Gloriously natural beaches, chic coastal towns, and holidaying con la famiglia in Tuscany with Lorraine Candy

We all know parenting is about gradually letting go of the things you love most: your children. This inevitable rite of passage happens over the years and then, rather unexpectedly it seems, your offspring suddenly fly the nest, and it feels like you hardly see them. Until, that is, you mention the word holiday. Then they swoop back in, suitcases packed and carry-on luggage brimming with phone chargers. 

So it was when we mentioned Porto Santo Stefano in Tuscany, our first holiday abroad together after our two eldest girls had left home in 2020 and 2022 respectively. These days it’s hard to find a family trip to suit all six of us, one that will satisfy four children, three girls and a boy, aged between 11 and 20. We needed adventure, relaxation, sun, beaches, good food (preferably pasta, nothing too spicy), a little shopping, sightseeing (but not too much, god knows teenagers hate a walk) and good wi-fi. 

We found it all, out of season on the part of the Tuscan coast where Italians take their getaways: Monte Argentario. It had everything we needed: a beautiful national park, miles of empty and gloriously natural beaches, chic coastal towns, bike rides, boat rides, elegant cafés overlooking super yachts moored in port, down-to-earth Italian eateries, a hot spring, medieval villages, wineries, walks, cheese, hikes, lagoons and even flamingos.  

If you have a large family, you’ll also know that food is one of the most important ingredients of your trip and we found the best supermarket we’ve ever been to in Europe (the Co-op) in Ortobello, a small town on the side of a national park and a lagoon. We couldn’t have asked for more.  

We flew into Rome’s Fiumicino airport and hired a huge van to transport all of us and our luggage two hours along the coastal road and across the bridge from Ortobello to the island town of Porto Santa Stefano. Then we wound our way high up into the hills and down a tiny path to La Madelenna Bassa, a stylish traditional villa literally perched on the edge of a cliff looking out to sea. 

The view was breathtaking and I spent every morning before the family woke up gazing out across the ocean, sipping my first coffee of the day. I was slightly worried that our eldest girls would find the pace of this trip too slow and the lack of nightlife a little frustrating but there is so much to do in the region they easily settled into that leisurely Italian time keeping.  

The villa’s owners, Roberto and wife Isa, made us feel extremely welcome. They called every day to check our needs; as midlife parents themselves they knew exactly what would keep everyone occupied in this remote, romantic location. 

Each morning, my husband and I made the most of late-sleeping kids to navigate the 15-minute walk down to the small private beach for a sun-up swim. It’s a trek for the hardy only but made more impressive when you learn Roberto built the path into the cliff almost by himself over a period of years. It was worth the effort to allow guests to swim alone out into the calming sea. Only one of the kids had the patience to come with us to the shingle beach but frankly having this little morning adventure alone was most welcome for me and husband James.

Once the kids were up, it was off on some sightseeing: we drove to the hot springs at Saturnia (take some coins for a shower after), wandered through the picture-perfect streets of hilltop towns like Montemerano, pottered around the small port of Porto Santa Stefano and the even tinier Porto Ercole nearby. We shopped in Ortobello and took an easy 20k bike ride around the lagoon through the pine forest to see pink flamingos. Occasionally, while the kids faffed about at the villa, my husband and I would drive to the little beach at Pozarello for a quiet swim and coffee before heading back for lunch in the small villa with it’s cute kitchen and comfy sofas.  

We all read books, my 18 year old completed a Russian essay for her university course, my 16-year-old son enjoyed the small pool overlooking the ocean and we feasted on fabulous home-made pasta in the evenings before playing cards and watching films. As anyone with adolescents will know, it takes them ages to get ready to go anywhere, which works in your favour in Italy where evenings don’t really get going until about 9pm. Be warned though, much of this region is shut for lunch between 1-4pm. Little happens during that time so focus on mornings and later in the afternoon for trips out.  

The best thing about Italy is of course the food. We had delicious ice creams and crepes from small cafés in pretty towns empty of tourists when we went in October half-term. The weather was a little windy for too much beach time, though we enjoyed an afternoon at Alberese beach which sits on the edge of a national park and is strewn with Hollywood film style drift wood.  

We ate out in family-run restaurants where we knew we could specifically satisfy the demands of picky eaters (one of ours, for example, won’t sit at a table with a real tomato unless it is on a pizza). At Paola & Rosita restaurant, down a small side street away from the centre of Porto Stefano, we thought we’d accidentally wandered into the owner’s front room, it was so cosy, but despite the language difference we had our best meal out of the week. Cooking at the villa was more of a challenge, due to the small kitchen, but we managed some spectacular meals with wonderful cheeses and gorgeous wines from the region’s numerous vineyards. 

This was one of the most relaxed holidays we have had as a family and we’re already planning a return journey to see more of this part of Italy. The villa is in a fairytale location and the morning on which a huge flock of tiny birds swooped down from the mountain top within touching distance as I savoured a cup of tea in the garden will stay with me forever.  

Lorraine’s pocket guide to Porto Santo Stefano, Tuscany

• Where to eat: We loved Il Cantuccio (for an upmarket meal) and La Taverna (for pizza) in Orbetello  
• Where to drink: In the small harbour town of Porto Ercole the bars are very glitzy and it feels like a more relaxed, less expensive Capri.  
• Where to shop: Orbetello has some lovely interior shops and we loved the little shops in Porto Ercole. 
• Where to walk: The national parks around the beaches at Feniglia and Alberese, are perfect for a walk and a picnic.
• Where to swim: Alberese has lifeguards in the summer but not out of season. We swam at the secluded cove at Pozerello on the road into Porto Santo Stefano. Fenglia is good too for a family dip. 

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