April 25, 2023

Best Sailing Holidays in the World

In search of a sailing holiday in 2023? Look no more!

Here, you will get my views on what I believe are the greatest sailing trips around the world. Get ready for an exciting voyage of exploration and discovery. Investigate some of the most spectacular places - all within reach of a sailboat!


Sailing is more than just fun. It's a way to explore crystal-clear waters, secret coves and stunning views - all accessible by boat.

My first ever sailing trip was a two hour sail as a child out of Weymouth harbour, in the UK. I was bitten by the sailing bug and soon after that I joined my local sailing club. (Redditch Sailing Club)

For over 20 years though I have concentrated on ocean sailing as that is where my passion lies.

So here I offer my opinion on the best sailing trips, and there are many places to pick from. The Caribbean and Mediterranean might come to mind, but there are also other off-the-beaten-path spots with just as much beauty and adventure.

My older brother has lived in Songkhla, which is southern Thailand so I have a slight bias towards the Gulf of Thailand as I see him and his wife as often as I can.

Croatia's Dalmatian Coast has dramatic cliffs, and the Seychelles have turquoise waters. Sailing holidays let you get away from it all and enjoy nature's best. So, pack your bags, grab your sunscreen, and sail off on a lifetime trip!

Table of Contents

What to Consider When Choosing a Sailing Holiday

Choosing a sailing holiday can be tricky. Here are some things to think about to make sure you pick the best one for you!

  • Crew: What's your sailing experience? If you're a beginner or want to take it easy, think about getting a crew. Experienced sailors should investigate bareboat chartering.
  • Destination: The destination is important. Climate, culture, attractions - all should be considered.
  • Time of year: Off-season or low season are great times to go sailing. There'll be less people in marinas and popular places.
  • Budget: Consider the total cost, flights, crew costs, and accommodation.
  • Finally - pick a boat in great condition, with insurance and maintenance.

Are you a sailing enthusiast looking for the world's best sailing holiday destinations? Check out these top 5 picks of the year!

Greece: Stunning islands, crystal clear waters, and a gentle Mediterranean breeze. Explore the Ionian Islands, Cyclades, and Saronic Gulf routes for a scenic cruise.

Croatia: History, culture, and natural beauty - Croatia has it all! Sail across over 1200 islands in the Adriatic Sea.

Thailand: Explore the exotic beauty of turquoise waters, white sandy beaches, and limestone cliffs. Sail in the Andaman Sea and the Gulf of Thailand.

British Virgin Islands: Aquamarine waters, fresh trade winds, and secluded bays. The Caribbean Sea offers cultural richness too.

Whitsunday Islands, Australia: Home to the world's largest coral reef system. Explore the rainforests, snorkelling hotspots, and secluded beaches.

Choose any of these destinations for a breath-taking sailing experience!

Types of Sailing Holidays

Sail away with five different types of sailing holidays! From luxurious yacht charters to thrill-seeking regatta races, there's something for all kinds of sailors.

  1. Live in luxury on a yacht charter - explore the seas and islands while being spoilt with five-star service.
  2. Enjoy the freedom of flotilla sailing - sail with your own fleet, with the same route and itinerary.
  3. Go bareboat chartering - take control and explore at your own pace with this option for experienced sailors.
  4. Learn to sail - get some help from an instructor to gain skills and confidence.
  5. Get the adrenaline rush of regatta and race charters - join a team and see how you fare against other sailors from around the world.
  6. Sailing holidays for singles.

Whatever you're after, a sailing holiday is sure to satisfy!

Benefits of Sailing Holidays

Sailing holidays provide a unique experience packed with adventure, relaxation, and a love for nature. Here are some great benefits of sailing vacations:

  1. Unplug from tech and the daily grind. Sail away and leave behind the hustle and bustle of modern life. This way, you can unwind and get some much needed rest.
  2. Connect with nature. With sailing, you get a close-up view of the sea, wind, and marine life. You can immerse yourself in the beauty of nature.
  3. Explore diverse destinations. Sailing holidays can take you to hidden islands, secret beaches, and untouched coasts that you can't reach by land.
  4. Get physical exercise and thrills. Sailing is a great way to get active. You can hoist sails, navigate, and steer. Plus, you can even ride the waves or spot wildlife.
  5. Respect nature. Sailing is eco-friendly and leaves a low carbon footprint.

Pro Tip: When planning a sailing holiday, choose a reliable and experienced charter company. Make sure they provide proper safety gear, training, and maintenance for the boat.

Tips for a Successful Sailing Holiday

Sailing holidays are the best to chill and explore! Make 'em unforgettable with these tips:

  1. Route research: Plan your route in advance to make sure you don't miss any must-see places.
  2. Weather check: Keep an eye on the forecast, and update it daily, so wind and waves don't ruin your trip.
  3. Pack smart: Pack light, and bring only the essentials like sunscreen, shades, comfy shoes, and a waterproof backpack.
  4. Learn sailing: Get familiar with basic sailing techniques and safety protocols.
  5. Get to know crew: Get to know the captain and crew, they've got great info and tips.

Pro tip: Enjoy the journey, not just the destination.

Common Mistakes to Avoid on a Sailing Holiday

Sailing holidays are brilliant! But there are a few errors to steer clear from. Let's list them:

  1. Don't set sail without checking the weather first.
  2. Don't take too many things; don't forget weight restrictions.
  3. Don't forget necessary sailing equipment.
  4. Don't underestimate the time needed to learn sailing basics.
  5. Plan itinerary in advance and don't try to fit too much in a short time.

That's it! Follow these rules and you'll have a great sailing holiday.


You should certainly check out our ultimate guide to "What to take on a Sailing Holiday".

All in all, sailing vacations present a special and thrilling way to discover the world's seas and shorelines. Ranging from the Caribbean's azure waters to the Mediterranean's rugged coast, there's a sailing getaway for everybody.

Not only do sailing holidays offer stunning sights and warm weather, they also enable you to take a break from technology and the worries of daily life while honing your sailing abilities.

Therefore, if you lean towards a bareboat charter or a completely equipped yacht, mull over including a sailing holiday on your bucket list for an extraordinary experience in the open ocean.

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  • John Sixthsmith

    I'm a freelance writer and avid sailor who loves to share my passion for the sea with others. I've written articles for various sailing magazines and websites, covering topics such as sailing destinations, boat maintenance, navigational tips, and marine wildlife. I went on a short sailing trip whilst on holiday as a child and was instantly hooked. I've been sailing ever since. Although I've done a fair amount of lake sailing in my time, my real passion is the ocean. I hope you enjoy reading this blog about sailing as much as I've enjoyed writing about it.

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