Looking for a Supersized Adventure? For serious sailors only...and offered only to those who have sailed on Alyosha in the past...

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 (who must contact us before booking) 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 is NOT a good trip to figure out whether you or your kids are susceptible to seasickness!

This trip is always limited to 6 people.

Trips on Alyosha depart promptly at the scheduled time from our brand new location at the "Olde Towne Marina" (address 307 Dorchester Street). Check in with our staff at our shed or come directly down to the boat at the end of the dock. (You can't miss Alyosha, we are the only sailing vessel around.) Parking can be limited, so arrive early.

This is 6 hours of sailing so make sure you plan on bringing lunch or heavy snacks for your comfort. Alyosha has plenty of water bottles for guests, but all other snacks and food are up to you. There is plenty of room onboard to store coolers, food and drink. That includes a refrigerator and a "cold box" for your supplies if you don't want to bring a cooler.

A Note Specific to The Big Blue re: The Weather:

This trip is also a bit more dependent on a good forecast for the full day. Full refunds will be made if the weather doesn't support a 20 mile offshore adventure OR you will be given the choice for a sail closer to share from 10am to 1pm or 1pm to 4pm. If this is the case, you will not receive any further refund- you will sail for only three hours, but with a limit of 6 passengers, which makes this a much more exclusive opportunity!

This trip is all about ocean sailing, so some preparations you should consider include an extra layer on chilly days (especially early in the season) and a dry change of clothes if you plan on chilling in the trampoline and the conditions are a bit rough... If you are prone to seasickness, it is highly, highly recommended that you take anti-seasickness medicine prior to the trip. If you are on the fence after reading this: Please take a look at our “Seasickness Guide!”

6 hours of sailing affords you the ability to really experience the sea, and if you want to bring additional items to pass the time no worries (a book? podcast? etc...)

There are restrooms ("heads") aboard Alyosha for use by customers. Keep in mind that the toilets on a sailboat are a little bit more sensitive than land based toilets… so plan accordingly.

Protection from the elements: Although Alyosha has a roomy salon area and cabins that our guests may use, the real action is outside, on deck! Therefore, we highly recommend plenty of sunscreen and sunglasses.

Aligned with the goal of ensuring all Sail Alyosha customers have a great experience, we will only run trips that are deemed safe by our Captains. Generally, the weather on the coast of the Ocean City area is very pleasant but sometimes storms and thunderstorms do occur.

In the event that your trip is cancelled, you will receive a full refund. Sometimes, the weather conditions, particularly high winds causing choppy seas, will allow us to run a safe trip that is a bit unpleasant.

Our captains will always strive to let people know when conditions will be less than ideal and if conditions warrant a possible refund you may choose to not take the trip. (But sometimes those rough passages make for the best experiences!)