Why I love traveling by boat
Hit the deck: let our travel experts state the case for traveling by boat.
Everything critics level at sailing vacations is true. A small boat is an inescapable, floating caravan on a Tower of Pisa tilt. You shower in very close quarters with the toilet, you have to take turns standing in the tiny cabins, sometimes your crisps blow away in the wind. Why, then, do I love it so much?
Like a boat that heels over but never capsizes, when you travel under sail you exist in tension between contradicting ideas. Our reviews capture this tension: “Peaceful, exhilarating,” reads one; “incredibly relaxing, yet adventurous, and deeply memorable,” says another.
It’s cramped – but what an incredible sense of space; it’s peaceful – but you find yourself in a constant altercation with the elements. There’s a rigid programme of relaxation, and countless pottering tasks. It’s romantic, but you have to empty the tanks and check the bilge. There are relentless rules – but the charts show infinite coastlines, and no impediments in sight. The world is your oyster, and you can have oysters for dinner.
Everything critics level at sailing vacations is true. A small boat is an inescapable, floating caravan on a Tower of Pisa tilt. You shower in very close quarters with the toilet, you have to take turns standing in the tiny cabins, sometimes your crisps blow away in the wind. Why, then, do I love it so much?
Like a boat that heels over but never capsizes, when you travel under sail you exist in tension between contradicting ideas. Our reviews capture this tension: “Peaceful, exhilarating,” reads one; “incredibly relaxing, yet adventurous, and deeply memorable,” says another.
It’s cramped – but what an incredible sense of space; it’s peaceful – but you find yourself in a constant altercation with the elements. There’s a rigid programme of relaxation, and countless pottering tasks. It’s romantic, but you have to empty the tanks and check the bilge. There are relentless rules – but the charts show infinite coastlines, and no impediments in sight. The world is your oyster, and you can have oysters for dinner.
Croatian Islands motor yacht cruise
Sail the Croatian islands on a luxury small ship cruise
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Split to Dubrovnik Luxury cruise, Croatia
Cruise Split to Dubrovnik in luxury via Croatia's islands
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£1615 to £2805
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Maldives vacations, Dhoni cruise
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Dubrovnik to Venice luxury cruise
Cruise the Croatian Islands before a bus journey to Venice
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South Argyll cruise in Scotland, history and nature
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What’s to love about going by boat on vacation?
There were genuine moments of pure timelessness!![]()
– Our traveler Sue Congram on our sailing in Croatia vacation.
True relaxation
“Once you leave the harbour, life becomes much simpler,” says Annie Antonatou, from our sailing partner in Greece, Mystic Blue. “Your day is shaped by the wind and the sea rather than by a schedule. I enjoy dropping anchor in a quiet bay for a swim, sailing into a small island port for dinner, and sharing those moments with guests.”
I love sleeping on deck, being barefoot. “The ability to purely relax and not worry about anything for four days,” as one of our travelers puts it.
You make your own fun – you swing on the halyard into the water, you have a diving competition, you race another boat upwind. When my grandpa joined one of our family sailing vacations, he arrived on the dock with a single holdall. Over the next few days, the contents revealed themselves: the smallest pair of bright orange swimming trunks known to man, and several large bottles of gin.
I love sleeping on deck, being barefoot. “The ability to purely relax and not worry about anything for four days,” as one of our travelers puts it.
You make your own fun – you swing on the halyard into the water, you have a diving competition, you race another boat upwind. When my grandpa joined one of our family sailing vacations, he arrived on the dock with a single holdall. Over the next few days, the contents revealed themselves: the smallest pair of bright orange swimming trunks known to man, and several large bottles of gin.
Learning something new
My granny taught my grandpa to sail, my dad learnt from them both, I learnt from my dad. I left home to work on boats, both motor boats and sailing boats, whimsically ‘running away to sea’ for three years.
I was not a natural skipper, but I enjoyed the ride. I’ll always be astonished by the journeys we made: the night crossings, the storms, and the sunrises, though I actually spent most of my time on board cleaning things and trying to learn the Morse code for all the flags.
You don’t need to know how to sail to help on a boat, and some of our most adventurous vacations are sailing expeditions where you can do something epic without the years of preparation that adventure often entails.
I was not a natural skipper, but I enjoyed the ride. I’ll always be astonished by the journeys we made: the night crossings, the storms, and the sunrises, though I actually spent most of my time on board cleaning things and trying to learn the Morse code for all the flags.
You don’t need to know how to sail to help on a boat, and some of our most adventurous vacations are sailing expeditions where you can do something epic without the years of preparation that adventure often entails.
Becoming a crew
“Sailing is a great leveller – there's one boss on board, the skipper,” says one of our reviews. At the same time, the skipper relies on their crew and there’s incredible camaraderie. What each of you did before you sailed, and your abilities and status on shore no longer matter on board (unless you can cook): for better or worse.
