decides on the route based on conditions.
On ocean nights, Alyosha heads out through the OC Inlet and sails along the coast as the sun drops toward the Ocean City skyline. Keep your eyes open for dolphins—they’re a regular feature on calm ocean evenings. On bay nights, we cruise behind Assateague Island along the channel, where the marshes light up gold and orange at sunset and the birdlife is incredible. We might try to get the sails up depending on the wind direction, but either way, the scenery is the main event.
By the time we return to the marina, you’ll wish this sunset cruise were longer—which is exactly how it should feel.
A Note on Motion Sickness
Alyosha is a 50-foot catamaran—an incredibly stable platform that sails flat. On bay evenings when the sunset cruise goes behind Assateague, there’s virtually no motion at all. On ocean evenings, there may be gentle swells, but the captain only chooses the ocean route when conditions are calm and comfortable. If you’re prone to seasickness and want to be extra cautious, take a Bonine or Dramamine before we leave the dock—but know that we’re always making the call with your comfort in mind.
A good rule of thumb: if you’re comfortable walking on a boat dock, you’ll be comfortable on this sunset cruise.
Pricing
Sunset cruises start at approximately $99 per person, with pricing varying by season and availability. Visit the booking page for current rates and to check open dates. Group rates may be available for private charters.
Weather & Cancellation
This sunset cruise is weather dependent. If Captain Steve 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.
We need a minimum of 4 people for this sunset cruise to run. If we fall short of the minimum, we’ll refund anyone who booked—but don’t let that discourage you from booking. We almost always hit the minimum, and if we don’t, we’ll find another time that works for you.
What to Bring on Your Sunset Cruise
Feel free to bring your own drinks and snacks—yes, including alcohol. This is a sunset cruise; a glass of wine or your favorite cocktail is entirely appropriate. Just bring beverages in cans or plastic containers (no glass bottles on the boat). Alyosha has plenty of bottled water onboard.
Sunscreen and sunglasses are a good call, especially early in the evening. The salon area and cabins are available if you need shade, but most guests want to be outside on deck for the whole sunset cruise. Bring a light layer if the evenings have been cool—it’s always a few degrees cooler on the water.
There are two restrooms (“heads”) aboard for guest use—just keep in mind the toilets on a sailboat are a little more sensitive than the ones on land.
Common questions about our sunset cruises in OCMD
The Ocean City sunset cruise aboard Alyosha is consistently rated as one of the best sunset cruise options on the Maryland coast. Unlike crowded powerboat tours, this sunset cruise takes place on a 50-foot sailing catamaran with space for just 12 guests. You’ll cruise the calm waters of Sinepuxent Bay behind Assateague Island, watch the sun set over the western marshes, and then enjoy Ocean City’s illuminated skyline on the return trip. It’s quiet, spacious, and aboard a real sailing vessel—not a tour boat. Most people who’ve tried multiple sunset cruises in Ocean City say this is the one they’d book again.
All sunset cruises on Alyosha depart from Olde Towne Marina at 307 Dorchester Street in downtown Ocean City, Maryland, right alongside Oyster & Scales restaurant. 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 about 5-10 minutes before your scheduled sunset cruise departure time.
The sunset cruise Ocean City MD is approximately 65-75 minutes on the water—long enough to fully unwind and soak in the scenery, short enough that nobody gets restless. By the time Alyosha turns back toward the marina after the sunset, you’ll wish this sunset cruise were longer.
The good news is we have longer trips and private charter options!
Absolutely. The Ocean City sunset cruise has quietly become one of our most popular date night experiences. The combination of a peaceful evening on the water, a gorgeous sunset, and the intimacy of a smaller sailing catamaran (versus a crowded tour boat) makes it ideal for couples. Bring a bottle of wine, settle into the trampolines or find your own spot, and enjoy the ride. This is hands-down one of the best romantic sunset cruises in Ocean City.
Yes! Let us know if you’re celebrating an anniversary, birthday, or special event when you book your sunset cruise. Sail Alyosha has anniversary and birthday flags—complete with a nautical number set—that we’ll raise during the sail. It’s a small touch that tends to make a big impression. We’ve hosted several proposals, weddings, and milestone celebrations on Ocean City sunset cruises.
