How to plan a trip by boat (with or without a boating licence)

Leggi in italiano 

Going on trip by boat is the exotic dream of so many sea-loving travellers who like to be in contact with nature!

Going on a boat journey to the main Italian islands and watching them from offshore, slowly getting closer to the coastline and then moving away again, looking for coves where you can dive into the deep blue water as well as stunning depths that leave you spellbound and… sunbathing on the bow of the boat just like celebrities (end of the day, we are celebrities), are only some of the cues that give us a dream picture of the trip by boat or present it as an experience we all need to have at least once in our lives, isn’t it?

Well, you should know that after the first time, there will most certainly be a second one.

This post is dedicated to those who would like to go on vacation by boat but haven’t had the chance to plan it yet or believe it is too complicated or even too expensive.

It’s actually easier that it might look and even less expensive than many more conventional holidays and trips on the mainland.

come organizzare una vacanza in barca a vela

First thing you certainly wonder about:

do I need a boating licence? 

Not necessarily.
It’s good news if one or more sailors are among the group of people you are about to leave with, because you could rent a charter boat without a skipper and save some money too.
Yet, if your group is made of boating newbies, you can definitely rent a boat with a qualified skipper, who stands for extra safety when it comes to those who love the sea but are also frightened by it.

Where can I find a boat? 

organizzare un viaggio in barca a vela

Clearly, you don’t need to own a boat for a vacation by boat.
There are many options to rent a manned or unmanned charter boat.

My suggestion is to look for a rental boat, either with or without a skipper, based on the port of departure and the supposedly ideal route.
If you’d like to leave from Sicily for instance, you can look for “boat rental in Sicily” and choose both the port of departure, the route and the boat.

But it costs a lot!!

No, it doesn’t! A week on a sailing boat can cost indeed even less than a week in a hostel or a three-star hotel.

If you rent for example a 9-10 mt unmanned boat for six people, you can spend less than 250 euros a week per person.
Usually, renting a manned or unmanned boat has a fixed price that increases or decreases for the single user according to the number of people on board.
It would be ideal (and funnier) to leave with a group of people and take the available seats, not just for money reasons but also and above all because the sailing boat is a very good experience to strengthen friendly relationships or even family ties. 

trip by boat_how to organize it

How to choose the route? 

Well, my dear In My Suitcase friends, we know well that a trip only partially depends on the means of transport: the route is actually the trip.

If your love relationship with the sailing boat has just begun, I suggest planning a trip to discover the main Italian islands, to enjoy the routes off the coast of Sicily or Sardinia as well as the wonderful Mediterranean coastline.

Practical tips: clothes, attitude, accessories.

Yet, how to dress for a boat trip?
I wish it was only a matter of clothes!  Renting a boat and leaving is actually easier than getting in the right boat mood.

Spaces are beautiful but limited so you need to remember not to leave your “things” around, from your phone charger to the slippers or bag of chips that you’ve just been munching on.

Take with you as few electronic devices as you can, for convenience and good manners reasons. For sure, you’ll always find a place to charge your phone, but if you also take a power bank with you, you won’t have to leave your phone in charge and will thus make room for the others.
Let’s leave the hair straightener home, my lady friends! Due to the salty air, your hair will look fine anyway, even if wild.
This applies to you too, my male friend: do you know that your unkempt beard makes you look way cooler, don’t you? Well, I picture you with a small beard and ruffled hair playing guitar at sunset, so please leave your beard trimmer at home.

Environmental sustainability tips

Every step we take in nature and, in particular, our presence at sea, leaves its mark. Whether it is noise or fuel, there can’t be no denying that even a wonderful boat trip has an impact on the environment.
Let’s try to make up for this technical impact depending on the means we have chosen with other almost zero-impact actions or consumption choices.

For instance, choose biodegradable materials over plastic for your lunches/dinners on board. There are wonderful (let me stress it) 100% biodegradable dishes and glasses made in bioplastics with corn starch, that help produce less highly polluting garbage and are also pretty elegant.

