Where to go on a sailing vacation

Sailing vacations map & highlights


The premise of a sailing vacation is to spend time on your boat – either on deck relaxing; getting hands-on and learning how to sail yourself; or a combination of both. You’ll be based in one country, sailing about the islands, coastline and fishing towns of your chosen destination during the day, before docking in a mixture of secluded bays and lively ports by night. Stopping at sights of interest en route, passengers have plenty of opportunities to hop onto dry land and experience the local landscape, be that via Roman ruins in Turkey, or sumptuous seafood in the restaurants of the glamorous Amalfi Coast.
Aegean Sea Croatia Cyclades archipelago Italy Turkey UK

Aegean Sea

Sitting pretty between Greece and Turkey, the Aegean Sea is a clear, bright, turquoise body of water scattered with remote islands, hidden coves and gorgeous sandy beaches. Sailing Greek waters out of Syros, the capital of the Cyclades, you can mix swimming and snorkeling in warm, Mediterranean waters with trips to mud baths, some great climbing, and unforgettable food from tiny fishing ports.


With an archipelago of over 1,000 islands that clings to its celebrated coastline, Croatia was made for sailing. The sea here it isn’t tidal, so you can cover large distances, and viewing the illustrious islands from the water lends visitors a glorious freedom and an entirely new perspective on the landscape. Plus you can head inland to try your hand at white water rafting, or explore each island’s cultural quirks.

Cyclades archipelago

The Cyclades archipelago is to sailing what ice cold beer is to sunny beach barbeques – the stuff of dreams – and you’ll experience both on an island-hopping sailing vacation here. Sail leisurely between deserted islands, stopping to snorkel, or feast on fresh waterside tavern dishes, and hike to traditional villages where you’ll eat and drink like only impeccable Greek hospitality allows.


Italy’s diverse waters are a game of two entirely different sailing halves. Head to the Ligurian Sea and you can join a whale and dolphin research team collecting data on species including sperm whales and bottlenose dolphins. Alternatively, cast adrift along the glittering Amalfi Coast and you’ll visit ancient Roman ruins, hike historic trails, and indulge in incredible regional cuisine at charming local villages.


Voyages on gulets – traditional sailing boats with wide sundecks and shaded afterdecks – are traditionally called 'Blue Cruises', in reference to the sea and sky that swathes guests along the Turquoise Coast from Fethiye, an ancient market town. Drop into secluded coves, idyllic island anchorages, ancient sites and beguiling fishing hamlets, along with all sorts of inland excursions.


We might not have the balmiest of climes, but sailing in the UK is an age-old pastime and you can peg a trip around our rugged coast onto all sorts of maritime events, or make the most of your boat to get up close to Scotland’s extraordinary wildlife. UK sailing trips are mostly participatory, so you’ll learn a lot of technique as well as meet new people – great for dragging teens from screens!

Sailing vacations travel advice


Sailing with teenagers

Becky Simmons, from our supplier, Adventure Under Sail, on screen-free time: “Teenagers come onboard and go into our saloon, which is the living area and chill out room, and there’s a TV in there and a DVD player, and immediately rejoice at the DVD player and talk about which DVDs they’re going to watch. After being onbard for an hour they’ve forgotten it’s there because they’re so engrossed in what they’re doing up on deck, pulling on ropes as part of a team and meeting new people. The TV never gets used, which is fantastic.”

Broaden your horizons

Becky Simmons, from our supplier, Adventure Under Sail, on the benefits of family sailing trips: “Some of our trips come under the umbrella of ‘sail training’, so they’re are all about broadening people’s horizons, challenge and adventure, and seeing different places, but also about coming out of your shell, learning to work as part of a team, meeting new people, and making friends for life. They’re great vacation for families with teenagers.”

Tips on getting stuck in

Annie Antonatou, from our supplier, Mystic Blue, on getting involved: “Our guests are welcome to get involved in sailing the boat if they wish, although it’s not compulsory. Our skipper gives all guests an introduction in sailing so you can help with trimming the sails and holding the helm, but there is also opportunity for other activities such as snorkelling and diving, walking, dolphin and bird watching... or you can sit back and enjoy the sailing, sunbathe, or just relax and read your book. There is something for everyone.”

Sailing vacations travel advice

Tips from our travelers who have gone on sailing vacations

At Responsible Travel, we think the best people to advise our travelers are often... other travelers. They always return from our tours with packing tips, weather reports, ideas about what to do - and opinions about what not to.

