Tailor-made Vacation · Greece
Classic Greek Island Hopping: The Highlights
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
Experience 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. With a dedicated guide, you can discover the celebrated Acropolis and delve into its fascinating history, before enjoying Michelin-starred Greek cuisine at a candlelit rooftop restaurant.
Read more
You'll head to the glamorous island of Mykonos next, your private oasis for four nights. Toast the purple sunset with cocktails at Little Venice's iconic waterfront bars, browse designer boutiques, and discover the incredible nightlife that makes Mykonos so renowned, before retreating to a grand suite at the exclusive Myconian Avaton.
Continue to the stunning Santorini aboard the Aegean's sparkling waters. Here, you can explore whitewashed villages on foot alongside intimate cave bars and tavernas. For the next three nights, Dana Villas will provide breathtaking caldera views, which you can enjoy from your private plunge pool.
Charter a private catamaran to discover Santorini's hidden coves and famous volcanic beaches, or visit the famous Santorini Wine Roads to taste the finest wines in the region.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Days 1-4: Athens
You’ll spend three amazing nights in Athens, staying at Ergon House. This accommodation features its own food market where you can sample some delicious Grecian cuisine, made with local produce. The interiors are cool and industrial, with a breezy, boho twist.
After breakfast at your hotel, you’ll meet your English-speaking gay guide who will take you on a private tour of the famous Acropolis. This historic spot is undoubtedly the crowning of the beauty and glory of Ancient Athens. Its many monuments include The Propylaea, the temple Of Athena, Nike, and the Erechtheion, with its Porch of Maidens.
Continue with a visit to the Acropolis Museum, considered one of the most important archaeological museums in Athens and ranked among the most important museums in the world. The Acropolis includes artifacts from Ancient Greece, as well as statues from the period.
Days 4-8: Mykonos
You’ll next head to Mykonos for a four-night stay at the breathtaking Myconian Avaton. You’ll stay in a Pure Room, one of the hotel’s entry-level rooms – or you can upgrade to have your own private plunge pool or jacuzzi on your balcony.
Enjoy a stunning champagne cruise on your first night in Mykonos – an incredible way of getting introduced to this gorgeous Grecian island. Sip and smile as you gaze out at the sun setting over the ocean.
While in Mykonos, be sure to engage with the nightlife and gay scene. You can even have a gay guide give you a tour of the island if you wish. Other than this, you’ll be free to explore the beach clubs, rooftop bars, swanky restaurants, and sandy beaches in your own time.
Days 8-11: Santorini
A glorious three-night stay awaits you in Santorini. Stay at the stunning Dana Villas & Infinity Suites, you’ll enjoy your own plunge pool on your balcony, with views towards the caldera. Indulge in this romantic retreat that is one of Greece’s most enchanting hotels.
While in Santorini, embark on a private tour along the Santorini Wine Roads. Visit three family-run wineries accompanied by a knowledgeable sommelier, who will guide you through each wine, sharing insights into the art of wine tasting.
If you’d like to further upgrade your stay, you can choose to explore Santorini’s secret coves and renowned volcanic beaches by chartering a private catamaran. This is the perfect way to get off-the-beaten-track and explore the lesser-known parts of the island – we’d recommend it to any traveler who would like to end their vacation with something really special.
Our Experts
Greece is one of our clients' most popular destinations. The combination of history in Athens and beach life in the islands is a brilliant combination.
Island hopping in Greece is one of my favorite travel experiences. The cobbled streets of Mykonos and the bright blue domes of Santorini are picture perfect.
Stellar 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.
Tiberiu
Similar trips
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 trip
Luxury Lesbos & Athens: In the Footsteps of Sappho
Tailor-made VacationThis itinerary pairs Athens with Lesbos, ending in Skala Eressos, the small beach town that has become one of the most important destinations for lesbian travelers anywhere in the world. It’s not just about where you go, but why you go. Athens brings the history. Lesbos brings something far more personal. Lesbos is not a typical Greek island add-on. You come here for a reason.
7 days tailor-made from $5,700 per person View trip
Athens & the Athens Riviera: A Luxury Week in Greece
Tailor-made VacationFor years, the Athens Riviera played second fiddle to the islands. That's changing fast. The 70-kilometer stretch of coastline south of the Greek capital has quietly become one of Europe's most compelling luxury destinations, anchored by the sleek enclave of Vouliagmeni and the glamorous suburb of Glyfada. You start in Athens, where the key sites are concentrated and easily covered with the right planning.
7 days tailor-made from $7,555 per person View tripTell us how you like to travel. We will shape the trip around it.
Frequently asked questions
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.
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.