What Sailing Greece Is Really Like: My One Week Sailing Trip from Athens

Hey there! This page may include affiliate links. If you click one and make a purchase, I earn a commission at no extra cost to you. Thanks for your support!

We were all gathered around the cockpit of the yacht one evening after dinner and a walk through town for gelato, drinking wine and chatting, when our newest best friend climbed aboard.

She was one of the many cats you’ll see around Greece. We first met her when we arrived in port, gave her a few treats from the kitchen, and somehow she ended up following us to dinner. By the time we got back to the boat, she had apparently decided she was part of the group.

That’s pretty much a typical evening sailing in Greece.

I’ve hosted sailing trips for five years in a row now, and my most recent trip took us through the Saronic Gulf, starting and ending in Athens.

If you’ve ever wondered what sailing Greece is actually like, whether you can do it solo, what life on the boat looks like, or what you should know before booking, this guide is for you.

I’m breaking down everything I’ve learned from years of sailing trips, including the questions you already have and probably a few you haven’t thought to ask yet, so you can decide whether a Greece sailing trip is right for you.

Greece Sailing Trip at a Glance

Route: Sailing from Athens you can choose the Saronic Gulf or the Cyclades
Trip length: 8 days, 7 nights, Saturday to Saturday
Time of year: High season is July and August, June and September are also very lovely and less busy.
Number of guests: 8-10
Boat type: You can charter a monohull or catamaran, 50 feet is the most common size. I typically charter a 50 foot monohull.
Cabins: Typically 4-5
Bathrooms: Typically 3-4
Crew: If you are chartering a yacht on your own, you generally hire a skipper and you have the option to hire a hostess or chef. On my trips you have our skipper Paul and myself as hostess on board.
Sailing experience required: None. Your skipper will give you a full safety briefing when you arrive, and you can get involved with sailing as much or as little as you’d like

Want to sail Greece with me? See my upcoming group trips and join the next sailing adventure here.

Jump Ahead to Your Question About Sailing Greece:

Is Sailing Greece Worth It?

Absolutely. While I was not new to sailing (I’d been sailing 4 years in a row in Croatia), this most recent summer sailing trip was my very first time in Greece. I couldn’t have picked a better way to experience it.

Sailing gave me the chance to visit several islands in the Saronic Gulf without constantly packing, checking into a new accommodation, or spending hours on ferries. Each day offered a small preview of a different island and what it had to offer.

There were definitely a few stops where I wished I had more time. But that is also one of the benefits of sailing Greece for the first time. Now I know which islands I would return to for a longer stay and explore more deeply.

For me, sailing was the perfect introduction to the Greek islands. Your accommodation and transportation are wrapped into the same experience, and you get a taste of several destinations without constantly packing, catching ferries, and checking into new hotels.

Why I Chose to Sail the Saronic Gulf From Athens

Because this was my first trip to Greece and I was hosting a group, I wanted to keep the logistics as simple as possible. Starting and ending the trip in Athens made the most sense.

Athens  has a major international airport, and several people in the group were able to find direct flights from the United States. This also made it easy for guests to extend their trip before or after sailing. From Athens, you can continue to other cities and islands throughout Greece by plane, bus, or ferry.

The two main sailing routes from Athens are the Saronic Gulf and the Cyclades. The Saronic Islands are closer to Athens, while the Cyclades require longer sailing days.

I chose the Saronic route partly because we were sailing in July. Winds can be much stronger in the Cyclades during this part of the summer, sometimes making sailing more difficult or even preventing boats from following their planned route. 

Note: If you are interested in sailing in the Cyclades, it is much better to plan your trip earlier in the summer in May or June or wait until the Meltemi winds have calmed in September. It’s still possible to sail in July or August, but be mindful that the itinerary may need to be more flexible to account for weather and sailing conditions. 

The shorter distances between the Saronic Islands also gave us more time to enjoy each day. We could stop for swims, occasionally visit an additional port, and still reach our overnight destination with time to explore.

For a first sailing trip in Greece, the Saronic Gulf felt like the right balance. The route was easy to reach from Athens, the sailing days were relaxed, and we had plenty of time to swim, explore, and enjoy each stop.

What Is a Greece Sailing Trip Really Like?

Sailing is an incredibly relaxed way to travel. Instead of thinking of the journey between destinations as travel time you need to get through, being on the water becomes part of the experience.

You might spend a few hours sailing, stop somewhere for a swim, have lunch on board, and arrive at your next island or port later in the afternoon.

The biggest thing to understand is that sailing requires flexibility. Wind, weather, and sea conditions can change your departure time or route, so the exact plan may shift from day to day.

If you’re curious about sailing itself, you can also ask your skipper how to get involved. I loved it enough that after five summers of sailing trips, I finally started taking sailing lessons myself.

What Does a Typical Day Sailing Greece Look Like?

