Private Charters on Alyosha
The Boat Is Yours — Make It Whatever You Want
Book early for the 2026 Summer Season — prime Saturdays and Sundays tend to book months in advance.
There is no better way to bring families and friends together than spending a few hours aboard a 50-foot sailing catamaran with room for everyone to spread out, relax, and actually enjoy each other’s company. Whether your group wants to sail the Atlantic Ocean, cruise the calm waters behind Assateague Island, or do a little of both — a private charter on Alyosha means the itinerary is entirely up to you.
Captain Steve and his crew will work tirelessly to make sure your entire group is taken care of. Alyosha can accommodate groups of up to 12 people. For groups larger than 12, consider the OC Bay Hopper.
New for 2026: Make Your Charter a Complete Experience
We’ve partnered with Oyster & Scales — the restaurant right next to Alyosha at Olde Towne Marina — to give your group even more options:
- Catering On Board: Have Oyster & Scales cater food directly to Alyosha for your charter. Show up, step aboard, and the spread is already waiting.
- Reserved Dining Before or After: Book a special table at Oyster & Scales for your group before or after your trip — turn your charter into a full evening out.
- Reserved Parking: Skip the stress of finding a spot downtown. Reserve parking right next to the restaurant and the boat for $50/car as an add-on.
- Arrive by Water: Worried about parking altogether? We can arrange for your entire group to be brought down to Alyosha by OC Bay Hopper. This needs to be coordinated separately, but it’s a great option — and a pretty memorable way to arrive.
What Makes a Private Charter Special
When you book a private charter, the boat is yours for that period of time. No strangers, no shared space, no compromise on what you want to do. You pick the experience — a real ocean sailing adventure, a relaxing evening cruise behind Assateague Island, or a combination of both if you book enough time (4 hours makes a great combo trip).
You can bring your own food and drinks and set up a spread on the table. Alyosha has a cold box, a refrigerator, and room for big coolers if you need them. There are two restrooms aboard. Trampolines for lounging, cushioned seating for groups, and a roomy salon if anyone needs shade or a break from the sun. It’s everything you need for a day — or evening — on the water with the people who matter most.
Perfect For
- Family Reunions & Get-Togethers: Room for up to 12, two restrooms, calm water options for kids and grandparents, and a platform everyone can enjoy together.
- Bachelorette & Bachelor Parties: And sure, for the right kind of group, Alyosha is perfect for this. Bring your own drinks, bring your playlist, and let us handle the boat.
- Birthdays & Anniversaries: We have anniversary and birthday flags — complete with a nautical number set — that we’d love to fly for you.
- Date Nights & Proposals: Nothing says “I planned something special” like a private sailing catamaran at sunset.
- Corporate Outings & Team Events: A unique team experience that’s nothing like the usual happy hour.
- Couples & Friend Groups: Sometimes the best plan is no plan — just good people, good drinks, and the water.
Two Ways to Book a Private Charter
Option 1 — Book All 12 Seats on Any Experience: Any of our listed experiences can be made private by booking all 12 spots on the boat. You’ll automatically receive a 10% discount when you book every seat. (Look for the link when booking.) As a private charter, you can dictate the itinerary — whether you go sailing or cruising behind Assateague Island.
Option 2 — Build Your Own Charter: Want something completely custom? Use our charter builder to design your own experience from scratch — pick your date, your time, your itinerary, and we’ll make it happen.
Special Events in Ocean City
Alyosha is a fantastic platform for Ocean City’s biggest events. The Air Show, the 4th of July fireworks (you can see 4–5 different shows from the water), and when conditions allow, the concerts Ocean City hosts each summer. All of these can be customized for your group — contact us for special event availability and pricing.
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. If you don’t see the boat, don’t worry—we’re probably off on another adventure and will return just before departure.
If You To Contact Us to Book Your Private Charter
Call: 410-376-5454 OR email: hello@sailalyosha.com