The Greek Islands have always been one of our top destinations that our clients visit often. With some of Europe’s most charming hotels, particularly in Mykonos and Santorini, Greece is home to many world-class hotels.
There are so many hotels to choose from on the Greek Islands and the Out Of Office Collection brings you a curated list of the best – whether you’re dreaming of a honeymoon in a cave hotel or planning a party trip to Mykonos.
Each Greek island has its own distinct appeal – our experts can help you find the perfect match based on your preferences and interests. Whether you’re seeking gay nightlife, complete relaxation, or something in between, the Greek Islands offer endless possibilities for a romantic trip.
Mykonos and Santorini are by far the most popular Greek islands. They’re close enough to visit both in one trip and many clients opt to pair both Mykonos and Santorini with Athens. If you’re interested in island hopping, we can plan the ideal itinerary for you. We can also help with some of the smaller and alternative Greek Islands which offer a more rustic and quaint experience.
If you’re interested in Greece’s ancient history, we’ll also suggest hotels and itineraries to match. You can discover Greece’s distant past at historical sites like Meteora, the Acropolis of Athens, and Delphi. Experience Greece’s renowned hospitality through folk dancing shows where you can even join in – and maybe even smash some plates at the end of the night (a Greek tradition, of sorts). Choosing the right hotel is crucial to ensuring your Greek Islands experience is unforgettable. Keep reading to discover some of our top picks.
Just a ten-minute walk from Mykonos Town, Myconian Naia is our top luxury choice in Mykonos. As well as being in an unbeatable location, it’s an endlessly stylish hotel. You’ll be greeted with direct sea views from almost any vantage point in the hotel. Myconian Naia is very much geared towards romantic, luxury trips. You can see the famous Mykonos windmills from the pool terrace. Myconian Naia represents the height of understated luxury.
Perched on a rock overlooking Elia Beach, Myconian Utopia is part of the Myconian Collection – along with Myconian Naia. They’re both tough to beat in terms of luxury and they’re located on different parts of the island. Either hotel can arrange transfers to or from Mykonos Town and Elia Beach. The infinity pool overlooking the beach is pretty spectacular. All of the furniture is made locally from natural materials. Expect whitewashed walls and understated luxury.
Boutique cave hotels have become more popular in recent years. You’ll find them in troglodyte destinations, such as Cappadocia and Matera. Perhaps the most stylish cave hotels can be found in Santorini. As a volcanic island with a huge caldera, Santorini is a natural home for cave hotels. It’s a very romantic experience to wake up in a cave suite with an indoor grotto pool. For the best cave hotel on the island, we’d choose Iconic Santorini.
Bill & Coo is one of the best luxury hotels in Mykonos. It’s an ideal choice for a gay honeymoon in Greece. Located just on the edge of town, you’ll be right in the heart of the action. Bill & Coo is a design hotel so it’s very chic. All of the furniture is handmade. The honeymoon suites are especially charming – with private jacuzzis overlooking the Aegean. Bill & Coo’s restaurant is considered to be one of the best in Mykonos.
Our standout hotel on the island of Rhodes is Lindian Village. Located at the beach of Lardos at the south-eastern tip of the island of Rhodes – the picturesque village of Lindos up the road. Lindian Village is set amidst 60 acres and an artificial river wends its way around the resort. This is an ideal choice if you’d like to stay in a larger resort in the Greek islands with more amenities. It may be a larger resort but it’s still very stylish and distinctly Greek.
Santorini is home to a unique selection of luxury cave hotels, offering an intimate and authentic experience with stunning views of the Aegean Sea. These hotels, built into the island’s volcanic cliffs, blend rustic charm with modern amenities. Notable properties include Perivolas, known for its private suites and infinity pool; Canaves Oia Suites, offering spacious suites with private plunge pools; Iconic Santorini, a boutique hotel with sweeping views and 19 cave suites; and Kapari Natural Resort, a secluded retreat with whitewashed cave dwellings and private infinity pools.
A question we get asked a lot by our clients. Mykonos and Santorini are two of Greece’s most iconic islands, each offering unique experiences. Mykonos is known for its vibrant nightlife, luxury beach clubs, and cosmopolitan atmosphere, drawing in travelers looking for glamour and excitement. It’s a hotspot for LGBTQ+ travelers, with a variety of gay-friendly venues and events. On the other hand, Santorini is celebrated for its stunning volcanic landscapes, romantic sunsets, and tranquil vibe, making it ideal for couples and those seeking a more relaxed escape.
While both islands feature incredible beaches, their appeal differs. Mykonos beaches, like Paradise and Super Paradise, are lively with parties and DJ sets, while Santorini’s beaches, such as Red Beach and Perissa, offer unique black and red volcanic sands, perfect for a quieter experience. Mykonos boasts luxury accommodations and a social atmosphere, whereas Santorini’s cliffside hotels and infinity pools cater to romance and breathtaking views.
The choice between Mykonos and Santorini ultimately depends on your travel style. Mykonos suits those seeking nightlife, LGBTQ+ inclusivity, and a vibrant social scene, while Santorini is ideal for honeymooners, nature enthusiasts, and anyone craving a serene getaway. Both islands provide unforgettable Greek experiences but cater to distinct types of travelers.
Tailor-Made Vacation
Experience the perfect blend of history and relaxation 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+...
Group Trip Departs: • 20th May 2025 • 1st June 2025 • 4th June 2025 • 11th July 2025 • 9th September 2025
Greece is the cradle of Western Civilisation, so it’s no surprise that it’s a popular tourist destination. The perfect weather, golden beaches and cuisine also help. Not to mention the magical Islands surrounding the mainland. On this trip you’ll get...
Tailor-Made Vacation
Indulge in an unforgettable honeymoon through the romantic landscapes of Italy and Greece on this 12-night luxury journey. Custom-designed for newlyweds, this tailor-made itinerary combines world-class hotels, private guides, and bespoke experiences across Rome, the Amalfi Coast, Santorini, and Mykonos....
We want to ensure you have the best experience with us so we’ll keep working on your itinerary until perfect. You will have your own personal dedicated member of our team who will help build a trip that is bespoke to you.
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