The Ultimate Gay Holiday Checklist

The Ultimate Gay Holiday Checklist: What to bring and what to expect?

The first step to having the most amazing gay holiday ever is going on any of the gay cruises organized through You can be among other gays enjoying all of the amazing places and people the planet has to offer. 


Choosing your holiday destination

Choosing a location can be a difficult task. However, with the locations are unlimited. Enjoy destinations like beautiful Brazil and the lovely British Virgin Islands, sunny St. Lucia, St. Vincent, and Martinique on one of our private gay cruises. If your taste is of something a little more exotic the join us in Seychelles, Tahiti, or in Thailand. I will never get enough of sailing in the Caribbean. 

Some of my favorite locations have been laying back and enjoying the white beaches of Puerto Rico, Saint Martin, and Saint Barth. Looking to explore the hidden jewels in the islands of Greece, ancient cities of Croatia and Montenegro. It does not matter where you would like to go for your gay cruises, all gays, all ages (18+) are welcome aboard to enjoy happiness and comfort. 

Where you choose to travel is most important but it’s just as important as who you are traveling with. Sometimes we travel and we are with complete strangers. The chances of those strangers not understanding your sexual orientation is very high. There were many times before this one where I have traveled with my partner and we were the only gay couple out of the bunch. Hot?! I think not we were like the hot topic in the hot tropics literally. After many experiences like this, I was left with the decision to choose a non-gay or gay holiday. I will always choose gay. I’m not alone because 600+ gay customers agree and choose to sail with 

Why choose a gay holiday instead of a non-gay? 

Gay holiday with pride diversity and sexuality

1. Pride 

Number one is pride because you get to be in an environment where everyone is truly proud to be who they are. This pride is a sense of confidence with the freedom to be you without stares or whispers. A pride that can truly be felt when shared with like-minded individuals. 

2. Diversity. 

When choosing a gay cruise, you find that there are people from all over with the same mindset. I love meeting a range of different people from different places in the world with different styles and personalities sharing the freedom to love who they want. Meeting new people from different parts of the world is easier when we all share a common interest in accepting and being ourselves all the time. 

3. Sexuality. 

This is a big reason if not the most important reason to choose a gay trip over a non-gay one. It will no longer be challenging to love who you love. Seriously to be able to kiss under a romantic sunset is priceless. Even the freedom to hold hands without unwanted stares is only available on a gay vacation. 

The Negative Sides of Non-Gay Trips 

One may choose to go on a holiday that does not cater to gay people because of their schedule and the availability to travel. I’m here to share that you can always and will always be able to find a trip for your convenience out of over 40+ gay sailing cruises or one of 15 private cruises we organize each and every year. 

If you still don’t know why you should choose a gay cruise, let me give you about 1 million reasons not to choose a non-gay cruise. I’m just joking, but let me give you some negative sides of choosing to go on a vacation that does not cater to gay people. 

Number one reason which I have experienced myself is that you may end up at a hostel where everyone is actually hostile because you are gay. Imagine being in a place where people do not understand your sexual orientation and actually feel that it is OK to use foul language towards you because not only are you foreign but you are a gay foreigner. 

You risk the chance of dealing with staff that is rude because you are gay. I have had the experience of being treated badly by staff because of my sexual preference. 

Bad experience on non-gay holiday

Another negative side is that being yourself will make others uncomfortable. I like to discuss this negative side more because the whole point of a holiday is to get away and enjoy yourself. Wherever you heart desires to travel and whatever you decide to do while traveling will be on display if you are the only gay personout of many straight people or staff. The most important part of enjoying getting away is to be able to be yourself. If being yourself makes others uncomfortable you too will start to feel uncomfortable. Feeling uncomfortable on a holiday defeats the whole purpose of taking a holiday. 

Showing love to your partner may make you or even your partner uncomfortable if everyone around you is uncomfortable and acting weird. What’s worse than paying for a trip and having a bad time? 

I agreed to go on a couples’ holiday with a group of friends only to be mistreated by staffed and whispered about by other couples who were not part of my group. Unfortunately, the negative sides of going on vacations not catered to your crowd, you will you risk the chance of you and whoever you are with being ostracized. 

How to prepare for a gay holiday? What should you bring with you? 

When you plan a holiday there are many things that you must keep in mind such as where you are going, what will you do there, where will you sleep, what will you eat, and do you need reservations? Also, what should you bring to wear and how are you planning to get there. Sometimes you think you got it all figured out and then it hits you “I forgot condoms and lube!”. There are many things we must remember before we sail but I’m going to give you my top ten. 

