Tailor-made Vacation · Greece
Luxury Greece: From Athens to Naxos
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
This journey through Greece combines history, island life and thoughtful luxury, moving at your own pace allowing the holiday to feel effortless. Beginning in Athens, the birthplace of democracy and philosophy, the itinerary introduces Greece through its most iconic landmarks and vibrant modern culture. From here, the journey continues to Crete, where ancient mythology meets rugged landscapes and a slower rhythm of life. Time on the island balances cultural exploration with rest, nature and exceptional local food.
The route then leads to the Cyclades, starting with Paros, an island known for its relaxed elegance, beautiful beaches and charming villages. Days here are shaped by sunshine, coastal walks and refined hospitality. The final stop is Naxos, an island defined by fertile landscapes, long sandy beaches and deeply rooted traditions. Here, the journey gently slows before returning to Athens.
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Throughout the itinerary, private transfers, carefully selected boutique hotels and immersive local experiences ensure comfort and ease. This trip is ideal for travellers seeking a well-rounded Greek experience that blends culture, scenery and relaxation.
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 1-2: Athens
Athens offers a powerful introduction to Greece, where ancient landmarks sit alongside lively neighbourhoods and contemporary culture. During your one-night stay, explore the Acropolis and its surrounding historic sites, then wander through areas such as Plaka and Monastiraki, where daily life unfolds against a backdrop of antiquity. Museums, markets and rooftop terraces provide insight into both the city’s past and its modern character. Staying centrally allows easy access to key sights while enjoying a refined boutique hotel experience. Athens sets the tone for the journey, grounding your travels in history while revealing a city that feels dynamic and alive.
Day 3-7: Crete
Crete offers a rich and varied experience shaped by history, landscape and tradition. Over four nights, you will discover archaeological sites such as Knossos, explore rural villages and enjoy time immersed in the island’s natural beauty. Staying on the quieter southern coast allows for rest and reflection, with opportunities to hike, swim or simply enjoy the surroundings. Local food plays a central role here, from olive oil tastings to traditional tavern meals. Crete’s scale and diversity create a sense of depth, offering insight into a Greece that feels authentic, grounded and deeply connected to its past.
Day 7-10: Paros
Paros captures the classic Cycladic feel with whitewashed villages, clear waters and a relaxed pace of life. During your three-night stay, explore towns such as Parikia and Naoussa, spend time on sandy beaches and enjoy evenings shaped by good food and gentle sea views. The island strikes a balance between understated sophistication and everyday island living. Your cliffside hotel provides privacy and comfort, making it easy to unwind between excursions. Paros is ideal for slowing the rhythm of the journey while still offering plenty to explore.
Day 11-13: Naxos
Naxos is the final stop and a fitting conclusion, known for its fertile landscapes, mountain villages and long beaches. Over three nights, discover historic landmarks such as the Portara, explore inland villages and enjoy the island’s strong food culture rooted in local produce. Your boutique hotel offers sea views and privacy, creating space to relax before departure. Naxos feels warm and unpretentious, blending tradition with comfort. It is a place that invites you to slow down, reflect on the journey and enjoy Greece at its most natural and welcoming.
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.