Five Easy Beginners-Friendly Sailing Trips And Destinations

One thing is sure when you are a beginner sailor – it’s crucial to find the ideal location for your first sailing vacation. You most likely have a lot of concerns about your skills, safety and responsibilities, and you should.

If you are looking for an beginner-friendly destination that won’t make you sweat for your first sailing trips, you are in the right place. Here are 5 of the most welcoming and breathtaking sailing locations for novices.

Why is it important to pick a beginner-friendly destination when sailing alone for the first time?

Picking a beginner-friendly destination is very important for a lot of reasons. Here are the main ones

An easy to sail destination will be a lot more relaxing

Let’s be honest, sailing is not always a very relaxing experience. Even the experienced skippers can find themselves in tricky situations that can bring a lot of stress on them, on their passengers or on the integrity of the yacht.

If it’s your first time sailing a boat alone, or if you are a casual sailors, you probably want to stick to an easy to sail destination for your first few trips, so that you do not find yourself in a situation that could jeopardize the relaxing aspect of your holidays!

Do not worry, you don’t need to sail in rough seas or to do a transatlantic to enjoy the speed and thrill of sailing. After all, you probably just want to have fun, not fear for your life or the ones on board.

Beginner friendly sailing destinations can have the infrastructure to help you out in case of problem

You surely are not hoping to have issue when you are sailing a new area, especially if you are a beginner sailor. But let’s face it, the sea is an unpredictable area, and you could be facing very stressful situations, even if you did everything right. Again, even the most experienced sailors sometimes found themselves in situations you’d rather not be.

Even if the likelihood of a problem with your yacht is quite low when you sail the right yacht in the right destination with the right skills, the risk is never non-existant.

When you have a problem at sea, help can be more than welcome. If you are sailing for the first time, it’s recommend that you sail in an area where help could be reached and come easily should you need it. Hopefully, you won’t. But you don’t want to be lost in the middle of nowhere with no help around when you are a beginner sailor with a serious issue.

Read also: How to sail upwind

A successful first sailing trip can build your confidence and experience

Sailing is all about experience. There is no magic formula: the more you sail, the more you will be good at it. The reason is simple: the more you sail, the more you are likely to encounter different situations that will challenge your knowledge and expand it.

But that doesn’t mean you should jump into the hard stuff straight away. Trying to reach new levels too fast is not going to bring you much results.

Start with an easy destination and build your experience slowly.

What Are The Main Criteria For Picking A Beginner-Friendly Sailing Trip?

The sea should be calm during the season you plan on sailing

A good easy to sail destination should have calm or relatively calm waters when you plan on sailing. First, it will be a lot more comfortable for everyone onboard with you. But it will also let you relax and enjoy your yacht charter a bit more instead of always stressing about the navigation, mooring and the weather.

Each destination has seasons where the seas are quieter:

  • For Mediterranean destinations, summer months (June to September) are the most quiet
  • For Caribbean destinations, winter months (November to March) have the calmest waters

Pick these periods and you are maximizing your chances of sailing a destination that is as beginner-friendly as it gets.

Keep in mind that the seas and oceans can be unpredictable, even in the best seasons. You might have windy days, rain, choppy waters and even storms in the best seasons. It is just much more unlikely than in the other seasons.

The winds should be suitable to your sailing experience and destination

The winds are very important when it comes to sailing, especially if you are a beginner.

Sailing upwind can be significantly trickier than downwind, and the wind can create a lot of chop on the water, and even waves, that can make sailing a lot more challenging for a beginner.

If you are sailing for the first time, try to pick a destination and an itinerary that will go with the wind and not against it. It’s usually better to just go with the flow than to try to reinvent the wheel and get stuck into difficult situations.

On this subject: How to Sail Upwind?

The (maritime) traffic should be light enough

Contrary to popular beliefs, the most popular sailing destinations are not always the most beginner-friendly ones. The reason? The maritime traffic can be an added source of stress for a beginner sailor.

That doesn’t mean you should pick a destination where no one is present either. Again, you would be very grateful to have someone around picking you up if you are facing a problem.

But if you are organizing your first sailing trip and are not so confident about your skills yet, try to pick a destination where maritime traffic is limited, so that you don’t sweat too much about crashing into somebody else’s boat.

Read also: Best Sailing Apps: 6 Apps You Should Be Using In 2022

Pick the Right Yacht and Pack Carefully

The yacht you are picking for your first sailing trip should be adapted to your skill level. In this department, size does matter, and the bigger is rarely the better. We highly recommend you to pick a boat you can easily maneuver to have a “pure” sailing feeling and to ease the mooring. That doesn’t mean you should pick a mini yacht either, simply pick one that reasonably match your abilities.

