Tailor-made trips for 2027 & 2028
Gay Santorini Luxury Tours & Vacations
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Every trip built from scratch around your dates, pace and preferences.
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Santorini is one of the definitive luxury islands in Europe. The caldera alone would make it famous, but what has turned the island into such a fixture for honeymoons, anniversaries and romantic trips is the extraordinary hotel scene built into its cliffs.
Some of Greece’s most distinctive hotels are here, from historic cave dwellings converted into suites to tiny properties where your terrace and pool look directly across the caldera.
More about Santorini
For LGBTQ+ couples, Santorini works particularly well for honeymoons and weddings, especially if you want romance and privacy rather than a dedicated gay nightlife scene.
Santorini does luxury differently from most Mediterranean islands. There are relatively few sprawling beachfront resorts. The hotels people travel across the world to stay in are built into the caldera cliffs, where former cave dwellings have become suites with private terraces, plunge pools and views across the volcanic basin.
Properties such as Perivolas, Canaves Oia Suites and Iconic Santorini have helped define the island’s hotel style. On Santorini, the room itself can be a major part of the trip, which is why the difference between the right hotel and simply a well-rated hotel matters so much.
There is plenty beyond the view. Akrotiri gives the island real archaeological weight, while Santorini’s volcanic soils have created one of Greece’s most distinctive wine regions. You can spend an afternoon tasting Assyrtiko, sail across the caldera or head down to the island’s black-sand beaches.
Santorini’s popularity does have a downside. Oia and Fira can become exceptionally busy at the height of summer, and choosing the wrong hotel or visiting at the wrong time can change the experience completely.
We know where to stay for privacy, which room categories are worth paying for and when Santorini is at its best without feeling overwhelmed by the crowds.
Trips in Santorini
Our itineraries are here to inspire you. Everything we do is tailor-made, so our team will customize one around your dates, pace and preferences.
History
Athens and Santorini in 7 Days: Luxury Greece Tour
Tailor-made VacationThis seven-day Greece itinerary combines Athens with Santorini, beginning with the country’s great ancient sites before moving out into the Aegean. You’ll start in Athens, where a guided tour takes in the Panathenaic Stadium, Hadrian’s Arch, the Greek Parliament and the Acropolis, followed by the Acropolis Museum. Before leaving the capital, spend a full day cruising the Saronic Gulf, stopping at Hydra, Poros and Aegina.
7 days tailor-made from $6,355 per person View trip
Classic Greek Island Hopping: The Highlights
Tailor-made VacationExperience the perfect mix of history and relaxation on this indulgent luxury island-hopping adventure through Athens, Mykonos, and Santorini on one of our most popular trips. Over eight days, this deluxe itinerary allows you to uncover ancient Greek ruins, explore cosmopolitan islands noted for their vibrant LGBTQ+ scenes, and unwind in ultimate style amid volcanic islands and azure Greek seas. Your personalized journey begins in the cultural heart of Athens.
11 days tailor-made from $5,120 per person View trip
Athens, Mykonos, Santorini & Naxos: The Four Faces of Luxury Greece
Tailor-made VacationDiscover four distinct sides of Greece on this tailor-made 13-day island-hopping holiday. From Athens, the birthplace of civilization, to the glamour of Mykonos, the romance of Santorini, and the authenticity of Naxos, this journey showcases the many faces of the Greek world. Designed for LGBTQ+ travelers who want a balance of culture, decadence, and relaxation.
13 days tailor-made from $4,205 per person View trip
The Best Luxury Hotels in the Greek Islands
Tailor-made VacationThe Greek Islands have always been one of our top destinations that our clients visit often. With some of Europe’s most charming hotels, particularly in Mykonos and Santorini, Greece is home to many world-class hotels.
7 days tailor-made from $3,705 per person View trip
Luxury Mykonos & Santorini Group Trip
Tailor-made VacationSpend seven days island-hopping between two of Greece's most iconic destinations. This trip strikes the balance between high-energy Mykonos and romantic Santorini — perfect for groups who want both nightlife and natural beauty. Your group stays in a private villa within walking distance of Mykonos Town's winding streets and whitewashed buildings.
7 days tailor-made from $3,550 per person View trip
Italy, Greece & Turkey: Luxury Gay-Friendly Cruise
Tailor-made VacationThis itinerary moves through Italy, Greece, and Turkey, combining Rome and Athens with a seven-night LGBTQ+ friendly cruise of the Greek islands aboard Virgin Voyages, closing with a stop in Bodrum along the way. The trip begins in Rome, where ancient ruins and Renaissance-era architecture sit within a short walk of the city's best shopping and nightlife.
11 days tailor-made from $5,080 per person View tripGay Group Trips in Santorini
Set departures with dates already fixed, organized end to end and traveling as a small group. Where a departure is full, dates are available on request. Extensions either side can be added, and we can plan something tailor-made instead if you would rather.
Most Popular
Gay Group Trip: Greek Island Hopping
Group TripGreece is the cradle of Western Civilization, so it's no surprise that it's a popular tourist destination. The perfect weather, golden beaches and cuisine also help. Not to mention the magical Islands surrounding the mainland. On this trip you'll get to explore the wonders of Athens, and then do some island hopping - including trips to Santorini, Mykonos and Milos.
