Sailing The Cayman Islands and Getting Around.

When you are planning a Private Yacht Charter Itinerary, you may consider Sailing The Cayman Islands as part of it. The following article will give you all the information about Sailing The Cayman island with a Private Yacht Charter. But also what you can expect when you set foot on any of the Cayman Islands.

When you consider to charter a private luxury yacht at Grand Cayman. Then the most common way to travel to the Cayman Islands is by plane. And from there you can rent a Luxury Private Yacht with crew or without crew.

Flying to The Cayman Islands.

When you plan to set sail the Cayman Islands from any of the docks of Grand Cayman. First you you have to travel to the Cayman islands. You can do this by flying to the Grand Cayman.

So the main airport is the Owen Roberts International Airport and this is located on Grand Cayman. However Cayman Brac also has its own airport known as the Gerard Smith Airport. Both these airports are the point of entry for visitors into the Cayman Islands.

Owen Roberts International Airport
Owen Roberts International Airport

Because the Cayman Islands is a very popular holiday destination. There are constant flights into the islands and it is always possible to book a variety of flight options. It all comes depending on where you are coming from and when you plan to visit the Cayman Islands. The main airlines that fly into the Cayman Islands include Cayman Airways. The Cayman Airways flies with the national flag of the Islands. Other airliners are American Airlines, Continental Airlines, Delta, Air Canada, and a host of others.

But keep in mind that the most popular Private Yacht Charter Brokers are located at Grand Cayman !.

There is also inter-island air travel and this will allow visitors to travel between the three main islands. These are The Grand Cayman, The Cayman Brac and The Little Cayman. Air travel between these islands is provided by two airlines only, Cayman Airlines and Cayman Express.

Below is the Google Map of The Caiman Islands starting from The Grand Cayman.

Sailing The Cayman Islands with a Private Yacht Charter.

When you and your companions plan to Sail The Cayman Islands with a Private Yacht Charter. Then this will be an experience you will never forget !. However you will need to plan your itinerary well and ensure that the captain of the private yacht charter is well aware of the safety issues with reference to the islands. Things to look out for include unfavorable winds, the coral reefs and the time of year in terms of weather.

When sailing The Cayman Islands, it is possible to rent a private yacht charter with crew and captain at Grand Cayman. I have described the best 5 Cayman Island Private Yacht Charter Brokers below.

The Best 5 Cayman Island Private Yacht Charter Brokers.

I created a brief description about the Best 5 Cayman Island Private Chart Yacht Brokers in this section. You can find the Yacht brokers contact information and websites (if I could find such) to visit them directly. My goal for you is to have a list of all the Private Yacht Charter Brokers that are established at Grand Cayman. So I hope you can make much of this information.

1. # Cayman Luxury Private Charters.

Sailing The Cayman Islands | Cayman Luxury Charters
Sailing The Cayman Islands | Cayman Luxury Charters

Well as the name of the charter broker says. You can charter luxury Private Yachts with crew and captain onboard !. And they offer the complete package for you and your companions. Their latest asset is the luxury catamaran ‘ Leopard 51 Power Catamaran’ named ‘La Vida’ !. And this no standard luxury Catamaran indeed. It can hold up passengers from 2 persons to 38 persons. So probably you can bring your whole family with you. Cayman Luxury Private Charters can arrange all your lunch and beverages directly on board.

Below is a Youtube video I found where you can see a ‘ Leopard 51 Power Catamaran Guided Tour.’ .

When chartering a Luxury Yacht at Cayman Luxury Private Charters, then snorkeling and diving destinations are part of your itinerary. You can expect private environments where you don’t see much crowd of even no crowd. They also offer amenities like water sports, jet-skiing, fishing and tubing. Also you can set foot on any island that is part of your itinerary. This all goes at an unforced way of sailing. Although you are not the Captain of the Private Yacht, you are actually in control of your Private Yacht Charter.

Besides the ‘La Vida’ Luxury Catamaran, they also have other Private Yachts to choose from. It all depends on how many companions you want on board, what amenities you expect and how long you are planning to sail. And not to mention, you can even have your luxury wedding on-board of your luxury private yacht charter !. They offer Bridal party ladies, bridal party gentlemen, trash the dress (you might not want to that ?). And also elude the wedding guests, photo shoots and well, get married of course !.

