Should you live on a sailboat?

Adventure 3 min read

The dream of climbing aboard a sailboat, leaving your problems at bay and sailing into the sunset is not an uncommon one. Life can become stressful, complicated and in several ways unfulfilling. The idea of sailing, for some, provides a means of escape, relaxation, freedom and a return to nature.

But how do you know if sailing into the sunset is for you?

Early in our marriage, my husband, Simon, and I decided to upgrade our usual weeklong sun and sea vacation to one that also included sailing. After making inquiries, we discovered that chartering a sailboat for a week simply required one of us to take a two day sailing basics course at a local sailing training school. Both Simon and I had some previous experience on a sailboat but it was very limited.

Simon took the local course over a weekend and a few months later we flew off to Cephalonia, an island in the Greek Ionian Sea, and took command of a 33’ Gibsea monohull sailboat. We were about to discover if sailing was right for us.

When booking a charter sailing vacation there are various options.

You can sign up for a flotilla, bareboat or private charter. The flotilla option is where 10 to 15 boats all leave and arrive at the same destination. This option is fantastic for newbies.

Every morning, a member of the lead crew gives a briefing about the next destination, discusses how the boat will need to be moored and outlines interesting places to stop for the day to swim, grab lunch or sightsee. After breakfast and the briefing, members of the lead crew help the boats get off their mooring and are available throughout the day if there are any problems.

After leaving the dock, anchorage or mooring field you can set your sails and enjoy a relaxing journey taking in the sights, smells and sounds of the sea OR you can play around with the sails to see just how fast you can make the boat go. All the other boats in the Flotilla scatter in separate ways, eventually coming back together at day’s end. When arriving at the designated destination for the evening, the lead crewmembers help all the boats get situated. Knowing that help is on hand provides newbies the opportunity to gain confidence without enduring a potentially stressful situation.

Flotillas are an excellent way to discover if sailing is right for you.

Bareboat and private charter options are available also. With bareboat and private charter, you can sail around an area unassisted. This means that you’re given full reign to decide where to go, when to leave, when to arrive and how long you want to stay in a particular location. Many boaters choose this option after they’re comfortable with a particular area – perhaps from doing a flotilla holiday in the past.

Aside from doing a flotilla or bareboat charter, you can hire a skipper to sail you and your family around. Furthermore, there’s a wide range of boat options to choose from. For example, you can try your hand at a monohull or catamaran; both boats have a variety of sizes.

Although Simon and I eventually had the confidence to do a bareboat charter, we continued to opt for flotilla vacations. We really enjoyed meeting new people and swapping stories during happy hour after a lovely day of sailing.

The range of people enjoying sailing holidays has no boundaries.

We’ve enjoyed the company of young couples, senior citizens, families with teens and babies in addition to people from a huge variety of nationalities.

Simon and I treasured the whole package – the sea, sun, sailing, new friends, excellent food and new memories. We’ve done over ten years of Flotilla vacations in Greece, Turkey and throughout the Caribbean. Every expedition was unique, fulfilling and left us wanting more!

Having many years of sailing flotilla vacations under our belt, and after welcoming a child into the world, we decided the time had come to buy our own boat. When our daughter was nine months old, we purchased our first boat, Selene, a 35’ Moody. And after over two years of sailing her locally, we traded her in for a 56’ Oyster and cut lines from land to head out around the world in our new vessel.

So how do you know if sailing into the sunset is for you and your family? Give a flotilla or bareboat charter a go. Who knows what might happen from there? Perhaps you’ll follow our footsteps, sail into the sunset and never look back.

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