10 Absolutes for the Ultimate Sailing Adventure

Travel Lists

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.

5. Less is More

Your charter company will send images of available boats. Yes, the cabins are really that small. Pack essentials only. Same goes for provisioning.

Moral of this story: don’t worry. You can pick up what you need along the way. And, on many evenings, you’ll hear music and laughter drifting from a beach shack and see locals grilling up today’s fresh catch. Guess where you’ll be?

6. Ride the Wave

It’s a good idea to have a destination and stops along the way in mind, but leave flexibility for detouring to interesting finds. Have a discussion with your captain about must-see stops, distances between islands and approximate sailing times so you can make decisions on how much time will be spent on the open sea and how much island flirting.

Having one long-haul day to experience the open sea and an array of sailing conditions before reaching an island chain can be grand. Some people may prefer short bursts between islands with more time for fishing, swimming, snorkeling and relaxing.

7. Spotting Boat Runners is Fun, but …

You’re savoring the first cup of coffee on deck when a parade of small crafts approaches offering wares and services. You’ll quickly find that those wares consist of beverages you probably shouldn’t drink (a plastic jug with purple-colored wine, for instance).

You settle for asking for an ice delivery. When they return hours later there’s no room in the coolers or fridge because you gave up twenty minutes ago and took the dingy to shore to get a few bags yourself.

8. Sailors are Special

From the hippie sailors in tiny boats who haven’t slept on dry land in years and flotillas of Europeans on summer-long outings to well-heeled mega yachters, every happy hour is an opportunity to collect great stories and make new friends. And, you’ll enjoy having new material to rehash with your mates when you’re back on the boat with a nightcap in hand.

As interesting as the fellow sailors are, be sure to make an effort and spend time getting to know the islanders too. You’ll encounter the most welcoming, fun-loving, friendly locals you’ve ever imagined and get a greater sense of the character of this beautiful world you’re gliding through.

9. Oh Captain, My Captain

The captain will be on deck when you stumble out in the morning, share every meal with you, tell you the most unbelievable stories and, most importantly, be your lifeline if anything goes wrong.

How do you get a captain who fits your crew? Communication is key. Share useful information with your charter company including what you hope to get out the trip. Also, provide the company with the age makeup of your crew. Then, once they have a few captains in mind, ask for bios. When you meet your skipper, have an honest chat about how you’d like to spend your days.

10. Sailing is Life

Some people experience a dose of melancholy on the last day. After a week you realize the boat quickly became your own private island. Your crew was your tribe and your captain, the fearless leader. As soon as you step onto land, it hits you that being on firm footing feels shaky and adjusting, both mentally and physically, will take some time.

You’ll likely glance over your shoulder for one last peak at her: the boat you’ve worked and come to know so well. After all, you weren’t just a passenger. You were a sailor.

Jess is a freelance writer and blogger with a passion for all things travel, art and the outdoors.

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