What is bareboat sailing in Greece's Ionian Islands like? — featuring FreeToRoam (Nautilus)

In this video: Sailing in Greece - The Ionian Islands -Kefalonia/ Meganisi/ Lefkados/ Ithaki (1st time bareboating)

FreeToRoam · 1 year ago

What is the difference between bareboat and flotilla sailing?

Bareboating gives you complete control over your route, daily schedule, and mooring choices; you plan each day independently.

At a glance

Length
23 min
Channel
FreeToRoam
Video from
Jul 2025
Rating
⭐⭐ Great video · 2/2
Best for
Sailors with prior experience considering independent bareboat chartering in Greece

What this video answers

  • What is the difference between bareboat and flotilla sailing?
  • Is bareboating safe for first-timers with some sailing experience?
  • How do I book a mooring at a restaurant or marina?
  • What is stern-to mooring with long lines?
  • When is the best time to bareboat in the Ionian Islands?
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A Week Bareboating in Greece's Ionian Islands

This video follows Andy, along with his son James and James's girlfriend Lyndsey, as they charter a 42-foot sailing yacht called Calypso for seven days around the Ionian Islands. Unlike their previous flotilla holidays, this is their first bareboating experience—meaning they navigate their own route, choose their own anchorages, and handle all mooring maneuvers independently. The journey begins at Palairos after landing at Preveza airport, then takes them through Kefalonia, Meganisi, Lefkados, Ithaki, and Kastos, with stops at bustling marinas and remote secluded bays.

This adventure is ideal for sailors who have some prior experience (Andy holds RYA and ICC certifications), want more freedom than a guided flotilla tour offers, and are comfortable managing daily logistics like finding dinner reservations and executing stern-to mooring with long lines—techniques that become crucial in tight Mediterranean harbors. The video honestly shows both the exhilaration and the stress of independent chartering, making it essential viewing for anyone considering a bareboat charter in Greece.

Key Moments

Highlights from Seven Days on the Water

  • Arrival and first night: collecting the boat in Palairos, stocking provisions, and anchoring in a quiet bay before dinner at a waterfront restaurant
  • Little Vathy and Karnagio: a pre-bookable mooring with restaurant, shower facilities (€3), and access to a small beach and village bar
  • Fiskardo on Kefalonia: mastering the stern-to Mediterranean mooring technique with long lines in a picturesque harbor, plus exploring a cave for diving
  • Goat Bay: a secluded anchorage in 300 meters of water where the team searches for wild goats and Andy cooks chili on deck
  • Sivota (Lefkados): navigating one of the busiest marinas, stern-to mooring at Stavros pontoon with restaurant staff assistance, and discovering how narrow the gap between pontoons is
  • Finally catching fish: four small sea bass on the last day, which they cook with lemon, butter, and parsley gathered from Little Vathy
Featured image for the guide to Sailing in Greece - The Ionian Islands -Kefalonia/ Meganisi/ Lefkados/ Ithaki (1st time bareboating) by FreeToRoam

What to Know Before Chartering a Bareboat in the Ionian Islands

  • Certifications required: Greece requires an ICC (International Certificate of Competence) at minimum; some charter companies also ask for proof of sailing experience. An RYA Day Skipper or equivalent is advisable but not mandatory.
  • Yacht specifications: Calypso is a 2017 Sun Odyssey 419 (just under 42 feet), with three double cabins, two heads, in-mast furling mainsail, and self-furling headsail—typical mid-range charter yacht with a draft of just over 2 meters.
  • Travel logistics: Flights arrive at Preveza airport; charter companies typically arrange a transfer (about 40 minutes) to the marina at Palairos where you collect the boat.
  • Mooring challenges: Be prepared for stern-to mooring with long lines, especially in busy harbors like Sivota and Fiskardo. Narrow gaps between pontoons can make maneuvering difficult. Arriving early or booking ahead at restaurants that offer mooring assistance is essential.
  • Daily planning: Unlike flotilla holidays, you must find and book your own evening mooring or restaurant anchorage each day. Popular spots fill quickly, so phoning ahead is recommended.
  • Crew advantage: The video shows that having four people (not just two) made daily tasks—like jumping ashore with lines or helping with maneuvering—significantly easier and less stressful.

Frequently Asked Questions About Bareboat Chartering in Greece

What is the difference between bareboat and flotilla sailing?

Bareboating gives you complete control over your route, daily schedule, and mooring choices; you plan each day independently. Flotilla holidays provide a guided group experience with a lead boat, structured itinerary, and daily briefings—better for first-time sailors and those who want less responsibility for navigation and logistics.

Is bareboating safe for first-timers with some sailing experience?