Morning on the Boat

What time your morning starts is completely up to you. You can wake up early and go ashore for a walk or jog around the port, grab a coffee, or sleep in and enjoy a slow morning on the boat.

On my group sailing trips, a full breakfast is included every day. We’ll have options like fresh eggs, omelets, Greek yogurt, local fruit, an assortment of goodies from the local bakeries, and everything you need to make coffee or tea.

Your skipper will let you know the evening before what time the boat needs to leave the next day. Departure times can change depending on the wind, weather, and route ahead, so some mornings may be extra relaxed while others get moving a little earlier.

Sailing to the Next Stop

Once you set sail for the day, it’s time to settle in and enjoy the journey. You can read a book, catch some sun on deck, or fit in a sneaky nap while the coastline passes by.

If you’re curious about sailing, ask your skipper how you can get involved. On my trips, our skipper Paul is a great teacher. There’s usually a job you can help with, and you can take a turn steering the boat if you ask nicely.

How long you’ll sail each day depends on the wind, weather, and distance to the next destination. Most days also include a swim stop somewhere along the way, giving you time to cool off in a beautiful bay before continuing to the next port.

Swim Stops and Lunch

The swim stops are always my favorite part of a sailing trip. They give you the chance to visit quiet coves, hidden bays, and places you simply wouldn’t be able to reach without a boat.

While sailing through the Saronic Gulf, one of our stops near Epidavros included underwater ruins that we could snorkel around. Other days, we anchored in beautiful bays with water so clear and bright blue that it almost didn’t look real.

Lunch will vary depending on who you book your sailing trip with. On my group trips, lunch is included and prepared by your lovely host, yours truly.

The menu is usually fresh, light, and perfect for a day on the water. We’ve served salads made with local produce picked up along the way, fresh fruit, simple pasta dishes, and full charcuterie spreads with meats, cheeses, crackers, and tinned fish.

Exploring the Islands

Most days, we reached our next island or port sometime in the afternoon. Where the yacht stays overnight will depend on the port and what space is available. You may anchor just offshore or secure to a buoy, which means taking the dinghy or a water taxi to land. In other ports, the boat may be moored directly at the jetty, allowing you to step right off and walk ashore. 

During my most recent Saronic Gulf sailing trip, we anchored just offshore on most nights and took turns heading to land in the dinghy. Our skipper, Paul, stayed on board, so whenever someone wanted to go ashore or return to the boat, they just let him know and he brought them across.

Once you’re on land, the rest of the afternoon and evening is yours to explore. Depending on the destination, you might visit historic sites, go for a hike, find a beautiful nature spot, browse local shops, or settle in at a restaurant or bar for good food and drinks.

The structure of your time ashore will depend on the tour operator or organizer you book with. On my trips, evenings are always free time. I share recommendations and let everyone know my plans, so anyone who wants to join in is welcome, but there’s never any pressure to stick with the group if there is something else you’d like to see or if you just need a little down time on your own. Shore time is really a choose-your-own-adventure type situation. 

Evenings in Port

What your evenings look like will depend on the operator you book with and the port you’re staying in that night. Our route through the Saronic Gulf included several quiet coastal villages, so the evenings felt very relaxed.

We still had plenty of late nights sharing wine and good conversation on the boat, but this wasn’t the kind of trip with loud parties going until sunrise.

Dinner is usually not included on my sailing trips unless stated otherwise. We typically spend one night anchored offshore at the beginning of the trip, when dinner is served on board. But, on all the other nights, I make a dinner reservation at a local restaurant for anyone who wants to join.

Dinner is always optional. You’re welcome to come with the group or choose somewhere else that catches your eye. Personally, I think eating at local restaurants is one of the best parts of sailing in Greece. It gives you the chance to try regional dishes, spend time in the port, and experience more of the local culture. Seriously, the food is one of the highlights of the whole trip.

When you’re ready to call it a night, your bed is already waiting for you. You can head back to the boat, walk downstairs to your cabin, and settle in. There’s something really nice about having your room travel with you. It’s always there when you need it.

What Was the Boat Like?

There are all kinds of sailing yachts and catamarans available in Greece, so the exact setup will depend on what you charter. I can only speak to the boats I’ve personally sailed on.

For my groups of eight to ten travelers, I typically charter a monohull around 50 feet with five cabins. On our most recent Greece trip, we sailed an Oceanis 54, which had a similar layout to several other yachts I’ve chartered over the years.

Cabins and Sleeping Arrangements

The yachts I’ve chartered over the past few years have all had fairly similar layouts. Our most recent boat was an Oceanis 54 with five cabins. Four cabins had double beds, while the fifth had two single bunks, with one bed above the other.

Because most of the travelers on my group trips book solo, I offer the option to reserve a shared cabin and be paired with a roommate. This makes the trip more accessible because you don’t have to cover the cost of an entire cabin when you’re traveling alone and don’t mind sharing.

