My first time taking a holiday alone

Alison James takes a leap of faith and heads to Cascais in Portugal – solo

Until very recently, there was something I had to address as a single woman. Whilst I was happy to go to the cinema solo, take in an exhibition on my own, or eat out at a table for one, I’d never found myself taking a holiday alone.

Since the demise of my long marriage, I have discovered that I quite like the single life. Not having to explain myself, or answer to anyone. Doing exactly what I like, when I like, and with whom I like. I’ve made new friends, taken up new interests and, I suppose you’d say, reinvented myself. Maybe not quite to the heights of a phoenix rising from the ashes. But I’m definitely in the fledgling category. 

I’m happy with all this, but the possibility of time away – a singleton holiday, if you will – remained on my ‘to do’ list. So, I decided it was time to do something about this. 

Where shall I go?!

It was already July but I didn’t want to hang about. I wanted to go soon. But before I did, I made another list of what exactly I was looking for. 

A short break in Europe, I reckoned, was the way to go for this first solo outing. I wanted to go somewhere warm but not too hot. A destination that combined a bit of beach life with a side helping of culture and history. And an aura of old-school glamour would not go amiss, either. Plus, the kind of destination where I might even try something else way out of my comfort zone. A new activity of the sporting kind, perhaps?

A short break in Europe, I reckoned, was the way to go for this first solo outing

While browsing on the internet for the place that would hopefully tick most of my boxes, I happened to chance upon the Portuguese coastal town of Cascais. Only half an hour from the capital, Lisbon, I gleaned that this picturesque former fishing village appeared to retain much of its maritime charm while combined with fabulous beaches. And also a noble, almost aristocratic feel, as befitted the go-to destination of many dethroned European monarchies during the first half of the 20th century. 

Beautiful blue cove with costal town building gathered around. A few boats float in the harbour. Taking a holiday alone to Cascais


It sounded right up my ‘rua’. When I read on one site that ‘It is not necessary to bring company to explore the wonders of this unique resort’, I felt myself warming to the idea of a short break in Cascais. And then when I noticed that one of my musical heroes, Van Morrison, just happened to be headlining at the Cool Jazz festival the very same weekend I planned to take off, well, it was pretty much a done deal. A triple-day trip, I reckoned, would be just the ticket. Three days would be just about right, with Van-the-Man playing on my final night. 

Getting there

Taking the early afternoon TAP Airways flight from Heathrow to Lisbon, I was excited yet apprehensive. I had never done anything like this before. What if I hated being on my own when everyone else seemed coupled (and loved) up? What if I felt like the ultimate Billie No-Mates? What if I felt unsafe at any point? What if my voice-box seized up due to lack of use? What if? What if? What if? 

I told the mad voice in my head to shut the f**k up. It. Was. Three. Days. That’s all. Three days was nothing. If the worst came to the worst, I could treat the break as a silent retreat. Or plot out the novel I’d always promised myself I would write. Or even read all the novels I’d downloaded onto my kindle.

I told the mad voice in my head to shut the f**k up. It. Was. Three. Days. That’s all.

Plus, I had my own bespoke tour guide. I had written myself a fairly detailed itinerary before setting off. I reasoned it would be good to have a set schedule so that I wouldn’t, at any time, find my mind wandering as I people watched, causing me to think, ‘Look at all those couples and happy families seemingly having the best time’ (even if they’re really not). 

I was picked up at the airport, having already arranged a transfer with my hotel, the almost-on-the beach Vila Gale. Something of a last-minute booking, the four-star hotel was a good choice being just a matter of seconds from the marina, just 10 minutes-walk from the historic centre of Cascais and also close to the Marechal Carmona Park where the Cool Jazz festival was taking place. I was delighted with my spacious third floor room and balcony. 

Exploring the locale

Image shows Cascais Marina full of boats in the sun, mountains in the background

Cascais Marina

Strolling into town for dinner was a feast for the eyes as I passed the marina with its resident fleet of swish-looking yachts, the imposing 16th century citadel, and the literally-on-the-beach, fairy tale castle-like Condes de Castro Guimaraes Palace.

Never once did I feel unsafe as a lone woman. I had pre-booked to eat at the Lota da Esquina, a restaurant housed in the former fish auction house. 

Read more: are retreats calling you?

The Museu Condes Castro Guimaraes. Beautiful building by a river with stone bridge running across it. Taking a holiday alone on Silver.

Condes de Castro Guimaraes Palace

The setting was stunning – as was the repast. The tomato and strawberry gazpacho, tuna ceviche, and sauteed fresher-than-fresh fish will remain in my memory food bank for a long time. 

…never once did I feel unsafe as a lone woman

As for the dining solo thing; or ‘comendo sozinho’ as they say in Portugal? Well, I’ll admit to feeling quite self-conscious when my fellow diners were made up of mostly two, three, and foursomes but I found that a couple of stiff G&Ts pre-dinner made this dissipate in a rather dreamy kind of way. Besides, the waiting staff were lovely and chatty, and didn’t once look at me with pity! 