No. The Ocean City sunset cruise stays entirely in the flat, calm waters of Sinepuxent Bay—it never goes out to the Atlantic Ocean. Alyosha is a 50-foot catamaran, which is an incredibly stable platform, and in these bay waters there’s virtually no boat movement to speak of. If seasickness has been keeping you off the water, this is the sunset cruise that changes that. A good rule of thumb: if you’re comfortable walking on a boat dock, you’ll be comfortable on this sunset cruise.
The Ocean City sunset cruise takes place aboard Alyosha, a 50-foot St. Francis sailing catamaran. Alyosha has crossed oceans, weathered storms, and logged over 50,000 nautical miles with Captain Steve at the helm. She features trampolines built for lounging, cushioned seating, a roomy salon area, and two restrooms. This isn’t a crowded tour boat or pontoon—it’s a real sailing vessel with room to spread out and get comfortable. Most people are surprised by how spacious and stable a catamaran feels compared to other sunset cruise boats.
Sunset cruises start at approximately $99 per person, with pricing varying by season and availability. Visit the booking page for current rates and to check open dates for Ocean City sunset cruises. Group rates may be available for private charters.
You’re welcome to bring your own drinks (including alcohol) and snacks—a glass of wine or your favorite beverage is entirely appropriate for a sunset cruise. Just bring drinks in cans or plastic containers (no glass bottles on the boat). Alyosha has plenty of bottled water onboard. Sunscreen and sunglasses are recommended, especially early in the evening. Bring a light layer if evenings have been cool—it’s always a few degrees cooler on the water. There are two restrooms aboard for guest use.
Yes, absolutely (assuming you are over 21!). Feel free to bring beer, wine, or your favorite cocktails on the Ocean City sunset cruise. Having a drink in hand is part of the experience. Just bring beverages in cans or plastic containers (no glass bottles on the boat). Alyosha has bottled water for all guests.
The Ocean City sunset cruise is weather dependent. If Captain Steve 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. We need a minimum of 4 people for the sunset cruise to run. If we fall short of the minimum, we’ll refund anyone who booked—but don’t let that discourage you from booking. We almost always hit the minimum, and if we don’t, we’ll find another time that works for you.
No sailing experience is necessary for the Ocean City sunset cruise. You’re a passenger the entire time—just sit back, relax, and enjoy the scenery. Captain Steve and the crew handle all aspects of the boat. All you need to do is show up, claim your favorite spot on deck, and watch the sun go down.
Yes. The Ocean City sunset cruise is appropriate for families with children. Alyosha is a stable 50-foot catamaran with plenty of room to spread out, and the flat bay waters mean there’s virtually no boat motion. That said, this sunset cruise has become particularly popular with couples and date nights, so families with very young children might also consider the Morning Assateague Tour, which is specifically designed with families in mind and runs during daylight hours.
Boarding Alyosha requires navigating a dock and stepping onto the boat, which may be challenging for guests with mobility limitations. If you have specific accessibility concerns about the sunset cruise, please contact us before booking and we’ll do our best to accommodate your needs.
Sunset cruises are popular, especially during peak summer season and on weekends. We recommend booking at least a few days in advance to secure your preferred date for the Ocean City sunset cruise. Last-minute bookings are sometimes available, but advance reservations ensure you get the date and time you want.
Most Ocean City boat tours run on powerboats with loud engines and pack 30+ people aboard. The Ocean City sunset cruise on Alyosha is different: it’s a 50-foot sailing catamaran (quiet and spacious), capped at 12 guests (not crowded), and runs on calm bay waters (zero seasickness risk). You get two experiences—sunset over the marshes and Ocean City’s illuminated skyline on the return—instead of just a sunset. It’s also one of the only true sailing vessels offering sunset cruises in Ocean City.
Absolutely. The Ocean City sunset cruise is a popular choice for proposals. The combination of a beautiful sunset, intimate setting, and peaceful atmosphere creates the perfect moment. Let us know in advance if you’re planning a proposal and we’ll do everything we can to make it special—including having the camera ready and maybe even a celebratory flag to raise afterward.
If you’d like to book the entire boat for a private sunset cruise, contact us about private charters. We can customize the experience for your group, whether it’s a family reunion, corporate outing, celebration, or just a group of friends who want the boat to themselves. Private charters give you flexibility on timing, route, and onboard experience.
Gratuities are appreciated but never required. If Captain Steve and the crew made your Ocean City sunset cruise memorable, tips are a great way to show your appreciation—but there’s absolutely no obligation.
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.