11 days group departure from $4,410 per person View trip
Gay Group Trip: Athens, Santorini, Naxos & Mykonos
Greece Group TripExperience the full range of Greece on this tailor-made eleven-day LGBTQ+ itinerary across Athens and three of the Cyclades. Designed for couples and honeymooners ready to take their time, the trip moves from the ancient capital to the quietest Cycladic island before ending on Greece's most established gay island, with stylish hotels, private guides and carefully curated experiences throughout.
11 days group departure from $9,900 per person View tripStellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
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Santorini in pictures
Is Santorini LGBTQ+ friendly?
In Santorini, same-sex relationships are legal, same-sex marriage is legal and discrimination against LGBTQ+ people is prohibited. Equaldex gives Santorini an Equality Index of 66 out of 100.
Source: Equaldex, checked September 29, 2026.
Greece legalized civil marriage for same-sex couples in February 2024, meaning LGBTQ+ couples can now legally marry in the country as well as hold symbolic ceremonies. Civil weddings involve the usual documentary requirements, so couples planning to marry in Santorini should allow time for the paperwork.
Santorini does not have the established gay beach and nightlife scene you find in Mykonos. Its appeal to LGBTQ+ travelers is different. This is one of Greece’s major honeymoon and wedding destinations, and same-sex couples come for the same reasons as everyone else: exceptional hotels, privacy and the caldera.
We work with hotels and suppliers we know are comfortable welcoming LGBTQ+ couples. If you want Santorini’s romance alongside a much more social gay scene, combining it with Mykonos works particularly well.
Things To Do in Santorini
Santorini Volcano & Hot Springs
Explore the natural beauty and wild scenery of the Santorini caldera.
Sailing Santorini’s Caldera at Golden Hour on a Private Charter
Swim beneath the volcanic cliffs, soak in the hot springs and watch the sun set from the water while Oia crowds its rooftops.
Walking to Skaros Rock from Imerovigli, Santorini
Hike out at sunrise to the rugged headland that was once Santorini's medieval capital, with the whole caldera spread around you.
Akrotiri
Visit the fascinating prehistoric settlement of Akrotiri.
The Red Beach
Discover the red lava cliffs and sands of Red Beach.Travel Guides in Santorini
Mykonos or Santorini – which is better?
Greece has around 6000 islands, and just over 200 of them are inhabited. Among them, Mykonos and Santorini stand out as the most popular destinations for luxury travel in the Greek islands. Combining these two with a couple of nights in Athens makes for a great luxury vacation itinerary.
Read
Santorini Island Guide
Santorini is the most romantic of the Cyclades islands. Located in the south Aegean Sea 120 miles from the Greek mainland, it’s one of the two locations in Europe to have a desert climate. The other is Anafi, also a Greek island. Santorini is instantly recognisable. Its blue domes and caldera sunsets can be seen in the background of so many posts by Instagram “influencers.” It’s a place to be seen and be photographed in.
Read
The Best Cave Hotels in Santorini
Santorini is one of the most romantic and exclusive destinations in Europe. It's home to a great selection of luxury boutique hotels. You won't find many sprawling resorts here. This volcanic island lends itself to a more intimate, authentically Greek experience. Cave hotels are unique to Santorini and a handful of other destinations. You may be wondering what a cave hotel is. They are, quite literally, hotels built within caves.
Read
Gay Greece: The LGBTQ+ Island Guide from Mykonos to Lesbos
Greece has been welcoming gay travelers longer than most destinations have had the vocabulary to describe it. Ancient Greece was among the first civilizations to normalize male same-sex relationships, and that cultural thread, however transformed by centuries of Orthodox Christianity and conservative politics, never fully disappeared. In February 2024, Greece became the first Orthodox-majority country to legalize same-sex marriage, granting full marriage and adoption rights to same-sex couples.
Read
Cyclades vs Ionian Islands: What’s the Difference?
Greece has an islands problem, and it's a good one. There are more than 200 inhabited ones to choose from, spread across two very different archipelagos, each with its own character, landscape, and pace. If you're trying to decide between the Cyclades and the Ionian Islands, the honest answer is that they're not really competing.
Read
The Best Gay Beaches in Greece for Luxury Travelers
Greece is one of our most popular destinations. For luxury beach vacations, Greece is difficult to beach - especially for gay travelers. Mykonos is the most sought-after destination in Europe for the international gay jet set. You’ll see them on Elia Beach, both in real life and on Instagram. What sets Greece’s beaches apart from other destinations is their variety.
ReadSantorini Travel Guide
General information
Santorini sits in the southern Cyclades and is built around one of the Mediterranean’s great volcanic calderas. Much of the island’s famous architecture follows the edge of that cliff, particularly around Fira, Firostefani, Imerovigli and Oia.
Oia has the greatest concentration of famous sunset views and some of the island’s best-known hotels. Imerovigli tends to feel quieter while retaining the dramatic caldera position, while Fira gives you easier access to restaurants, shops and the center of the island.
