Five days on a boat with people we’d never met
You might remember that two years ago I went sailing in Thailand on a women-only trip. I spent a week on a catamaran with strangers, learning what it’s like to discover a new destination from the perspective of its coastline. The one thing missing the whole time was Mal. I kept noticing things I wanted to show him and so at the back of my mind I hoped a midlife sailing holiday was something we might do together one day, perhaps with the boys or maybe with friends.
So when an invitation arrived from More Sailing to sail the Croatian coast for a few days in May, way before all of the sadness happened, the sailing itself didn’t worry me. I know roughly which end of a boat is which and what to do if someone starts shouting about ropes. What I didn’t know was whether it would work for the two of us. In Thailand it was just me on a catamaran with other midlife women and I think women work hard to accommodate each other. This time it would be me, Mal and a handful of strangers of different ages sharing four cabins and the question I couldn’t answer in advance was whether you can join a trip like that and still come away feeling as if you’d had a break.
My head filled up with reasons not to do it… we’d be trapped… there might be forced jollity… someone might want to play games all day. The risk to me as an outgoing introvert was that we’d spend a fortnight’s worth of social energy in five days and come home needing a holiday from the holiday. And that sounds horribly middle-aged and risk averse but I know some of you will understand. Above all there was the worry that a group trip means handing over your ‘self’. That you go away as you and come back having spent the week being ‘agreeable’.
However we said yes – partly because I wanted Mal to experience the freedom I’d felt in Thailand and partly because I’ve reached the point where being overly cautious feels like the start of the great midlife ‘disappearing’ which is something I really want to avoid. It’s too easy to stay on the sofa with biscuits. The whole point of my gearing up to 60 project is to open my mind to new things so I’d have felt I was failing from the start if I’d shied away.
Dolce Vita tee (this year’s version); Jeans (this year’s version); Jacket
And so it began
What I’ve discovered each time we’ve done group travel with strangers is that more often than not it can be lovely – not in the relentless, organised way I dread with a rota and somebody else’s playlist to suffer. It’s just lovely in the way that casually good company can be when there’s no obligation to keep it going.
We arrived on a gloriously sunny Saturday afternoon having spent three very wet, cold days in Split on our own.
Patch pocket shorts; Zip voile blouse (this year’s version)
We found we were to travel with three other couples, all travel bloggers and younger than us ranging from their early twenties to mid-forties. So although they were strangers to begin with, by the Thursday they were people we had a lunchtime cocktail with. I could tell from the outset that they were going to be easy and interesting company so as we raised the anchor it already felt like an adventure.
One of the few rules on board was no drinking before eleven which meant that on some days a glass of something chilled appeared at roughly five past! Not every day though, it wasn’t remotely a booze cruise. We soon got into a rhythm of sharing a sumptuous breakfast and then relaxing on deck as we headed out to sea from wherever we’d docked overnight.
There was a dinghy for fun and a certain amount of getting in and out of it with minimal dignity which turns out to be a powerful social leveller.
And we pulled into tiny coves for long lunches where the conversations spun into completely new directions as they do with people you haven’t met before. We often found ourselves still sitting at the table three hours later.
What surprised me was that it didn’t feel like a big effort. I’d braced myself for being sociable and the performance of it all but as with my Thailand experience, I found that being on a boat changes that. You’re all in the same small space so there’s nowhere to hide but there’s also nowhere to go which paradoxically takes the pressure off. When you do a trip like this nobody is expecting you to host, nobody’s keeping score, you drift into conversations and when you’ve had enough, you drift to the other end of the boat to look out to sea and nobody takes it personally.
Patch pocket shorts; Bikini top (this year’s version)
Going away in a single boat like this gives you more freedom than being part of a flotilla. If people are enjoying one harbour you can stay there a little longer, if the weather turns you move on. Like last time I wondered if it would feel claustrophobic, whether there would be a certain amount of teeth gritting for the sake of the scenery. However, as I discovered in Thailand there’s a distinct pleasure in sailing in company – one good thing is that the day has to be organised around the wind and the next harbour rather than anybody’s opinions. And when you’re constantly on the move there’s always something new to look at that isn’t each other.
Beach dress (from here)
And then, every evening, our own holiday
The thing I liked more about this trip than the Thailand one was that every evening we docked in a new location. So once the boat was tied up and the day’s sailing was done, the group dispersed into its component couples. We wandered off into whichever small Croatian island harbour we’d washed up in and so the evenings were just for the two of us.
Linen shirt (this year’s patterns); Jeans
We sat at a different table in a different harbourside restaurant every night with a bit of a smug feeling that we’d earned it by sailing there even though we’d done very little. Being back alone together made it feel utterly romantic as we sat in a tiny, twinkling harbour on a completely different island to the night before.
After dinner we’d wander back to the boat in the dark as would everyone else and sometimes the cards came out. That added yet another dimension to it all. It almost felt like a family holiday with the whole crew on deck under a dim light, dealing another hand… accusing each other of cheating… full of dinner and feeling windswept and happy. So we spent the days loosely together with the evenings firmly apart and then often there we all were again, by choice, with nobody having organised it.
I’d expected to have to choose and that was the whole reason that I dithered over this experience. Company or privacy… the group or time together… other people or ourselves. Often when you go on a group trip you sign away the second to get the first.
But on these sailing trips you don’t. You can have the cards and the cocktails and the strangers who become friends and you can also have the quiet dinner for two at the end of the day – and they sit side by side quite happily. The company is there when you want it and you have time for your own holiday too.