Ultimate Gay Holiday Checklist: top 10

1. First, remember to make a list. Making a list will help you remember the most important things that you need to buy, bring and do. It will help you have a stress free holiday. If you are not the type of person that easily remembers, like me, a list is perfect for you. Even if you have a great memory having a list and checking it twice is my best advice. 

Don’t want to make your own list? Download the Ultimate Gay Holiday Checklist!

2. Get your finances in order. Make sure you call your credit card companies and let them know that you are traveling. Check to see if there are fees related when using your card and the safeguards your credit card company may offer when traveling. Contacting the companies will give you a better understanding on using your cards out of the country and it will also prevent the companies from putting a hold on your account because of unrecognizable out of the country charges. 

3. You may want to make sure that you have cash. Having cash will help you with travel expenses when cards are not accepted. Also having local currency for the place you are visiting will be beneficial in saving money and communicating. 

4. Pack wisely by bringing things that you know are necessary for the trip. This includes your wardrobe. Make sure your clothes match the destination. 

5. Condoms and lube. To be prepared for a holiday make sure you have condoms and lube. Yes, it’s better to be safe than sorry. 

6. Print out any necessary documents. Also make copies and put them in each of the bags that you plan to carry and keep them with you at all times or somewhere safe on the trip. 

7. Plan your travel day. If you know that you’re going to be traveling somewhere that might have a major change in the weather, then make sure you have any necessary sunscreen or outerwear that you may need and make sure it is easily accessible. Make sure that you have important documents somewhere with easy access. If you use any type of medication you want to make sure you have what is needed during your travels on your personal belongings. If you like to play games, read, write, draw or eat while traveling make sure you have what you need so you don’t have to go searching for it. 

8. Bring the necessary medication. Or things you will need to prevent or cure motion sickness. 

9. Last but not least, make sure you let someone know that you are traveling because you might need them in case of an emergency. You can also use them to check on your home while you are gone. While letting them know your amazing plans for your gay cruise don’t forget to take advantage of their knowledge and ask them if there is anything that you might need to buy, bring, or do before your trip. 

10. Book with! 
No explanation required 😉

What to Expect on a Holiday Cruise Catering to Gays 

You can expect to not be viewed as different but instead, you will be surrounded by people with like minds. Coming on a holiday with we will make sure you feel welcomed and not out of place. Booking your holiday with you can expect a gracious staff that will respect you and treats you like a guest should be treated. 

You can expect gay skippers and gay cooks onboard making sure you have a great vacation experience. 

If you take advantage of the several labels you can expect much more. 

With the GaySail Special, your service will include a gay cook and skipper. It will also come with accommodations on board, breakfast meals, lunch, harbor fees, taxes, end cleaning, and gasoline. 
More about GaySail Special.

If you choose the GaySail Exclusive, it will include everything in the GaySail Special along with accommodations on board on a new exclusive luxury sailing yacht or catamaran. 
More about GaySail Exclusive.

Coming along with us on a holiday you can expect a wonderful time with truly great people not because we are gay but because we are truly happy to be free to be who we want to be.

Comfort is always number one to me on vacation. To meet people and not be treated poorly for who you are or who you are with is the most important thing when you’re traveling. You want to enjoy the luxury of seeing new things, maybe learning new languages, eating new foods, and relaxing on beautiful beaches. 

“If I can choose a gay versus non-gay vacations I will always choose gay”

If showing love to my partner offends someone I will not want to be in their presence. The chance of running into that on a holiday with my lover is high. If I can choose a gay versus non-gay vacations I will always choose gay. If you are gay, I would recommend you do the same. By doing so you can avoid the negative side of choosing a non-gay trip for yourself and whoever you are traveling with. Remember some people are miserable just to see other people happy and getting some. 

Feel free to download our ultimate checklist. Also be sure to: 

  • Make a list and check it twice
  • Getting your money in order 
  • Pack wisely (e.g. condoms and lube 😉)
  • Print out important documents 
  • Bring all needed medication 
  • Let someone know about your amazing cruise 
  • Last but not least, remember when planning your holiday. 

I will most rather take a vacation where I can be around people who also agree to love who they want even if it’s the same sex. has been voted the Number One Worldwide Leader and Specialist for Gay Sailing Cruises. So, do not forget to make your first place when planning your next gay vacation. You will be part of an environment where everyone is like-minded and genuinely are there to celebrate the pride, diversity, and sexuality of themselves and others.

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