Tailor-made Vacation · Greece
Greek Island Hopping: Milos, Paros and Mykonos
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At a glance
Milos, Paros, and Mykonos make for a brilliant Greek island trilogy. This route takes you from under-the-radar beaches to charming village life, finishing with Mykonos's signature glamour.
Begin in Milos, the Cyclades' best-kept secret (though the word is getting out). With over 70 beaches—many only accessible by boat—this volcanic island delivers dramatic coastlines, lunar landscapes, and crystal-clear waters without the crowds you'll find elsewhere. The fishing villages are genuinely picturesque rather than picture-perfect, and there's proper history here: this is where the Venus de Milo was discovered. Fly or ferry in from Athens and settle into one of the island's boutique hotels, preferably near Pollonia or Adamas.
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Paros strikes the ideal balance between authentic island life and upscale comfort. The main town, Parikia, and the hilltop village of Naoussa both offer excellent restaurants, wine bars, and shops tucked into whitewashed Cycladic alleyways. The beaches are lovely—Golden Beach particularly—and the whole island has a relaxed sophistication that makes it easy to linger. This is where you slow down, have long lunches, and remember why you came to Greece in the first place.
Finish with Mykonos, where the energy ramps up considerably. The island's reputation precedes it: world-class beach clubs, designer boutiques, exceptional restaurants, and nightlife that runs until sunrise. For LGBTQ+ travellers especially, Mykonos remains unmatched in the Mediterranean, with a vibrant gay scene centered around Elia Beach and the bars of Mykonos Town. Whether you're here for the party or just the polish, Mykonos knows how to deliver luxury with a dose of hedonism.
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: Milos
Begin your Greek odyssey in the captivating island of Milos, accessible via ferry or plane from Athens. Famed for its connection to the ancient statue of Aphrodite, Milos is a paradise of natural beauty, boasting over 70 beaches.
Each beach offers its own unique landscape, from the moon-like terrain of Sarakiniko to the emerald waters of Kleftiko.
Spend your time here discovering hidden coves and enjoying the island’s serene ambiance, perfect for unwinding and soaking in the Grecian sun.
Day 3-5: Paros
After savoring a leisurely breakfast in Milos, prepare for your next destination: the charming island of Paros. A ferry ride will bring you to this gem in the Cyclades, where the blend of traditional architecture and contemporary life creates a captivating atmosphere.
Spend your afternoon wandering through the narrow streets of Parikia, the island’s capital, or relaxing on the golden sands of Kolymbithres Beach, renowned for its natural granite sculptures.
Day 5-7: Mykonos
Continue your journey with a ferry ride to the renowned island of Mykonos. Known for its vibrant atmosphere and welcoming spirit, Mykonos is a kaleidoscope of scenic beauty and lively entertainment.
Upon arrival, immerse yourself in the charm of Mykonos Town, with its iconic windmills, whitewashed buildings, and bustling waterfront. As the sun sets, experience the island’s renowned nightlife, from the chic bars of Little Venice to the lively clubs scattered throughout the town.
Whether you prefer lounging at the stylish Jackie O’s Beach Club, sunbathing on the pristine shores of Elia Beach, or exploring the gastronomic delights in local tavernas, Mykonos offers endless opportunities for enjoyment.
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.