When sailing as a beginner, you should also always include the essentials, such as clothes, sun protection, a waterproof bag, first aid supplies, food, water, and appropriate attire and shoes. A phone, GPS, map, and compass are a few additional essential items to purchase. You may also wish to carry medication if you are susceptible to travel sickness.

Read also: What Are The Different Parts Of A Sailboat?

The Five Best Destinations For A Beginner Sailing Trip

Croatia: a good beginner friendly destination in Mediterranean

Many refer to it as the “new Greece,” “new Riviera,” or “new Tuscany.” Travelers’ best-kept secret, Croatia, continues to be genuine and beautiful with its received attention. This stunning location, one of the most well-liked bareboating locations, provides the ideal circumstances for any novice. Croatia is the destination you should visit because of its year-round sunshine, comfortable temperatures, and calm northerly winds. Also, May and September are ideal for carrying out that task.

Greece: plenty of islands to explore as a beginner

Without stunning Greece, no list of sailing locations is complete! Greece is undoubtedly one of the best locations to begin exploring the fantastic sailing world, and this position is no exception. But among all the stunning locations in Greece, we strongly advise hiring a boat on Lefkas.

Beginner sailors should head to this island, which is located in the Ionian Sea off the western coast of Greece. The ocean is calm and serene, and there is a light northwest wind from April to November. The temperature, which ranges from 24 to 28 degrees Celsius, is enjoyable.

You can also travel to Santorini, Mykonos, or Corfu if you have an upbeat attitude and wish to experience all that Greece offers in terms of natural beauty. Their world-class resorts, stunning beaches, and vibrant nightlife won’t disappoint you.

The British Virgin Islands: a perfect winter destination for a beginner sailor

The practice of saving the best till the last is common. These locations, each distinct and lovely in their way, thoroughly merit exploration by boat. We must admit, though, that whenever the words “beginning” and “sailing” are combined, the British Virgin Islands come to mind.

The BVI is one of the top sailing locations for experienced and novice sailors. You might have already made your vacation travel plans by this point. The queries you had likely vanished as well. Who wonders, perhaps you’ve already seen Croatia’s lavender farms while sailing in the Ionian Sea. However, whatever the experience level, visiting these islands is a must for all sailors.

Turkey: an up and coming easy sailing destination in Summer

Turkey‘s sailing season lasts from April to October. The Mediterranean climate’s merciful temperature is the first factor that makes this one of the most accessible places for novice sailors. The Aegean Sea and Turkey are excellent for novices because of their clear visibility, long, hot summers, and sparse rainfall. They can take leisurely boat rides and explore breathtaking scenery in Turkey.

Try and visit Fethiye when sailing the tranquil Aegean Sea. The 2,300-year-old tombs cut into the steep cliffside are only one of the many historical gems that make up this town. The city features a harbor protected by a tiny island in addition to culture, delicious food, and breathtaking vistas. Its 12-meter-deep waters and several anchor spots make it ideal for beginners. A location where you may practice sailing while admiring Turkey’s natural beauty.

The Bahamas: a good playground for a beginner sailing trip

One of the best sailing vacation destinations for beginners is the Bahamas. The Bahamas see more than 340 days of sunshine annually with a consistent trade wind at 16 km/h.

A team and a captain can be hired for a little extra, or sailors can rent a boat and take a quick sailing lesson.

Deep sea fishing, reef fishing, or spearfishing off the coast of Nassau are all options for sailors who enjoy fishing.

There are additional shipwreck dives near Long Island, Andros Island, and Bimini, and coral reefs near Nassau for those with an adventurous spirit.

If you feel like forgoing your yacht in favor of sunset beach strolls on actual pink beach sand, you may wish to check out Harbour Island’s Pink Sand Beach.

Crewed Yacht Charters: A Great Alternative For A First Safe Sailing Trip

If you are unsure about your sailing skills, a great alternative is to charter a crewed yacht, or at least a yacht with a skipper.

The captain or the skipper can bring you everywhere you want to go… safely. If you are starting out, you can learn a lot from them by looking at what they do and why they do it. A great way to gain experience without the responsibility of sailing a yacht yourself.

A crewed yacht charter is also very comfortable. The crew is taking care of everything, including the parts about sailing a yacht that are not so fun.

Read also : 10 Sailing Myths And Bad Advice You Shouldn’t Listen To


Picking an easy to sail destination is very important if you are a beginner sailing without a crew.

Make sure you pick a destination with calm waters, favorable winds and help nearby for your first few sailing trips. The point is to enjoy the thrill of sailing and not to get yourself scared.

Many sailing destinations can be perfect for beginners: Greece, Croatia and Turkey can be quite easy to sail in summer months. In winter, the British Virgin Islands or the Bahamas are also serious contenders.

If you are unsure about your sailing abilities, a crewed and / or skippered yacht charter can be a great way to gain confidence and experience alongside experienced sailors, with the comfort that comes with the crew.