11 days tailor made from £ pp
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Classic Greek Island Hopping – The Highlights
Trip Summary:
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At a glance
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Don't forget that all of our itineraries are totally customized and so this is just an idea of what we can build for you.
Experience the perfect blend of history and relaxation with Out Of Office on this indulgent luxury island-hopping adventure through Athens, Mykonos, and Santorini. 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 personalised 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.
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 check out the incredible nightlife that makes Mykonos so renowned – and then retreat 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.
This indulgent, luxury itinerary takes in Athens’ ancient allure and the Greek Islands’ Mediterranean beauty all while staying in Greece’s most exclusive hotels. Allow our experts to handle every detail – travel options, local LGBT+ guides, alluring dinners for two with scenic vistas – to help craft your ideal escape of a lifetime.
In detail
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Don't forget that most of our itineraries can be totally customized. Our expert team will be able to talk you through all the options.
Day 1 - 4 Athens
You’ll spend three amazing nights in Athens, staying at Ergon House. This accommodation is a foodie’s dream – it 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.
You can also choose to enjoy a food tour of Athens with a dedicated guide, who will show you the best spots to enjoy some authentic Greek food.
Day 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.
We’ll organize a stunning sunset champagne cruise for you to enjoy 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 check out 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.
Day 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 – it’s 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.
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