And I had company. Not my ubiquitous smartphone – I purposely left that in my bag – but a book. 28 Portuguese Poets: A Bilingual Anthology, which I’d ordered online before travelling. A tad pretentious? Perhaps, but just the thought of that made me laugh. The poems were generally absorbing, and turning the pages between forkfuls of delicious food made me feel like the lead in a moody foreign movie.

Day two – heading out

Day two of my solo short break was spent in Sintra, a historic, Unesco World Heritage site about 45 minutes-drive from Cascais. As per my bespoke itinerary, I had pre-booked an organised tour of this magical kingdom – think fairy tale, pastel-coloured-palaces set amongst lush, undulating emerald forests in the foothills of the Sintra Mountains, with Shortcuts Tourism. 

Did I arrange to meet up any with my lunch companions again? Er, no. While I’d had fun in their company, when you know, you know

A good choice, even if I do say so myself. We were a group of six in all and our guide Andre was everything you could wish for in a tour guide. Full of information, very funny, and his English was probably better than mine. The fantastical Monserrate Palace was a particular highlight. Beloved by romantic poet Lord Byron and featured in his poem Childe Harold’s Pilgrimage, this Taj Mahal-like edifice in miniature, combines gothic, Indian, and Moorish influences. While the gardens are spectacular, and home to species of trees and plants from all over the world. 

Sintra, Cascais – Pena Palace Turismo

We ended up in the very picturesque if rather touristy town of Sintra itself. Where we, as a group, sat down for a light lunch at a café by the main town square. It was nice to chat to the other members of the group – although it was the hugely entertaining guide Andre who did most of the talking. Did I arrange to meet up any with my lunch companions again? Er, no. While I’d had fun in their company, when you know, you know. And I felt extremely OK about dining solo again that evening.

Monserrate palace. Grand cream palace with terracotta roofs set amongst lush greenery. Taking a holiday alone to Cascais

Monserrate Palace

Returning to by mid-afternoon, I spent a couple of hours on the beach, braving a dip in the bracing but not overly rough Atlantic, before eating that evening at sublime seafood restaurant Marisco na Praca at Cascais Marina. 

Meeting new friends

It was here that I happened to get chatting to a group of uber-friendly women on the table next to me who were in the area on a golfing trip. I don’t know if it was because I’d already chatted to strangers earlier in the day – or because the Sangria I was drinking gave me a bit of Dutch courage – but I had no qualms about starting the conversation off. 

Tiger Woods I most definitely wasn’t but I did enjoy the experience

The woman sat nearest to me was wearing a lovely necklace which I complimented her on. Within minutes, they’d asked me to join them for a nightcap. My meeting with this group of girls led me in turn to decide on just what my aforementioned sporting activity would be – a category left blank on my itinerary. Why not take a shot at the game my late father had been obsessed with? 

The next morning saw me on the driving range of the nearby Quinta da Marinha Golf Resort, taking an hour-long ’taster’ lesson, alongside another single lady. Tiger Woods I most definitely wasn’t but I did enjoy the experience. Especially when our teaching pro informed us that golf was as beneficial to the body as Pilates.

Two mature friends at a driving range with gold clubs posed. Taking a holiday alone and making friends

Time for Van Morrison

After an afternoon people-watching and sunning myself by the hotel pool, it was time for Van the Man at the Cool Jazz festival in the park. I’ve done some festivals in my time, but I can honestly say I have never attended a gig in such a stunning setting. We’re talking palm trees, grassy knolls, evening sunshine and an altogether languid vibe. This was cool with a capital C. 

Van Morrison playing at Cascais - pic Alison James

Van Morrison playing at Cascais – photo: Alison James

I’d spoiled myself with a VIP ticket which included wine and delicious canapes – such a treat but I am worth it, I’d decided. As was Van himself. At an amazing 77-years-old, he sounded as good as ever – even if he hardly said a word between numbers and didn’t perform any of his hits! Not that I’d really expected him to. He is, by all accounts, famous for this. 

I was happy just to watch him perform but I found myself chatting to a group of Portuguese fans, who looked a good decade younger than me. No matter about, that, though. Experience and a growing confidence that maybe only comes with age – in addition to surviving a ruined marriage – has taught me that if you are open and interested in people, it’s not hard to get talking to them. My night ended at the festival’s 80s disco with me and the Portuguese 40-somethings getting into the groove. 

So how do I look back on this foray of stepping out on foreign soil for the first time on my own? 

I can honestly say it was one of the best short breaks I’d ever had. In a relatively short time, I’d done so much. I travelled solo, but I never felt lonely; I also felt a massive sense of achievement. 

Taking a break after a break-up? Intrigued by the idea of a solo trip? Just do it. Pack an open mind and a spirit of adventure in addition to a micro-holiday wardrobe. You have nothing to fear, and only exciting new experiences to look forward to. 


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