If we can’t help using plastics, my advice is to wash it and reuse it during the journey.

When offshore, we should avoid playing loud music, not just because loud music is incredibly rude but also due to the very delicate bio-balance of the sea, which is strictly related to silence.

Refrain from using the engine as much as possible.

Get in the right mood

There’s always a lot to do on a boat, therefore you should alternate between relaxing moments on the bow, taking pictures for your Instagram posts, and volunteering for doing the dishes or cooking (or, even better, each one can be assigned to a task before leaving).

Speaking of Instagram, the kittenish girls like me will be happy to know that our beloved light and large dresses are particularly recommended on a boat, along with hats to protect from the sun, whose strength is often underestimated due to the breeze.

On the other hand, leave your heels at home and bring with you a pair of moccasins or low sandals with a flat sole, better if bright-colored.

Last but not least, you should bring along the desire to sing at sunset, the ability to have fun even without getting drunk (a hangover on the boat is definitely unpleasant) and to feel free within small and cozy spaces, as well as being able to not feel lost in front of endless horizons.

So, make sure to pack some essential items like pain relievers, electrolyte drinks, or even IV for hangover to help combat any potential symptoms while on the boat. Additionally, it’s a good idea to designate a sober captain or skipper to ensure everyone’s safety during your sunset singing sessions.



  • Sandra Williams

    My plane for a trip by boat. That was interesting for me. You share many information on trip by boat. I will try to do.

  • Karla

    This inspired me to have a trip by boat! I really thought it’s pricey but considering the adventure, I think it’s worth the price. All your tips are very informative!

  • Blair villanueva

    I learn a new thing again avoid boating and thanks for your blog. I want to experience boating!

  • Kacie

    I would love to rent a boat and skipper and sail around the Caribbean – I think I had better start saving.

  • Cristina

    I’d love to rent a boat but I don’t know how to sail! Always feel so peaceful when at sea – there’s nothing more relaxing on holiday.

  • David Allen Elliott

    I love going out boating and being on an adventure out there. But you really do have to take it all seriously or something can go seriously wrong. So at least getting a class in boating basics I would believe is essential.

  • Renata -

    This is a nice post and I’d really love to do an extended sail boat tour. But although I’m living adjacent to one of Europe’s largest harbors, I’m getting sea sick really easily; so…no boat for me 🙁

  • Samantha Carraro

    I’ve definitely always thought that renting a boat would cost a lot more but 250 euros sound very reasonable and even less expensive than some other more usual vacations.
    I’ve always wanted to spend some days on a sailing boat, it must feel so good to wander through the sea, careless and under the sun.

  • HilLesha

    I used to go boating a lot with my family when I was a child and haven’t done this ever since. I would love to go on more boat trips in the future!


    I had never thought to go on a boat trip. Handy to have an idea of what to do if I did though, thanks for sharing. I bet it must be amazing.

  • Wendy Lemeric

    Very informative. Definitely not for me, though. I’m scared of the water. I can’t swim haha!

  • simpleindianmom

    That’s interesting. Never thought about but it sounds fascinating. Should give a try 🙂

  • Elizabeth O

    This sounds like such a great experience. It looks super relaxing to just go float somewhere peaceful and enjoy the sea and scenery

  • Alison Rost

    I have never thought about doing this before but it seems so exciting to be able to experience it. Going on a trip by boat and just enjoying the experience! WOW! Thanks for the info about it too!

  • Celestial B Purposed

    Such a great idea. Going sailing or boating would be a great and relaxing vacation. But, I did find it useful for the number of resources to bring to be polite to the others on the boat. Great idea and I also did not know about the silence issue when on the sea. Great post. (FB: Addie Cotoure)

  • Nina

    I don’t know I always get sick but thank you for all the suggestions. it can be relaxing and entertaining for sure

Lascia un commento

Il tuo indirizzo email non sarà pubblicato. I campi obbligatori sono contrassegnati *