Sailing vacations 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 vacation out there to suit everyone. From hands-on trips around Scotland where guests are invited to hoist the sails and fish from the decks, to 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, enjoy activities as diverse as skiing and whale watching, kayaking and cycling. All trips share an emphasis on sociability, fun and freedom, though. After all, this is a vacation, not an epic ocean-going challenge. Drinks will be served, new landscapes explored, sunsets admired and sea legs discovered.

Navigate your way with our sailing vacations travel guide.

Is a sailing vacation for you?

Responsible Travel recommends

Go on a sailing vacation if…

… you like to be active. A sailing vacation is easily paired with walking and cycling on shore, kayaking, swimming and snorkelling off the boat, and even manning the rigging on board. There’s always time for lounging on deck, too, but that’s not the whole sailing story.
… you believe good food makes a vacation. Meals prepared with local produce on board, plus the chance to moor in a quiet harbour so you can eat in small restaurants, well off the tourist trail, or a beach barbecue with the catch of the day – food is good, plentiful and fresh on a sailing trip.
…you love variety. Sailing glides you past ever-changing landscapes and delivers new sights, sounds and opportunities for exploring each day.
…you want access all areas. Some destinations can only be reached from the water – Myanmar’s Mergui Archipelago, a scattering of tiny Greek islands and wild Scottish isles like Ailsa Craig, for example.

Don’t go on a sailing vacation if…

…you’re a stickler for routine. There will generally be an itinerary, but it’s more a suggestion than a schedule. Most sailing vacations take a go with the flow approach, to adapt to weather conditions, passenger preferences and wind direction.
… you get seasick. Most sailing vacations 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 vacation.

When to go on a sailing vacation

Catching the trade winds

In the UK, sailing trips tend not to run Oct-Feb, especially in Scotland, with Apr-Sep the best time to go, when the weather is clement and seas less choppy. Sailing in southern Europe generally follows suit, taking advantage of the blue skies and sunshine of late spring and summer, but with trips running during the balmy autumn, too, until late Oct. Factor in high summer heat, though, if you’re planning active land-based activities, too, such as hiking or cycling. Sailing further afield opens up the calendar. Drift around the Mergui Archipelago in Myanmar from Nov-Mar, take a skiing and sailing trip to Norway in the winter or cruise the Virgin Islands or Maldives any time of year.
Photo credits: [Top box: Alessandro Caproni] [Helpdesk - Little boat red sail boat: Ian Burt] [Best time to go - UK with windmill: Fimb]
Written by Joanna Simmons
Sailing in Croatia

Sailing in Croatia

A multi-activity adventure sailing cruise in Croatia

From 580 4 Days ex flights
Greece sailing holiday for families

Greece sailing vacation for families

Sailing trip for families/friends in Greek islands

From £750 8 Days ex flights
Arctic sailing voyages, North Spitsbergen

Arctic sailing voyages, North Spitsbergen

Spitsbergen tall-ship wildlife and natural history sailing

From 3045 8 Days ex flights
Skye and the Small Isles sailing vacation

Skye and the Small Isles sailing vacation

Sail Scotland's Small Isles and visit spectacular Skye

From £1520 9 Days ex flights
Family yacht charter sailing vacation in Greece

Family yacht charter sailing vacation in Greece

Private sailing with fun games, reliving mythical tales

From 2100 8 Days ex flights
Cyclades sailing & walking vacation in Greece

Cyclades sailing & walking vacation in Greece

Combine a sailing & hiking adventure around the Cyclades

From £785 7 Days ex flights
Photo credits: [Page banner: Markos Mant]