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The Cayman Islands has its fair share of nightlife. Most of the activities take place on Grand Cayman, the largest island in the chain. There are a series of bars and clubs that cater mostly to the tourists. You will not find many of the locals hanging out in these bars and clubs. For one thing, they charge a lot of money. You can spend a good amount of dough through one night of drinking in the Cayman Islands. If you want to go where the locals go you either need to ask around or just look for a place that doesn't look too built up. The drinks will be cheaper and you will get to hang out with the locals. If you want, you can head down to the beach and relax by the water and look up at the stars. This is a nice way to enjoy the night in a safe environment with family or friends. There are also some cinemas and game stores as well. There are a bunch of activities for kids set up at night that will keep them entertained.
If you like to go out and relax on nice lounges and bars, you can try Macumba Lounge on Seven Mile Beach in front of the Westin Hotel, it's a martini bar and lounge with entertainment every night. Also Havana club Cigar Lounge on west bay road if you are a Cuban cigar lover, and if you like dancing you can try JET Night club and O Bar both on Seven Mile Beach as well.
As of January 2011, some of the most popular night spots for young adults are as follows:
1) Calico Jack's - Open Mic Night
2) The Wharf - Salsa Night
1) Royal Palms - Industry Night, Wednesday Night
2) The Attic - Wednesday Night Drinking Club (Pub Crawl)
1) Aqua Beach - Open Mic Night
2) Royal Palms - Open Mic Night
1) Triple Crown - Karaeoke (Busier earlier in the night)
2) Aqua Beach - regular hangout for expats from Canada, United States, Europe, South Africa, Australia, etc.
3) Various other venues
Saturday (note: bars close at midnight)
1) Fidel Murphy's - Irish pub, karaeoke
2) Calico Jack's - House night
As mentioned above, O Bar and JET are the popular nightclubs. O Bar is located in Queens Court Plaza, and JET is beside Aqua Beach. A new nightclub, Elements, has recently opened as well and is located at The Strand.
Legendz is the most popular sports bar on the island, due to it's large number of TVs, well-priced food, and $2 pints of Caybrew after 10pm. The Dog House is another decent Sports Bar, but is not located on Seven Mile and requires a small drive (approx. 10 minutes). Most bars have satellite TV, so you could likely catch the game at most bars. If you're looking to catch English Football on a Saturday morning, Centre Spot Bar & Grill in George Town will be playing it.
Margarataville is a popular bar for visitors, as it is near the cruis ship terminals. With a waterslide and swim-up bar inside, it likely makes for a fun afternoon with all the visitors. Margaritaville also hosts all sorts of events, from boxing to comedy shows to foam parties.
Hammerheads and Rackhams are great water-front bars that are within steps from the cruise ship. Hammerheads has an in-house distillery (Seven Fathoms), where you can get a quick tour and a shot of rum. They both offer decent happy hours that are sure to get a bit lively.
For those who don't like change, there is also the Hard Rock Cafe downtown. A number of other local establishments exist.
Billy Bones is the best swim-up bar, as it is regularly staffed and is right in the centre of the action at Treasure Island, which is one of the cheaper places to live on Seven Mile Beach. Due to the low rent, service industry staff (bartenders, waitresses) tend to live in this area, making it a lively spot during the day and on off nights. It is your best bet for catching some rays while enjoying a rum punch in a pool.
Royal Palms has also recently built a swim-up bar.
Margaritaville's swim-up bar is open during busier cruise ship days, located beside the waterslide.
The Ritz offers dinner and drink service to tables set in the middle of the ocean.
Westin Casuarina's Beach Bar also has a swim-up bar during the day.
The bars at most of the higher-end hotel restuarants tend to be upper-class. From Blue/Periwinkle/7, to Hemingways and Bamboo, there are many choices to pay for an over-priced drink in a more sophisticated setting. Wine Bar in Governor's Square is newly opened and offers a good bar area that is well decorated, and a great selection of drinks.
Camana Bay is the king of sophistication. Whether it's a Bellini or Mojito surrounded by the White-on-Black feel at Abacus' patio, or a drink over at Michael's Genuine, Camana Bay has been about sophistication since the day the idea of Camana Bay was conceived.
Tiki Beach, just down from the beach bar Calico Jack's, is a more sophisticated version of Calico Jack's, and offers up theme nights as well.
Coconut Joe's is a very casual, laid back environment. Their $0.20 chicken wings on Sundays and Mondays are hard to beat, and their food is well-priced all around. The actual bar is small, but the patio gives a very islandy feel.
Lone Star has been newly renovated and offers a good menu as well as a patio to enjoy a beer on.
Macabuca in West Bay, an all-patio bar, is also a relaxing area on the water that will provide you with a unique experience. Try the cracked conch on their menu if you're looking for a bite to go with a beer.
Rum Point - A true escape from the more modernized Seven Mile Beach. As everyone will tell you, make sure you try the mudslides, and then enjoy it on a hammock overlooking the crystal blue water.
Kaibo - close to rum point, Kaibo offers more of an actual bar and has the ability to host parties. There is also a restaurant on site. Similar to Rum Point - enjoy a drink on a secluded beach.
Full Moon Party - A popular tradition at Calico Jack's that brings all types out - happens every full moon. Kaibo also offers a full moon event.
Disco Night - The Wharf, second and last Friday of every month