Tripadvisor Trust ranking – Cayman Luxury Private Charters.

As for trust, on Tripadvisor they rank number 4 when it comes to ‘ The Best Family Vacation in the Caribbean and Mexico ‘ . But also they rank at number 18 for the Best Destination in the World !. Also their sailing destinations are wide. So you can plan your itinerary sailing the western Caribbean sea and all that is in between.

As for prices when renting a luxury charter, I have put the most low range and the most high range. It depends on what kind of luxury yacht you want to charter and for how long. You can think of prizes between $825 US to as high of somewhere around $4200.00 US.

Overall this seems to be a good Private Yacht Charter Broker. Maybe their website is a little out of date when it comes to design, but their reviews are great. So maybe you don’t have to judge them by the quality of their website, but through their quality of service they have to offer.

I will keep these Yacht Charter Brokers Reviews short, but I can write a lot more about them. And maybe I will if I have the time to do so. I hope I have giving you the information about this broker to get you on your way !.

  • You can visit The Cayman Luxury Private Charters official website at Or you can reach them directly at Cayman Islands . Their telephone number is . | Google Maps –

2. # Cayman Yacht Charters.

This Yacht Charter Broker is surely one of the best you can find at Grand Cayman. They offer boats up to 4 cabins for the guests, professional crew with captain and a range of luxury private yachts. In their inventory of boats, you can choose from Luxury Sailing Catamarans, Motor Boats, sports boats and dive boats. So there is always a boat that can satisfy your needs.

Cayman Yacht Charters | Sailing The Cayman Islands
Cayman Yacht Charters | Sailing The Cayman Islands
  • Their Private Catamaran Yacht.

Their Private Catamaran Yacht is ideal option if you want to spot Eagle Rays, Turtles and Stingrays. The front deck of the Catamaran Yacht is perfect when you want to want to enjoy the sun. Also the Catamaran Yacht has spacious rooms for guest in the rear cockpit. Or you can enjoy yourself and your companions on the lounger. And when you the sun is getting to much for you, then you can hide in the shade under the gull-wing roof.

  • The Sea Ray Sports Boat.

This Sports Boat can accommodate up to 12 guests. This is a popular Private Sport Boat that has an expansive cockpit, which you can use as a social area. Also this boat has aft facing lounger. And guess what, you can expand the facing lounger to a sunpad as well. When it comes to music ?. Well this boat is equipped with a Premium Audio System, so you can start the party right away.

  • The Sea Ray Sun-Dancer crewed motor yacht.

This crewed motor yacht can accommodate 14 persons and is most popular for day charters. When it comes to luxuries. This motor yacht has a lot of space with lots of comfort, so you can enjoy a day you will never forget. You can enjoy the sun on the deck or you can take a dive in the clear blue sea from the swim platform. This motor boat has 2 cabins and it comes with 2 crew-members.

Sailing The Cayman Islands with the Sea Ray Sunseeker 46
Sailing The Cayman Islands with the Sea Ray Sunseeker 46


Amenities ?. This boat charter offers all kinds of amenities. Some of them are Jet-skiing, paddle boards, snorkeling and lots more. Also most of the boats for charter, drinks, snacks or a BBQ is included.

  • The Cayman Yacht Charters Broker is also located at Grand Cayman. Their address is Cayman Island Yacht Club, Yacht Drive, Grand Cayman B.W.I. You can reach them by calling the following phone number: +1 (345)917-9855. And probably you want to read all the information about The Cayman Yacht Charter. Well their official website is https://

3. # Mainstay Sailing.

When you’re looking for a tailor made Sailing Trip ?. Then Mainstay Sailing is offering just right that. Because this is a relative small Yacht Charter Broker. Mainstay Sailing has a great service and you can be assured that they will do anything to give you an unforgettable day a sea !. You can even have your wedding on board. Everything will be arranged by Mainstay Sailing. Also they are experienced in staff parties kids birthdays and even disabled groups.

When reading their reviews of people that have sailed with Mainstay Sailing, you will get reliable feeling. And not to forget, they have a 100% 5 star certificate of excellence from Tripadvisor. Following are their two Mainstay Sailing Boats.