Santorini is not primarily a beach destination in the way Mykonos is. Its appeal comes from the cliffs, cave architecture, volcanic landscape, wine and hotels. The beaches are distinctive rather than conventionally glamorous, with dark volcanic sand and pebbles.
Santorini LGBTQ+ rights
Greece legalized civil marriage for same-sex couples in February 2024, meaning LGBTQ+ couples can now legally marry in the country as well as hold symbolic ceremonies. Civil weddings involve the usual documentary requirements, so couples planning to marry in Santorini should allow time for the paperwork.
Santorini does not have the established gay beach and nightlife scene you find in Mykonos. Its appeal to LGBTQ+ travelers is different. This is one of Greece’s major honeymoon and wedding destinations, and same-sex couples come for the same reasons as everyone else: exceptional hotels, privacy and the caldera.
We work with hotels and suppliers we know are comfortable welcoming LGBTQ+ couples. If you want Santorini’s romance alongside a much more social gay scene, combining it with Mykonos works particularly well.
What to do in Santorini
How We Book The Trip
Hotel choice matters enormously in Santorini. Two properties can be only a few minutes apart and offer completely different experiences. One might put you among the crowds in Oia, while another gives you a private terrace in Imerovigli where you barely need to leave the hotel.
Room category matters too. Santorini is one of those destinations where paying for the right suite, pool or caldera position can materially change the trip. We know which upgrades are worthwhile and where the marketing photographs do not tell the whole story.
Timing is the other big consideration. At peak times, narrow streets and popular sunset spots become extremely busy. We can arrange your days so that you see the island without spending the entire trip following everyone else around it, and we can advise when traveling slightly outside July and August will give you a better experience.
If Santorini forms part of an island-hopping trip, we also arrange the ferries, transfers and sequence of islands so you are not sacrificing entire days to logistics.
Three Things You Cannot Miss
See Oia without only seeing the crowds
Oia deserves its reputation, but arriving with everyone else immediately before sunset is rarely the best way to experience it. Stay nearby, visit earlier in the day or give yourself enough time to explore after the busiest period has passed.
Get out onto the caldera
Santorini looks completely different from the water. A sailing trip gives you the scale of the cliffs, the volcanic islands in the center of the caldera and a perspective you simply do not get from a hotel terrace.
Visit Akrotiri
The Bronze Age settlement was preserved beneath volcanic material following the island’s ancient eruption and remains one of Santorini’s most important archaeological sites. It gives some context to the landscape you have been looking at all week.
Weather in Santorini
Temperatures converted from Celsius.
Getting to Santorini
You can reach Santorini by air or ferry, and the best option depends on the rest of your itinerary.
If you are coming directly from Athens, flying is usually the quickest option. Ferries also operate from the mainland and connect Santorini with other Cycladic islands, making them useful if you are combining the island with Mykonos, Paros or Naxos.
Santorini’s ferry port at Athinios sits below the caldera and can become extremely busy, so transfers are something we arrange rather than leaving you to negotiate on arrival.
For longer Greece trips, we will work out whether it makes more sense to fly, take the ferry or change the order of the islands entirely. A good island-hopping route should feel like a vacation, not a transport timetable.
See the whole trip, priced in full, before anything is confirmed.
You will have the itinerary and the price in front of you, and the final word on both.
Frequently asked questions
About Santorini
Is Santorini LGBTQ+ friendly?
In Santorini, same-sex relationships are legal, same-sex marriage is legal and discrimination against LGBTQ+ people is prohibited. Equaldex gives Santorini an Equality Index of 66 out of 100.
Can my trip to Santorini be tailor-made?
Yes. Everything we plan is tailor-made. Our suggested Santorini itineraries are starting points: your specialist shapes the route, the hotels, the pace and the length around your dates and preferences. As a guide, our suggested Santorini itineraries run from 7 to 13 days.
Which luxury hotels do you recommend in Santorini?
Our specialists' current picks in Santorini include Erosantorini, Nobu Hotel Santorini and Charisma Suites, each handpicked for how it welcomes every guest.
What are the best things to do in Santorini?
The experiences our specialists recommend in Santorini include Santorini Volcano & Hot Springs, Sailing Santorini’s Caldera at Golden Hour on a Private Charter, Walking to Skaros Rock from Imerovigli, Santorini and Akrotiri.
Is Santorini good for a honeymoon?
Yes. We plan honeymoons in Santorini, with 11 suggested honeymoon itineraries as starting points, such as Athens and Santorini in 7 Days: Luxury Greece Tour and Classic Greek Island Hopping: The Highlights.
Can I combine Santorini with another country?
Do you run group trips to Santorini?
Yes. Our next small-group departure is Gay Group Trip: Greek Island Hopping, leaving on May 23, 2027. Tailor-made trips run year-round.
Traveling with Out Of Office
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
Our Experts
Santorini is simply gorgeous. It's perfect for romance, with its whitewashed buildings, blue-domed churches and stunning sea views.
I always recommend Santorini to those who want the quintessential Greek Isle experience. Those views at sunset have to be seen to be believed.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.