Gay Caribbean Cruise – Outings and Adventure

An all Gay Caribbean Adventure? Yes! I had one of the most amazing adventures of my life sailing in the Caribbean!


As you already know, I partnered with Outings and Adventures this October. I flew to the Caribbean and enjoyed a Gay Sailing cruise on a windjammer for one full week… and it was simply amazing!

First of all… do you all know what is a windjammer (in Italian, veliero; in Spanish, velero)? In order to make sure I am giving the right definition (as you all know I am not a native English speaker), I quote Wikipedia: ” A windjammer is a type of large sailing ship, with an iron, or for the most part, steel hull, built to carry cargo in the nineteenth and early twentieth century…. The windjammers were cargo ships designed for long voyages. They usually carried bulk cargo, such as lumber, guano, grain or ore from one continent to another, usually following the prevailing winds and circumnavigating the globe during their voyages”.

Yes the one you see just above is Vela, the amazing windjammer I had the fantastic opportunity to sail aboard in the Caribbean! It felt so magic: it was like sailing back in time!

For me the adventure started on Friday, October 7th, due to long intercontinental trip. I arrived on the beautiful island of Grenada on the Saturday afternoon, directly from Europe (British Airways flies directly to Grenada and Saint Lucia from London Gatwick). I was welcome in the beautiful True Blue Bay Resort, where I met most of my fellow shipmates: it was clear since the very first dip in the Infinity pool that we were going to make an all gay Caribbean experience!

Gios in the Infinity Pool - True Blue Bay
Gios in the Infinity Pool – True Blue Bay

On Sunday morning from the resort we reached the port and finally got on board Vela! It was like a dream: we were 20 gay guys, most of us virgins (I am talking about sailing with Outings and Adventures…), starting a dream experience on a windjammer!

We were welcome by the crew with snacks and drinks, of course, just an appetizer of what we enjoyed throughout the week: we have been pampered by the crew with incredibly great food, drinks, and attention to details! Great breakfasts in the morning, energetic lunches at midday, rich Happy Hours with snacks and signature cocktails (Vela Colada, of course!), and a luxury dinner every night on deck, open-air under the stars! I was impressed by the efficiency of the crew and the high quality of the organization.

But most of all, we had the luxury of experiencing a great week in some of the most beautiful areas in the world! It was my first time in the Caribbean Gulf: it was beautiful beyond any expectations!

How did we spend the week? Thanks to the amazing weather (luckily enough, we have not been touched by the hurricane, nor the storms, although being storm season) we have made the most of the cruise. We swam (and snorkeled) in beautiful seas, while visiting some of the most charming beaches (and bays) of the world: Sandy Island, Union Island, Tobago Cays, Les Pitons in Saint Lucia… all of them breathtaking and a pleasure to discover!

We had also the opportunity to visit nice little towns along the way, such as Bequia and Saint Vincent, full of history and charm. But above all we enjoyed the life on board of Vela! And yes, we made the most of it: jumping from the deck into crystalline waters, paddling around the ship, swimming to the closest islands, from where to trek and enjoy amazing sights all around, dancing around like crazy monkeys at sunsets, bonding on deck while sipping drinks and playing Cards Against Humanity soon after dinner…

And I had the gift to meet a great bunch of good guys, which I have now the honor to call friends! Yes, this amazing Gay Caribbean Cruise gave me the opportunity to meet with great like minded people: so many memories who will stay with me forever! And so many new friends!

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Sailing in the Gay Caribbean with Outings and Adventures was such a treat! Do you want to discover more? Drop me an email with all your questions! I will be happy to persuade you to join their next big trips!

Buongiorno :) What are you thinking?