Booking the perfect charter
Do you need a Yenta for a good match?
Scott Ralston
Booking a sailing vacation charter can be a little like searching for the perfect mate- and I mean a love match made in heaven.
It’s all about finding the best boat, climate, itinerary, getting value for your investment- and avoiding the perfect storm.
It can be daunting the first time around- like a blind date.
But don’t worry smooth sailing can lie ahead.
Here are some simple tips to navigate in unchartered waters.
• Ask friends and family, even strangers who have chartered vessels in the Caribbean.
• Find an operator based where you want to go. i.e. Don’t expect an operation in Alaska to know the islands – even if its principals sailed the Caribbean for years. Better get someone you can contact in the Caribbean, where and when you need them.
• Ask yourself, if you are a seasoned sailor or do you really need someone to help you navigate? Get rid of the ego. This is a safety issue, and can make or break your holiday if you're not honest.
The difference between a bareboat and a crewed charter is night and day.
• If you want to go bareboat, consider what size works well for you.
Determine if you want to work at sea or lay back with a rum punch- or a lot of rum punches.
Do you want to explore islands by land or just savor some peace at sea?
• Call or e-mail a few charter companies. Ask about thier expertise. Tell them what will make you happy, and ask them to play Yenta, so you can match your expectations with what is out there.
Their initial response will speak volumes about the service, and move you a lot closer to your dreamboat.
Scott Ralston has charted a few boats, and learned to sail before he could drive a car.