The video demonstrates that bareboating is manageable for sailors with prior experience (Andy had done flotilla holidays before and holds RYA/ICC credentials), but it does require confidence in executing maneuvers like stern-to mooring, especially in windy or busy conditions. Having a skilled skipper and a capable crew makes a significant difference in reducing stress.

How do I book a mooring at a restaurant or marina?

Phone ahead to confirm availability and express your estimated arrival time. Many locations—like Stavros in Sivota, Karnagio at Little Vathy, and restaurant pontoons—will hold a spot and often provide assistance with mooring as long as you dine at their establishment. This is crucial in high-season months.

What is stern-to mooring with long lines?

Stern-to is a Mediterranean mooring technique where the boat drops anchor in deeper water ahead, then reverses stern-first toward the dock. Long lines secure the stern to shore or bollards while the anchor holds the bow. It requires practice, coordination, and often extra crew members to handle lines ashore.

When is the best time to bareboat in the Ionian Islands?

The video was filmed during what appears to be peak season (given the busy harbors and warm, clear water), likely late spring or summer. This offers reliable wind and warm swimming conditions but also means marinas and anchorages are crowded. Shoulder seasons (April–May or September–October) may offer less congestion and gentler conditions for new bareboaters.

Bareboating
Renting a sailboat without a professional skipper or crew, allowing you to navigate and moor the boat independently.
Stern-to mooring
A Mediterranean docking technique where the boat reverses stern-first toward shore while an anchor holds the bow, with lines securing the stern to the dock or shore.
ICC (International Certificate of Competence)
A recognized sailing qualification required by many countries, including Greece, to charter a sailboat.
Lazy lines
Pre-rigged mooring lines attached to shore or buoys that boats use to secure themselves without requiring crew to jump ashore.
In-mast furling mainsail
A mainsail that rolls up inside the mast for easier deployment and stowing, reducing the physical effort of raising and
A still from the video Sailing in Greece - The Ionian Islands -Kefalonia/ Meganisi/ Lefkados/ Ithaki (1st time bareboating) by FreeToRoam
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Justin’s Take

This video is invaluable because it shows the real experience of bareboating—not just the glamorous sailing and sunsets, but the anxiety before mooring maneuvers, the tight harbor gaps, the daily planning, and the relief when everything goes right. The honest commentary from Andy and his family about stress levels, mistakes (like dropping a fender), and the satisfaction of independence gives potential charterers a genuine sense of what they're signing up for.

What I appreciated most was seeing the progression: they start cautious and clearly nervous, but by midweek they're executing complex maneuvers and enjoying the freedom to anchor in remote bays like Goat Bay. The mix of dining ashore, cooking on deck, impromptu fishing, and exploring villages reveals the full texture of a bareboat week. If you've sailed before and crave more control than a flotilla offers, this is essential viewing before you book.

Great video · 2 out of 2

Justin
Justin

Years on the front lines of helicopter tour coordination — not as a travel blogger, but as the person responsible for making every guest experience go right. Managed 2,000+ cruise guests weekly as Shore Excursions staff aboard the Pride of America in Hawaii Personally coordinated with helicopter tour operators to confirm age, weight, and safety requirements.

Video by FreeToRoam on YouTube. If you enjoyed it, please subscribe to their channel and show your support for the great video.

Description

Hi in this video we are joined by our son James and his girlfriend Lyndsey, as we charter a yacht ( Calypso ) and sail for a week around the Ionian islands in Greece.

We flew into Prevezo airport and had a transfer organised to take us to Palairos to collect our yacht for the week.

We sailed around to the islands of Kefalonia, Meganisi, Lefkados, Ithaki and Kastos.

We experience for the first time the joy of bare boating (chartered yacht). Mapping our own route staying in busy marina's and off grid secluded bays. Eating in restaurants and eating on deck. Trying manoeuvres with stern to mooring with long lines.

Places we visited :
Sivota - Lefkados - Stavros pontoon - Phone ahead and they will help you in as long as you eat in their restaurant

Fiskado - Stern to with Long lines - Opposite the main harbour. Gets quite busy get their early.

Little Vathi - Just outside at Karnagio - Book ahead, they also help you moor up. Free mooring but you have to eat in their restaurant



Andy has a skipper qualification through the RYA and ICC certificates

We have done flotilla holidays before which are great if it's your first time sailing in the med. Bare boating was brilliant as it gave you so much more control over where to go, however you do have to find somewhere to stay each night and you have to have the confidence to be able to complete all the manoeuvres which are not always easy in a busy marina particularly if the wind picks up.

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Video transcript for “Sailing in Greece - The Ionian Islands -Kefalonia/ Meganisi/ Lefkados/ Ithaki (1st time bareboating)” Accessibility

A full written transcript of this video, provided for accessibility. Select any timestamp to jump the video to that moment.

