How to organize a Sailing Holiday

But no worries, such a crisis can be contained and even prevented if you follow this simple step-by-step guide we have prepared for you. Also if you are an experienced sailor, sailing solo or with your close family is different than sailing with a big group of friends. An adventure that can be so amazing you don’t want to miss out on it just because you are uncertain if you can manage all the organizing that comes with it.

This is where we come in to remind you that you are not alone and the Tubber Charter Experts are always here to help you! Furthermore, this guide will tell you everything you need to know about organizing a sailing holiday. From choosing your crew to selecting the route and the destination. We got you covered, so check out the overview of the topics we will discuss and dive in!

  • Step 1 – Choosing Your Crew
  • Step 2 – Choose the Right Destination
  • Step 3 – Find the Right Budget for Your Crew
  • Step 4 – Figure Out How to Get There
  • Step 5 – Search & Charter

Choose Your Crew

This first step may sound obvious, and you probably have a bunch of names in your head already. However, we advise you to think twice, because it’s not as simple as it seems. Simultaneously, choosing the right friends to bring together on this sailing trip is the most critical step.

The first thing you need to realize is that you are on a boat, in the middle of a sea or an ocean, there is probably nowhere to go but to be together. You probably think that’s great now but put together on that boat, people who used to be in a relationship, have some kind of beef, or only came because they like one of the girls, but she’s more interested in another guy and just looks at hell breaks loose.

On a boat, where space is not that much, and there are moments where you just can’t walk it off on the beach, you have to take into consideration what are the relationships between the people there and if they are likeminded. So the ultimate advice here is:


Furthermore, when it comes to the number of people you should bring, it all depends on how crowded you would like the boat and your budget. Of course, more people means fewer expenses per person, but it may not be what the collective wants. The number we often see on these friendly sailing holidays is from 8 to 10 people with around 4 cabins and a whole blissful week of sailing. That makes the trip relatively cheap per person, especially compared to staying in crowded hotels.

Choose the Right Destination

Choosing the right destination is the next crucial step in organizing a fantastic sailing holiday. Some of the questions you should ask yourself and the group here are: Which country fits the best with your crew’s sailing abilities? What is the best destination for having fun experiences? To provide an answer to this, there are several factors you can consider…


If your friends are coming from all over the world you should consider what are the connections to the destination from different countries? Do they all have the possibility to fly or drive easily to the place where you are picking up your boat?


Different destinations require a different set of skills and experience in sailing. Consider how people will react to heavy sailing in case they don’t have much experience. Of course, some destinations offer easy sailing conditions that are perfect for beginners. You can check out some of them here. Or you can charter a yacht with a skipper. He is not able to sail the boat alone but will provide enough guidance for all of you to be ready to sail with no worries.


Talk with your friends and decide whether you are looking for hot spots where you can enjoy the nightlife and festivals. Or are you looking for a very serene and relaxed place where you can just chill on the beach all day without crowds? Also, figure out what facilities and amenities you are looking for regarding marinas and surrounding towns. Some of your friends might want to spend a night at a luxury hotel or have a meal at a high-class restaurant nearby.

To make things even easier for you, we have a few suggestions and great itineraries you can follow. Check them out and pick what fits best for you and your friends.

Find the Right Budget for Your Crew

After you have figured out the crew and the destination, you basically have the essentials ready. Now all that’s left to do is just set some overall budget or a price per person. That way, when you start looking for a boat, you will be prepared and know what offers you can give to your friends. Here you should probably also consider extra costs, such as groceries, taxes, and expenses for marinas. That doesn’t play a significant role in choosing the boat, but everyone should be aware of it before getting on board.

If you decide to hire a skipper as well, include that in the price as well. Most websites, including Tubber, have that option and you can see exactly how much it will cost you for the indicated period.

Figure Out How to Get There

We already mentioned this in Step 2. So you already know you have to consider how easy it is for your friends to get to the destination where you will pick up your boat. The easiest way to travel is most probably by plane. So look at flight prices and consider the time you are arriving.

A little trick we can share with you is picking the right month and season. There are so many locations that have perfect weather and sailing conditions at times you wouldn’t expect. This could work to your advantage since the prices of flight tickets vary depending on the season and the month. It may require some time in research. But we are sure it will be worth it when you find those exclusive flight deals that cost near to nothing.

Search & Charter

The last step is simple if you have everything else figured out. Do a Google search and pick a website that offers all the things you re looking for and more. Of course, we would recommend Tubber, because we have more than 12 000 yachts at more than 600 locations worldwide. Furthermore, we offer secure payment, global insurance for all our boats, and customer support 24/7.

To conclude this guide on organizing a sailing holiday, we would like to show you some options already. For us, an ideal sailing holiday would be with 10 amazing friends. On board of a spacious catamaran, sailing in the waters of the Ionian Sea in Greece. This is a dream destination beloved by many that offer endless possibilities and multiple settings, both relaxed and exciting. Check out our suggestions that fit these requirements perfectly and feel free to explore further.

So, what do you think? Are you ready to embark on the adventure of a lifetime and try organizing a sailing holiday with your friends? Tell us in the comments below or on our Facebook Page. And remember, if you need help with chartering a yacht, the Tubber Experts are always here to help!