What to Expect on Your First Sailing Holiday and How to Prepare

Beautiful sailing of a sailing yacht during the golden hour at sea

Start by waking up to the lovely sound of the sea, making a fresh cup of coffee and then stepping out on the deck to see the sun brightening the sea – these are the simple things that draw us most. Making the decision to charter a sailing yacht for your holiday will be a genuinely transformative experience. A sailing holiday onboard a yacht could offer you much more than a simple trip to the beach and the all too familiar tourist resorts. You might discover a deserted beach, a tiny fishing village, or even an unknown bay that only the locals know.

This way, if you are a novice at planning a sailing holiday, the idea alone might get you excited initially but at the same time, you will have your apprehensions as well. For example, you might be thinking about how it really is living on a yacht, what you should actually bring with you, and whether sailing knowledge is necessary. Having a bit of planning and being positive are what it takes to make your first sailing holiday your love affair with the seas.

Which Kind of Sailing Holiday to Pick

Choosing the right sailing holiday is mainly a matter of your comfort and experience level.

A Skippered Charter

If you are a novice in sailing, a skippered charter will be a nice pick. A professional skipper takes care of sailing, docking, monitoring the weather, yacht handling, and you just enjoy the trip whilst your mind is completely at rest.

You can always go for sailing lessons if it is something you want. The skipper will teach you the essentials, and you can have a relaxing holiday as well.

Flotilla

Sailing is a great way to combine freedom and assistance. You have the freedom to sail your own boat while still following the lead boat which gives guidance, route planning, and help throughout the journey.

If you are a beginner and want to experiment with independent sailing but also are not willing to be left alone completely, then this option is just right for you.

Crewed Yacht Charter

The crewed yacht is the epitome of luxury. In most cases, the skipper will be joined by other members of the crew – a chef, the person responsible for the maintenance of the yacht, and the one in charge of ensuring that everything is running smoothly.

If you are the type of person who wants to completely unwind without any worries and at the same time be pampered with excellent service, then this is the best option for you.

Bareboat Charter

A bareboat charter is mostly for those who are expert sailors. Captaining the yacht yourself means you will have no one to share the responsibility with. A professional skipper, however, is usually the one to take off the stress of docking and undocking the boat, assisting with navigation, and managing the crew.

If you don’t have a skipper, then you must be fully prepared to bear the responsibility and risk of sailing without assistance.

Packing Smart for Life at Sea

When you are planning a sailing holiday, packing skills may have to be quite different from when you do a hotel stay, for example, in a couple of ways. For one thing, space onboard a sailing boat is usually very limited and so you should think carefully about packing as few items as possible.

The best suggestion about luggage is not to take a big hard-shell suitcase – a pain in the neck concept for a sailing holiday, isn’t it? If you must bring a duffel bag or something foldable, which you can roll up and hide away in such a small space onboard, where it will not get in the way.

Besides, don’t forget that the key to dressing for a sailing trip is to have several layers of clothes you can put on or take off quickly according to the shifting weather.

Your basics to bring are:

  • Lightweight, breathable clothing
  • Waterproof windbreaker
  • Comfortable shorts and quick-drying clothing
  • Non-slip shoes with light-coloured soles
  • Swimwear and beach towel
  • Hat or cap
  • Polarized sunglasses
  • High-SPF sunscreen
  • Reusable water bottle
  • Personal medications

If you’ve a tendency to suffer motion sickness, then seasickness tablets or wristbands are worth considering.

Whether or not you are prone to seasickness, it’s always safer to prepare yourself. Fresh air, staying well hydrated, and focusing on the horizon are effective remedies for those prone to motion sickness.

The Truth About Life on Board

Most newcomers to sailing find it one of the biggest surprises that life on board suddenly starts feeling so much a part of them.

The vessel will naturally roll and sway as the day passes. You might feel a bit of the rolling at first, mainly when you are trying to sleep or eat. Still, most people get used to it after the first one or two days and many even come to find it soothing.

