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10 Absolutes for the Ultimate Sailing Adventure

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10 Absolutes for the Ultimate Sailing Adventure

For many, sailing is the ultimate dream adventure. But, thankfully, making this dream a reality is easier and less costly than you might think. The biggest factors in determining price are when, where and how.

When: Consider a shoulder season—even just a week before or after peak season—when prices drop considerably and weather conditions are still favorable.

Where: Winter is high season in the Caribbean; summer in the Mediterranean. The Med offers cultural experiences, great food and wine. The Caribbean can’t be beat when it comes to exquisite snorkeling, free anchorages, and a relaxed vibe. To cut costs, consider a less traveled, yet no less alluring destination, like the Adriatic.

How: If you have a certified captain among your mates, you may choose to go “barefoot” or self-contained. But even if you decide to hire a captain, you still have a range of self-sufficiency options.

For my trip last year, three newbie couples chose a launch from the Southern Caribbean island of Grenada for a weeklong sail through the Grenadines on a 38-foot catamaran. We hired a “teaching” captain to lead us through level 1 certification, but chose to cook for ourselves to cut costs considerably.

Here are a few things we learned along the way:

1. Sailing is Work

Yep, work. Your days will be spent lifting the sails, jibbing, tacking, navigating, steering and mooring, and then repeating the whole process again, until you anchor for the night.

You’ll learn a new vocabulary and skill set, sweat alongside your friends, feel challenged and invigorated, and have a whole lot of fun in the process. To get a jumpstart, be sure to read a sailing manual and learn basic vocabulary before the trip.

2. Sailors Sail

Duh, that’s obvious. Not so fast. It’s not until you’ve sailed that you grasp the meaning. A sailboat is not a floating hotel where days are spent island-hopping. That’s a great way to spend a vacation; it’s just not this vacation.

The purpose of sailing is to be on the water not on the shore. In the pre-sail meeting, have an open and honest conversation with your captain and mates about what everyone hopes to get out of the trip and how your ideal day would look. Then get ready to be flexible and divvy up chores and jobs.

3. Size Matters

The question of size should be “where will I spend most of my time?” The answer: topside—so you can’t go wrong by choosing a boat with ample outdoor or deck space.

You’ll also need to decide between a catamaran or a monohull. Some sailors prefer the way a single hull maneuvers through the water and like the feel of its gentle rocking motion when anchored. Others prefer the stability and layout of a cat. Do your research and ask the charter company for advice.

4. Don’t Be a Dope

Save the heroics for hoisting sails. When it comes to preventing seasickness, being smart and playing it safe wins every time. You’ve put ample planning and resources into this trip, so make the most of it by doing yourself and everyone on the boat a favor, take the Dramamine.

To ensure you don’t spend the day hanging over the side of the boat in agony, or watching your mate do the same, encourage everyone to take a pill first thing in the morning at least 30 minutes before lifting sails.

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