On my most recent trip, I shared one of the double cabins with another solo traveler. We each had our own side of the bed and our own bedding, and the cabin felt surprisingly spacious. Honestly, we probably could have fit a third person between us if we really wanted to. 

Your pillow, bedding, and towels are all provided, so you don’t need to pack any of those. If you prefer more privacy or simply want extra space, I recommend booking a full cabin for yourself.

Bathrooms and Showers

There are full bathrooms on board with toilets, sinks, and showers. On our most recent sailing trip, the yacht had three bathrooms, each with hot water for showering.

We also had electric-flush toilets, which felt like a nice little upgrade from the standard marine toilets I’ve used on other boats. Marine toilets aren’t difficult to use. They simply have a hand pump instead of an electric flush.

The bathrooms are compact and function a lot like the ones you’d find in a camper or RV. You have everything you need, just in a smaller space than you may be used to on land.

Common Areas

Most of your time on board will probably be spent hanging out in the common areas rather than in your cabin.

Below deck, you’ll find the kitchen, or galley as it’s called on a boat, along with a dining area with long cushioned benches around a table. It’s a comfortable spot to eat, relax, or hang out if you want a break from the sun.

Up on deck, the cockpit has plenty of seating for everyone on board. While we’re sailing, I prefer to be up top on the deck to see the view and catch the breeze. Personally, I love bringing a towel up and stretching out on deck to read, nap, or soak up some sun while we sail.

If you want to stay outside without sitting in direct sunlight, the cockpit is covered by a bimini. You still get the breeze and the views, but with a little added shade.

Electricity, Charging, Wi-Fi, and Cell Service

Your access to electricity, Wi-Fi, and cell service will vary depending on the yacht, what your operator provides, and where you’re sailing. If you’re farther offshore or in a more remote area, cell service may be less reliable.

On my most recent sailing trip through the Saronic Gulf, I had surprisingly strong cell service almost the entire time. I usually had at least three bars while we were moored and even while sailing. There were a few pockets where the signal dipped, but because we stayed relatively close to the mainland and larger islands with cell towers, connectivity was never a major issue.

Electricity will depend on the yacht itself. Some boats have solar panels, a generator, or both to provide power when you aren’t connected to shore power. I’ve chartered yachts both with and without a generator. Having one is definitely convenient, especially for keeping everything charged, but diesel generators can be loud, so we usually turned ours off before bed.

Even if your yacht has a generator or you expect to connect to shore power at night, I still recommend bringing a power bank. It’s an easy backup for keeping your phone, camera, and other important electronics charged when electricity isn’t available.

Luggage and Storage

Space on a yacht is limited, especially on the roughly 50-foot boats commonly used for group sailing trips. A full-size hard-shell roller suitcase is not going to fit on the boat, so I definitely recommend packing your sailing essentials in a smaller soft-sided bag, like a duffel or backpack.

If you’re sailing out of Alimos Marina in Athens, there is luggage storage available at the marina. As of 2026, it cost €5 per piece of luggage for the week. This works perfectly if you’re traveling before or after your sailing trip and need more with you. You can leave your larger suitcase behind and bring only what you need onto the boat.

And honestly, for a week of sailing, you really don’t need that much. You’ll spend a lot of the day in a bathing suit and cover-up, then change into something nicer for dinner.

The vibe on most of the islands is pretty casual. For women, think sundresses, linen pants, and breezy tops. For men, linen pants, shorts, T-shirts, or a lightweight button-down all work well.

I’d also skip the heels. Many of the port streets are cobblestone, and some are made from smooth marble, so flat sandals or other comfortable shoes are much more practical.

If you want to dive a little deeper into packing tips, check out my packing guide for a sailing trip. (The article does mention sailing in Croatia but the packing tips remain the same for Greece as well.)

Frequently Asked Questions About Sailing Greece

Do You Need Sailing Experience to Sail Greece?

Absolutely not. My first sailing trip was also my very first time on a sailboat, and that’s been true for many of the travelers who have joined me over the years.

On the first day, your skipper will give you a full safety briefing and explain the basics you need to know while you’re on board. If you ever have questions about safety or how something works during the trip, ask your skipper.

If you’re interested in learning more about sailing, this kind of trip is also a great way to get a feel for it and practice a few basic skills along the way.

And if you have zero interest in learning to sail and just want to relax, swim, explore the islands, and enjoy the experience, that’s completely fine too.

Can You Join a Greece Sailing Trip Alone?

Absolutely. Solo travelers are a huge part of why I started organizing these trips in the first place. Before I began hosting my own, I joined a group sailing trip myself, so these trips have always been designed with solo travelers in mind.

