Trips and Experiences

Click an experience to view a description of the experience and see the scheduled trips.

Join Captain Steve and the crew of Alyosha for a trip that very intentionally skips the Atlantic Ocean and stays in the flat, calm Sinepuxent Bay west of Assateague Island. No need for dramamine on this trip, as Alyosha provides a very stable platform for couples, friends and/or families to enjoy some time on the water. Lounge on the trampolines or one of the many comfortable seating options- there is plenty of room for everyone!

We offer this trip for anyone who is longing to get out on Alyosha- the 50' catamaran sailing out of Ocean City, Maryland during the summer- but is concerned about getting seasick out on the ocean. Alyosha will slowly glide along the channel, potentially affording a view of Assateague's wild ponies, under diesel power for the entirety of this journey. You will watch the sun melt into the marsh along the west bank of the Sinepuxent and then be treated to a magnificent view of OC's night time skyline as we return to port.

Just a reminder: there is no sailing on this type of trip! 

Note on Birthdays and Anniversaries:

One of the great surprises of our first year of operations was how many people decided to celebrate their anniversaries and/or birthdays with us! (There were a few weddings and a proposal as well...)

Let us know if you are celebrating something with your cruise: We now have anniversary and birthday flags- complete with a nautical number set- that we hope you will consider raising during the sail.

More Information

Crew the boat that sailed the world!

Join us for a hands on sailing adventure that will include some very simple lessons on the basics of sailing. Captain Steve Butz has over 35 years of sailing experience and recently completed a circumnavigation on Alyosha. He has logged over 40,000 nautical miles on the boat. Expect to participate in raising, lowering and adjusting the sails as Alyosha gracefully glides under wind power!

Steve will do his best to explain the physics behind sailing and is happy to “go deep” with answering any and all of your questions.

No question is off limits as Steve is happy to pursue whatever topics interest sailors looking to boost their knowledge or stoke the interest of newbys to the sport. This trip- which is a longer experience at 4+ hours- is for those wanting more than just a ride in the Atlantic Ocean. You will leave with a deeper appreciation of the sport of sailing and the physics behind it.

Please note: If you just want to get out there and sail, and this is the most convenient time for you, by all means please book the trip! We have many “Hands On” sailors who actually prefer to just chill out and relax and let others do the work. This trip is exactly as engaging as you want it to be.

Note on Birthdays and Anniversaries:

One of the great surprises of our first year of operations was how many people decided to celebrate their anniversaries and/or birthdays with us! (There were a few weddings and a proposal as well...) Let us know if you are celebrating something with your cruise: We now have anniversary and birthday flags- complete with a nautical number set- that we hope you will consider raising during the sail.

We must have 4 people booked in order to go out on this trip. We also allow only 8 people on this trip to ensure everyone is able to get some "hands on" experience.

More Information

The premise of this trip is simple: Get out on the water for around 2 hours and experience the chill of relaxing on a 50’ catamaran while cruising through OC’s West Harbor, along the iconic OC inlet, and through the coastal bay adjacent to Assateague Island. We will supply the boat, the music, and the expertise in guiding the vessel- you supply your favorite cocktails and the party vibe!

This trip does not go out into the Atlantic Ocean, unless the conditions are extremely calm. Additionally, it is likely that the sails on Alyosha will not be raised during this particular experience. 

This is about relaxing, chilling, and enjoying friends and the beautiful scenery of the waterways surrounding Ocean City.

A “Happy Hour” you won’t forget. Consider topping off the evening with dinner at Pier 23!

More Information

There are only about 5-6 nights over the course of a summer where everything falls into place for a truly magical experience: sailing under the stars and moon in the Atlantic Ocean… If the Atlantic is too rough, we have also had incredible experiences sailing under a full moon behind Assateague Island.

A personal favorite of your captain, sailing under a full moon provides an unforgettable commune with nature that will have you reflecting on all of the sailors who have bravely gone to sea in search of opportunity. This trip will only be conducted if the conditions are perfect: light winds, clear skies, and a gentle sea. If we don't get the right conditions, your trip will be fully refunded, no questions asked! But if we do: prepare yourself for a once in a lifetime experience!

More Information

Sail the boat that sailed the world! 

Join Captain Steve Butz and prepare yourself for a very different Ocean City attraction! This is not the Sea Rocket! Sailing on the Atlantic Ocean is sometimes very exciting and often very relaxing, depending on the conditions. Don’t worry, you will have a great time either way…

The adventure will begin promptly at the scheduled start time and Alyosha will head out for an unforgettable sail on the Atlantic Ocean. Watch OC fade into the horizon as the crystal clear Atlantic Ocean waters surround the boat. The fun really begins when the diesel engines cut off and the boat moves along effortlessly under only sail power. Yes, this trip is about sailing! Pods of dolphins often playfully swim right off the bow of the boat, making a once in a lifetime natural experience! There is plenty of room aboard Alyosha for you to spread out and enjoy yourself- we encourage guests to utilize the wide trampolines in front of the boat for lounging.

