One of the great things about operating a sailing school and being a yacht broker is seeing people’s dreams come true. Here at Windward SeaVenture we have had numerous people arrive at our door with the dream of taking off and going sailing. To go cruising on a sailboat is truly one of the most rewarding opportunities life has to offer. Speaking from my own experiences, I feel I have seen things, had experiences and met people while sailing and cruising that no other opportunity in life could have offered.
Cruising on a sailboat offers you the opportunity to go to the places you want to go and stay as long as you want. Unlike standard travel and vacations where you’re most likely staying in a tourist-oriented location and you’re only there for a set amount of time. While cruising you can go to the out of the way places. You find yourself interacting with the locals by going to the grocery store to provision or the marine chandlery looking for parts to fix your boat. Either way, it’s opportunities like these where you really learn what the place is about.
With our busy lives and packed schedules air travel is our standard mode of transportation for vacation destinations. While this is most convenient, sailing across mother ocean is a life changing experience in and of itself. For one it’s simply personal satisfaction that you have done it. You crossed a body of water using your skills as a sailor, navigator and personal endurance. But more importantly, flying at 38,000 feet you miss seeing the whales, the stars, the sunsets and all the beauty that mother nature has to offer.
It is rewarding to have the opportunity to pass this passion and dream onto those who cross our path. While much of this sounds daunting and intimidating, I can attest that many people have done it. We have had people send us an email inquiring about our classes, take them, practice a bit and eventually buy a boat and take off. The main regrets we encounter are those that wait till it’s too late. They have worked till they have reached some imaginary monetary number to feel secure and then they’re too old and health problems interfere. So, if you want my advice, life is short. Get out there, see this beautiful world, fulfill your dream and set sail.





