CHILL 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. (we might try to get the sails up, but this will depend on the time and wind direction!)

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. Bring your camera!

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

An Experience Unlike Anything Else...

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 have had incredible experiences sailing under a full moon behind Assateague Island. This will be the Captain's choice based on conditions.

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! This trip generally happens less than 50% of the time it is scheduled- BY DESIGN! In some ways it is a perfect guarantee: Either you get great moon viewing, peaceful sailing conditions, OR YOU GET A REFUND.

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. When this trip happens, it is magical- easily our favorite experience to offer customers!

More Information

All the "chill" of sailing, without the uncertainty of the Atlantic Ocean!

So you want to enjoy a few hours on the water and experience sailing without the uncertainty of what the Atlantic Ocean serves up? This experience is for you... Several times during the summer, the tides and currents behind Assateague Island afford the most pleasant sailing imaginable: a quick trip south, with a strong current heading into the predominantly south winds. This gets Alyosha down to the Verrazano Bridge pretty quickly. Then, we turn around and the magic happens: a long, beautiful spinnaker run with those south winds behind us, into the current! Flat sailing, no motors, and you and your family/friends take in the scenic views from a choice seat on the trampoline or on Alyosha's spacious deck.

If you like the idea of sailing, but maybe not the actual seas and boat movement, try this trip out. It is fantastic!

More Information

Take in a Sunset on a spacious, 50' sailing catamaran!

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 65-70 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

View all trips and experiences (not just CHILL)