The SAILAER Experience
Skippered & Crewed sailing holidays in Greece by Andrew & Erin, shaped by the sea, the season and how you want your time to feel.
Life at sea, the Greek way
A week with SAILAER isn’t about racing from place to place or sticking to a rigid plan.
It’s about finding the rhythm of the sea… the kind of rhythm Greece has always lived by.
Some mornings start slowly. Coffee in hand.
A quiet swim before breakfast.
Other days begin with a clear destination and the excitement to explore somewhere new.
Each day is shaped by the weather, the light, the wind and our experience of the area.
We choose routes, anchorages and harbours that suit the conditions and the moment, allowing the week to unfold naturally rather than forcing a plan to fit.
There’s time to swim, paddleboard, read, rest, wander ashore, or simply sit and watch the landscape change colour.
Most evenings are spent ashore, wandering into villages as the day cools and tables fill in the square. We handle the dinner reservations on your behalf, leaving you free to explore, shop, eat well and settle into the rhythm of Greek life.
If there are places you’re hoping to see, we always take them into consideration. Ultimately, the route is guided by the sea/wind and by good judgement built on experience.
Your sailing holiday, in good hands
From your first contact with us through to the end of your week on board, everything is handled with us in one place… thoughtfully & smoothly so you can relax knowing nothing has been missed. We take care of the sailing, the weather decisions, the logistics and the daily flow of life on board… quietly, calmly and with experience.
The Fully Crewed Sailing Experience
If you’ve never experienced a fully crewed sailing holiday before, you might be wondering exactly what that means.
Simply put, it means having both a professional skipper and a cook-hostess/first mate onboard to look after you throughout your holiday.
With Andrew taking care of the sailing and navigation and Erin managing meals, provisioning, hospitality, housekeeping and assisting with the sailing, you can enjoy your time in Greece without worrying about the day-to-day responsibilities of running a yacht.
Wake up to breakfast prepared onboard, spend your days swimming, exploring the islands or relaxing on deck and enjoy freshly prepared lunches without having to think about shopping, cooking or cleaning up afterwards.
And because Erin is also an experienced first mate, she works alongside Andrew during docking, anchoring and sailing manoeuvres.
It’s a team effort that allows you to spend more time enjoying your holiday with the people you’ve brought along.
Skipper-Only Sailing Holidays
For guests who prefer to take care of their own meals and daily life onboard, skipper-only holidays with Andrew may also be available on selected dates. You’ll still benefit from his sailing experience and local knowledge while enjoying the freedom to organise the rest of your holiday yourselves.
Andrew – Your Professional Skipper
An RYA Yachtmaster Offshore with over 100,000 nautical miles of sailing experience, Andrew brings extensive knowledge and experience to every charter. He takes care of the sailing, navigation, anchoring and manoeuvres, while his local knowledge of Greece helps us plan each day around the weather, sailing conditions and the places you’d like to explore.
Erin – Your First-Mate Cook & Hostess
Erin looks after life onboard, preparing freshly made breakfasts and lunches, with the occasional dinner onboard too. She also assists Andrew with sailing and manoeuvres, keeps the shared spaces comfortable and tidy, and helps make sure everyone can relax and enjoy their holiday.
Together, we take care of the practical details, leaving you free to swim, explore the islands, enjoy good food and spend quality time with your family or friends.
Originally from South Africa (Andrew) and Australia (Erin), we’ve sailed and worked in different parts of the world before making Greece our home. With over 30 years of combined experience in the sailing, tourism and hospitality industries, we bring a wealth of knowledge and a genuine love for life at sea to every holiday we share with our guests.
SAILAER is designed for travellers who value ease, good judgement and time well spent. For those who want to feel safe, well looked after and free to relax into the week, without rigid plans or performative service.
If this way of sailing resonates, we’re always happy to start the conversation.
Different seas, different experiences
Greece offers very different sailing experiences, depending on the region, the season and the prevailing winds. Part of our role is to help guide you on the sailing areas for your group, always prioritising comfort, safety and the overall feel of the week.
The Ionian
Known for their lush green landscapes, turquoise waters and picturesque coastal villages, the Ionian Islands offer a beautiful setting for a sailing holiday. From Corfu and Paxos in the north to Lefkada, Kefalonia and Ithaca further south, each island has its own character and charm.
The Ionian is particularly popular during the summer months, with lively harbours, busy anchorages and hot Mediterranean days, especially in July and August. Sailing here offers a wonderful mix of swimming, exploring traditional villages, waterfront dining and discovering the islands from the sea.
The Saronic Gulf & Peloponnese
Just a short sail from Athens, the Saronic Gulf is home to some of Greece’s most beautiful islands, charming harbour towns and sheltered bays. From the colourful waterfront of Poros and the car-free streets of Hydra to the crystal-clear waters around Agistri and the historic coastal towns of the Peloponnese, there’s so much to discover.
With generally more sheltered sailing conditions than the open Cyclades, the Saronic Gulf is a wonderful choice for families, groups of friends and those experiencing their first sailing holiday. Enjoy a mix of swimming, exploring ashore, waterfront tavernas and relaxed days onboard, with each day’s route shaped around the weather and your interests.
The Cyclades
are shaped by the Meltemi wind, which is stronger at certain times of year and varies week by week. In settled conditions, especially in the Smaller Cyclades, sailing here can be beautiful, authentic and deeply rewarding. When conditions are less favourable, we’ll often favour more sheltered areas, such as the Saronic, to ensure the week remains enjoyable rather than demanding.
Where We Sail Throughout the Season
As a dedicated sailing crew, we spend different parts of the season based in specific sailing regions across Greece, rather than moving between distant destinations from one week to the next.
This means that if we’re operating from Athens and exploring the Saronic Gulf, for example, our charters during that period will depart from that area. As the season progresses, we may move to other regions, depending on our sailing schedule.
By spending time in each region, we can make the most of our local knowledge, plan each charter carefully and focus on providing the best possible experience for our guests.
If you have a particular island group or sailing area in mind, just let us know when enquiring. We’ll be happy to explain where we’ll be operating during your preferred dates.
Who this experience suits
SAILAER is for people who value space, ease and authenticity over formality.
It suits guests who enjoy being well looked after, but don’t need constant attention to feel comfortable. We’re present, professional and always nearby — but we don’t hover.
If you like:
A calm, relaxed atmosphere onboard
Crew who know when to step in and when to step back
Turning up the tunes, pouring a few drinks, and settling into holiday mode
Feeling completely at ease without being watched or managed
Conversations that feel human, not scripted
Luxury that feels natural rather than choreographed
…then you’ll feel right at home with us.
We create an environment where you can genuinely switch off. Whether that’s reading a book, taking a nap, swimming, laughing over a drink, listening to your favourite music as the sun goes down, or disappearing into your own rhythm…knowing everything is quietly taken care of in the background.
Good service and good seamanship go hand in hand. Safety is part of the experience. We make sound, experienced decisions at sea, which allows guests to fully relax, confident they’re sailing with crew who take their responsibility seriously.
