Mastering luxury family travel, from stylish packing to local discoveries
Getting your packing right can make or break a holiday, especially when travelling with children. We spoke with luxury family travel expert Jillian from Compass Roam for some expert tips on how to make family travel look effortlessly luxurious. Having stayed at two of The Thinking Traveller’s villas in Puglia and Sicily, she has some great idea for what to pack for the perfect villa escape, from versatile wardrobe items and shoes, to activities and snacks for the kids.
Travelling in luxurious style isn’t just about what you pack, however: it’s also about what you find when you arrive. So, along with Jillian’s top tips, we’ll also explore the charm of local shops and markets, and highlight how supporting local businesses can enhance your overall travel experience. Whether it's finding the perfect, handcrafted piece in Puglia or uncovering hidden gems in Sicily and Greece, we’ll help you experience a holiday that is both well-prepared and culturally immersive.
Read on to find out more.
Holiday packing tips from a luxury family expert
For mums on the go on holiday, what wardrobe items are a must-have?
I’m all about comfort on the road – especially when traveling with kids.
For the beach - I like to bring a comfortable one piece that allows me to play with the kids easily. I also always bring a cover up that could pass for a simple sundress – just in case we hop from the beach to a restaurant.
For going out in the summer, sundresses are a must, but I’ve learned it’s best to bring “low maintenance” outfits – dresses that can easily fold and roll up in the suitcase. Those outfits make it easier to get ready quickly and have time to get the kids ready too.
For walking around/exploring - I always have a good pair of sneakers and a small backpack that doubles as my diaper bag/snack bag for the kids.
Do you have any recommendations to keep children engaged during a stay or day experiences?
Good question! It’s a balance because you want to have some “tricks up your sleeve” just in case they need a small break or distraction on a tour – but at the same time, you don’t want them to be distracted the entire time. You’re in Italy after all!
On our boat tour in Puglia, I packed a few coloring books, mermaid and truck sticker books, a few small toys, and a small picture book. These activities were helpful to have handy when we were sailing from one spot to the next – to help the kids pass some down time. There was a full dining table and shaded section on the boat, which allowed everyone to sit comfortably and play until arriving at our next stop. Then it was a mad rush to stow away crayons as we raced to jump in!
What is your top book recommendation for a getaway?
The Seven Husbands of Evelyn Hugo by Taylor Jenkins Reid is a great vacation book!
View our holiday book recommendations
How do you like to pamper yourself on a villa holiday?
At L’Argentiera we were always pampered! But I absolutely loved coming downstairs everyday and seeing the breakfast spread laid out on the table – freshly baked tarts and bread, delicious fruit, coffee/tea and eggs to order. It was a true luxury to have that meal waiting for us everyday. I could relax on the patio as the kids played, while my husband went and jumped in the sea for a quick dip.
What easy-to-take beauty items are a must for mums on holiday?
I always use a face lotion with good SPF, I’m all about waterproof mascara for the pool days, and I always have a baseball hat in my bag. While I do love a good wide brim hat, they aren’t the easiest to pack, so I leave those for home.
Did you have any go-to local foods you had over and over?
I became pretty obsessed with the fresh cheese in Puglia. I’d eat fresh mozzarella and ricotta for breakfast everyday - so much so that mozzarella and ricotta became their own food group for me.
We also tried Tiella- which is a mix of mussels, rice, cheese, and potatoes baked together. I’ll admit, I wouldn’t have ordered this on my own, but our guide highly recommended it. He did not lead us astray - we devoured every bite.
At L’Argentiera, guests can have a pizza chef come to prepare local pies in an authentic pizza oven. We loved this experience! Our pizza chef spent the whole afternoon just getting the oven ready. I never knew what went on behind the scenes to make pizza! We learned about the process – including how he heats the inside and preps the ingredients.
We walked away from that night really appreciating the craft behind pizza making – it’s not just spinning pies, but rather putting into practice a method that’s been passed down from generation to generation.
Read our holiday packing checklist
Shopping with purpose: supporting local communities and sustainable choices
If you do forget anything once you arrive, our Local Concierges will be happy to help and fill in the gaps. Or, it’s just a great excuse to explore the local stores and engage with the communities you visit.
From speciality markets to artisan shops, supporting local businesses on holiday can create lasting memories and often be a more sustainable way to find unique items that tell a story.
Here are top recommendations from our Local Concierges on where to shop whilst you’re away.
Our favourite shops in Puglia, Italy
Where to shop in the Salento
Le Costantine - A textile workshop using traditional techniques to create beautiful woven and embroidered homeware, clothing and accessories.
Tulsi Shop - Produces timeless clothing and accessories by hand, with an array of delectable colours.
Vico dei bolognesi concept store - In the historic centre of Lecce, working with local designers to bring premium “no logo” products to the fore.
Where to shop in the Valle d’Itria
Asselta - In Bari, a women's clothing and accessories store for elevated everyday and party wear.
Antica Sartoria - in Bari, clothing for women, men and children.
Abbracciavento - in Martina Franca, a boutique that provides luxury daily fashion and a tailoring service.
Underground Boutique - in Polignano a Mare, a women's boutique with a “rock character but a romantic soul”, with pieces to differentiate your style.
Tessitura Artigiana - in Ostuni, a family-owned business specialising in traditional embroidery techniques with local fabrics for their homeware items.
Numeri Primi – For the best local, Italian and international food products there are Numeri Primi stores in Monopoli, Polignano a Mare, Bari, as well as Brindisi.
Our favourite shops in Sicily, Italy
Massimo Izzo - A jewellery store in Siracusa. The stunning pieces that Izzo crafts are inspired by Mediterranean culture.
Fratelli burgio – A delicatessen in Siracusa for local produce including sauces, wines, caponata, conserves and more.
Bonajuto – In Modica, a boutique chocolate shop making the perfect stop for gifts for your loved ones.
Fiasconaro – Celebrating 70 years of Sicilian pastry making – in Castelbuono near Cefalu. Visit for their famous panettoni and chocolate/pistachio spreads.
Boudoir 36 - A boutique perfume store in Catania that makes signature scents on request.
Domenico Pellerino - A Sicilian artist who makes splendid light signs based on traditional Sicilian festive lights (luminarie).
Patrizia Italiano - A local ceramic artist crafting chic decorative "head vases”, symbollic of Sicily.
Colori del Sole - The brand has various boutiques in Sicily and makes home décor, and textiles with colourful designs for the table.
Camparia - A shop on the island of Favignana that carefully curates its selection of design objects, cosmetics and accessories, sporting local craftsmanship and sustainable resourcing.
Our favourite shops in Paros, Greece
Hamam People - Working directly with skilled weavers to produce beautiful and vibrant hamam towel collections with a contemporary twist.
Eclectia - On Paros as well as Hydra, a local boutique offering Greek linen clothing and designer resort wear.
Atelier 1935 - A family-owned business making leather sandals by hand.
In Antiparos:
Morethanthis – A design shop featuring goods from selected “aesthetically interesting” designers, specialising in jewellery, furniture, ceramics, artworks and accessories.
Sandali Antiparos - A local designer crafting handmade leather sandals and accessories to complete your holiday looks.
