The Mediterranean instantly says “slow down”, so you’ll want something that suits the pace – and the heat. Plus, if you’re moving from boat to island to boat again, weight might not be your best mate. Linen breathes in heat, dries fast after saltwater swims and looks intentional, whether you’re fresh or rumpled. Swim shorts that you don’t need a change of clothes for are essential. So is a versatile jacket that works for dinner. Then, comfortable sandals for walking and a pair of suitable shoes for water-adjacent activities.

There’s an unspoken dress code in these towns, even when casual. You’ll move between beach lunches and dinner parties, so your pieces need to read as thoughtful without looking overdressed. Canvas sneakers, polo shirts and tailored shorts can handle daytime, while the evenings require a little more formality. Don’t forget a striped sweater for cooler evenings.

Cities demand flexibility, so pieces that can do both are everything here. Think of dark-wash jeans and neutral T-shirts or shirts for your base. Choose fine knit sweaters for air-conditioned spaces, a pair of smarter trousers that move from lunch to dinner and soft loafers that dress up well. And finally, a lightweight jacket is essential for unpredictable weather.

Whether you’re off camping or hiking at higher altitudes, it’s all about the balance between practicality and aesthetics. Think checked shirts – from God’s True Cashmere, for instance – sturdy shorts with proper pockets, sneakers, boots or approach shoes that have been broken in before you leave. Don’t forget moisture-wicking layers for temperature shifts and a backpack to fit them all in.

The humidity can be relentless, so let your clothes breathe. Cotton or viscose shirts in vibrant prints or neutral hues look just as good solo as they do open over a tank top with tailored swim shorts you can wear beyond the beach. Pack a lightweight coverup for resorts and restaurants, along with flip-flops for poolside and something more structured for walking. Heavy rains aren’t uncommon, so don’t forget to bring a very lightweight rain jacket.

You shouldn’t abandon style for function by any means. ON, lululemon and Satisfy offer pieces that are crafted for performance but also look intentional once the workout is over. For running, yoga or Lagree, pack tops and bottoms that wick moisture and dry quickly as well as shoes to match the activity. If tennis or golf are more your bag, Brunello Cucinelli, Polo Ralph Lauren and Mr P. have plenty of options.

From Cotswolds farmhouses to Wyoming ranches, comfort is the brief here. Pack what feels good against the skin – soft linens and brushed jerseys, broken-in leather, pieces that have settled into themselves (or feel like they have). You can leave the city wardrobe behind but expect to dress up occasionally. You’ll still need some tailored trousers and a button-down shirt for that, just forget structure.