Sailing travel guide

Maybe you don’t own a sou’wester and yellow wellies. Perhaps the Dover-Calais ferry is your longest voyage to date. No matter! There’s a sailing holiday out there to suit everyone. We have hands-on trips around Scotland where guests are invited to hoist the sails and fish from the decks. On the other hand, you’ll also find luxury cruises down the Croatian coast or around Greek islands, where swimming, snoozing on deck and feasting on fresh food in quiet quayside restaurants is as arduous as it gets.

The choice of location and type of boat is vast, and between bobbing along, you can enjoy activities as diverse as freediving and whale watching, kayaking and cycling. All trips share an emphasis on sociability, fun and freedom, though. Drinks will be served, new landscapes explored, sunsets admired and sea legs discovered.

Navigate your way with our sailing holidays travel guide.

…you’re a stickler for routine. There will generally be an itinerary, but it’s more a suggestion than a schedule. Most sailing holidays take a ‘go with the flow’ approach, to adapt to weather conditions, passenger preferences and wind direction. … you get seasick. Most sailing holidays glide through calm summer seas, so rolling waves are not generally an issue, but if you suspect you’re sensitive to the bob-bob of a boat, try a sailing daytrip before you book, and bring seasickness tablets, too. …you want to be alone. Sailing is small group travel in reasonably confined quarters, so you need to feel comfortable sharing space with others. Cabins are only really for sleeping in, not hanging out. …you like to go deep. Exploring a town or region in depth or returning to the same beach each day isn’t going to happen on an ever-moving sailing holiday.

Around six to eight guests and a small crew of two or three are typically on board, although our really exclusive, luxury holidays might feature a yacht with space only for a couple. We have private charters too, so a family or group of friends can book out the entire boat, giving you complete freedom to tailor make the trip, adding on days or tweaking the itinerary. On our standard small group sailing holidays with fixed departures, sociability is key as space is limited. Make friends with your fellow passengers and, if travelling alone, be ready to share a cabin with another solo shipmate of the same sex.

Expect comfy accommodation on board, but not acres of space; this is sailing, not cruising on a floating hotel. Cabins are for sleeping in and that’s about it, often with twin beds and shared bathrooms. This shouldn’t be a problem, though, as you’ll be spending most of your holiday on deck, in the sea or exploring on land. In fact, it’s the intimate, personal nature of a sailing holiday that sets it apart from our small ship cruises with 40 or so passengers. You’ll get to know everyone on board and also the crew, who can really bring the whole experience to life. Learn about sailing from the skipper and local food from the ship’s host, be directed to the best family run restaurants, find out more about marine wildlife and listen to local yarns and myths as the sun sets over the wide horizon.

Sailing is usually in small boats, so there’s limited space. Pack minimal luggage in soft bags that are easy to haul up and down ladders.

You don’t have to be super fit to go on a sailing holiday, although activity levels all depend on the type of trip. You might have to set a sail or – on offshore sailing trips – be awake for a night watch, so ask for more details if you’re unsure. Anyway, there’s always a team of willing shipmates to lend a hand.

What makes it so fun? “It’s the sense of freedom! When you hoist the sails and let the wind do the work, the only noise you’ll hear is the sails blowing in the wind and the waves splashing against the side of the boat,” says Diane Muldoon from our partner Intrepid Travel. Relaxation is mandatory, too. “For many trips there will be a couple of hours without WiFi. You are ‘forced’ to relax; you get to watch the world go by, talk to your fellow travellers, read a book, listen to music or catch up on some sleep.”

Many of our relaxed sailing trips are coastal trips, where you’re never too far from shore. We also sell offshore sailing trips. Offshore sailing takes you further out to sea, on longer voyages. You might sail for multiple days at a time non-stop without coming to shore, and experience less sheltered conditions: more wind, more waves. These are hands-on trips where you’re not just a guest, but a member of the crew. Some trips might be ‘mile builders’: designed to give you more nautical miles under your belt so you can work towards a sailing qualification. Others are adventurous voyages: sail in the Atlantic Ocean between the Canary Islands and Madeira, or, on the other side, between Saint Lucia and Saint Vincent in the Caribbean. You can even cross the Atlantic.