Whether your tipple of choice is a tropical cocktail, craft beer or crisp white wine, when the working day is done are there any two words quite as enticing as “happy hour”? Luckily, Cayman has no shortage of watering holes offering generous deals to tempt you in for a glass or two. Cheers!

Grand Old House

With its dramatic location on the craggy shore of South Sound, historic Grand Old House is one of our favorite spots for a sunset libation. The daily Happy Hour at its “On the Rocks” bar serves up special drinks deals as well as a 20 percent discount on the delectable tapas menu created by their award-winning chefs.
Daily 5 – 7 p.m.

George Town Yacht Club

Watch the yachts bobbing in the marina and the planes soaring up from the airport at this relaxed venue, away from the hubbub. Make the most of its daily “321” special – that’s $3 off spirits, $2 off wine and $1 off beers.
Daily 5 – 7 p.m.


Happy hours aren’t only an early evening affair: This slinky Seven Mile bar lays on an extended happy hour every Friday, with 50 percent off drinks. Remember its usual daily deal of $4 beers, $5 wells (house liquors) and $6 wines, and for those who are feeling peckish there is even a $11.95 pizza and beer meal deal.
Daily 5:30 – 7:30 p.m.; Fridays 9 – 11 p.m.

Da Fish Shack

Head down to George Town’s waterfront for discounted appetizers, drink specials and live music from late afternoon to early evening. The relaxed and rustic Caribbean vibes are just what the doctor ordered after a stressful day. You could opt for a $6 glass of Mondavi Cab Sav, a $10 pitcher of Caybrew or $5 Appleton rum, while nibbling on a plate of tacos, calamari or fritters at just $7.
Monday to Friday 4 – 7 p.m.

Tortuga Beach Grill and Bar at The Westin Grand Cayman

Get into the holiday mode with a signature Cayman Lemonade or local draft beers at the Westin’s daily happy hour. We love those gorgeous beach views and mellow Caribbean-influenced music providing the soundtrack come sunset.
Daily 5 – 7 p.m.


One of the chicest new additions to Cayman’s dining scene, Venetian-inspired Bàcaro lays on a tempting happy hour. Seated on the terrace or at the bar, overlooking the water, take advantage of the half price cichetti (small plates) and crudo (raw seafood) along with carefully crafted cocktails and other drink specials.
Tuesday to Friday 5 – 7 p.m.

Legendz, Eats, Yoshi Sushi

This trio of eateries in Cayman Falls may offer rather different menus (from American classics to Japanese), but they share the same great happy hour offers. It’s a purse-friendly $3.25 for beers, $4 wine, $5 Prosecco, $3.25 highballs and $4 cocktails. Three is better than one!

Daily 4:30 – 7 p.m.

Royal Palms

Getting the week off to a bang, Mondays at Palms mean Sunset Sessions where it is 2-for-1 on all drinks. As the DJ plays Ibiza-style chilled house music, this feels like Cayman’s answer to Cafe Del Mar. The venue has also just started a recycling initiative and switched from plastic to paper straws. Hurrah!
Mondays 5 – 7 p.m.

Margaritaville Beach Resort

New kid on the block, Margaritaville, has a license to chill and is not afraid to use it. All drinks are half price when the weekday happy hour is rolling.
Monday to Friday 5 – 7 p.m.

Anchor & Den

Sample the latest craft cocktails and house infusions at the Apothecary Happy Hour, where the bar’s talented mixologists get creative with fresh botanicals each week. A live DJ spins the tunes to add to the chic lounge atmosphere.
Friday 5 – 7 p.m.


Up on the tip of West Bay, draw up a chair at this tiki bar and savor the sunset with a discounted cocktail in hand. The deals run later into the night on a Friday, when there is also live entertainment and $15 buckets of beer to take advantage of.
Daily 5 – 7 p.m. or Friday 5 – 9 p.m.


Find yourself on the East Side? Happy hour happens early here with Tukka’s afternoon food and drink deals – in fact, the earlier you arrive, the cheaper you can eat. Between 3 and 4 p.m., nibbles like coconut shrimp and conch fritters cost as little as $1.25 each. Wines and cocktails are a palatable $6 all afternoon and beers are $3.50.
Monday to Friday 3 – 6 p.m.


Of course, Camana Bay also has plenty to offer in the happy hour arena, with one of the most popular being tapas restaurant Karoo. Indulge in signature cocktails, wine or beer for 20 percent off the regular price.
Daily, 3 – 7 p.m.