Cabins on yachts are usually quite small, but the layout is such that every inch is put to good use. Another factor for why it pays to bring less is that there is not a lot of room for storing things.

One of the best perks of staying in shared spaces is that it really rounds out the entire experience. When you travel with your family, friends, or even fellow travellers, you will naturally learn to work together without even realising it. Almost all of you will do the communal chores like cooking, cleaning the dishes, and arranging the equipment.

Don’t be in a mindset that common chores are going to be a bother to you because most of the time, you will see that they not only make the trip more enjoyable but also help to build bonds and give a sense of unity.

A Typical Day at Sea

Unlike fast city holidays, sailing holidays are more about taking it easy. One of your options is breakfast at a peaceful marina and a sail towards a neighbouring island. On your route, you may swim, snorkel, paddleboard, or simply drift in the crystal-clear water.

There is a good chance on most days that you will experience visits to delightful fishing villages, eat fresh fish at restaurants right on the waterfront, or discover some of the islands’ beaches which are totally isolated and only reachable by boat.

During the night, you can either be anchored in a protected bay or return to a marina and have dinner while enjoying the view of the sunset over the sea.

It is always something different each day. Yet, the sailing lifestyle is probably one of its greatest appeals.

Must Have Things Checked Before a Trip

Before going on board, a few important administrative tasks have to be done. Check that your passport, visas, travel insurance, and other necessary documents are valid well in advance of your departure. Regarding your sailing skills and skipper qualifications, make sure they align with the requirements of the destination if you’re a bareboat charterer.

Besides, getting to know local sailing restrictions, marina regulations, expected weather, and emergency contact numbers of the area you are going to will definitely be worthwhile.

In fact, there are quite a few who underestimate the necessity of obtaining proper Boat Insurance which in reality is the most important item on your pre-departure checklist. Without a doubt, having sufficient insurance that covers both the boat and the liability in case of a marine accident is a must.

Sharing a copy of your itinerary with a trusted friend or family member is also a good idea, so that at least one person is aware of your route and the day you should be back.

Great Sailing Spots for Beginners

In general, those who have just started to sail quite often find it difficult to get used to some locations. For this reason, beginners benefit most from choosing destinations that suit their experience level. Besides natural calming factors like smooth water and regular weather patterns, a supportive sailing community and facilities also strongly determine a sailor’s experience.

Mediterranean Coast

It is still the Mediterranean Sea which is considered one of the world’s most sought-after sailing areas. Hot climate, fairly stable wind conditions, nice beaches, and beautiful villages along the coast constitute a perfect setting for novices.

Algarve, Portugal

The coastline of Algarve is a combination of beautiful cliffs, vast beaches, hidden caves along the coast, and locations perfect for lying at anchor safely. Beyond its many protected anchorages ideal for cruising, the region also offers stunning landscapes along every route.

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Griekse eilanden

The islands of Greece run high on the list of dream holiday destinations thanks to their lovely blue waters, iconic architecture of simple white buildings, and many islands that remain undiscovered. An advantage for novices is that they usually sail in calm waters given the season and location. Besides that, you can also swim and enjoy cultural exposure. 

Kroatië

In the last few years, Croatia has been one of the leading sailing destinations in Europe. With its Adriatic coastline, numerous islands, historic port towns, clear waters, and short sailing routes, Croatia is an ideal destination for beginners. Happy sailing awaits.

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Enjoy the Journey 

Every first sailing holiday is a learning experience. Maybe the weather does not cooperate, the meals are a little chaotic, or something is forgotten. These little things eventually become the stories you will laugh about in time.

The things that may very well remain etched in your memory are those serene mornings on the water, the secluded bays, which are only accessible by boat, the breathtaking sunsets, and the wonderful feeling of freedom that comes from the ability to go in any direction that the wind and the sea allow.

With some good planning, reasonable setting of goals, and a willingness to embrace your adventurous spirit, the very first zeilen cruise can be both delightful and remarkable. Most sailing novices find that one trip is never enough. In fact, they are already planning their next sailing holiday to explore new places, try different sailing routes, and spend more time with water.

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