Overall rating: ★ ★ ★ ★ ☆ – 4 adventure travel stars

Sailing adventure

Sailing the ocean blue

Sailing offers something that everyone wants in the worst way: freedom. That’s why sailing adventures are so popular all over the world.

Some take this freedom to extremes and sail around the world on adventures where they don’t see land for days or weeks on end. That may be beyond the scope of what most people are looking for, but taking a couple of weeks to sail from island to island in the Caribbean is something many of us would love to do.

If you want to captain the sailboat yourself you’re going to need considerable skills and experience.

However, even if you have no skills whatsoever you can still fulfill your dream without delay by hiring someone with the skills necessary to take charge of the vessel.

And if you suffer from motion sickness just put one of those travel patches behind your ear, and stay above deck. You’ll be fine.

Risk Factor
Rating: ★ ★ ★ ☆ ☆ – 3 adventure travel stars

Sometimes you’ll hear about people who have survived a terrible ordeal on the water. The media certainly loves to showcase sensational stories like that. However, statistically speaking, sailing has a much lower risk factor than getting in your car to drive on the freeway to work. That is when it’s done safely, because there are risks that need to be considered.

Five significant risks include collisions, grounding, capsizing, falling overboard and fires. The top risk, by far, is collision, so you’ve got to be alert at all times and have the maneuvering skills to avoid other boats and miscellaneous hazards.

A few things that will lower your risk factor are light to moderate winds, warm waters, an experienced crew and knowing the area where you like to sail. Things that will increase your risks are heavy weather, bad equipment and pushing the limits of your sailing abilities.

You might also want to avoid the Bermuda Triangle if you plan to go sailing off the eastern coast of Florida.

Skill & Physical Factors
Rating: ★ ★ ★ ★ ☆ – 4 adventure travel stars

Sailing requires a lot of skill and experience if you want to stay safe and enjoy it to the fullest.

You’ll need to learn how to master the maneuvers such as tacking, gybing and docking, and you’ll need to know how to navigate. But who knows, maybe the navigation thing is overrated. Christopher Columbus thought he was going to Asia and look what he discovered.

You’re also going to need to learn how to tie some good reliable knots. The last thing you need on a sailing adventure is to find yourself adrift because you didn’t know the correct way to tie your boat up with a round turn and two half hitches. Not only could that cause some expensive damage to your boat, it could also prove to be very embarrassing.

When it comes to the physical factors you’re going to need to be strong, agile and have a good sense of balance to move about the deck while your sailboat is rolling on the seas.

Fun Factor
Rating: ★ ★ ★ ★ ★ – 5 adventure travel stars

You’re heading out to sea with the wind filling your sail, yours friends are on board and there’s plenty of food in the cabin for a weekend on Catalina Island. As you tack back and forth you watch the orange sun settle on the highest peak of the island as you prepare to moor your boat.

I used that example because I used to go sailing with a friend on his boat off the Southern California coast and head towards Catalina. Those were the days, and I can tell you from personal experience that the fun factor for sailing adventures is definitely a five-star experience.

Christopher Cross may have said it best in his song: Sailing… just a dream and the wind to carry me, and soon I will be free.

20 popular places for sailing adventures

There are certainly numerous places all around the world for some great sailing adventures, and following is a list of some of the best.

  • French Polynesia
  • British Virgin Islands
  • Belize
  • The Grenadines
  • The Bahamas
  • Cape Horn, Chile
  • Norway
  • Balearic Islands, Spain
  • Scotland
  • Wales
  • Ilha Grande, Brazil
  • Tahiti
  • Tonga
  • Turkey
  • Greece
  • French Riviera
  • Corsica and Sardinia
  • Balearic Islands
  • St. Barts
  • New Zealand