Start Sailing Now: Introduced to Sailing on the Mediterranean

It all started with a sailing trip in the Greek Islands

I booked a sailing trip in the Greek Islands several years ago and liked it so much that I booked another trip almost every other year! I was in my early 50s the first trip, which consisted of spending a week sailing island to island in the Mediterranean aboard a 50-foot monohull with approximately 10 guests from various parts of the world. We were all strangers at first and best friends at the end. In addition, the boat had a captain and a cook/first mate. 

I was not part of the crew, but we were all asked from time to time to assist in various roles, such as helping with fenders, lines, and the helm. I had previously thought sailing was all leisure; just sit there and enjoy the view. Although there was a lot of that, I soon realized how active we all had to be during the journey. 

Boat ownership

After doing the Greek Isles trip several times, I decided to buy my own boat to sail on the Chesapeake Bay. I searched for about six months until I found the starter boat I was looking for. I did not want to spend a lot of money, since I wasn’t even sure if I would enjoy owning a boat. However, I knew that I wanted a boat that would be big enough for me to spend weekends on it and had some comfort features, such as air conditioning and heat, hot water, full galley with oven/stove/microwave, electric toilet, sleeping for four to six people, swim platform, outdoor shower for after swimming, and a stereo. I also wanted it to be small enough to singlehand. Finally, I found what I was looking for and made the purchase from Yacht10 Yacht Sales.

When I bought my 2000 Hunter 340 Elias about two and a half years ago, it took a bit of work making updates to get it to where I wanted it. Now Elias is docked at Horn Point Harbor Marina. Although I am a DC resident, I decided on Annapolis for my boat slip because my two sons live there, and as a realtor I have had some real estate sales in Annapolis. 

Initially I took the boat out with experienced sailor friends to learn some basics. I also took American Sailing Association (ASA) 101 and 103 courses through SailTime, with a private instructor aboard my boat, along with one of my sons and a friend.

sailing with friends and family
Sailing brings family together: Omar Vidal, center, with his son and his son's fiancee, aboard Omar's sailboat.

Overnights, singlehanded sailing, and more chartering

I plan to continue learning and practicing on my boat, primarily around the Chesapeake Bay, doing day trips and hopefully overnights as well. I am still not able to singlehand my boat, so that is a goal too. I will also very likely go back to Greece. I just went again this July, but this time sailed on a catamaran.

Advice for someone who wants to learn to sail 

I think everyone should at least take the basic ASA 101 to start. Then they should practice as often as possible. It should be a fun activity every time.

aboard his sailing vessel
Vidal's sailing adventures have included charter cruises, boat ownership, ASA courses, and bringing a coach aboard his own boat.

What surprised you about sailing?

Probably sticker shock. Everything marine is pricey, including the classes to learn. With budgeting and careful planning, it has been possible. It is also very challenging to find professional help when something needs fixing. Everyone is booked so far in advance, and it comes with a hefty price tag. Yet, I have no regrets, and I am truly enjoying this new phase in my life. I am even considering becoming a liveaboard in the future. That is how much I love being on the water, in my boat.

by Omar Vidal

edited by Beth Crabtree