Tailor-made Vacation · Greece
Luxury Mykonos & Santorini Group Trip
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
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At a glance
Spend 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. After settling in, head to BAOS for grilled octopus and fresh Greek salads overlooking Little Venice.Spend your days beach-hopping — Psarou for the scene, Agios Sostis for something quieter. In the evenings, watch sunset from the windmills before heading to Jackie O' Beach Club, where the party goes until sunrise (if your group can keep up).
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A private guide takes you beyond the tourist spots: family-run wineries in Ano Mera, the archaeological site at Delos (a 30-minute boat ride), and the best spots for that perfect Cycladic photo.
Ferry over to Santorini and check into your villa in Oia or Imerovigli — both have those famous caldera views you've seen on Instagram, but they're genuinely stunning in person. Book dinner at La Maison for modern Greek cuisine (the fava purée and slow-cooked lamb are standouts). Spend an afternoon visiting three family wineries — Santorini's volcanic soil produces distinctive Assyrtiko wines you won't find elsewhere.
Rent ATVs to explore the black sand beaches and hilltop villages at your own pace, then end with a private catamaran cruise along the caldera at sunset. The skipper stops at hot springs and secluded swimming spots away from the crowds.
What's included: Private villa accommodation, airport transfers, welcome reception, guided Mykonos tour, wine tasting experience, ATV rental, and sunset yacht charter.
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: Arrival in Mykonos
Begin your Grecian odyssey with a warm welcome at one of our handpicked private villas in Mykonos. Each one is chosen for its exquisite beauty and suitability for large groups. As you step into the world of luxury, a champagne reception awaits, signifying the start of an indulgent stay.
Our team expertly handles all logistics, including flight arrangements and private transport, to ensure a smooth and relaxing arrival. Settle into your sumptuous villa, where a pre-stocked fridge filled with your favorite treats and beverages awaits.
Spend the evening in the comfort of your lavish accommodation, reconnecting with your group and basking in the elegant surroundings that define luxury travel in Greece.
Day 2: Mykonos Exploration
Wake up to a day of exploration in Mykonos, known for its stunning landscapes and rich cultural heritage. Embark on a private guided tour to discover the island’s renowned attractions and hidden gems, including its picturesque beaches and iconic landmarks.
After the tour, enjoy a spot of shopping in the designer shops and stylish boutiques of Mykonos. Then, indulge in the authentic flavors of Greek cuisine at BAOS Greek Restaurant, a culinary haven on the island. In the afternoon, unwind in the tranquility of your villa before diving into the vibrant nightlife of Mykonos.
Experience the renowned Jackie O’ Beach Club and Restaurant, a hotspot for the LGBT+ community, and continue the night’s adventures in the lively LGBT-friendly bars and nightclubs of Mykonos, such as the famous Babylon.
Day 3: Serene Sailing in Mykonos
Enjoy a leisurely morning and afternoon in the comfort of your villa before setting off on a magical sunset catamaran cruise. Glide along the stunning Mykonos coastline, sipping champagne and savoring a gourmet dinner on board with your loved ones.
As the evening unfolds, visit The Piano Bar, one of Mykonos’ oldest and most beloved gay bars, where live music and expertly crafted cocktails create a perfect end to an exquisite day.
Day 4: Journey to Santorini
Transition to the mesmerizing island of Santorini, traveling by ferry or private yacht. Upon arrival, immerse yourself in the elegance of your private villa in Santorini, where you’ll find luxuries such as a private pool, caldera views, and traditional Cycladic decor.
Like in Mykonos, your villa is thoughtfully prepared with a selection of your preferred gourmet items. In the evening, experience the culinary excellence of La Maison, an incredible restaurant offering fine dining with breathtaking views of the caldera.
After your meal you can explore Santorini’s vibrant nightlife, discovering the charm and allure of local bars and the island’s unique ambiance.
Day 5: Vineyard Ventures
Delve into the rich viticulture of Santorini with a private tour of the island’s acclaimed wine estates. This immersive experience allows you to sample a variety of the island’s finest wines, deepening your understanding and appreciation of the local wine culture.
Conclude the day with a private dinner at your villa, prepared by a personal chef. Enjoy the evening accompanied by sundowners, as the Santorini sunset provides a stunning backdrop.
Day 6: Santorini Sunsets
Embark on an exciting private guided ATV tour of Santorini, an adventurous way to explore the island’s stunning landscapes and historical sites.
In the evening, set sail on a sunset yacht tour along the picturesque coastline and caldera. Raise a glass of champagne to toast the breathtaking beauty of the Aegean Sea and the unforgettable memories made on this luxurious Grecian getaway.
Day 7: Farewell Santorini
On your final day, as you prepare to depart, reflect on the unforgettable experiences shared in Mykonos and Santorini.
You’ll be comfortably transported to Santorini airport for your journey home, bringing to a close a remarkable luxury group vacation that has perfectly blended the enchanting allure of the Greek islands with the finest aspects of luxury travel.
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.