Mainstay Sailing | Sailing The Cayman Islands
Mainstay Sailing | Sailing The Cayman Islands
  • The Enchantress Private Luxury Catamaran.

This Private Luxury Catamaran has four double en-suite cabins and has all the luxury you can expect when renting this boat. Actually when it comes between action and relaxing, it’s all up to you !. You can enjoy the sun and have some drinks and beverages. But you can also swim with Stingrays, paddling, knee boards, fishing and lots more.

When it comes to safety and professionalism. The Catamaran Yacht Enchantress is sailed by the experienced Captain Jon. Captain Jon is a Sailing Instructor and have bin sailing the seas for 17 years.

  • The Leopard Power Cat Luxury Catamaran Yacht.

This luxury Catamaran Yacht is equipped with a fridge, freezer, satellite cell, AC, and has 4 en-suite double cabins. Because Mainstay Sailing has no sailing packages, they offer just all you want. It all depends on the purpose of your sailing trip. So if you would like a birthday party, new years eve or Christmas party. Then Mainstay Sailing will create a package of wishes and you can a the prefect day sailing the sea.

4. # Crystal Charters.

This Yacht Charter Broker is also high rated on Tripadvisor. Their mission is to give you the best experience when sailing the sea for a day. They own three Luxury Charter boats which you can rent for your family, friends and other companions. Following is a little review about the Crystal Charters Luxury Boats.

Crystal Charters to book your Private Boat in The Cayman Islands
Crystal Charters to book your Private Boat in The Cayman Islands
  • The Sea Ray Sundeck Luxury All-Round Boat.

This luxury all-round boat can accommodate up to 8 persons. This Luxury boat is an all-round boat for any family and is equipped with all the luxury that you can expect a luxury boat has. You have plenty of space to move around and has a shading top that offers you the shade that you might sometimes need. Also this luxury boat has a convenient platform and ladder. So you when you are done swimming the sea. You can easily climb on board.

  • The World Cat Luxury Power Catamaran.

The World Cat Luxury Power Catamaran can accommodate up to 14 persons !. When it comes to speed and the luxury, then this luxury Catamaran is the boat you are looking for. This luxury power catamaran is equipped with showers and a top entertainment media center. Also this Luxury Catamaran has a extended swim platform and a reinforced ladder where you can climb back on the boat. So when you want your kids or adult party going on straight away, then the World Cat Luxury Power Catamaran might be the boat you are looking for.

  • The Bank Draft Luxury Power Boat.

When you are looking for a boat that can hold large groups. Well then the Bank Draft Luxury Power Boat is probably the boat you are looking for. This is the Crystal Charters premium Luxury Power Boat !. This is a boat especially for large groups with little extras.

All the boats are equipped with a licensed captain and crew, drinks and beverages. They offer additional extras like Pick-up form your resort (Rum Point, Kaibo), deep fishing and reef fishing. But also wake-boarding, water-skiing, tubing and even a professional photographer.

5. # Sail Cayman Ltd.

Well Sailing the Caymans is an experience you and your companions will never forget. Sail Cayman Ltd makes your dreams come true. Sail Cayman Ltd has experience for over 25 years. They have lot of sailing experience and offer you the best sailing experience when it comes to day trips.

Book your Private Yacht at Sail Cayman Ltd
Book your Private Yacht at Sail Cayman Ltd
  • The Stingray Bio Bay Night Snorkel experience.

In this Sailing Package they offer the Luxury Power Boat Lazy Daz and a specialized adventure. You leave the Grand Cayman Yacht Club sailing to the Stingray City Sandbar. From there you sail with a slow pace to the barrier reef. At this point the crystal clear waters turn black because of the dusk that is coming. This will be a great experience because the natural sea creatures will com to live. You are equipped with LCD lights, so you can become part of the life in the sea. The Lazy Daz can accommodate up to 8 people and you can sail for 3.5 hours to 4.5 hours. The price for this experience is between $800 US to $950 US.

  • The Cayman Private Luxury Catamaran Tour.

You can have a unforgettable day on the Luxury Catamaran Yacht ‘ Leopard39 Powercat’. This luxury Catamaran Yacht can accommodate up to 20 persons. I will keep this short because there is to much information to cover. In a nutshell, they offer Sunset Sails, Half Day Sails, Full Day Sails and Multi Day Sails. When following the link from you are redirected to . I don’t think this has to do anything about phishing, but just another domain Sail Cayman Ltd has created. Anyway on their link you can read everything about what they offering when it comes to chartering a package with a Private Luxury Catamaran.

