Cayman Islands

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Cayman Islands dating guide advises how to pick up Caymanian girls and how to hookup with local women in Cayman Islands. Travel, enjoy and have fun with hot single girls and you might even meet the love of your life. Read more on how to date Caymanian women, where to find sex and how to get laid in Cayman Islands, Caribbean, North America.

View of Grand Cayman

Located in the Caribbean sea, the Cayman islands compromises of three major islands - Grand Cayman, Cayman Brac, and Little Cayman. All of them are located a bit south of Cuba and northeast of Honduras.

The islands are visited by millions of tourists every year who come here to enjoy some of the most beautiful beaches in the world. More details about the islands, the culture, nightlife, girls, and more are provided under the different sections in this guide below.

Cayman Islands Top 10 Overview:

Chance of picking up girls: 4.0 / 5

Picking up at daytime: 3.7 / 5

Picking up at nighttime: 4.3 / 5

Looks of girls: 4.0 / 5

Attitude of girls: 4.0 / 5

Nightlife in general: 4.0 / 5

Locals' English level: 3.5 / 5

Transportation: 3.5 / 5

Budget per day: US$259 - $1000

Accommodation: US$182 - $500

Caymanian Girls

The girls in the Caribbean are known to be extremely hot and it is generally agreed upon that the hottest girls in the entire area belong to the Cayman Islands. The girls here love to party and most of them have beautiful exotic bodies that will ensure you won’t be able to take your eyes away from her.

Other than having excellent bodies which they love to show off, most of the girls here love to party and have a really great vibe that is almost infectious which is why people all over the world consider these girls to be raw examples of hotness and beauty.

Other than the local girls, you’ll also have a lot of chances to meet hot tourists who come here to party from all over the world! Every day is a party in the Cayman Islands and you can meet some of the hottest girls in the entire world here!

RatingLooks Looks of girls: 4 / 5

The local girls here usually are tall and have beautiful slender figures. Most of them have a slightly tanned complexion and perfectly shaped bodies with long legs and great assets. There’s no shortage of beautiful and hot local girls on the islands here.

RatingAttitude Attitude of girls: 4 / 5

The attitude of girls here is pretty great and that is a reflection of the atmosphere that exists all the time here in the Cayman Islands. Most of the girls here are very free-spirited and love adventure. Overall, they’re a pleasure to approach and most hot local girls are usually okay with getting approached on the islands here.

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How to Pick Up Girls

The Cayman Islands are some of the best places to meet hot girls from all over the world and not just from the islands. However, the local girls are still pretty hot and you can have a lot of fun picking them up both during the night and the day here.

There are a lot of things that make picking up girls here much easier. If wide-open beaches filled with people who are in the mood to party and a vibrant nightlife doesn’t get you in the mood for some fun then almost nothing will!

Most of the girls here are usually looking for something casual and fun. If you can ensure that your approaches have a casual vibe, you can have a really great time when it comes to hooking up with girls in the Cayman Islands.

RatingPickup Chance of picking up: 4 / 5

You will have a pretty great chance of picking up girls here. You can find more details about how to pick during the day and the night under the different sections below.

Tips for Daytime

The beaches are the best places to pick up girls during the day here. You can find hot local girls showing off their perfect bodies on the many beaches filled with white sand here. Approaching them is also pretty straightforward and most girls have a lot of time here so they’re very likely to entertain your approaches.

How you dress up will also largely affect your results when it comes to hooking up with girls here. It is very important to be well dressed when you approach the girls here because your image is just as important as your pick-up skills when it comes to the local girls here.

RatingDaytime Chance of picking up at daytime: 3.7 / 5

You will have a pretty great chance of picking up girls during the day here. Not only are there tons of amazing venues where you can meet girls all day and the party-infused atmosphere only helps your results here when it comes to your dating life.

