Tailor-made Vacation · Greece
Athens, Mykonos, Santorini & Naxos: The Four Faces of Luxury Greece
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At a glance
Discover 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.
Athens — Origins & Heritage
Your journey begins in Athens, where the Acropolis and Parthenon stand as symbols of Greece’s ancient legacy. Explore world-class museums, take a private guided tour through the historic Plaka district, and savor Michelin-starred dining with views over the city. Athens sets the tone: timeless history combined with luxury travel perks.
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Mykonos — Glamour & Nightlife
Next, fly to Mykonos, the island of energy and indulgence. By day, unwind on chic beaches and explore boutique-lined alleyways; by night, experience one of the world’s most vibrant LGBTQ+ scenes, with beach clubs, cocktail bars, and nightlife that lasts until sunrise. Mykonos delivers pure hedonism wrapped in high style.
Santorini — Romance & Beauty
Then it’s on to Santorini, where romance takes center stage. Stay in a cliffside suite overlooking the caldera, hike between the villages of Fira and Oia, and take a sunset sailing trip around the volcano. Santorini is the Aegean’s ultimate backdrop for love and luxury.
Naxos — Authenticity & Escape
Your journey ends on Naxos, the largest and most authentic of the Cyclades. Here, time slows down: stroll through traditional villages, discover Byzantine churches, hike mountain trails, and relax on wide golden beaches. Naxos adds depth and balance to your itinerary — a reminder of Greece’s quieter charms beyond the spotlight.

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.
Day 1-3: Athens
Fly into Athens where you’ll be met by a driver at the airport. You’ll stay at the stunning Ergon House.
On your first morning, you’ll meet your English speaking guide who will take you on a private tour of the highlights of Athens. Starting your visit to Panathinaikos Stadium, you’ll also explore the National Garden, Hadrian’s Arch, Greek Parliament and the tomb of the unknown soldier, and then visit the famous Acropolis, undoubtedly the crowning of the beauty and glory of Ancient Athens. Its many monuments include The Propylea, the temple Of Athena, Nike and the Erechtheion, with its Porch of Maidens.
Continue with a visit the Acropolis Museum, considered one of the most important archaeological museums in Athens and ranked among the most important museums of the world. The Acropolis includes artifacts from Ancient Greece, statues from the period and caryatids which are sculpted female figures used as architectural support instead of columns.
You’ll see the Parthenon as well as the ruins of Ancient Athens City, revealed during archaeological excavations on the site of the museum.
Day 3-6: Mykonos
Following breakfast, you’ll check out from Ergon House and be driven to Piraeus port for the ferry to Mykonos which takes a few hours. You’ll stay at the stunning Myconian Utopia.
With its iconic whitewashed buildings, vibrant nightlife, and picturesque cobblestone streets, Mykonos epitomizes the glamour and energy of the Greek Islands. Stroll through the chic shops and oceanside cafes of Mykonos Town, relax on famous beaches like Paradise and Super Paradise, or escape to the secluded coves and hilltop villages around the island.
Don’t miss watching the sunset from Little Venice, where the whitewashed buildings glow against the sea. Whether you seek culture, indulgence, natural beauty or nonstop fun, Mykonos promises gorgeous Aegean views and lively Greek island ambience.
You’ll spend the next three days on the beautiful island relaxing and visiting some of Mykonos Town’s best nightlife, restaurants and gay bars.
Day 6-9: Santorini
After breakfast at your hotel you’ll check out and be driven to Mykonos port to take a ferry to Santorini. Once you get to Santorini, we’ll take you to the beautiful gay-friendly Canaves Oia Suites Santorini where you’ll have your own Junior Suite with a private plunge pool from where you can watch the beautiful sunset.
Santorini’s unmistakable landscape of whitewashed villages perched atop volcanic cliffs overlooking the sea has made it Greece’s most visually stunning island. Take in the famous sunset views from villages like Fira and Oia, with the sun’s rays casting colorful hues across the caldera below.
Relax on black sand beaches only accessible by boat, sample wines from vines grown in volcanic soil, and feast on fresh Greek cuisine enhanced by island ingredients. Santorini’s romantic atmosphere, ancient sites like Akrotiri, and indulgent cave hotel suites beckon travelers seeking a quintessential Greek island escape.
Day 9-13: Naxos
After breakfast, you’ll be driven by to Santorini port to take the ferry to Naxos. A quieter island than the other two, this itinerary will see you stay at the Naxian Collection Naxos in its Honeymoon Villa.
The largest of the Cyclades islands, Naxos captivates with its gorgeous beaches, atmospheric old-town charm, and mythological legacy.
Walk the winding lanes of historic Chora dotted with Byzantine chapels and Venetian mansions. Relax on stretches of powdery white sand like Agios Prokopios and Agia Anna. Hike through the interior’s lush trails to encounter chapels and marble quarries. Take a boat to smaller islands like Koufonisi for secluded turquoise coves.
With opportunities for active adventures as well as luxurious resort getaways, Naxos offers an authentic Greek island experience beyond the more famous destinations.
Day 13: Depature
It’s time to bid farewell today and you’ll return to either Santorini or Athens for your onward flight.
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
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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.