We have selected some of the most useful sailing vacation travel tips that our guests have provided over the years to help you make the very most of your sailing vacation – and the space inside your suitcase.
“Research the area you will be visiting, but also be open visiting new and unexpected places. In Greece, understand the differences in the islands: Mykonos and Santorini are larger and more touristy with more amenities, while Kimolos and Irakleia are smaller and less visited, but charming. Have an idea of what you would like to do or see, but also be willing to trust the captain and crew to gain an understanding of you and your style and guide you in a wonderful direction.” – Danielle Romme

“Pack Light. I mean really pack light, and use a small soft-sided bag and/or SMALL backpack. You won't end up wearing half of whatever it is you've packed.” – Melandee Brown, on a sailing vacation in Greece

“Know that you are living on a sailboat for the week and your sleeping accommodations are tight. This is not a problem at all as you are only in your room to sleep and get cleaned up for dinner. There is too much beauty above to spend any awake time in your room.” – Janice Layne, on a Bahamas Windjammer sailing vacation

“Be prepared to muck in and experience everything on offer. Being a working boat there are potential hazards and getting in and out of the dinghy involves good co-ordination so think carefully if you have limited mobility.” – Roy Owen, on a wildlife sailing vacation in Scotland

“Be aware the yacht a small space to live in - comfortable, clean, and safe, of course, but small - and it's an active vacation. Be prepared to go up and down ladders, haul ropes, and do the washing up. Bring anti-seasickness medication - better to have it and not need than otherwise!” – C Appleby, on a sailing vacation in Greece

“Bring waterproofs! We had five solid days of sunshine, but even in these conditions, a waterproof coat and trousers come in very handy for dingy launching and riding, lobster pot launching and retrieval etc where splashing at the very least is inevitable.” – Sophie Hood, on a wildlife cruise in Scotland

“Keep an open mind, and just enjoy the sailing, seeing new things and meeting great people.” – Jade Lam
Photo credits: [Map intro: Harold Litwiler] [Aegean Sea: Fisherga] [Croatia: Mario Fajt] [Cyclades archipelago: Mark Goebel] [Italy: FrontierOfficial] [Turkey: Chris_Parfitt] [UK: John mcsporran] [Sailing with teenagers: Port of San Diego] [Tips on getting stuck in: _dChris] [Helpdesk - Little boat red sail boat: Ian Burt] [Review 1 - Mathias Bredvei: Graeme Churchard] [Review 2 - Debbie Maitland: Andy Powell]
Written by: Polly Humphris
Sailing vacation in the Ionian Sea

Sailing vacation in the Ionian Sea

An unforgettable sailing adventure

From £416 7 Days ex flights
Dartmouth Royal Regatta on a Tall ship

Dartmouth Royal Regatta on a Tall ship

Be part of the 172nd Dartmouth Royal Regatta!

From £625 5 Days ex flights
Sailing vacation in the Aegean Sea

Sailing vacation in the Aegean Sea

Uninhabited islands in a 6 person boat

From £458 7 Days ex flights
Wildlife sailing holiday in Scotland

Wildlife sailing vacation in Scotland

Extraordinary wildlife above and below the waves

From £750 6 Days ex flights
Cyclades sailing & walking vacation in Greece

Cyclades sailing & walking vacation in Greece

Combine a sailing & hiking adventure around the Cyclades

From £544 7 Days ex flights
Sailing cruises in Norway

Sailing cruises in Norway

Sail Troms and Finnmark. A once in a lifetime expedition!

From NKr 89000 7 Days ex flights
Greek Islands bicycling and sailing vacation

Greek Islands bicycling and sailing vacation

Bicycle and sail around the Cyclades Greek Islands

From US $1920 8 Days ex flights
Virgin Islands cruise vacation

Virgin Islands cruise vacation

Romantic Virgin Islands sailing vacation for a loving couple

From US $7700 7 Days ex flights
South coast of England tall ship sailing tour

South coast of England tall ship sailing tour

Visit historic ships around Portsmouth and shop!

From £425 4 Days ex flights
Sailing vacation in Portugal

Sailing vacation in Portugal

A memorable sailing vacation in southern Portugal

From 600 7 Days ex flights
Cuba sailing vacation, Canarreos Archipelago and Cayo Largo

Cuba sailing vacation, Canarreos Archipelago and Cayo Largo

All-inclusive diving yacht tour in Cuba.

From 1200 7 Days ex flights
Mull vacation while staying on a boat, Scotland

Mull vacation while staying on a boat, Scotland

Discover beautiful Isle of Mull from the anchored St Hilda

From £750 7 Days ex flights
Lisbon to Cadiz tall ship sailing vacation

Lisbon to Cadiz tall ship sailing vacation

The start of the 2nd Tall Ships' Race in Lisbon!

From £810 6 Days ex flights
Sailing vacation in Turkey & Greece

Sailing vacation in Turkey & Greece

A blissful week of sailing and family adventure in Turkey.

From £1800 7 Days ex flights
Whisky and wildlife sailing holiday in Scotland

Whisky and wildlife sailing vacation in Scotland

Malt Whisky and Wildlife Cruise to Mull, Jura and Islay

From £1200 9 Days ex flights
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