Best Places to Meet Girls

There’s no shortage of great places to meet girls during the day in the Cayman Islands. Here are some of the best places to meet girls here:

  • West Shore Center
  • Countryside Shopping Village
  • The Strand
  • Camana Bay
Camana Bay Canal, Cayman Islands
  • Grand Harbor Shopping Center
  • Seven Mile Beach
Seven Mile Beach, Cayman Islands

Tips for Nighttime

You can get much better results during the night when it comes to picking up girls than you’ll get when you do it during the day. Most of the nightclubs are filled with hot local girls almost every night of the week.

Do note that the clubs here are usually pretty loud and if you are not a fan of that environment, hanging out at the bars near the beaches might be a better fit for you. While there are fewer hot girls in this environment, you can still find a lot of stunners here!

RatingNighttime Chance of hooking up at nighttime: 4.3 / 5

Most guys should have a pretty great chance of hooking up with girls during the night here. As long as your approach is direct and casual, you can get a lot of results here and most girls will entertain your approaches during the night here.

Best Nightclubs to Meet Girls

Here are some of the best nightclubs to meet girls in the Cayman Island:

  • Bacaro
  • Coccoloba
  • Lobster Pot
  • Ristorante Pappagallo
RatingLooks Nightlife in general: 4 / 5

The nightlife here is pretty great and there are new nightclubs opening up regularly here. Currently, there are a lot of big nightclubs and smaller bars and pubs all over the islands here. Overall, the nightlife is really vibrant here and you can expect to have a great time during your night outs on the islands here.

Mature Ladies and Cougars

A large number of tourists come into the Cayman Islands every year. One of the major types of tourists who visit the island includes cruise-ship passengers. A significant percentage of all those passengers are mature ladies and cougars. You can find them usually at the smaller bars and pubs on the island and the tourist-friendly areas.


Cayman Islands regions map.png
Grand Cayman
The largest island and home to most of the population and tourist facilities. The other two islands are called the Sister Islands by locals and are also tourist destinations.
Little Cayman
Cayman Brac


  • George Town - the capital


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Top Dating Tips

One of the most important things that you should keep in mind when it comes to dating the girls here is that you should have a cool and casual vibe throughout your approach to get the best results. A lot of guys do not get great dating results here as they usually do not have fun personalities that can alienate the girls here.

Unlike other parts of the Caribbean, the Cayman Islands are pretty well developed economically. Most of the girls here usually not be impressed by your spending power but are usually just looking to have fun with a cool guy on a temporary basis.

Relationships and Love

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Online Dating

You can meet a lot of great girls using online dating in the Cayman Islands. Most of the younger girls here use online dating a lot when it comes to finding guys to hook up with. You can find tons of hot girls using online dating during your time here.

Some of the best online dating apps to use here include:

  • Tinder - One of the best dating apps in the world, you can meet a lot of great girls using Tinder in the Cayman Islands. It is the most used app here.
  • Bumble - Bumble is also a pretty great online dating app to use during your time here. You can find tons of hot local girls on that platform.
  • Happn - Lastly, Happn is the best dating app to use when it comes to meeting girls who are traveling through the area. The app tries to match you up with girls who might have crossed your paths in the last 24 hours.

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What Kind of Guys Have the Best Chances

Guys with a fun personality will have the best chances of hooking up with the local girls here. Even though learning how to dance is not vital when it comes to hooking up with the girls here, it can still be pretty helpful.

Risks while Gaming

The islands are pretty safe but you should still maintain a healthy level of caution whenever you’re out gaming during the day or night here. Basic things such as not trust strangers too quickly or going into dark shady areas with girls you barely know should be avoided during your time here.

The local population is also pretty chill when it comes to the girls getting approached here and white knights or cock blockers are rarely encountered here which means you don’t have to worry about a lot of things while gaming here.

How to Get Laid as Soon as Possible

There are two main ways of getting laid really quickly here. The best places to find girls here are the world-famous beaches and nightclubs here. Since these venues cover both day and night, you can spend your entire vacation approaching girls and having fun.

It is also a good idea to rent accommodation close to the beach or in the nightlife district to make it really easy to go from the nightclub or beach back to your room.

