Mykonos-Santorini-Mykonos: May

GaySail: Come along for a Mykonos-Santorini-Mykonos adventure! A whole week of exploring and sight seeing awaits you! This sailing cruise is one that takes you along the southern cyclades Island to the spectacular island of Santorini!

Sail with the new spacious air conditioned Bavaria 56 feet sailing yacht with room for 11 guys as you explore Mykonos. This cruise is a one that will send you throughout various spots of Greece.

This is your chance to explore islands and mountains that give way to low, rocky hills which combine with superb beaches! Book your next adventure to embark on a new journey this Spring!


  • Clothing optional
  • Islands and rocky mountains to explore
  • Breakfast and lunch
  • Historical sites to visit
  • Adventure with fellow shipmates
  • Chance to meet new people



Day 1: Mykonos
Boarding starts by 5 pm in the afternoon. After meeting with your Gay Crew in the afternoon we do the welcome drink, introduction round and first briefing. Then it is time to unpack your stuff and have a swim and/or a shower before we go to town for dinner.  Of course we pay a visit to the famous gay piano bar Montparnasse as well and if you like we go for partying afterwards in one of the gay bars. It is no coincidence that this, the most cosmopolitan of all Greek islands, attracts so many gay visitors from the entire globe. Here the steep mountains to be encountered in most of the Cyclades islands give way to low, rocky hills which combine with superb gay beaches. The capital Hora, with its colorful harbor in which little fishing boats nest happily side by side with luxury yachts, presents quite a different picture from that of the majority of Aegean island towns. Mykonos is spread out over a flat area, and the whitewashed streets stand as brilliant white cubic houses with stepped walls for sitting on.

Day 2: Mykonos & Paros

Departing from Mykonos in the small hours of the morning and heading for Paros. The first thing you notice when in Paros is the blue transparent sky floating inside dazzling white sunlight. Look on the island for the white Cycladic houses built next to the Aegean Sea. The two large natural bays of the islands Parikia and Naoussa, have beautifully protected sandy beaches. We will anchor for lunch and swim and then move to the port, in one of the bays, depending on the wind.

Day 3: Paros & Ios

Early this morning we pull anchor and start sailing to Ios. A lazy day ahead filled with sun tanning, listening to music and on board meals. We stop at an ideal swimming spot on the way to Ios – the famous tourist destination. Visitors come for its golden beaches and the characteristic Aegean architecture. Ios is well known as the party island with the lively atmosphere and the endless fun. The capital is built at the point where the ancient city was, where white houses unfold and its windmills and narrow small roads can be seen on the hill tops. We make a private sunset party on the church hill and afterwards we have dinner in the only gay (friendly) restaurant of Ios, Lord Byron.

Day 4: Ios & Santorini

As the sun comes up we head for the magic summer madness of Santorini. On our way we anchor of for lunch and swim at the south side of Ios. It has been said that the sunsets in Santorini are the best in the world. From the Caldera, watch breathtaking views of the volcano & neighboring islands. Santorini is one of the major tourist attractions of Europe with its marvelous climate and perfect observation conditions, you will experience a wild beauty created from a volcano that lies in the middle of the bay. Today you will have enough free time to explore the town. Still shaky Santorini needs no introduction, being a 1 million year old volcano that remains in active/dormant state until today. Its breathtaking beauty both historically and geologically are awe inspiring making it one of life’s true highlights. The island was home to a Minoan settlement that was obliterated by an eruption around 1650BC which sent tsunamis through the eastern Mediterranean. The colossal eruption displaced 30 cubic kilometers of earth jetting a cloud of ash 36 km into the sky creating the foundation of what we see today. Centrally located in the 300 meter deep 5 -mile wide crescent moon shaped caldera harbor are two new cones, Neas Palaias & Kammenis. Like Paros our anchor stop for the night depends on the wind direction, either close to Fira, the main town or Oia in the north of the crater.

Day 5: Santorini & Iraklia

As the sun comes up we head for the small local Island of Iraklia or its even smaller neighbor Schninousa. Both are lovely little bays with only a few local Greek restaurant. A really peaceful atmosphere after all the hustle and bustle of Santorini. The population – much reduced by emigration – lives by farming and fishing. Ferries are not frequent, which explains the surprising low numbers of tourists.

Day 6: Iraklia & Naxos

After breakfast in the island we’ll sail to Naxos. The island of Naxos is the largest and most central island in the Cyclades. Approaching the island by boat, you can see two small islands to the left and right of the harbor, one with the little church of Myrtidiotissa, and the other called Palatia which is linked to Naxos Town. The imposing gate, Portara is ab ancient marble temple dedicated to Apollo. Ligdamis ordered this to be built in the god’s honor in the 6th century B.C You will have enough  free time to explore the town and to swim in the warm waters of the Aegean Sea or watch the sunset at the Arch.