“Perhaps the best part is seeing what happens within a small group after several days at sea,” says Jouke Lemmers, founder of our partner Offshore Yacht Charters, “Sailing together creates a real sense of teamwork and friendship. People return home not only with wonderful memories of beautiful places, but often with new friendships as well. That, for me, is the real joy of these sailing vacations.”
It’s a gentle sort of fun, with a lot of ribaldry: I sewed a sea-goat flag out of a couple of polo shirts to be flown from the main masthead on my last trip. “I thought it was an ugly mermaid,” someone said.
“Perhaps the best part is seeing what happens within a small group after several days at sea,” says Jouke Lemmers, founder of our partner Offshore Yacht Charters, “Sailing together creates a real sense of teamwork and friendship. People return home not only with wonderful memories of beautiful places, but often with new friendships as well. That, for me, is the real joy of these sailing vacations.”
It’s a gentle sort of fun, with a lot of ribaldry: I sewed a sea-goat flag out of a couple of polo shirts to be flown from the main masthead on my last trip. “I thought it was an ugly mermaid,” someone said.
Settling into new routines
“Just enjoy, be chilled and relaxed,” says our traveler Debbie Shuttlewood, reviewing our Dubrovnik to Hvar sailing vacation.
You can derive a lot of vacation pleasure from a new routine, and boats are full of routines: deciding where to go over coffee on deck, consulting the forecast again. Preparing to get underway, motoring out of the harbour. Unzipping the sail bag and raising the main.
You turn the engine off (and run down to switch off the fridge, which runs off the engine). There’s complete silence. Then the wind fills the canvas; you start to move. A period of adjustment: winches, lines. A period of calm: time to be on the foredeck on dolphin-spotting duty. Someone draws the short straw and goes below deck to bring up drinks. Everyone slaps on another round of suncream. One day, someone’s hat blows overboard whilst you’re at anchor and you retrieve it with the boathook.
You can derive a lot of vacation pleasure from a new routine, and boats are full of routines: deciding where to go over coffee on deck, consulting the forecast again. Preparing to get underway, motoring out of the harbour. Unzipping the sail bag and raising the main.
You turn the engine off (and run down to switch off the fridge, which runs off the engine). There’s complete silence. Then the wind fills the canvas; you start to move. A period of adjustment: winches, lines. A period of calm: time to be on the foredeck on dolphin-spotting duty. Someone draws the short straw and goes below deck to bring up drinks. Everyone slaps on another round of suncream. One day, someone’s hat blows overboard whilst you’re at anchor and you retrieve it with the boathook.
A respect for nature
“It’s a beautiful outdoor life for a week,” says Maurya Wickstrom, reviewing our Aegean sailing vacation. “Prepare to get wet from waves, dress very casually, not mind if you don’t get a shower for a few days, and surrender to the winds.” Surrender comes up again and again in our reviews. “Sailing really is dancing with the weather!” says our reviewer Sue Congram, “and a lot of fun!”
Whistle all you want, you can’t force the wind to come when you’re becalmed, or calm a storm – as I found out when trying to sail to the Dominican Republic from the Turks and Caicos in time for Christmas: as we left the harbour, the waves became higher than we were – and we had to turn back. You must be philosophical in the face of danger. “Even with modern weather forecasts, nature always has the final say,” says Jouke.
Whistle all you want, you can’t force the wind to come when you’re becalmed, or calm a storm – as I found out when trying to sail to the Dominican Republic from the Turks and Caicos in time for Christmas: as we left the harbour, the waves became higher than we were – and we had to turn back. You must be philosophical in the face of danger. “Even with modern weather forecasts, nature always has the final say,” says Jouke.
A love for life
“Even after all these years, I still find that sailing gives me a sense of freedom and perspective that is hard to find anywhere else,” says Annie.
Jouke was born on a boat. “I come from a family with a long maritime history. My father was one of the pioneers of the Dutch sailing charter industry.” Other ancestors included a rear admiral in the Napoleonic Wars, and some whalers. “Sailing is truly in my blood.”
If you love traveling by boat, you’ll always love it, and you’ll love it for all its frustrations and inefficiencies. One of the last books my grandpa read before he died was The Last Grain Race – Eric Newby’s very funny account of transporting goods from Australia to Europe by sailing boat in the 1930s. Reading it after him made me wistful. Thinking about sailing – even with all its frustrations – always does.
Jouke was born on a boat. “I come from a family with a long maritime history. My father was one of the pioneers of the Dutch sailing charter industry.” Other ancestors included a rear admiral in the Napoleonic Wars, and some whalers. “Sailing is truly in my blood.”
If you love traveling by boat, you’ll always love it, and you’ll love it for all its frustrations and inefficiencies. One of the last books my grandpa read before he died was The Last Grain Race – Eric Newby’s very funny account of transporting goods from Australia to Europe by sailing boat in the 1930s. Reading it after him made me wistful. Thinking about sailing – even with all its frustrations – always does.
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