The Best Bars in Oia, Santorini

When you picture Santorini, you’ll likely visualise pools on steep terraces that seem to merge with the blue sky. If you weren’t lucky enough to snag accommodation with a pool, head to the family-friendly Lioyerma Lounge, where you can spend an afternoon in the water. Hire a lounger or reclining chair, and make a day of it. The drink menu is fairly straightforward, but you’re really here for the pool. Bring a towel.

When you’re sipping a glass of Domaine Sigalas wine, you’re tasting the landscape of Santorini itself. Fruity yet bursting with minerality, the grapes grown by this winery just outside Oia benefit from a terroir unique to the island. Old vines of native Greek grapes – assyrtiko, athiri and aidani for white and mandilaria and mavrotragano for red – grow from volcanic soils in intense sunshine and are cooled by sea-salt-rich breezes. Tasting flights come with cheese, double-baked bread and cherry tomato paste. Alternatively, upgrade to a more extensive food and wine pairing session, and sit on the patio beneath vine-covered pergolas with an Oia sunset view.

Housed in a former butcher’s shop, Hassapiko – also known as Marykay’s by those in the know – is often described as the only true bar in Oia. With simple furniture and soaring vaulted ceilings, the tiny space has a wide range of drinks and regular DJ sets, rightly attracting a diverse crowd. Indeed, its website declares that its clientele comprises “local and foreign celebrities, fashion victims, modern and classic people, retro fans or whoever else you can think of”. It’s open all day, so pop in for an early-morning coffee and finish the day with a nightcap.

This cosy favourite is hidden away in a traditional Santorini home, complete with an original grape press and underground wine cellars. Sit in the cool courtyard with its rust-red walls, and sample the best of the island’s produce as you soak in the hippyish vibe. In addition, there’s a shop, a restaurant and an art gallery, and it hosts various performances. As for the drinks, the ancient vines on the island are unique, and there are more than 180 wines from 19 Santorini wineries to work through here.

Tramonto describes itself as an oasis away from the crowds. Decorated with cacti and seagrass and with rattan chairs under shaded bamboo canopies, it’s a relaxing pit stop at any time of day. The food menu spans from breakfast to dinner, with pizza and pasta always in high demand. Drinks-wise, cocktails are made to a high standard and range from the classics to unique creations inspired by Greek flavours. Order a spritz and watch the sunset, or start the day right with a boozy brunch.

Taking modern mixology to its most creative and showy conclusion, the Catch Bar-Restaurant is deliberately understated in its all-white decor. It only draws more attention to the outrageous, theatrical cocktails served in glass birds, perfectly spherical glass orbs or smoked under glass domes. The menu itself is organised around the elements of earth, air, fire and water. Try the Madama, made with black peppercorn-infused gin, rose liqueur, fresh lemon juice, hibiscus syrup and egg white. Make a meal of it at the restaurant, which offers Mediterranean comfort food, including slow-cooked meats and seafood.

Drinking sundowners beside windmill sails, gazing down across the caldera, is a Santorini must. Sun Spirit is the perfect spot for sunset drinks. The terrace has two levels, but grab a seat on the higher one as the views from the lower level tend to be obstructed by gathering crowds looking for the perfect sunset photo op. The drinks are on the pricier side, but you’re paying for that all-important view. Arrive early for the best seats.