Tailor-made Holiday · Greece
Greek Island Hopping: The Cyclades
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At a glance
Experience Greece's dazzling azure seas and sun-drenched islands aboard a private luxury yacht on this indulgent island-hopping adventure. Set sail from vibrant Athens into the heart of the Cyclades, an archipelago perfect for an off-the-beaten-path gay or lesbian getaway.
Over seven relaxing days, your captain will navigate to hidden coves and secluded beaches on islands few tourists reach like Sifnos, Serifos and Kythnos. Swim in crystal waters and explore sleepy fishing villages and harbor-front shops before retiring to your suite aboard this well-appointed yacht, equipped with three spacious double cabins and decadent amenities.
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Each day presents new possibilities - perhaps you'll spend the afternoon at a wine tasting at an undiscovered vineyard, or a sunset dinner at a rustic taverna serving the freshest Mediterranean seafood. The freedom of having your own private boat and crew means you can customize your perfect island-hopping itinerary at every stop.
Picture yourself sipping champagne under clear blue skies or stargazing on deck after a day filled with discoveries. An LGBTQ+ yacht charter through the Greek Isles delivers all the romance and adventure of your wildest getaway dreams.
Let us handle every detail, from crew and catering to exclusive excursions, leaving you to simply relax and enjoy paradise. Contact our luxury travel experts today to start planning your blissful Grecian escape.
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
The Cyclades are made up of about 39 islands – the major ones include Paros, Mykonos, Santorini, Ios & Milos whilst the smaller ones include Kythnos, Folegandros, Sérifos, Sífnos & Koufunissi, and many other uninhabited islets.
Alimos Marina in Athens will be your starting point. Board your boat in the afternoon and enjoy the kitchen and bar for your first Greek sunset. Overnight on board.
Day 2: Sounio
Sounio will be your first contact with ancient Greece. Admire the beauty of Greek civilization when you see Poseidon’s temple, and be astonished by the magnificent sunrise.
Day 3: Kythnos
Today it’s Kythnos. Bays provide good shelter in pleasant surroundings whilst its white sandy beaches boast crystal clear waters.
Kythnos is a barren rocky island that’s hardly been touched by tourism. The hot mineral springs in Lutra have been well-documented throughout history. Near Cape Kafalos you’ll find the ruins of a medieval citadel and town.
Day 4: Serifos
Serifos is best known for Livadi Village, a beautiful harbor village where you can find extra provisions that you might need for your trip. It is also highly recommended for its nightlife.
Serifos has a modern tourist trade in summer, with its white houses of the Chora on the hill above Livadi Bay being the highlight. The view from the chora down onto the bay and over the sea and islands beyond is well worth the trip alone.
Day 5: Sifnos
Sifnos is known for its medieval village of Kastro which has been continually inhabited for over 3000 years.
The west coast of this hilly island is barren and burnt, but on the east side of the island – where most of the population lives – it is greener and cultivated in places. Its beaches on its southeast coast are very popular.
Day 6: Kea
Kea is mostly barren with patches of cultivated woodland near the coast. The lyric poets Simonedes and Bacchlides come from this island. The picturesque hamlet of Vourkari is most popular and has excellent restaurants. The beautiful chora on the hill has a huddle of glaring white houses and is well worth a visit. A large lion carved from the rock face is attributed to an Ionian sculptor from around 600 B.C.
Day 7: Aegina
Aegina is a small town based around a harbor and is a pleasant homely sort of place. The single column on Ak Kolona is all that remains of the temple of Aphrodite that formerly stood on the cape. You’ll find beautiful tavernas around the waterfront, as well as good boutiques.
Day 8: Athens
Today you’ll return to Athens to complete your wonderful journey.
About your Greece private yacht charter and crew
Each boat comes with a skipper who will navigate the yacht between islands.
Each day you will need to allow around £75/$100 per person which allows for food, gasoline, harbour fees and mooring fees.
The boat rental includes insurance, cleaning and fresh linen and towels.
Included
- Yacht rental
- Three double cabins
- Two toilets
- Yacht insurance
- Skipper
- Linen and towels
- Hostess/Chef (June-Sept only)
Not included
- International flights
- Travel insurance
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 favourite 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 specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, 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 personalised 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 travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, 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, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
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 personalised 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+ travellers 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 travelling 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 enquiry to homecoming. No call centre, and nothing is charged until you decide to book.