Birthdays, Anniversaries and Special Events:

One of the great surprises of our first year of operations was how many people decided to celebrate their anniversaries and/or birthdays with us! (We have had weddings, first dates, and proposals as well...) Let us know if you are celebrating something with your cruise: We now have anniversary, birthday and special event flags- complete with a nautical number set- that we hope you will consider raising during the sail.

There is always a four person minimum for all Ocean Sailing trips.

More Information

Enjoy the sights and sounds of the Oceans Calling Music Festival while relaxing comfortably aboard Alyosha! 

If conditions allow, we will anchor the boat as close as possible- in the Ocean!- to the main stage of the Oceans Calling Music Festival with all of the trimmings of a 50' catamaran! Restrooms are available and feel free to bring your own food and beverages. There is also a coldbox and refrigerator available onboard. The plan would be to stay out for 3.5-4 hours and listen to the music. But the conditions will have to be JUST PERFECT.

If there is wind or choppy seas, then you can count on this being a shorter trip (more like a Sunset Cruise with a music festival "sail by") about 2 hours in length and we will refund 1/2 of your money!!!

More Information

Join Frannie, Solomon and Steve for a chill, Jamaican-themed tour behind Assateague Island with food and beverages included! We will provide the boat, the scenery, the food and the soundtrack: You bring the sense of adventure!


Alyosha will stay behind Assateague Island for the entirety of this two hour tour but we will hopefully put the sails up and kill the engines to enhance the party vibe! This trip is only for adults over 21 years old. Plenty of other options for kids on Alyosha.


The spread of food- provided by local favorites One Love Cafe- will include the option of a Chicken or Tuna salad sandwich with Caribbean Slaw chips and a pickle all served on toasted Brioche bun.


And Solomon promises to put everyone in the right mood with his Jamaican- inspired playlist!

More Information

Book Alyosha for your next event or group outing! Private charters for up to 12 people are available on request. This specific offering- usually on Saturday afternoons, is our longest available private charter outings for groups of up to 12 people. The time will run at least 1pm to 4pm and could run as long as 4:45pm depending on whether your group wants to go sailing, enjoy the nature and serenity of the bays behind Assateague Island or just set up an afternoon party on the water!

More Information

It’s everything you might imagine a Saturday Night Sunset Cruise to be, and even a bit more! We have added some time to this adventure to make it a worthwhile “date night” excursion. This trip is about double the length of our normal sunset cruise!

Cruise on Alyosha, a 50ft sailing Catamaran, out into the Atlantic for a beautiful view of the Sunset. If you are worried about your comfort during our longer "Ocean Sailing" and "Hands On" trips, then this shorter trip out into the Atlantic might be something to consider. Generally, the sunset cruise will depart about 45 minutes before sunset and will return at dusk. (about 65-75 minutes) Watch the sun set on Ocean City from the Atlantic Ocean as you glide along the coastline under sail. Lounge on the trampoline or enjoy any of the other excellent seating options that this 50' boat has available. This is a "must do" experience in Ocean City!

Note on Birthdays and Anniversaries:

One of the great surprises of our first year of operations was how many people decided to celebrate their anniversaries and/or birthdays with us! (There were a few weddings and a proposal as well...) Let us know if you are celebrating something with your cruise: We now have anniversary and birthday flags- complete with a nautical number set- that we hope you will consider raising during the sail.

More Information

Sail the boat that sailed the world!

Cruise on Alyosha, a 50ft sailing Catamaran, out into the Atlantic for a beautiful view of the Sunset. If you are worried about your comfort during our longer "Ocean Sailing" and "Hands On" trips, then this shorter trip out into the Atlantic might be something to consider. Generally, the sunset cruise will depart about 45 minutes before sunset and will return at dusk. (about 65-75 minutes) Watch the sun set on Ocean City from the Atlantic Ocean as you glide along the coastline under sail. Lounge on the trampoline or enjoy any of the other excellent seating options that this 50' boat has available. This is a "must do" experience in Ocean City!

Note on Birthdays and Anniversaries:

One of the great surprises of our first year of operations was how many people decided to celebrate their anniversaries and/or birthdays with us! (There were a few weddings and a proposal as well...) Let us know if you are celebrating something with your cruise: We now have anniversary and birthday flags- complete with a nautical number set- that we hope you will consider raising during the sail.

More Information

Are you looking for something different? Want to watch the land fade away and really get out there to experience open ocean sailing? We have you covered! This is the longest sailing experience we offer and is a great chance to get away from it all. 

We will depart from our West OC headquarters and sail straight out into the blue beyond. The goal here is not only to really soak in the ocean sailing experience but also to watch the water change colors as the Ocean City horizon fades and then disappears!

This 6 hour+ trip is for those who have sailing experience, have been sailing on Alyosha before OR, for those extremely adventurous types! Alyosha is a 50 foot St. Francis catamaran that has sailed around the world with Captain Steve at the helm, so you are in capable hands out there in the ocean.  

This trip is limited to 6 people.


More Information