And when it comes to drinks and beverages. Sail Cayman Ltd. offers it all. Like a full bar menu, cocktails and a BBQ.

  • Like all the other Yacht Charter Brokers, Sail Cayman is established at Grand Cayman. Their address is Yacht Club, Dock #15, Seven Mile Beach, Grand Cayman. Their phone number is +1 345 916 4333 and their official website is | Google Maps –

When searching their site, their tours are little on content. So I did my best to describe this review. If you think differently or you want to ad more information, you can always send my a mail to Or you can leave a comment below.

Sailing the Cayman Islands when you are the Captain of your Private Yacht.

When you are sailing your own Private Yacht form anywhere else in the world to the Cayman Islands and anchor at one of the docks. You will need to seek clearance from the relevant authorities of course. Since the authorities on the Cayman Islands tend to be rather strict in enforcing the rules. Ensure that you know the latest procedures and requirements before Sailing The Cayman Islands.

Procedural, the moment you enter Caymanian waters, it is necessary to fly the Q flag. In addition mosquito control officers will spray your vessel at a cost of USD$25 before you can enter the islands. When arriving the first step is to communicate with the port Security on VHF Channel 16. They will then inform customs and immigration of your arrival and advise you about yacht boarding procedures.

As with all other ports of call, no weapons of any form are allowed and these must be submitted to customs. Fresh fruit and plants are also not allowed on the islands. It is also important to be careful with anchor chains that may damage the coral, and of course no dumping is allowed.

You can also go for Cruising The Cayman Islands.

Another option when it comes to Sailing The Caribbean and Sailing The Cayman Islands is via a cruise ship. There are cruise ships that arrive at the Grand Cayman every day. These cruise ships have a stopover on the Grand Cayman which normally lasts about 6 hours while on their way to Jamaica or Cozumel.

There are different cruise ships that service this destination including the Carnival Cruise Line, Princess Cruise Line, and several others including the Disney Cruise Lines. If you are opting to cruise into the Cayman Islands, it is useful to remember that you can choose the cruise class that you will be interested in. there are premium cruises and luxury cruises available and if you are not on a luxury budget, the premium cruise is worth considering as you will get value for money.

The Disney Cruise Lines
The Disney Cruise Lines with all the luxury on board

If you are opting to cruise into the Grand Cayman, it is unlikely that you will be able to spend much time there. While on the island, the common activities are shopping and you will find many shops selling good quality imported goods near the port.

What can you expect when anchoring your Private Yacht Charter at one of the Cayman Island Docks ?

Island hopping – Cayman Island style.

The best way to travel between the islands is either by Sailing a Private Yacht Charter or by using The Cayman Ferries.

Using The Cayman Ferries
Using The Cayman Ferries is a good option to travel

The best way to travel between the islands via Private Yacht Charters that are available at the brokers established at Grand Cayman. But you can also pay about USD$25 per trip to travel between Cayman Bra and Little Cayman with a ferry and this journey will take about 25 minutes. This is of course the more affordable option when it comes to Sailing The Cayman Islands. The disadvantage is that you can’t arrange your own itinerary.

There is just one ferry service that operates between Rum Point and North Sound in Grand Cayman and takes about 40 minutes each way. The best Cayman Ferry company established at Grand Cayman is Cayman Ferries. You can visit their official website directly at

If you opt to travel by air, small aircraft are the best way to do this. It is possible to hire a flight or if you are a licensed pilot, to charter a plane at one of the airports.

Traveling the Cayman islands on land ?.

When you anchor your Private Yacht Charter at one of the docks of The Cayman Islands. Well Taxis are plentiful on Grand Cayman and the taxi drivers are usually friendly and very accommodating. If you would like a more eclectic transportation mode. Then it is also possible to get on the buses that ply most routes.

On the smaller islands, Cayman Brac and Little Cayman there is actually no public transportation. Therefore if you are hoping to travel on these islands, the best means is by renting a car or bike or even a moped.

In addition, if you would like to test your seafaring skills, you can also go for charter yachts or catamarans to explore the islands. These vessels usually come with a trained crew who are able to guide you on your sea adventure.

