With summer around the corner, there are plenty reasons to raise a glass and celebrate the best that Cayman has to offer. Whether you’re into carnival vibes, craft cocktails or a vino with friends, this year’s lineup of ‘spirited’ summer events has something for everyone.
Arguably the most anticipated event of the summer, CayMAS 2025, runs from 28 June to 7 July. With the tagline, ‘Experience the carnival, discover the islands’, CayMAS is a dazzling display of cultural pride and community spirit. The week-long boutique carnival experience comes alive with parades, elaborate costumes, soca rhythms and a series of fêtes. And while CayMAS isn’t officially about drinking, anyone who’s done carnival knows that the drinks flow just as freely as the soca music.
For those seeking something a little more laid-back (and with air conditioning) to whet the appetite a few weeks before the carnival festivities begin, Sip, Savour & Support Our Seas offers a chance to toast for a cause. Taking place at The Tasting Room at Camana Bay on 4 June, the wine tasting experience supports the Central Caribbean Marine Institute’s coral reef conservation efforts. From noon to 8pm, guests can sample up to nine wines for just $45, with a portion of all proceeds going towards CCMI. For tickets, email [email protected].
Now in its fourth year, the Cayman Islands Margarita Festival is back on 26 July, and organisers say this will be “the biggest year yet”. Set on Seven Mile Beach, this year’s event will feature the launch of Margarita Masters, a live bartender competition where Cayman’s best mixologists will go head-to-head in front of an internationally acclaimed judge. Expect creative margaritas, a food court packed with tacos and other Mexican bites, and a high-energy atmosphere that truly captures the spirit of Mexico, right here at home.
The celebration continues on 16 Aug. with the Cayman Islands Rum Festival, taking place at Sand Bar. From 5pm to 11pm, sample a wide range of rums, from local favourites to globally renowned labels, paired with flavourful tapas. This festival sets out to showcase the rich variety and unique flavours of rums from around the world. Tickets start at $100.
To bid farewell to summer, Grand Old House is hosting a Summer Break Party on 22 Aug. From 5pm, guests can enjoy waterfront dining, music by a live DJ and specials on drinks, tapas and wines. It’s the perfect way to enjoy one last sunset soirée before the season winds down. Reservations are required.
Ongoing summer events
Cayman’s wine scene is always in full swing with ongoing tastings for enthusiasts.
On 30 May, The Brasserie presents an exclusive Joseph Phelps Vineyards dinner with a Champagne Krug reception, a four-course tasting menu, and three vintages of the acclaimed Insignia blend for $150. Book a table at [email protected].
For those who want to keep the good times flowing, The Brasserie also offers a monthly wine club curated by Master Sommelier Simone Ragusa, delivering top global picks straight to your door. Retailers like The Tasting Room, Jacques Scott and Blackbeards also host regular tastings.
For a more hands-on experience, the Catalina Cocktail Club is an interactive mixology night held at Hotel Indigo on the last Monday of each month. For just $30, guests get a welcome drink, a cocktail tutorial, a live demo and a keepsake to take home — but with only 16 spots, it fills up fast.
And, of course, Sunday brunch remains a beloved Cayman tradition. Restaurants and hotels across the island, from The Ritz-Carlton, Grand Cayman to Tillie’s, offer a range of brunch packages, some with bottomless beverage options. Whether you’re into mimosas, bellinis or a custom Bloody Mary, brunch continues to be the perfect way to toast the weekend.
Cayman’s lineup of spirited summer events offers something for every taste. As always – drink responsibly.
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