Day 7: Naxos & Mykonos

Time to sail back to Mykonos. If we are in time we anchor of in front the famous Elia gay beach for swim stop and a drink. Mooring in the marina.. It’s a nice way to end this week over a cocktail watching the drag queen shows next to the pool in Elysium while the sun is going down. Dinner and party (if you like) in town

Day 8: Farewell Friends

Our trip will end here (10:00 am) in the stunning waters of Mykonos. After an on board breakfast we say goodbye to our new friends, and disembark the vessel.
This itinerary is subject to change. Local circumstances such as weather may influence the itinerary.



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Sailing Yachts and Catamarans

All cruises in Greece we sail with one or two spacious well equipped 56 feet (17 meter) Bavaria 56 Cruiser sailing yachts “Prometheus” and “Protheus”. These sailing yachts offer accommodation for a maximum of 11 guests, with six huts and three toilet/shower cabins. Three huts have twin beds, one hut has two single beds, one hut has a bunk bed and there is one single hut in the front with access from the deck.

In Croatia we sail with similar yachts for the GaySail and GayNudeSail cruises. On all GaySail Exclusive and GayNudeSail Exclusive cruises we only use catamaran sailing yachts, also in Croatia. See our complete Croatia program. If we have bigger groups, we organize more similar yachts and we will sail together.

On all GaySail Exclusive and GayNudeSail Exlusive cruises in Croatia, Saint Martin & Saint Barth, Puerto Rico, Virgin Islands, Bahamas, Seychelles and Thailand we only sail with one or two luxury catamarans yachts. See our GaySail Exclusive program and our GayNudeSail Exclusive program for more information.


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One Review

  1. Sandy Miller15 Sep
    Sandy Miller

    I am so excited to write this review of the GaySail of Greek Isles. I can tell you that now having completed the GaySail cruise that departed Mykonos on September 1st, to Paros, Ios, Santorini, Naxos, and back to Mykonos, it was the best vacation we have had in our 12 years as a couple. It was so much more than we expected.

    The GaySail trip consisted of two boats, and a total of 23 guys, counting passengers and crews. The crews were professional, safety minded, and caring. Our crew was Mark, Kia, and Brett. The passengers were of many nationalities, but predominately American. Our ages ranged from about 25 years old to about 65 years old, and everyone on our boats got along really well.

    You will spend most of the time during the day with just the group of guys on your boat, but there is still plenty of time where you are able to meet and mingle with the other boat’s passengers, so you get to know them as well. Every night you go as a group to dinner on the island, and you will see some of the most fantastic sunsets you can imagine. During the day you will stop for lunch in a cove. Both boats will anchor and you will have time for a quick swim before lunch. Lunches vary depending on the cook. Each boat has a different cook and their daily lunch menus vary as well. One night in the week everyone will gather on a secluded beach for a BBQ. That was actually one of my favorite activities. It was awesome – a very fun time.

    Each night you will go on the island to have dinner. The food was amazing. Our captain, Mark, has made wonderful contacts on the islands and he knows great restaurants and unbelievable places to go to get the best sunset views. Places that you would not know about if you were just traveling on your own. And if you are traveling with your bf, partner or husband, there are so many romantic spots to get that special sunset picture.

    Life on the boat would best be described as close quarters. Just understand that when you book. If you have ever been in a camper or motor home, everything is designed to make the best use of the space that is provided. This is the same for the sailboats. They are sailboats where you have all the basic necessities – all of your basic needs are met. The sleeping quarters can accommodate couples or they can accommodate singles very comfortably. You will have sleeping arrangements for 9 passengers and 2 crewmembers.

    The food on board is fresh and lunch is cooked fresh daily. If you have a special dietary need, just let the cooks know and they are very willing to make special arrangements for you. Breakfast is your basic continental breakfast consisting of yogurt, cereal, breads, and juice. Anytime you are docked in a marina, there are usually little coffee cafes and bakeries close by for you to go grab something if you have that craving.

    We left the boat on the last morning with emotional hugs of goodbye with new friends that we made. It felt like we were saying goodbye to family members. It truly was an awesome experience.

    After our experience on this vacation, we are already discussing booking one of the Croatia GaySails next year.

    Note: Don’t forget, besides the website, checkout the GaySail Facebook page too. It is filled with great information about specific cruises.

    #gaysail #gaysailing #gaycruises #greekislecruises