I know how frustrating it can be to have a trip you’ve been dreaming about stuck in the group chat because no one else will commit. Sailing is an incredible way to experience Greece and visit multiple islands in a week but it can be challenging to coordinate a group of 8-10 friends to commit to the same week to actually get a yacht charter booked. If the group yacht trip won’t leave the group chat, go solo.

On my trips, you can book solo and choose to be paired with a same-gender roommate. That way, you only pay for your portion of the cabin. If you prefer having your own space, you can also book the entire cabin for yourself.

Most of the folks who join my trips come solo and opt to get paired with a roommate, but you’re also welcome to bring a friend, family member, or partner and share a cabin together.

I promise you by the end of the very first day, we will all be best friends on-board. 

What Is It Like Traveling With a Group on a Sailboat?

The vibe on every sailing trip I’ve taken or hosted so far has felt a little like a floating hostel. You’re sharing a small space, so everyone has to be mindful about keeping common areas neat and pitching in when needed.

As the host, I plan and prepare the meals, but people usually jump in to help with breakfast, lunch, setting things out, or tidying up afterward. It really does become a shared, communal effort pretty quickly.

That’s one of my favorite parts of these trips. You’re spending a week sailing with people who may have started out as strangers, but by the end you realize you took a trip with your best friends. You just hadn’t met them yet.

How Much Free Time Do Guests Have?

Even when we’re all together on the boat, you’ll still have plenty of opportunities to have some quiet time to yourself. You can relax in your cabin, find a comfortable spot on deck, read, nap, listen to music, or just enjoy the view.

Once we arrive onshore, your time is completely your own. You’re welcome to join any group plans or activities, or head off and plan your own solo adventure.

What Do You Eat on a Greece Sailing Trip?

On my sailing trips, breakfast, lunch, and snacks are included each day.

Breakfast is usually simple and filling, with options like eggs, bread or pastries from a local bakery, Greek yogurt, and fresh fruit. Lunch is typically a light Mediterranean-style meal with fresh salads, a charcuterie assortment, fresh fruit, bread, and light pasta dishes.

If you have any dietary needs or allergies, just let me know when you sign up so I can accommodate for those. 

Coffee, tea, still and sparkling water, beer, and wine are also included on board. 

Dinners are separate and are usually enjoyed at local restaurants in the islands and ports where we stop, which is honestly one of my favorite parts of the trip. If you ever want to make dinner yourself on board, the galley is always open. 

Will I Get Seasick Sailing Greece?

It’s hard to know how you’ll feel on a sailboat if you haven’t spent much time on the water before.

If you already know you’re prone to seasickness or motion sickness, it’s a good idea to come prepared with whatever medication or remedies you normally use. Some travelers on my past trips have used prescription motion sickness patches, so that may be something worth asking your doctor about as well. Talk with your doctor before the trip about what they recommend for you.

Always check with your doctor before taking any medication.

What Happens If the Weather Changes the Itinerary?

Sailing is dependent on the weather, particularly the wind and sea conditions, so changes to the itinerary are always possible.

Your skipper may adjust departure times, spend longer in one destination, or change an overnight stop depending on conditions. It’s simply part of sailing, so the best thing you can bring is a little flexibility and a willingness to enjoy wherever the route takes you.

Who Is a Greece Sailing Trip Best For?

A Greece sailing trip is probably for you if you love the water, spending time outdoors, swimming, and visiting places that aren’t always as easy to reach by ferry.

It’s especially good for travelers who prefer a relaxed trip over a packed itinerary. You need to be comfortable with a little flexibility because the wind and weather ultimately have a say in the schedule.

If spending your days swimming, sailing, eating good food, and soaking in the Greek island vibes sounds amazing to you, you’ll probably love it.

Final Thoughts on Sailing Greece: 

After five summers of sailing, I can confidently say this is still one of my favorite ways to travel. There’s something about waking up somewhere new, spending the day swimming in clear blue water, sailing past the coastline, and ending the evening with dinner in a small Greek port that never gets old.

What I love most is how much you get to experience without the trip ever feeling rushed. Your transportation, accommodation, and part of the adventure are all wrapped into the same experience. You can visit several islands in a week, swim in bays you’d never reach from shore, and still have plenty of time to slow down and enjoy where you are.

You do have to be flexible. The wind may change your route, your arrival time might shift, and life on a yacht means sharing a smaller space than you’re probably used to. But for me, those things are part of what makes sailing feel like an adventure rather than just another vacation.

And if you’ve been waiting for the perfect group of friends to commit before you finally book that Greece trip, you really don’t have to. Some of my favorite memories from these trips have come from watching a group of solo travelers arrive as strangers and when we leave at the end of the week, it feels like we’ve known each other for years. 

If swimming in quiet bays, exploring Greek islands, eating your way through local restaurants, and spending a week living on a sailboat sounds like your kind of trip, take a look at my upcoming Greece sailing trips and come sail with me.