Tailor-made Vacation · Greece
Greek Island Hopping: Mykonos, Ios & Santorini
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At a glance
Mykonos, Ios, and Santorini have become the holy trinity of Greek island-hopping—and for good reason. Each island brings something different to the table: Mykonos serves up glamour and all-night parties, Ios delivers a more relaxed setting, whilst Santorini provides those postcard-perfect sunsets and caldera views. String them together over nine days and you've got yourself a perfect Greek summer.
Start with three days in Mykonos, where the iconic windmills and sugar-cube houses are just the beginning. Spend your days exploring the boutique-lined streets of Mykonos Town, watching the sunset from Little Venice with an Aperol in hand, then diving into the island's legendary nightlife scene.
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A short ferry ride brings you to Ios. Two days here means long stretches on Mylopotas Beach by day, followed by bar-crawling through Chora village once the sun goes down. Don't miss sunset from Cape Gero Angeli—it's worth the trek. Ios has shed its hardcore party reputation slightly but still knows how to have a good time.
Finish with three days in Santorini, where the drama quotient goes up considerably. The caldera views from Fira and Oia are genuinely breathtaking—yes, even with the crowds. Hike the clifftop path between towns, book a sunset sailing trip around the volcano, and spend at least one evening watching the sun drop into the Aegean from Oia's castle ruins. It's touristy for a reason: it's spectacular.
Nine days, three islands, endless blue-and-white views. This route gives you the full Greek island experience without rushing, with enough time on each island to settle in properly before moving on to the next.
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: Mykonos
Welcome to Mykonos. Spend your first day relaxing on the huge selection of pristine beaches. The stunning island attracts a wide variety of people and has lovely beach clubs ideal for cocktails and dancing with parties that continue well into the night. The restaurants and tavernas offer many different cuisines but when in Greece it’d be foolish not to try some of their specialities.
Day 2: Mykonos
Hop on the ferry to the island of Delos to discover one of the most extensive archaeological excavations in the Mediterranean. Immerse yourself in history at this hugely important archaeological, historical and mythological site. Evening cocktails whilst watching the sunset and cabaret and drag shows at the Elysium Hotel are a must.
Day 3: Mykonos
Look around the quality jewellery and clothing boutiques in the old part of Mykonos Town, Hora. Visit the stunning, Byzantine-era church Panagia Paraportiani, in the signature Mykonos whitewashed style. For waterfront dining and picturesque views head to Little Venice.
Day 4: Mykonos to Ios
How long is the ferry from Mykonos to Ios? It takes under two hours. Check out Mylopotas Beach for excellent gastronomy, bars and clubs. White houses and narrow streets of the old town are home to boutique shopping, spectacular views and is where you’ll find the classic Greek experience.
Day 5: Ios
Relax and unwind at the secluded beaches of Manganari or Kalamos. For the ultimate sunset experience and best end to your day, sip tropical drinks on the cliff edge at Pathos sunset bar.
Discover ancient ruins and tombs at the far end of Ios all set against a magnificent ocean backdrop. For this evening’s meal, the old town of Katogi offers some of the best Greek, taverna style gastronomy.
Day 7: Ios to Santorini
For quintessential Greece, head to the enchanting village of Oia, pronounced Ia, where whitewashed walkways lead off to sun-bathed verandas, blue-domed churches and charming houses. For some of the island’s best gastronomical experiences, head to Amoudi Bay harbour located just below Oia.
Day 8-9: Santorini
The sulphur, steam and hot stone await you at the active volcano Nea Kahenh. Arrive at the volcano by boat and hike and learn all about the tectonic history from an experienced tour guide. A mammoth volcanic eruption in 1450 BC caused the middle of Santorini to fall into the ocean and created the spectacular Cantera which is best viewed from island’s clifftops.
Thira is the ancient city on top of the steep Messavouno mountain comprising temples and buildings from 11th Century BC and is well worth a visit. Go even further back in time at the Akrotiri Archaeological Site, a remarkably well preserved Minoan settlement.
Day 10: Departure
As you come to the end of your multi-centre Greek island hopping holiday, make your way to Santorini airport for your onward flight.
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.
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Anthony S.
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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.
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