Top 5 Tips for Your First (or Favourite) Sailing Holiday

From Croatia to French Polynesia, here’s what to pack, expect, and embrace

A sailing holiday is one of the most relaxed, rewarding, and soul-restoring ways to travel. Whether you’re hopping between medieval harbours in Croatia, discovering hidden coves in Sardinia, or swimming alongside humpbacks in French Polynesia, the rhythm of life at sea is something special.

If you’ve booked your first trip — or are dreaming of your next — here are five essential tips to help you make the most of it.

1. Pack soft (and light)

Leave the wheeled suitcase at home — you won’t need it. Space is always at a premium on board, and a soft-sided duffel or sailing holdall is much easier to tuck away. Brands like Musto make excellent water-resistant options that are both durable and stylish.

Aim for light layers, swimwear, and a good sun hat. And while it’s all about barefoot comfort during the day, a casual, nice outfit is great for dinners at shore-side restaurants.

We provide towels onboard, so no need to bring extras unless you want a quick-dry one for the beach.

2. Shoes? Optional (but non-slip if you bring them)

Most people go barefoot onboard — it’s safer, cleaner, and honestly feels better. If you prefer something underfoot, non-marking deck shoes or sailing sandals are a smart choice.

You won’t need hiking boots or heels. Comfort is the name of the game here.

Woman relaxing barefoot on the bow of a yacht wearing a sunhat, enjoying a sailing holiday in the sun.

3. Be flexible and go with the flow

Unlike fixed tours, sailing trips are often shaped by the wind and weather. That island you didn’t expect to visit might turn out to be your favourite. Trust the skipper, enjoy the spontaneity, and let the ocean lead the way.

Each day may include time to swim, paddleboard, read, or just lounge on deck with a drink in hand — the pace is wonderfully unhurried.

A seaside taverna in Greece

4. A few extras worth tossing in

Dry bags or zip-locks for electronics and travel docs
Reef-safe sunscreen — it protects the planet and your skin
A good book or two (though conversation usually steals the show)
Travel adapter or power bank, especially if you’re camera-happy

5. The vibe is everything

On a Water By Nature trip, there are no huge cruise ship crowds or noisy itineraries. It’s just you, a small group of like-minded adventurers, and the sea.

Whether you’re sailing through Croatia’s Dalmatian Islands, Greece’s Sarionic Gulf, Sardinia’s secret coves, or the outer atolls of French Polynesia, the trip is about connection with people, with nature, and with a slower way of travelling.

Ready to Set Sail?

Whether you’re booking your very first sailing holiday or coming back for another round, we’d love to help you choose the perfect trip.

Explore our sailing holidays
Start dreaming about French Polynesia
Sail Croatia trip

by Hamish McMaster

Hamish McMaster is the Water By Nature owner. He has spent the past 25 years exploring and playing on the world's great rivers. He still loves nothing more than getting out there and sharing adventures.

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