Spending time on a sailing boat is an experience unlike any other. It combines freedom, unpredictability, and just enough challenge to keep things interesting. Before stepping on board, though, it helps to know what to expect and how to prepare. Over the years—and after several sailing holidays—I’ve learned that life on a boat requires a balance of order, respect, flexibility, and a sense of humor. Here are my tips for making your first sailing adventure as smooth as possible.
The Reality of Sailing Holidays
A sailing trip can be exhilarating one moment and frustrating the next. The wide-open horizon offers a sense of limitless freedom, yet the cramped living quarters can feel restrictive. You may bond with strangers instantly, while old friendships can be tested by the lack of personal space. The truth is, sailing magnifies emotions—joy, tension, and wonder all coexist in the same day. That’s part of its magic.
Priorities on Board
Keep things organized. Space is limited, and clutter quickly becomes everyone’s problem. Always stow your belongings neatly and avoid leaving items in communal areas.
Respect others. Be mindful of noise, especially at night. Freshwater is precious, so use it sparingly. Even small courtesies—like brushing long hair in private rather than in the common space—make life easier for everyone.
Stay flexible. Routes, schedules, and tasks can change with little notice. The captain’s word is final, and while not every decision will suit you, going with the flow prevents unnecessary tension.
Pay attention. Boats are full of moving parts: ropes, winches, and the swinging boom can all cause injury if you’re careless. Protect your feet with proper shoes unless told otherwise, and always walk on the higher side of the deck when the boat heels.
Manage seasickness wisely. While I’ve never personally struggled with it, many friends have. The best advice is to keep busy on deck and avoid sitting idle below. Simple foods, bread with lemon, or even Coke can sometimes help. If all else fails, listen to the skipper and rest where it’s most comfortable.
Prepare for “land sickness.” Oddly enough, some people feel dizzy after returning to solid ground, as if everything is still moving. It’s not dangerous—just a reminder of how immersive sailing can be.
What to Pack for a Sailing Trip
Cabins are tiny, so soft luggage like a duffel bag or backpack is essential. Hard suitcases are impractical and take up too much space.
For warm-weather sailing, my essentials are:
- Swimsuit
- Underwear and socks for each day
- T-shirts and a couple of pairs of shorts
- A sarong that doubles as a towel
- A sweatshirt for cooler evenings
- Something dressy for going ashore, plus appropriate shoes
- Flip-flops and deck shoes (white-soled sneakers work too)
- Lightweight rain jacket
- Microfiber towel
- Silk sleeping bag liner
- Toiletries with sunscreen, after-sun lotion, and marine soap
- Sunglasses, hat, or headband
- Sailing gloves
- Camera, phone with waterproof case, and e-reader
- Chargers, power bank, and car adapter
- Baby wipes (more practical than toilet paper on boats without flush systems)
For colder seasons, add:
- Long-sleeved shirts
- Fleece or warm sweater
- Full-length trousers
- Waterproof jacket and pants
- Sneakers or boots
- Beanie and gloves
- A heavier sleeping bag (with silk liner inside for comfort)
A Small Travel Medicine Kit
I always carry a compact kit with basics: pain relievers, motion sickness tablets, allergy medicine, stomach remedies, antiseptic cream, insect repellent, throat lozenges, plasters, and sanitizer gel. It’s better to have these on hand than to scramble for them later.
Final Thoughts
Sailing isn’t for everyone, but even a short trip is worth trying. It offers a mix of adventure, teamwork, and serenity that no land-based holiday can replicate. If you’re curious, start with a weekend trip—you might discover a passion that keeps drawing you back to the sea.
