Last weekend I went sailing with friends and, as usual, my chats with friends filled up with horizon shots, salty hair, and that smug little “look at me, I’m living my best sea life” vibe.
Then the questions arrived.
What do you pack?
How do you survive in a cabin the size of a wardrobe?
Do you need special shoes?
Is it romantic or is it… basically a floating group project?
Here’s my honest answer: a sailing holiday can feel like absolute freedom and a tiny prison, sometimes within the same afternoon. You go from the immensity of the ocean outside to the limited space inside. You might discover surprising affinity with strangers and unbridgeable differences with long-time friends. You can feel powerful emotions, and also feel personally offended by a wet towel left in the wrong place.
I am on my tenth long sailing holiday, plus plenty of shorter trips, and I have learned a few things the hard way.
So here’s my practical guide to life on a sailing boat, including what to pack, how to behave, and how not to become the person everyone silently wants to throw overboard.
First: the unglamorous truth about sailing with friends
A sailing boat is not a hotel. It is not even a well-organised Airbnb.
It is a moving space with:
- limited freshwater
- limited electricity
- limited privacy
- and unlimited opportunities for small irritations to become “a conversation”
If you go in with the right mindset, it’s magic. If you go in expecting comfort and autonomy, you might spend a week negotiating your relationship with humidity and storage.
The golden rules of sailing life
1) Order is not optional
Space on board is shared, and it is tight. “I’ll just leave it here for a second” is the quickest way to create chaos.
- Keep common areas clear
- Put your belongings away immediately
- Do not leave shoes, bags, chargers, books, wet swimwear, or your entire skincare routine in pathways
- Think of the boat as a minimalist studio flat, except it moves and tilts
This is not about being strict. It’s about not making life harder for everyone.
2) Respect is not a slogan; it’s a survival skill
Sailing is teamwork and cohabitation. Respect on a boat includes things you never think about on land.
- Keep your voice down when others sleep
- Be mindful with freshwater, especially at anchor
- Ask before using shared storage
- Do not turn the cabin into a hair salon
- If you have long hair, brush it in private and definitely not upwind
Also, choose your battles. A sailing holiday is not the moment for dramatic debates about politics, money, or who was right in 2019.
3) Flexibility is the price of the horizon
Weather changes. Plans change. The skipper makes decisions you might not fully love.
Sometimes you will sail less, sometimes more. You might change the route. You might anchor earlier. You might stay in port.
If your happiness depends on everything going exactly your way, sailing will teach you humility very quickly.
Also, you may be asked to do tasks you do not enjoy. I personally have a complicated relationship with galley life and meal prep on a moving boat, but I have learned that resistance is futile.
4) Attention is everything, especially above your head
The boom is not a metaphor. It is a real object that can hit you.
- Watch the boom
- Watch ropes and winches
- Watch where you put your feet
- Wear shoes unless the skipper explicitly says otherwise
- When the boat heels, move to the higher side unless instructed differently
Sailing is beautiful, but gravity is always employed.
Seasickness and “land sickness”: yes, both exist
Seasickness: the quick, realistic approach
I am not the best reference because I’ve never really suffered from seasickness, but I’ve sailed with people who love the sea and still struggle.
If you start feeling off:
- stay on deck, look at the horizon
- keep busy, ask the skipper for a simple task
- eat small, bland things regularly
- avoid being down below, especially in stuffy cabins
- hydration matters more than you think
Old sailor remedies include lemon, bread, cola, and salted anchovies. The main truth is simpler: fresh air, horizon, and a job to do.
Ground sickness: my personal speciality
I can get dizzy as soon as I disembark. It feels like the world continues to move under your feet.
It usually fades within hours, sometimes a day. It’s not dramatic, but it is very real and slightly ridiculous. Walking in a straight line becomes an ambitious concept.
Sailing is still worth it.
What to pack for a sailing holiday
Start here: bring a soft bag
This is the non-negotiable part.
Take a duffel bag or a backpack. Do not take a hard suitcase or trolley.
Cabin storage is limited and shaped like a puzzle designed by someone who hates you.
A soft bag compresses, fits in corners, and won’t become the enemy of everyone sharing your cabin.
Warm-season packing list (Mediterranean, Canaries, Lanzarote, summer trips)
Clothing and essentials
- swimsuit
- underwear and socks for each day, plus extras
- t-shirts for each day
- 1 to 2 pairs of shorts
- a light layer for evenings (sweatshirt or thin jumper)
- one “going out” outfit and shoes, if you plan dinners ashore
- flip-flops or sandals for onboard
- sailing shoes or trainers with white soles (Converse or Superga work well)
- lightweight waterproof jacket or windbreaker
- microfibre towel
- sarong: towel, cover-up, emergency blanket, makeshift pillow, everything
Sleeping and comfort
- silk sleeping liner or light sleeping bag liner
Cabins can be humid, bedding standards vary, and you will sleep better with your own layer.
Sun and protection
- sunglasses
- cap or headband
- high-SPF sunscreen
- after-sun lotion
Toiletries
- compact wash kit
- marine-friendly soap if you are rinsing with seawater
- hand sanitiser
- tissues
- baby wipes
A quick note about boat toilets: they are not your home bathroom. Many systems cannot handle paper or anything that is not, well, what your body produces. Wipes are practical, but dispose of them correctly and never in the toilet.
Tech
- phone with waterproof case
- e-reader with waterproof case, if you love reading
- car charger and cables
- power bank
Electricity can be limited depending on whether you are sailing, motoring, or moored in port.
Cold-season upgrades (winter sailing or windy destinations)
Swap and add:
- long-sleeve tops
- warm fleece
- proper trousers
- waterproof jacket
- warm socks
- beanie and gloves
- warmer shoes
Even in mild climates, mornings and evenings at sea can surprise you, especially with wind. If your craziness is similar to mine, you might even plan a Lofoten sailing holiday in February…
You might also want to check out my extreme cold-destination packing tips.
My “travel pharmacy” for sailing
This is not medical advice, just the basics I tend to carry:
- pain relief
- antihistamines
- anti-diarrhoeal
- anti-nausea tablets if you are prone to seasickness
- antiseptic cream
- anti-inflammatory gel
- plasters
- insect repellent
- something soothing for bites
If you take prescription meds, bring more than you need and keep them accessible.
A few practical tips that make sailing easier
Pack in pouches
Cabins are small and messy quickly. Use:
- one pouch for underwear and socks
- one for swimwear and beach stuff
- one for toiletries
- one for charging cables
You will feel organised even when the boat isn’t.
Assume everything gets slightly damp
Even with good weather, salt and humidity are constant. Choose fabrics that dry fast and don’t take up precious space.
Eat and drink sensibly
Skipping meals and dehydration make everything harder, including mood. And on a boat, the mood spreads.
Be useful, even if you are tired
You do not need to be a sailor to be helpful. Simple actions count:
- tidy shared spaces
- wash dishes efficiently
- offer to handle easy tasks
- keep an eye on others if they look unwell
A sailing holiday is a shared life. That’s the point.
Is a sailing holiday for you?
If you love nature, big skies, and the feeling of being tiny in front of the horizon, yes.
If you need privacy, predictable schedules, long showers, and full control of your environment, maybe start with a short trip first. A weekend sailing trip is the perfect test. It’s long enough to understand the rhythm, short enough not to become a crisis.
Either way, I always say this: do not be afraid to try. Sailing is one of those travel experiences that teaches you something about yourself, sometimes with surprising honesty.
If you want, tell me where you’re sailing and in which season, and I’ll adapt the packing list and the “what to expect” section to your exact route, Lanzarote included.
Fair winds (and calm seas)!
