From Your First Ocean Sail to Epic Offshore Adventures
Looking for ocean sailing in Ocean City? The real thing happens out on the Atlantic—through the OC Inlet, onto open water, where the engines cut off and the sails take over. This is where you watch Ocean City fade into the horizon, where pods of dolphins swim off the bow, and where the only thing powering the boat is wind.
Sail Alyosha offers four distinct ocean sailing trips, all departing from Olde Towne Marina in downtown Ocean City, Maryland. Every trip runs aboard Alyosha—our 50-foot sailing catamaran that’s circumnavigated the globe and logged over 50,000 nautical miles. She’s big, she’s stable, and she’s the real deal. But the experience you have on her depends on which ocean boat tour you choose.
Whether you’re looking for your first taste of ocean sailing, a longer offshore adventure, a hands-on learning experience, or an all-day expedition 20 miles out—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 ocean sailing experiences that cover a wide range of interests and skill levels. We also offer calm-water bay sailing trips behind Assateague Island, and if you have a larger party or don’t see what you want here—check out our Private Charter option
Ocean Sailing on Alyosha
The Gateway — Your First Taste of Real Sailing
This is where most people start their ocean sailing adventure, and honestly, it’s where a lot of people fall in love with sailing. About two hours on the Atlantic Ocean aboard a boat that’s circumnavigated the globe. You’ll head out through the OC Inlet, feel the sails go up, and experience Ocean City from a perspective most people never see. No experience necessary, no prior booking required. Just show up, hang on, and enjoy the ocean boat ride.
Depending on the weather, you’ll get either the “chill” or the “thrill” of ocean sailing. Typically, June through August features gentle, rolling swells as a sea breeze builds throughout the day. But not every day is typical. This is real open ocean sailing—the captain and crew have yet to be able to control the wind and seas.
Best for: First-timers, families, vacationers, anyone curious about what it’s like out there. This is your “let’s try it” trip.
Ocean Sailing Advanced
More Time, More Ocean — Sail the Boat That Sailed the World
You’ve been out with us before and you want more. Three hours on the water instead of two, pushing further offshore and spending more time under sail. This oceanside sailing tour is for return sailors who already know they love it and want a bigger dose. The captain may keep the trip inside the inlet if Atlantic conditions aren’t cooperating—but when the ocean is calling, this trip answers.
Prepare yourself for a very different Ocean City attraction. Sailing on the Atlantic Ocean is sometimes very exciting and often very relaxing, depending on the conditions. Don’t worry—you’ll have a great time either way. Pods of dolphins often swim right off the bow—a once-in-a-lifetime natural experience.
Best for: Return guests who want a longer sail and aren’t done exploring what Alyosha can do. Requires a prior booking with Sail Alyosha.
Hands On Sailing
Command & Crew the Boat — You Do the Work
This is the trip for people who can’t sit still. Three hours of real ocean sailing where *you* handle the helm, raise the sails, and set the course—with Captain Steve directing the action from the cockpit. Limited to just 6 guests so everyone gets meaningful time at the helm and on the lines. You’ll leave understanding the physics of sailing and with a real sense of accomplishment. This trip is exactly as engaging as you want it to be.
On Hands On Sailing trips, we make an effort to get all the sails working. There’s a 10–15 minute safety orientation at the start, and after that, you’re put to work. No question is off limits—Steve is happy to pursue whatever topics interest you, whether you’re looking to boost your sailing knowledge or just getting started in the sport.
Best for: Doers, learners, aspiring sailors, and anyone who’d rather be pulling lines than holding a drink. Requires a prior booking. Ages 13+. Fitness waiver required for participants.
The Big Blue
The Ultimate — 20 Miles Offshore, All Day on the Atlantic
This is the one. Six hours on the open Atlantic, sailing 20 miles offshore into deep blue water. The coastline disappears. The water changes color. Dolphins show up. It’s the kind of ocean sailing most people only read about, and you’re doing it on a boat that’s crossed the Pacific. Limited to 6 guests because an experience like this deserves space and attention.
You’ll watch Ocean City shrink behind you, the water will change colors beneath you, and eventually the horizon will be nothing but open Atlantic in every direction. Six hours affords you the ability to really experience the sea—and if you want to bring a book, a podcast, or anything else to pass the time between tacks, no worries.
Best for: Experienced Alyosha guests ready for a full-day ocean adventure. People who’ve done Ocean Sailing and said, “I want to keep going.” Requires a prior booking with Sail Alyosha.
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 ocean sailing trips departs through the OC Inlet and onto the Atlantic Ocean. This is real open-ocean sailing—engines off, sails up, wind doing the work. You’ll watch Ocean City fade into the horizon as crystal clear Atlantic waters surround the boat.
They all depart from Olde Towne Marina at 307 Dorchester Street in downtown Ocean City, Maryland. They’re all aboard Alyosha—a 50-foot sailing 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). Alyosha has plenty of bottled water for all guests.
Pods of dolphins often swim right off the bow. The real action is outside on deck—bring sunscreen and sunglasses. And keep in mind: this is the Atlantic Ocean, so there can be motion. If you’re prone to seasickness, take preventative medicine before we leave the dock.
