Gay Sailing Week

Aeolian islands, Sicily

From €1140 or USD $1290 per person in double cabin shared

17 – 24 July 2021 

16 – 23 July 2022

Other Dates are available for private charters for small groups. Please inquire

  • All Gay Sailing Experience
  • Gay Sailing trip across the Aeolian islands, Sicily
  • Discover beautiful islands
  • Swim, snorkel and relax in crystal clear blue waters
  • Get to taste fresh cuisine from Italy
  • Get to know the locals at the ports where we stop
  • Recharge, relax and switch off from the business of everyday life
  • Learn tips from the experienced crew
  • Make new friends
  • Professional skipper included
  • Get pampered by Italy Gay Travels hosts

Aeolian Islands, Italy

€1140 or USD $1290 per person in double cabin shared

At the moment of Booking a Deposit (€500) is required. Final Payment is due no later than 60 days before Departure.

4-8 people

Fly in and out of Catania, Italy, or Palermo, Italy

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Price per person (based on shared double cabin €1140 or USD $1290

At the moment of Booking a Deposit (€500) is required. Final Payment is due no later than 60 days before Departure.

Services included

  • 7 nights accommodation on the boat
  • Professional Skipper for the whole week
  • Professional Italy Gay Travels Host / Cook
  • Briefing on safety onboard
  • Bed linen and bath towels
Services not included
  • 3.5% Credit Card Commission Fee
  • Return flights
  • Transfer IN and Transfer OUT
  • Meals, mooring buoy or harbor fee, petrol for the jetty or for the boat when motoring (kitty will be arranged, around €350 – 400 per person)
  • Insurance, tips and everything not listed as Included


  • 8 days / 7 nights
This tour is accessible to anyone who can swim. You need to be in relatively good shape.
Onboard sharing in double cabins.
You will have 24/7 support during the trip.

Gay Sailing Week in the Aeolian islands!

On your marks, get set, SAIL!

Yes Christopher Columbus and his gay entourage have a gay sailing cruise! Okay minus Chris 😊 This is gay sailing like no other. From the moment you step on board Italy Gay Travels will float your boat (Spritz anyone?)! Discover the amazing Aeolian islands, off Sicily, and its crystaline waters!

The Sailing Week starts and ends in Milazzo, reachable easily from Catania airport. Another option is also flying into Palermo airport and get a private transfer.

We will embark in Milazzo port on Saturday afternoon. You will be welcome with a glass of Prosecco of course!

We will drop off our bags on the boat and explore Milazzo town, getting to know our fellow sailors. After dinner and a few drinks we will head back to the port to sleep on the boat, ready for the gay sail adventure that lies ahead.

On Sunday morning we will leave Milazzo. There will be a safety briefing and some basic training to ensure that everyone remains safe through the trip. After tugging at the strings (of the boat) we open the sails and head out into the open sea. If you have never sailed, fear not, we will show you the ropes to ensure you don’t go overboard. We have selected only the best (and hottest) crew to keep you afloat as we cross the sea and head to the beautiful Aeolian islands.

In the next days we will explore these amazing volcanic islands: Alicudi, Filicudi, Lipari, Vulcano, Panarea to name a few*. The exact itinerary will depend on the winds, as you can imagine: we will have a professional skipper with us, and a host/cook.

We will usually sail during the morning. We will have breakfast and light lunch on board. In the afternoon / evening we will explore the islands and have dinner in local restaurants.

On the Friday we will sail back to Milazzo, where we will arrive in the afternoon. We will sleep on board on Friday, disembarking on the Saturday, early morning.

We have selected only the best (and hottest) crew to keep you afloat as we cross the Mediterranean sea sea and head to the beautiful Aeolian islands. The only criteria for this cruise is the ability to swim. Of course, the crew are here to help you a little and show you how things work. They do all the hard work of course 😊 Picture lying on the front deck, wind through your hair, a beer in your hands and gazing out into the Mediterranean.

This exclusive gay sailing adventure is a 8 day, 7 nights adventure stopping at islands and ports on the way where we can explore, sunbathe, swim, meet the locals, eat out and plenty more!

Our gay sailing yachts are modern with space to relax. The cabins are comfortable and there is a fully equipped galley and 2 bathrooms. This gay sailing trip is a great opportunity to relax, enjoy, taste local cuisine, meet new friends and explore cultural. Make new friends from all over the world!

If you have any other questions about this gay sailing trip please email

* Please note that the itinerary is flexible depending on the weather.