Small ship sailing cruises

The first time the captain cuts the engine is always a magical moment. You can feel under your feet when the sails of your boat begin to fill. Soon, you’re leaning on the breeze, and the wires holding the mast begin to hum.

With the sails up, everything feels different. Your boat has undertaken a beautiful metamorphosis. It is a new creature – a quiet one, that can approach wildlife with suitable stealth. You can hear the seabirds; you can hear a whale blow.
With the sails up, everything feels different.
The best part is that you don’t need to know how to sail to be on board. That’s what the crew are for. Small ship sailing cruises are all about sharing the joy of being under sail without needing to know the ropes. If you like the sound of silence and seabirds when you’re underway, or cosy chatter around the dinner table, then these kinds of trips might just be for you.

Sailing vs motoring – which cruise to choose

In a motorised world, a sailing vessel is not the default. But there are lots of advantages to going on a small ship cruise under sail.

Sailing cruises give you an environmentally friendly way to travel; they use less fuel because they can rely on wind power for parts of their passage. Sailing vessels are living history. They’ve often served past lives as fishing vessels and racing ships and come with all the battle scars and wood panelling to prove it. Sailing cruises can be peaceful and great for unobtrusive wildlife observation. Sailing vacations can be very intimate. Some boats only have room for two to six passengers, plus a crew of two. Sailing folk have a reputation for being relaxed. Sailing vacations are social and casual and there’s little segregation between crew and guests. Your captain isn’t shut away in a bridge – they’re on deck with you. Sailing boats can be more comfortable than small motorboats. Because you travel with the weather, you’ll experience less of a rocking motion underway.
There are disadvantages to consider too. Makes sure these aren’t dealbreakers before you book.

Sailing vessels are less spacious, partly because they have apparatus to stow, and partly because they generally must be narrower to perform well in the water. Space constraints mean your boat might have steeper a staircase than a motorboat, or use ladders. This means certain vessels might be less suited if you have mobility issues. Sailing vessels need bigger clearances. They have a keel below the water, so they cannot go into as shallow seas as similarly sized motorboats – this may affect where they can anchor, and how close to shore they can stop. They also have a mast – so no going under bridges. They’re still a hundredfold more agile than your average cruise ship, though. Sailing vessels may have less shade availability on deck – which is great for sunbathers, of course. Because of the masts and sails, there are fewer places on deck to string a canopy, especially when you’re underway. There is always shade at the back of the boat in the cockpit.

Best places to go on a small ship sailing cruise

The only sadness about sailing vacations is that when you’re on board you can’t fully see how magnificent your boat looks with all her sails up.
There are places in the world where sailing vessels come into their own. Where there are short distances, reliable winds, and flat seas, you can get some great cruising, and maximum time with the sails up. For this reason, vacations spent roaming among islands groups are where sailing vessels really shine. That’s why there are lots of these trips dotted around Croatia’s Dalmatian Islands, and the Greek islands.


Leave the lightest of touches on the Arctic when you visit under sail, keeping engine noise and fumes to a minimum. It might be icy out there, but below deck everything is cosy and quiet, and you might see a whale out of the porthole.


One of the most popular sail cruising destinations thanks to the Dalmatian Islands, which are a perfect playground for boats. Pinball between pretty ports. The Adriatic water has a special, mesmerising clarity – you’ll want to jump in at every stop.


Sailors love Greece: lots of gorgeous islands, calm seas and reliable winds, plus fantastic food and a thriving harbourside taverna culture. The Cyclades, the Ionians: the island groups are full of tourist hotspots, but by small boat you can sneak out of the spotlight and find its hidden coves, too.


You’ll be the envy of everyone on the Turquoise Coast if you’re sailing in a romantic gulet (pronounced ‘goo-let’) – a traditional wooden converted fishing vessel that’s commonly seen swaying at anchor off the Turkish coast.


There are short, leisurely sailing distances between most of the islands in this Indian Ocean archipelago, making it a relaxing cruising destination. That means plenty of time for swimming – essential when the water is this inviting.


Slip across the sounds and around the mulls in search of dolphins and golden eagles. You won’t be sunbathing on deck, you’ll be standing on watch, looking out for more wonderful wildlife in the water.
Travel Team
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What do small ship sailing cruises entail?

These boats are small – if you’re on board with strangers, then be relaxed and respectful about sharing each other’s space, as you’ll be in close quarters. You may be sharing bathroom facilities with other guests and crew. Conditions below deck are cheerful, but cosy, and you’ll be getting to know each other well.

On small ship sailing cruises there’s lots of time spent on deck, as well as plenty of stops on land, opportunities to go out in the tender (smaller accompanying motorised boat) and in warm climes, swim stops, so you won’t be cooped up.

Your captain and crew are there to sail the boat and keep you safe. These are sailing cruises, so you won’t have to do any of the sailing for yourself – just sit back and relax.

You may go into harbours for dinner in the evenings, or, in remoter regions, make use of an on-board chef.

You won’t always have the sails up. You’ll stick the motor on to manoeuvre in and out of moorings and harbours, and you may go under power if the weather is not in your favour. You may motor sail, too – that is, have your motor on whilst the sails are up, to travel faster.

Sailing cruise vacation tips

Pack light, with your luggage in soft bags, as they can be squashed into the boat’s oddly-shaped storage facilities. Don’t forget to pack adequate, reef-safe sun protection – the sun is reflected off the sea, and you might want to sunbathe on deck. Don’t forget deck shoes – any pair of clean, non-marking shoes that you can slip on to wear on deck. Mainly so that you don’t stub your toe. As with any cruise, pack seasickness tablets, just in case. If seasickness hits, sometimes it’s best to stay out on deck – but if this doesn’t work, go and have a lie down. If you’re traveling solo, you’ll usually share a cabin with someone of the same sex. If you want a private cabin, a single supplement will likely apply.
Written by Eloise Barker
Photo credits: [Page banner: Markos Mant] [Main intro: Michael Held] [Arctic: Dylan Shaw] [Turkey: Jorge Franganillo] [Tips: Craig Cameron]