Hands On Sailing
Command & Crew the Boat That Sailed the World
Ever wonder what it’s like to actually maneuver a 50-foot sailboat in a tight harbor? Want to experience the thrill of manning the helm, raising the sails, and setting a course for adventure? Or maybe you’re just the kind of person who can’t sit still—who’d rather be doing something because that’s how you’re wired to relax. If any of that sounds like you, this is your trip.
This is a hands-on sailing adventure where you and your fellow guests handle every aspect of a 3-hour ocean sailing experience. You’ll be at the helm, on the sails, and in a variety of other capacities—with Captain Steve using his voice (and kind, patient demeanor) to direct everyone through a real Atlantic Ocean sail. Limited to just 6 guests to make sure everyone gets meaningful time at the helm and on the lines.
We also have other ocean adventure trips here.
What to Expect on Hands On Sailing Trip
Close to 3 hours of real ocean sailing. We’ll head through the OC Inlet—often the roughest part of the entire journey—and then let the wind dictate the triangular course we sail. 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 you’ll be expected to review a brief safety guide beforehand (we’ll send it to you). 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. You’ll leave with a deeper appreciation of sailing and the physics behind it.
Captain Steve Butz has over 35 years of sailing experience and recently completed a circumnavigation on Alyosha. He’s logged over 50,000 nautical miles on this boat. You’re in good hands.
Hands On Expectations
Participants choosing the hands-on experience should be in good physical shape and willing to sign a fitness waiver. You’ll have a chance to re-confirm your desire for the hands-on experience at the start of the trip—it’s no problem at all if you decide, based on the conditions, to participate a bit less than planned. We understand that not everyone aboard wants to work the lines, and that’s fine.
Extra credit: Sailing gloves. If you have them, bring them. We do have a few extra pairs onboard. Not required.
Who Is This Trip For?
This trip requires a prior booking with Sail Alyosha. It’s designed for return sailors who know what they’re signing up for and want to go deeper. Whether you’re a seasoned sailor looking to sharpen your skills or someone who fell in love with sailing on your first trip and wants to understand the mechanics behind it, this is the natural next step.
That said—if this is simply the most convenient time for you and you just want to get out there and sail, by all means book the trip. We have plenty of “Hands On” sailors who actually prefer to just chill out and let others do the work. We also have many couples where only one person wants the hands-on part—and that’s perfectly fine. This trip is exactly as engaging as you want it to be.
We prefer no youth under 13 for this experience.
A Note on Motion Sickness
Alyosha is a big, stable sailing catamaran, and she sails flat. But there can be motion in ocean sailing, and if you’re prone to seasickness, you should plan to take preventative medicine before we leave the dock. Once you’re feeling sick, it’s too late. We recommend Bonine or Dramamine.
If you’re on the fence, take a look at our Seasickness Guide!
Weather & Cancellation
This trip is 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. Unlike some of our other trips, there’s no bay alternative here—there’s not enough hands-on sailing to be had behind Assateague Island.
What to Bring
This is a 3-hour sail, so come prepared. Alyosha has plenty of bottled water, but feel free to bring any food or drinks you’d like onboard. Sunscreen and sunglasses are a must—the real action is outside on deck. If you plan on being active on the boat, we recommend bringing sailing gloves if you have them (if not we have a couple pairs).Restrooms (“heads”) are aboard for customer use—just keep in mind the toilets on a sailboat are a little more sensitive than the ones on land.
There are restrooms (“heads”) aboard for customer use—just keep in mind the toilets on a sailboat are a little more sensitive than the ones on land. For sun protection, the real action is outside on deck, so we recommend plenty of sunscreen and sunglasses. Alyosha also has a roomy salon area and cabins if you need a break from the sun.
You’ll be as hands-on as you want to be. Some guests handle the helm, raise the sails, and participate in every aspect of the sail. Others prefer to observe and let fellow passengers do the work—and that’s perfectly fine. We have many couples where only one person wants the hands-on experience, and we also have guests who book this trip simply because it’s the most convenient time slot. Captain Steve will check in with you at the start of the trip to confirm your level of interest, and there’s no pressure either way. This trip is exactly as engaging as you want it to be.
No prior sailing experience is required for Hands On Sailing. This trip is designed for both seasoned sailors looking to sharpen their skills and complete beginners who want to understand how sailing actually works. Captain Steve will guide you through every aspect of operating Alyosha—from raising the sails to manning the helm—with clear instruction and patience. You’ll learn by doing, and by the end of the trip, you’ll understand the physics and mechanics behind ocean sailing. That said, this trip does require a prior booking with Sail Alyosha, so you’ll already know what it feels like to be out on the Atlantic before you take the helm.
Absolutely. Captain Steve Butz has over 35 years of sailing experience and recently completed a circumnavigation on Alyosha, logging over 50,000 nautical miles on this boat. He’ll be directing every aspect of the sail from the cockpit, ensuring safety while giving you meaningful opportunities to operate the boat. There’s a 10-15 minute safety orientation at the start, and you’ll review a brief safety guide beforehand. The trip is limited to just 6 guests, so everyone gets personal attention and real time at the helm and on the lines. Participants should be in good physical shape and willing to sign a fitness waiver, but sailing experience is not required—just a willingness to learn and participate.
Getting Here
Trips depart promptly at the scheduled time from our slip at Olde Towne Marina (307 Dorchester Street, Ocean City, 21842). Plan to arrive about 5 minutes before departure—there’s no formal check-in. But please know: if we have other guests and you’re late, we will still leave on time. It’s not fair to punctual guests to make them wait. Parking can be a challenge, so arrive early and maybe have a drink at the restaurant next to the marina.