Join us as we embark on our sailing adventure in the Ionian Islands. We've been on fertils before, but this is our first bearboat charter. We are here with James, our son, and his girlfriend Lindsay. So, in this video, you'll see us do a little bit of sailing, trying out new maneuvers in bays, having

fun in the water. [Music] Staying in secluded bays and busy marinas where we could stock up, eat great food and wine. Oh, and lots and lots of fishing. But did we catch anything? Watch the video and see.

I hope you enjoy. [Music] We've just landed at PZO airport. This is the start of our sailing adventure. We landed in Proves airport and Nautilus who we chartered the boat from had organized a transfer um to Polaris where we were collecting the boat. Hope we are not just the only

people on this. We have the bus to ourselves. As you can see, the journey took us around about 40 minutes. Wow, just coming into Polaros now. We were dropped off at the Odyssey's office where we signed all the paperwork and then it was off to the boat.

So, here she is, Calypso. Calypso is a 2017 Sun Odyssey 419. And she's just under 42 ft long, 13 ft maximum beam with three double bursts, two heads and a draft of just over 2 m and comes with an inm furling man and self furling heads out. The boat wasn't quite ready for us, so as we'd had such an early

start, we decided we'd go and have some lunch and a wand around the town. Leaving Amdi to do the inventory and we are going to go and buy food. So, there's a supermarket apparently further up in the village. We're just wandering through to see if we can find a supermarket. But first, we had to find a

fishing rod. So, we got the provisions that we required and then the decision was whether we would stay in the marina in Polaros or we would move to the bay opposite. It was quite windy. Um, so it was quite a big decision and other than me stupidly dropping a fender and the wind trying to drag us into another

boat, we were out and off on our adventures. [Music] Lindsay and James went off in the tender to find out if there were any restaurants we could go to that night. Beautiful evening. We're going to go over to a restaurant for some supper. Look at the water there. It's glorious.

Found this restaurant. Come over on the boat. It's really cute. Not very many people. It's nice. Service is very good. You see the boat is out there. And then it was back to the boat for one of our many games of card Monopoly.

The water's so clear this morning. First thing, Lindsay, James, and I went off in the tender uh to the village of Pagonia to get provisions for the next couple of days. And this little jetty. So it's a 8 minute walk up a hill to the supermarket. Well signposted. Here we go. Supermarket.

Just walking back down the hill now. And a friend. He's now coming with us. And we Supermarket was quite good, wasn't it? Yeah. Where are we going to? Uh we're going into a little back home back and then we're going to go to the north coast of Manganessi and have a look into the bay

there. Lovely swim. First attempt at fishing. Very little wind today. So we are motoring. Just coming into little Bathy and we're just going to look um at a small cove. on the right hand side just

over here that has a restaurant that you can book ahead and book a moing as long as you eat there. Restaurant booked uh for tonight. So, we're going to now go and do a bit of sailing, find a bay, have some lunch. So, we've stopped in this little bit. Boys are got the flippers out. Lindsay's

just had a little swim down there. [Music] Okay, that's it. It's quite tight now. Let's go. We're going to bounce. [Applause]

So we are now stern mowed onto a pontoon at little little bassy. Just going to have a wander down here.

So at Canadio there is a lovely small beach, a restaurant, a bar, a tiny shop, showers which cost €3 each. So a great location to spend the evening. Andy's just going to have a go with the drone. Just had a wonderful shower. €3. Worth every penny.

And now sitting having going to have an apperal spritz. To charter a sailing yacht in the Mediterranean, you will need as a minimum an ICC, an international

certificate of competence. Some countries like Croatia also require a VHF radio license, but others like Greece don't. Most charter companies ask for a sailing rum to confirm your experience. Andy also has a R ya day skippers license, but although the theory and testing is more stringent than an IC, it

is not recognized. The R YA will provide an ICC for free to any R YA skipper. [Music] And then we decided we after supper we

would walk into little bass down here. [Music] [Applause] [Music] Chocolate ice cream in Vathy. The boys did have a whiskey. [Music]

So cute. Oh, just outside Little Vathy, which is just around the corner. Fishing this morning. So, Skipper, where are we going today? Scardo. Scardo. That way. That way. So, another new maneuver this morning. Yeah. Leaving on lazy lines. Yeah. So, today

we've got another new one. Stern two with an anchor. Okay. More fishing. This time trolling. I know. I think you should. Sometimes they do see them on the coming in to Fiscardo.

