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Is this going to be like a Gay Cruise?

No! This trips is the opposite of a gay cruise- well don’t worry it’s still gay! Cruise ships are like giant floating hotels that only let you do so many activities and go to certain ports. On an OLSA adventure you sail your private 40 to 60 foot long Sailing Yacht between your ports of call that are greatly expanded due to our yachts being able to sail shallower waters than cruise ships. You get to go exactly where you want to.

Do I need to know how to sail?

Nope- but you can learn if you want! All OLSA adventures are fully crewed by professional staff that can handle the boat themselves, or jump in to help if you’re a seasoned sailor. If you’re interested in learning, just say so and you can learn a new skill on your adventure!

How stable is the boat going to be? Is it going to be leaning over while we sail?

Our yachts are extremely stable. All of our adventures utilize top of the line luxury catamarans that sail without heeling (Nautical term for a boat leaning over due to the wind) because of their width and twin hull design.

Can our straight friends come?

Sure!… Why not? We love bringing like-minded allies into the community – as long as they know what they’re getting themselves into!

I’m booking just one cabin, who else will be on my boat?

We fill our boats and cabins with people from all walks of life who are part of and friends of the LGBT+ community! You may be meeting strangers when you get on board, but you’ll become close friends by the time you depart!

Is this just a trip for young twinks?

Not at all! We encourage the diversity of the LGBT+ community to shine on our adventures.

Yeah that’s great and all, but I’m not at all young and have some health complications, can I still come?

As long as you can move around the boat, dinghies, and docks, then yes! Healthcare can be a consideration as well. Check with your insurance company to know if your covered in the territory of your ports of call but also be aware that to get to those medical services can be a lengthy and/ or expensive ride away.

Will I be able to post everything on the trip to Instagram?

Check with your cellphone carrier for their international plans- do your homework first to make sure you can connect and you’re not over paying. WiFi will be available at some locations ashore that we will be visiting. WiFi on board your yacht is included with your adventure in the BVI, Mediterranean, Seychelles, and Thailand. Connectivity and internet speed may vary throughout the cruising grounds.

Where do we sleep?

On the boat! Your yacht becomes your home away from home on your adventure. This is where you eat, sleep, (or not sleep ;), shower, and live. Your cabin and head (Bathroom for your land lubbers) will have most of the same comforts of your own home! Take a look at the details of the yacht your on at this link: [insert link to yachts page]

Also remember that if your arrival or departure dates are before/ after your yacht’s dates, you must make your own accommodation arrangements. There are lots of places to stay on St. Thomas and Tortola – ask us for a recommendation!

Can I get my own room?

Yes, you can! If you’re chartering the whole boat, then you can divide your crew among the staterooms as you wish, which depending on the number of crew and which boat you charter could include your own room. If you are chartering by the cabin, the default price is for a double occupancy cabin, with an option for single occupancy.

What’s the deal with showers?

Your yacht has showers on board that you are welcome to use throughout the trip though some of them can be a bit cramped and fresh water supply can be limited. Other shower options include outdoor showers on the swim platforms for getting the salt off after your swim, and showers on shore at many of the ports you’ll be visiting.

Where do we eat? … Who prepares the food?

You eat meals on your yacht prepared by your personal on-board chef for your adventure. In preparation for your adventure you will be asked about your dining preferences that your chef will use to provision the boat and in selecting meals to cook. Make sure to report food allergies accurately as well. All meals of the trip are provided on board, if you want to go out to eat in town, that expense is on you.

How do you get around between boats/ moorings/ docks?

You get between your yacht, islands, and other yachts by dingy- a smaller boat you take everywhere with you! The dinghies that come with our yachts are generally 10 to 12 feet long rigid hull inflatable (aka RHIB or RIB) boats with an outboard motor on the back.  Just be careful getting in and out – particularly after a few drinks!


There is no smoking at all inside the yachts, doing so will result in extra cleaning charges. Smoking is allowed on exterior parts of the boat as long as you’re considerate of the others on the boat. Remember to be downwind of others and don’t leave traces of your ashes or butts. It is our policy that smokers must responsibly extinguish and dispose of their cigarette butts and trash – No littering, no one wants to come to our beautiful cruising destinations to swim with trash. Hired yacht crew have final say, follow their instructions.

Will my things be safe on the boat?

Yes. Theft is not normally a problem in our cruising destinations. Additionally, your hired yacht crew will always have a trusted crew will always have a crew member on the boat who is “on watch” meaning they are keeping the boat safe including for theft. That being said- un plug for the week- leave your valuable electronics at home, and don’t bring your finest jewelry, the most dressed up you’ll need to get is shorts and a polo.

Where should I fly into? Where should I book my travel?

Never book your flight until you’ve gotten confirmation of your yacht or cabin booking from us which will include a welcome packet. This welcome packet will contain travel details for your individual trip. This will ensure you avoid the potentially costly change fees and other SNAFU’s.

Do I need a passport? Visas?

In general: you will definitely need a passport, and sometimes a Visa – but check on your home and destination countries’ laws on travel. More information will also be provided in your welcome packet. Also make sure your passport is up to date- to be on the safe side and avoid other headache’s, make sure the expiration date is at least 6 months after your adventure.

What should I pack?

A full detailed packing list will be in your welcome packet of trip information. Some guidelines: Don’t pack as much as you need- you’ll end up spending most of your time in your swimsuits! If you prefer smaller swimsuits, be sure to pack some quick dry shorts as well to easily slip on over your swimsuit for going to shore in public, and can be more comfortable moving around between yacht to dingy to shore and back. Overall our destinations are very casual so don’t worry about bringing fancy clothes- shorts, polo, and flipflops are enough for dinner or drinks on the islands- sometimes even overdressed! And finally, don’t bring your big hard-shell wheeled suitcases! On board the yacht, space will be limited so ditch the hard- shell for a duffle bag you can fold and store out of the way!