Gold Diggers and Sugar Babies

Cayman Islands is full of hot girls looking for a mutually beneficial hookup with travellers. There are lots of girls who don’t charge by the hour but who will do anything for a guy who is willing to help them pay their bills. If you are looking for a more personal and less transactional alternative to escorts, a good place to find these sexy open-minded girls in Cayman Islands is SecretBenefits.


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Swinging and Naturism

Unfortunately, there are no official nude or topless beaches in the Cayman Islands but unofficially there are some parts of the island such as the Orient Beach that are known to be naturism-friendly.

There are also no official swinger clubs here but you can easily find listings online for local swinger clubs where you can meet a lot of hot local girls and get laid lots of times!

Costs of Living

The Cayman Islands are a pretty expensive place to live in and the costs of living clearly indicate that. More details about the various aspects of the costs of living here are provided under the different sections below.

CostsDay Single traveler’s budget per day: US$259 - $1000

For most single travelers, a budget of at least $259 per day is required to have a decent trip here. The islands are one of the most expensive places to live or even to have a vacation in and some people might end up spending a lot more during your time here. An upper limit of $1000 per day should be more than enough for most people here.

CostsAccommodation Accommodation per night: US$182 - $500

The cost of accommodation in the Cayman Islands can range anywhere from $182 per night to $500 per night. These are the prices for normal hotel rooms and other accommodation here. There are some luxury resorts here that can charge a lot more than that but they usually include additional services and luxuries in the price.

CostsBeerBottle Beer in a grocery shop: US$2 - $4

The cost of a beer in most grocery shops here can range from $2 to $4 depending on the brand of the beer and the location of the grocery shop.

CostsBeerBar Beer in a bar or restaurant: US$6 - $7

The cost of a beer in a bar or restaurant here is usually $6 or $7. You can find cheaper prices during happy hour at most establishments here.

CostsMeal Meal in a restaurant: US$10 - $100

There is a wide variety of restaurants available here and the price of a meal can depend on the quality of the place, from budge to super luxury. Most basic restaurants here will charge you between $10 to $30 for a meal. Higher-end places can charge up to $100 for a great meal for two people here.


While there are a lot of options when it comes to accommodation in the Cayman Islands, the costs can be a bit too expensive. There are a lot of luxury resorts here that provide all the amenities you might need during your stay here.

There are also some budget accommodation options that you might find here such as Jeff’s Resorts and Rocky Shore Guest House but they are often overbooked if you visit the islands during the tourist season.

Overall, you can get some really nice accommodation here but you will definitely have to pay a steep price for it. On the plus side, most accommodation options here, even the really low-cost ones provide a really good quality of service and amenities.

Marriott Resort and Beach, Cayman Islands

How to Get There and Move Around

While getting into the islands can be a bit challenging, you can still find a number of options when it comes to moving around the region. More details about the different ways to get into the island and move around the region are provided under the different sections below.

By air:

Owen Roberts International Airport is the main airport serving the islands. It is a small international airport that is located outside George Town. There is only one runway and one terminal and every flight use the same runway.

There are a lot of airlines that operate flights on the airport including Air Canada, American Airlines, British Airlines, Cayman Airways and others that connect the city to a number of destinations within the country and outside.

You can easily find taxis that can provide to be an adequate way of transporting yourself from the airport into the city and vice versa.

Owen Roberts International Airport, Cayman Islands

By bus:

Due to the geographical limitations of the island, it is not possible to enter the Cayman Islands by bus. When it comes to moving around the area, the Grand Cayman Public Bus Transport provides a number of routes that cover the entire area which makes traveling around the region by bus a comfortable and good experience.

By car:

As the islands are surrounded by water, it is not possible to enter the islands by car. However, you can still move around the region by car easily as there are tons of taxis that cover all the island areas.

All the major car rental companies also have a presence on the islands so you can also rent a car and drive it around the island yourself. The traffic conditions are good but it can take a while to get used to it so definitely drive carefully here. You also must obtain a local license that requires you to have an international driving permit.

