I’ve been planning sailing trips for several years now in conjunction with this SailTime business and learned some lessons worth sharing along the way. One of the big benefits of the SailTime program is that Members are free to take sailing vacations without feeling guilty that they left the boat they own at home for bluer pastures abroad! While our PLUS program, alone, opens up a world of sailing adventure, there is nothing like traveling to a distant sailing mecca to immerse yourself in a cruising vacation.

Now, we are 60 days away from our next sailing trip. But the planning for our Fourth Annual Captains Cruise began in ernest last Summer right after the Third Annual concluded. Thanks to the internet we have a boundless resource for planning vacations and preparing. Over the next several weeks, I will share with you my process for planning our sailing trips. Keep in mind that I plan for a flotilla which has to take into account more points than if you were just making plans for you and your friends or family on one boat. I plan two trips a year for our Members to participate in if they so desire. The good thing about that is I am always in a state of planning…there is always the next trip to plan for!

Some people don’t like planning trips. I love to. So that makes this “tough job” easier to handle. There is something to be said for last minute travel. Especially in a down economy. You can save some major bucks if you can go spur of the moment. But most of our trips are to foreign lands never visited before that require more than casual planning. Also, there are generally easier places to sail and more challenging places to sail. You need to tailor that into your plan. Here is my process for planning:

• One of the most exciting sailing trip decisions is where to go. I like to decide where to go as far out as a year before. This gives me 3-4 months to make the boat reservation.
• After you decide where you need to decide when. We go during shoulder seasons. It’s not the “off” season, but the shoulder between high and low. It merges the best price with the best potential for good weather. There is a shoulder season nearly universally in the Spring and Fall.
• As soon as you know when, its time to research what charter operators are available. We like to work directly with the operator because of our flotilla situation, but you may want to use a charter boat agent or broker. If in doubt, working with a 3rd party could help you if things don’t work out. I do as much research as I can about operations and finally try to have 2-3 to get quotes from.

In many instances the operator decision will be easy. There may only be one! But in cases like the Mediterranean or the Caribbean you may have several factors that go into your choice of operator. For instance, a popular method of getting the most bang for your buck is to do a “one-way” charter where you pick the boat up in one place and drop it off in another.

That is what we are doing this Spring. I found a Sicilian charter operator who was able to put all the pieces together for us. We are sailing for two weeks leaving the NE Sicilian port of Portorosa for a cruise of the Aeolian Islands and the North Coast of Sicily, dropping the boats at the NW end of the island in Palermo.

With only 60 days before departure I am at the fun part of the planning. Digging deep into the internet to become familiar with our sailing destinations. With a little You Tube and Google Translate, I know more about our first stop at Vulcano Island than I could have ever imagined!

Baia Levante Centro Nautica, Vulcano Island in the Aeolians

In my next installment of these Sailing Trip Planning Tips we will choose an awesome crew and reserve the boat!

Read the whole series ::: Part 2 ::: Part 3 ::: Part 4

Tags: 2010, bareboat, charter, flotilla, itinerary, planning, sicily, vacation

Trackback URI | Comments RSS