The Trips At A Glance
| Ocean Sailing | Ocean Sailing Advanced | Hands On Sailing | The Big Blue | |
| Duration | ~2 hours | ~3 hours | ~3 hours | ~6 hours |
| Distance Offshore | Up to 3nm | Up to 3nm | 1nm to 6nm | 20 miles |
| Your Role | Passenger | Passenger | Active crew | Passenger |
| Max Guests | Up to 12 | Up to 12 | 6 | 6 |
| Best For | First-timers & everyone | Return sailors | Hands-on learners | Ocean adventurers |
| Prior Booking Required? | No | Yes | Yes | Yes |
| Minimum Age | All ages | All ages | 13+ | 8+ |
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 ocean sailing tours and boat rides from Ocean City, MD
Sail Alyosha offers four ocean sailing trips from Ocean City, Maryland: Ocean Sailing (a 2-hour introduction perfect for first-timers), Ocean Sailing Advanced (3 hours for return sailors wanting more time on the water), Hands On Sailing (a 3-hour hands-on experience where you crew the boat), and The Big Blue (6 hours sailing 20 miles offshore). All four trips depart through the OC Inlet and sail on the Atlantic Ocean aboard Alyosha, a 50-foot catamaran that’s sailed around the world.
No experience is necessary for Ocean Sailing, our 2-hour introductory trip. It’s designed for first-timers, families, and anyone curious about sailing. Ocean Sailing Advanced is for return guests who’ve already been out with us. Hands On Sailing is perfect for those who want to learn—whether you’re a seasoned sailor looking to sharpen skills or someone new to the sport who wants hands-on instruction. The Big Blue is for experienced Alyosha guests ready for a full-day offshore adventure.
Ocean Sailing and Ocean Sailing Advanced typically go up to 3 nautical miles offshore. Hands On Sailing can range from 1 to 6 nautical miles offshore depending on conditions and the learning objectives for the day. The Big Blue sails 20 miles offshore into deep blue water where the coastline disappears completely.
Ocean Sailing is a 2-hour trip designed as an introduction to ocean sailing—no prior booking required, open to everyone. Ocean Sailing Advanced is a 3-hour trip for return sailors who’ve been out with us before and want more time on the water. Advanced pushes further offshore when conditions allow and gives you a bigger dose of what made you fall in love with sailing the first time around. Both are passenger experiences where you sit back and enjoy the ride.
Yes—on our Hands On Sailing: Deep Immersion trip. This 3-hour ocean sailing experience is designed for guests who want to actively crew the boat. You’ll handle the helm, raise the sails, and set the course with Captain Steve directing from the cockpit. Limited to just 6 guests so everyone gets meaningful time at the helm and on the lines. If you’re an experienced sailor looking to sharpen skills or someone who fell in love with sailing and wants to understand the mechanics, this is your trip.
All our ocean sailing trips involve real open-ocean sailing on the Atlantic—engines off, sails up, wind power only. We head through the OC Inlet and sail a triangular course dictated by the wind. On Hands On Sailing trips, we make an effort to get all the sails working to give participants the full experience. Conditions vary: June through August typically features gentle rolling swells as sea breezes build throughout the day, but the Atlantic always keeps things interesting. Alyosha is a 50-foot catamaran that sails flat and stable.
Yes. Ocean Sailing, our 2-hour introductory trip, is appropriate for most children above age 4 or 5. There’s plenty of room aboard Alyosha to spread out—trampolines for lounging, cushioned seating, and a sheltered cockpit. Two restrooms are aboard. The trip is designed as an introduction to ocean sailing and works for families, seniors with fair mobility, and first-timers. For longer trips: Ocean Sailing Advanced and Hands On Sailing are all ages and 13+ respectively, while The Big Blue has a minimum age of 8.
Bring sunscreen and sunglasses—the real action is outside on deck. Alyosha has plenty of bottled water, but feel free to bring any food or drinks you’d like. For longer trips (3+ hours), consider bringing lunch or heavy snacks. There are two restrooms aboard. If you’re prone to seasickness, bring Bonine or Dramamine and take it before we leave the dock – making sure yo have checked with your physician. Sailing gloves are helpful for Hands On Sailing if you have them (we have a few extra pairs). For The Big Blue, bring an extra layer for chilly days and a dry change of clothes if you plan on lounging on the trampoline in rough conditions.
Alyosha is a big, stable sailing catamaran and she sails flat. But this is real open ocean sailing on the Atlantic, so there can be motion. If you’re prone to seasickness, take preventative medicine (we recommend Bonine or Dramamine) before we leave the dock. And you have checked with your physician. Once you’re feeling sick, it’s too late. For those highly susceptible to motion sickness, consider starting with our calm-water bay sailing trips behind Assateague Island—they offer the sailing experience with virtually no motion.
On certain ocean sailing trips when conditions are favorable, we may fly additional sails. Hands On Sailing trips make an effort to get all the sails working to give participants the full sailing experience. Captain Steve has over 35 years of sailing experience and recently completed a circumnavigation on Alyosha, logging over 50,000 nautical miles—he’s happy to explain sail trim, points of sail, and any technical questions you have about how the boat performs.
All Sail Alyosha ocean trips depart from Olde Towne Marina at 307 Dorchester Street in downtown Ocean City, Maryland (21842). Alyosha is docked at the end of the pier—you can’t miss her, she’s the only sailing catamaran around. Plan to arrive about 5 minutes before departure. There’s no formal check-in, but if we have other guests and you’re late, we will leave on time—it’s not fair to punctual guests to make them wait. Parking can be limited, so arrive early. Consider having a drink at the restaurant next to the marina before departure.
Ocean sailing trips 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.