By train:

It is not possible to enter the region using trains or move around it by train as the islands don’t really support a railway network.

By boat:

Cruise ships often stop at George Town and the town is considered to be a destination for most western Caribbean itineraries.

Cruise Ship in Cayman Island

Visas: The visa policy of the Cayman Islands is pretty relaxed and nationals from a lot of countries like the United States, Canada and Australia can enter the islands without the need for a visa. It is still prudent to check the Cayman Islands’ visa policy before visiting the island.

Digital Nomads and Remote Work

The Cayman Islands may seem like a Carribean paradise, it is not the best destination for digital nomads or if you want to live here long-term. There are a lot of things that are wrong with the islands such as a really high cost of living and bad medical facilities.

Even though everyone speaks English, the quality of education of the locals is pretty low. The weather is also very humid and it can get too hot in the summer for most people here. Lastly, not a lot of remote workers come here which can make you feel a bit isolated during your time here.

Internet and Mobile Operators

Even though the internet connection here is not fast at all, you can still get decent cell phone coverage in most parts of the islands here. There are quite a few internet and mobile operators that provide service in the region. Some of the best internet and mobile operators in the Cayman Islands include:

  • Flow
  • Digicel

Gambling and Casinos

Unfortunately, gambling is not legal in the Cayman Islands and following this rule, all casinos have been declared illegal and had to shut down. So there are not really any casinos in any of the Cayman Islands and you should not expect to face any kind of gambling action during your time here.

Weed and Drugs

Cannabis is not legal in the Cayman Islands. However, you can still find a lot of weed here if you take some time to look around. Do understand that you can still land in some serious trouble if you are caught with weeds or other drugs here by the local cops as they’re not known to be kind of foreign tourists in these types of situations here.

Health, Fitness, Gyms and Massage

The local hospitals here do not provide the best medical services but they can treat most of the common problems that you might face when you’re here. The local hospitals are still hygienic and well-staffed though and you can expect a really good quality of treatment for the basic problems here. Some of the best hospitals in the Cayman Islands include:

  • Health City
  • Faith Hospital
  • East End Health Centre
  • Cayman Clinic

If you would like to work out during your time here and keep up with your fitness regime, there are a lot of gyms located here where you can work out. Most of these places also hire well-trained trainers who can help ensure all your workouts will be on-point. Here are some of the best gyms located on the island:

  • Anytime Fitness
  • World Gym Fitness Center
  • Universal Fitness
  • Fitness Connection

Lastly, there’s rarely any places in the world that are as great for relaxing as the Cayman Islands are. Not surprisingly, there are a lot of amazing spas that operate in the region and provide a wide range of high-quality massage, therapy, and relaxation services. Some of the best spas in the Cayman Islands include:

  • Eclipze Hair Design and Day Spa
  • The Westin Grand Spa
  • Perfectly Pampered Cayman
  • Tips ‘N’ Toes

STDs and HIV

The Caribbean is considered to be heavily affected by HIV and it is a pretty big problem here. In order to stay healthy and circumvent any potential problems in the future, it is a good idea to use protection whenever you’re hooking up with local girls here.

Stay Safe

The Cayman Islands is a "relatively low-crime area, especially compared to other vacation destinations in the Caribbean". However, that being said, crime is on the rise on Grand Cayman. Walking or riding a bicycle at night along dark roads (for example, along Courts Road) puts one at risk for assault and/or robbery. Pedestrians also need to worry about being hit by cars along soft-shouldered roads. Drunk driving and hit-and-run accidents have been a problem. The police regularly conduct roadblocks to deter and detect drunk driving, making numerous arrests most weekends. DWI/DUI is a serious offense in Cayman.

The capital city of George Town is generally safe. Tourists should avoid certain areas (Rock Hole, Swamp, Jamaica Town/Windsor Park, Courts Road, and Eastern Avenue) and this shouldn't be a problem as these areas are all well out of the way for most activities. In addition, George Town is virtually deserted at night as there are few centrally located restaurants, bars, or nightclubs.

See Also