As the days grow colder and shorter, it’s difficult not to crave a holiday somewhere sunny and filled with the beauty and opulence of summer. To escape for a winter break is to rise above the natural order, and to refuse to be dragged down with the death of the year. It is to flex your muscles as a man refined to say no to feeling chilly, no to stressing over the looming Christmas period, and no to chastely refusing yourself some relaxation and sensory pleasure.

After all, is there any feeling as liberating and deeply enjoyable than feeling the sun on your skin? Is there any sense of decadence to match the pleasure of drinking cocktails through the long, warm evenings, or exploring a new city by foot and sampling its treasures? Somehow, doing all of this after rejecting staying at home in the winter months serves to accentuate those pleasures manyfold, and makes the whole experience of holidaying so much more satisfying.

There are many, many places you can head to between November and March on any given year. But where are those locations which truly hit the sweet spot for a gentleman on holiday? Which offer culture alongside azure seas, gastronomy alongside beach bars, and stand out as something unique amid the mess of package holidays populated by the unimaginative and uninspired? As ever, A Man Refined is on hand to help you out, and we’ve picked our favourite winter sun locations (as well as one alternative to the sunshine we think you’ll love), and have even given you some fashion suggestions to try out while you’re over there. Enjoy!

Havana

Winter Break Ideas Havana

The past few years have seen Cuba become a seriously hot ticket when it comes to winter tourism, and it isn’t difficult to see why. No longer considered something of a pariah-state, the Cuban government has woken up to the fact that tourism is key to its future success, and has gone well out of its way to ensure that visitors to this beautiful, sunny, fascinating island find everything they could possibly hope for.

The main draws of the city of Havana are clear. Not only does it sit on a spectacular stretch of coastline, where the warmer quarter of the Atlantic Ocean brings sunbathing, swimming and surfing possibilities aplenty, but it is also jam-packed with extremely romantic, decadently crumbling Hispanic architecture that can take your breath away. On top of that, you have a vibrant, affordable and unique culinary culture and a set of clubs and bars in which to dance until the early hours. Unforgettable.

Don’t forget to pack: What else is there to wear in Cuba but a high-quality linen suit in white, ivory or beige? Pair it up with a pair of dark brown leather boots or brogues and a matching belt, and you’ll be ready for the promenade and the salsa club in one outfit!

Costa Rica

Winter Break Ideas Costa Rica

If you’re looking for a real escape from everything, then there are few places on earth better than Costa Rica. It’s a genuine tropical paradise, a country which has a bit of everything: dense rainforests, incredible untouched beaches, the chance to see some amazing wildlife, and a burgeoning urban scene in the capital, San Jose.

If you’re into spending time among the waves, then Costa Rica is hard to beat. You get a choice of not only dipping your toes into the Pacific Ocean on the west coast but also the Caribbean Sea on the East. You’ll be spoilt for choice!

Don’t forget to pack: You’ll need a sturdy pair of walking boots, as this will be a winter sun holiday that would be a total waste if you just spend it by the pool. However, make sure you also pack a stylish pair of designer swimming trunks (such as those made by Sanwin Beachwear) as there’ll be plenty of opportunity for practising your front crawl in the waves, too.

Cape Verde

Winter Break Ideas Cape Verde

The Canary Islands are so last year. What few people realise, however, is that only an hour further by plane is one of the world’s greatest island locations, quickly becoming a must-see destination for sun-worshippers: Cape Verde.

This volcanic peninsula sits 350 miles west of Senegal and is ideal for the gentleman looking for a seriously laid-back winter holiday, with few plans other than checking out the local scene and picking up a healthy tan. If you feel so inclined, you can do a bit of island hopping to the culturally fascinating Sao Vicente, or the rugged Santo Antao, Sal or Boa Vista. Generally regarded as the Atlantic’s best-kept secret, get over there before the masses descend!

Don’t forget to pack: The blazing sun of Cape Verde will require you to pick up a good hat and a pair of shades. Use this opportunity to get some that will receive some envious stares: a tailor-made fedora, straw hat or boater, and great pair of aviators to match.

Phuket

Winter Break Ideas Phuket

Despite the fact that Phuket earned an international reputation as a hippy retreat that was later overrun with gap-year students in the 90s, it has gone to great lengths in more recent years to attract the luxury sector, too. If you’re looking for guaranteed great weather and plenty of opportunities to seriously kick back and relax, there are few better places in Asia to head to during the long dry season between December and April.

While there are beaches aplenty and hidden paradises to explore, one of Phuket’s main draws is its gastronomy scene. It’s said that one cannot eat badly in Thailand, and this island’s distinctive cuisine – made using the freshest fish – is well worth travelling for in itself.

Don’t forget to pack: a sharp, light, summer suit will help you stand head and shoulders above the rest in Phuket, and will no doubt help you get the best tables at the best restaurants. For the rest of the time, a sturdy pair of stylish sandals will help keep your feet from overheating on the sand!

Essaouira, Morocco

Winter Break Ideas Essaouira Morocco

Many travellers are somewhat put off from visiting Morocco after hearing horror stories from the crowded souks of Marrakesh. However, Essaouira offers something quite different, and we’ve seen a considerable spike in interest in recent years in this western outcrop of North Africa. It’s perfect for those looking for temperatures solidly in the low twenties – warm enough to spend long evenings enjoying drinks on the coast, cool enough to stay active and spend all day in town.

Essaouira is a historic city, packed full of crumbling 18th-century fortifications perfect for strolling around. However, most people head to this part of Morocco to take in the water sports it specialises in: it’s a haven for surfers, kite surfers, jetskiing and more.

Don’t forget to pack: Morocco loves to assault your senses with an amazing array of fragrances. Make sure you stand out yourself by wearing a strong, spicy, woody perfume of your own. Also, take a good quality wool jacket to throw over your shirt in the evenings, so you can look sharp as the temperature falls.

Tallinn, Estonia

Winter Break Ideas Tallinn Estonia

So, maybe you aren’t the kind of person who looks for sunshine and sandy beaches during the winter. Maybe you’d like to revel in a bit of wintry wonder… and there are few cities as spellbinding for a short winter break than Estonia’s capital of Tallinn.

Featuring possibly the finest restored medieval city centre in all of Europe, Tallinn’s old town is a genuine wonder. The cobbled streets give way to 13th-century townhouses and merchant halls, and the city boasts a thriving restaurant and nightlife scene among the castles and towers that dominate the skyline. Eat and drink like a medieval lord at Olde Hansa – their authentic 15th-century ales are considered by many to be the finest beers in the world. Plus, the women of this city are widely agreed to be the most beautiful on earth, so any gentleman is guaranteed to have an eye-opening experience in this frosty wonderland.

Don’t forget to pack: A trip to Tallinn in winter is going to be a chilly one, so make sure you pack your cashmere scarf and full-length woollen overcoat.

Benjamin Norris

Benjamin Mitrofan-Norris is an author and journalist from Bristol, England, specialises in luxury lifestyle writing and wine reviews. He is a lover of life's finer things and has a particular fondness for Alsatian and Eastern European wines, which he fell in love with during his three years working in Budapest.
Benjamin Norris

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