Patch pocket shorts; Bikini top (this year’s version)
Mal, of course, took to the whole thing with enthusiasm. He arrived with our rucksack like a proper boy scout…
… and spent his time on board plunging into the icy cold Adriatic at every opportunity. He loves the cold and I think only I noticed the small smile on his face as he climbed back on board each time – the secret triumph of a midlife man who’s proved to himself that he can still go further/deeper/longer than the much younger men he’s travelling with.
I, meanwhile, am a creature of the warmth, never happier than during the recent heatwave which has now departed from the north. As I type I’m next to the radiator again – this part of the UK is beautiful apart from the bloody weather. Anyway, while Mal was in and out of the icy water I found my happy place at the front of the boat, doing nothing much more than reading in the sunshine.
Linen shirt (this year’s patterns); Patch pocket shorts
My biggest daily output was having to find a new patch when the sun moved round.
There was one evening ashore when the skies turned grey and the heavens opened. We found ourselves trapped in a cocktail bar (oh no!) and it was one of those heart-lifting moments when it struck me that we were on the island of Hvar – completely unexpectedly – because there was no itinerary when we set off, we were told the skipper would just follow the winds. I’ve always wanted to go to Hvar and so despite the rain, it felt like a blessing out of the blue.
Shorts; Blouse (closest here)
What our midlife sailing holiday taught me about travel
If there’s a lesson in any of this (and I’m a bit wary of trips having to have a lesson) it’s about finding new ways to travel in midlife. This is an option where there’s enough company to feel part of something but also enough room to stay yourself. You can engineer them both at once if you choose the right sort of thing. The mistake I’ve been making (partly from the experience of some of the group travels we’ve been on) is treating those things as mutually exclusive In my mind there were three distinct options – we either had to protect our relationship and go away on our own… or risk a friends’ holiday and end up like the brilliant “Two Weeks In August” drama… or throw ourselves into the social deep-end of an ‘always on’ group tour and accept that we’d see each other at the other side. It hadn’t occurred to me that if you look carefully you can balance a bit of everything.
So here I am, recommending the very trip I’d felt a bit worried about. Not sailing specifically, although the sailing was glorious and you couldn’t possibly find a better operator to go with than More Sailing. But beyond that saying yes to a trip that has other people in it and trust that it will be all right. It was more than all right. We had a great few days specifically because of the blend of company and solitude. I do think it’s worth finding one that has time carved out for you alone though rather than a sixteen hour itinerary.
As you know I’m slowly building Midlifechic Experiences and in a minute I’m going to give you the booking details of the next one that I’ve organised on the principle of time with likeminded people and time alone to relax. But first I’m just going to tell you a little about More Sailing because if you fancy a trip like ours, you couldn’t choose a better operator.
Patch pocket shorts; Striped half sleeve tee (closest here)
About More Sailing
More Sailing is a Swedish company that specialises in lots of different sailing trips both in Europe and The Caribbean. You’ll find your boat is crewed by jolly young Swedes who handle everything for you – sailing, cooking, keeping things clean, bringing drinks round at different times. You can pitch in if you want to with the sailing side of things or you can leave it to them.
The itinerary is planned according to the winds and the weather so all you need to focus on is relaxing and looking forward to the surprise of your evening destination.
Included in the cost of your trip is accommodation, an outstandingly good breakfast and lunch every day as well as unlimited drinks. Unlike on my trip to Thailand, the drinks fridge is open from 11am and fully stocked with good local wines and beers. This doesn’t happen on most group trips I’ve experienced so it’s an absolute bonus. You have a double cabin to yourself with a decent sized bed and your own bathroom. As always with sailing you have to be careful with the water supply and so we showered when we got to the harbours – each one had warm showers that were free to use. You organise your own flights and meals in the evening are at your own cost.
My trip with More Sailing was far more relaxed than the one I had in Thailand. There were fewer rules and the meals with wine were far more generous. Plus of course you’re free to spend the evening out on your own. I think these things really matter when you’re travelling with people you don’t know.
Midlifechic Experiences – Marrakech
Sorry – this sold out faster than I could ever have imagined – we’re in touch with our friends in Marrakech to see if we can plan another one in
Booking is now open for our trip to Marrakech next March. Eighteen of us will have a trip that mixes local experiences with time to relax in the sunshine. Please read the details on the page before making your booking and there’s one thing I ask of you.
Now I have my teacher voice on here. There are only seventeen places and we’ve arranged for the payments to our certified tour operator in Marrakech to be phased so that you don’t have to spend a lot of money all at once. However, if you’d like to come I’m trusting you to commit. Obviously sometimes big life events hit you and we understand that when that happens, cancellations are unavoidable and we will do everything we can to fill your place.
However over the last few events we’ve had people changing their minds quite late on which leaves me to cover the cost of the trip I’ve committed to personally every time – sometimes the cost is significant. When I commit to an event in the UK or abroad I have to underwrite the cost and so if you cancel, it’s my problem and it’s been painful at times this year. I’m not a tour operator, this is a friendship group that I’m trying to build – so in the spirit of friendship I need to be able to rely on you.
As soon as we have enough bookings to fill the trip we will make the commitment. If there isn’t enough interest, your deposit will be refunded.
There, that’s the serious bit out of the way – now let’s make a plan to have some fun together next year. You can find all of the details here: Midlifechic Reader Trip to Marrakech, 2027