Things To Do in Cayman Islands.

If you are thinking about things to do in Cayman Islands you should know that there are many things for all possible tastes in this area. It is perfect for those that love to relax and there is no denying that most tourists visit the islands because of this very reason. However, if you love adrenaline and if you want to go through many Cayman Islands Attractions that you are going to always remember due to the thrill felt. Well this is also possible !. Let us look at some of the most common things to do in Cayman Islands based on what most people actually do when they come here.

Fishing Grand Cayman.

If you love relaxation, there is a huge chance that you are going to enjoy fishing. Fly fishing is recommended in different areas and you can catch so many interesting fish. One will surely want to visit Grand Cayman so that they gain access to dozens of incredible fishing spots. We recommend that you also consider Bayside as it offers deep sea fishing. Make sure that you talk to a local tour operator to see exactly what places you want to visit for this activity when there.

Golf Activities and Coruses.

What can be more relaxing than golf? The answer is pretty simple. Playing golf in a surrounding that is exotic as what is offered by Cayman Islands will definitely be a tremendous delight. This is one of the Cayman Islands activities that only some enjoy but if you are one of them, you are surely going to have a blast. There are two tremendous golf courses that you will surely want to take into consideration: North Sound Golf Course and Britannia Golf Club. Enjoy a unique golfing experience in luxurious tropical oasis.

Golfin in The Cayman Islands
Golfin in The Cayman Islands

The Cayman Islands Scuba Diving.

You cannot come to Cayman Islands and not go on a Scuba Diving trip. This is an adventure in itself and the waters here are clear while giving access to hundreds of different species of tropical fish and a tropical reef like nowhere in the world. Keep in mind that at the moment there are around 200 different dive sites and the temperature of the water is ideal at around 80 degrees. Numerous tour operators will offer this opportunity and you are most likely going to be offered 2 tank dives while in the morning. We recommend this time of the day as everything is more special. While on a dive you can expect to see corals, sponges, eagle rays, tarpon, turtles and nurse sharks, not to mention the already mentioned tropical fish species.

The Cayman Tours and Sightseeing.

The truth is that when you go on a vacation, you are most likely interested in sightseeing. At the moment there are dozens of different local tour operators that you can take advantage of. Combine this with numerous offers built by travel agencies from all around the world and we are faced with a real delight. All that you basically need to do is make sure that you look at all the offers that are available and you will surely find something that you are going to love. Make sure that you visit exotic and unique destinations like Stingray City or Hell.

Sailing The Cayman Islands.

The Northeast side of the Cayman Islands is perfect for sailing as the water will reach a 15 knots average speed. The breeze is more than suitable for different water sports like windsurfing, sailing and parasailing. You do not need to bring anything with you since different local operators are going to cater for all the specific needs that you might have.

Sailing The Cayman Islands is a dream come true
Sailing The Cayman Islands is a dream come true

The Cayman Islands Nightlife !.

Those that are younger would most likely want to have fun during the night. Even if most establishments are going to close at around 3 AM, this does not mean that you are not going to have different dance halls, bars, pubs and similar locations where you can hang out with friends during the night until dawn. All is usually set in a very exotic surrounding and you are definitely going to love the nightlife here.

I have created an article about The Cayman Nightlife and Dining. You can follow this link —

These are just some of the most popular activities that you can enjoy in the area. The truth is that there are also other possibilities and you can even invent your own fun day. Cayman Islands has everything from hiking tours to swimming with stingrays so you can imagine the possible diversity that you can enjoy here. Make sure that you learn as much as possible about the activities so that you can have a tremendous vacation.

Cayman Islands Sailing Weather Overview.

The prevailing trade winds bring lovely, cool breezes to the Cayman’s during the winter, and tourists may even need a light sweater in the evenings. However, the proper attire for pretty much any time of the year is shorts, t-shirts, sundresses, and sandals during the day, and nice casual clothing in the evenings for going out, as the Cayman Islanders are often conservative.

The Cayman Islands lies in the farthest parts of the Western Caribbean, quite close to the Equator. And at a latitude of between 19 and 20 degrees North. What this means is that tourists need to take care not to expose themselves to the sun too much during the late morning and early afternoon, since the sun at this latitude is much more direct that in the US. Sunburns can happen very quickly, which will effectively ruin any vacation. Also, the sunlight is very direct, so take care to wear a hat and sunglasses, as well as sunscreen, when you are outside.

The Cayman Islands Rainy Season.

The wet, or rainy season, runs from May until December. This is the Cayman Islands “summer.” The months of May and June and September and October are frequently the rainiest months. There are many thunderstorms in the afternoons during the summer months, which brew up, drop significant amounts of rain in a short period of time, and blow out to sea in record time. These thunderstorms are caused by “Tropical Waves”, pressure systems which drift through the entire Caribbean region during the summertime.

These tropical fronts can increase in intensity and become tropical depressions, storms, and eventually hurricanes, which will be discussed further on. Other rain showers are generated locally by the condensation of hot, humid air over the mangrove swamps in the interior of Grand Cayman, causing thunderheads. The western side of Grand Cayman gets the lion’s share of these heavy rains, as this is the direction of the local prevailing winds.

The wettest day in the Cayman’s on record was November 30, 1993, when 7.8 inches of rain was depositing in less than 24 hours. The average annual rainfall is around 46 inches.

You may contact the Cayman Islands National Meteorological Service in Georgetown, Grand Cayman, for the current weather forecast and local conditions at (345) 949-4528.

Average Monthly Rainfall The Caribbean
Average Monthly Rainfall The Caribbean

Cayman Islands Temperatures.

The winter months in the Cayman’s are from January until April, with the coolest temperatures recorded during the months of January and February. When the average daytime temperature is in the high 70s to the lower 80s, and nighttime lows in the mid060s to lower 70s. The temperatures peak in the months of July and August. But it usually go no higher than the mid-90s during the day and the lower 80s during the evening. The summer is often quite humid. With the heat index seeming to add another ten to twenty degrees to the actual air temperature. The sea breezes will alleviate much of this on the coast. But the interior of Grand Cayman can become uncomfortably muggy, especially in the mangrove swamps. The lowest temperature on record in the Cayman’s was in January of 2000, when 58 was registered.

Winter (Dry Season)- November to April.

  • 72°F to 86°F during the daytime
  • 64°F to 72°F in the evening
  • Water temperature varies between 78°F & 82°F

Summer (Rainy Season)- May to October.

  • 85°F to 90°F during the daytime
  • 73°F to 85°F in the evening
  • Water temperatures between 82°F & 86°F
  • Relative humidity varies between 68% to 92%.

The Cayman Island Hurricanes.

The Cayman’s are located in the path of the Caribbean Trade Winds, and receive their fair share of severe storms. They are blown in by the Nor’Westers. Which are high winds bringing cooler air from the mainland to clash with the hot, humid air generated by the islands. The hurricane season runs from the beginning of June to the end of November. With the most storm activity for the Cayman’s being during September through November.

During these months, storms often form in the southern part of the Caribbean. But also are swept north by the prevailing winds of the Gulf Stream and into the path of the Cayman Islands. The nation has good disaster plans in place !. So if you plan on traveling during this time period you need not worry about becoming trapped. Additionally, hurricanes and tropical storms often skirt the Cayman’s altogether. Frequently, the nation is not really touched, even by the biggest storms.

The last big hurricane that really affected the Cayman’s was Michael in 2018. But also the hurricanes like Hurricane Harvey 2017 and the subtropical storm Alberto 2018. Luckily The Cayman Islands where not impacted by Hurricanes like Irma and Maria. You can read more about the exact Cayman Island Hurricanes at

My Conclusion about The Cayman Islands.

So when it comes to Sailing The Cayman Islands. Well generally there is much to do and if you have an opportunity to explore the different islands. I think the best journey is to visit the Cayman Islands is with a Private Yacht Charter. When chartering a luxury yacht or sailing your own yacht, you can experience everything The Cayman Islands has to offer. This is what flying between the islands can’t give you for sure.

So I hope you can make any use of this information in this article and I hope my goal is reached by describing all the topics in this article that I could think off. But if you have any questions left, or you have any information that you want to add to this article. Please don’t hesitate to send me a mail to

My wise words for this article is ” The pessimist complains about the wind; the optimist expects it to change; the realist adjusts the sails. ” —-

Write A Comment