Stern two. Mediterranean moing with anchor is a technique where the boat drops anchor ahead, then reverses stern first towards the dock or shore. The anchor holds the bow while the stern is secured with lines either to the dock or in this instance long lines tied to the shore. Now try fishing without the fishing rod.

Should we keep him? Yeah. Well, we might not get another one. So, let's just keep him. Can you? So, we're coming into Fiskard now. Viscardo is a picturesque village located on the northern tip of Kefalonia. It's known for its charming harbor,

colorful buildings, and crystal clear waters. Viscard attracts yachts, tourists, and those seeking a peaceful yet upscale atmosphere. Isn't that This is nice here, isn't it? All of those. Oh yeah. So, I've just got some food water. Ice water they do here, which is really handy when you're on a boat. It

keeps everything colder in the fridge. In the afternoon, we went out to a cave where you can walk through and dive from.

Make sure you get my And then it was off over for supper.

This would have been us 3 years ago all in Eflatilla. Not sure that Andy's enjoying it as much bear boating. Are you the relief when we um successfully mowed up in here? The Panorama's Tavern has amazing views and great cocktails.

Cocktails tonight. We got to go back to our boat in the dark and we've had probably too much rosé.

Day four was Fiscardo over to Castos and finally a beautiful bay called Goat Bay. So, what are you doing there, Lindsay? I'm putting a lever on. We're going to attach to the floor. Yeah. And Andy stopped the boat in 300 m depth of water.

He's coming. Okay. Two. Three.

So there's Calypso. Just swam across to uh this little beach. Climbed up to get some pictures. As you can see, [Music]

[Music] And then this was our secluded cove for the evening. Goat berry over to look for the goats. They are free roaming apparently friendly. We brought some food with them. You could hear the bells ringing and we could see a couple further up the hillside, but that was all. There we are. just

there. Wow, that's amazing. [Music] [Music]

Go down and see the chef. But we are It's Andy on duty tonight. We're having What we having, Skipper? Chili. Chili. Smells good. Smell. Yes. We caught a fish, but too small. He had to go back.

navigation system is a bit array this morning. Today we're on our way to Civot and some more fishing. [Music] So we're just coming into Sabota. So we've radioed ahead. We have booked a

moing outside a restaurant called Stavros. It was very tight to get onto the pontoon. This time Stern 2 with Lazy Lines, but the team from the Tivera were fantastic and helped a lot. And then it was most definitely time for a beer. Come on then.

Right, showers. See where we've got to go. So, I'm going to wait now for a shower. It's still very hot. Just about 6:30. Done the shopping for the next two days. Can't believe it's Thursday already. Time's going too fast. Very, very busy.

Marina. This is Civot. And see, we are on um the Stavros Pontoon. So, we have to eat there. Just want to give you an indication of how how busy it is. Glorious morning in Savota. Lots of color. It's half past 8.

Supermarkets are open here. Good supermarket. You can get anything you want. [Music] Look. Sponge.

gap between the two parallel pontoons was so narrow that you couldn't actually maneuver yourself which meant tenders pulled us out in the morning. Thank goodness just leaving Civot. Um we should be able to have a sail around before anchoring somewhere for lunch.

So we're stopping from for lunch in between Civot and Vathy, little Vathy. Uh quite a few boats that have found this. Ready? We found the most adilic bay on the north side of Meganissi. It was quite tight. Um took a little bit of maneuvering, but we got there in the end. Again, anchor with long lines to

shore. Nice spot. Very nice. There we are for the night. [Music] [Music]

I [Music] [Music] do. [Music]

And more fishing and still more fishing. And on the last day, there was a success. Four little fishes. So, and I decided we would walk into Little Pathy to get some lemons, butter, and parsley ready for the fish.

Hot walk into Vafy. Treat might be a definitely. How have you found it then this week of skippering? Yeah, it's been okay. The crew have helped. Yeah. Uh James has been useful especially with the long lining from the strong and fit jumping ashore with lines and everyone else. You've been reliable. Yeah, he's

been good. And we've done things that we wouldn't have done before. Definitely done things we wouldn't have done before. And there's been some stress and probably like anything, isn't it? the uh anxiety ahead of doing something's worse than me actually doing it. So, how's it been for

you? I've enjoyed it because I really wanted to try bare boating rather than a flatilla and being able to be have the combination of on on anchor or in a marina was fab. I felt I obviously didn't feel as nervous as you did, but I could feel the anxiety and knew that some of the things would be harder,

but I think after the event, it feels feels really good that we achieved this. Yeah, totally. Uh and I think I realized as well that we did need I would have found it hard if it was just the two of us. Yeah. Um having James and Lindsay made it easier. Well, although maybe if there were just two of us, we wouldn't

have had such a big um thought. No, that's true. That's true. So, we're walking into little bath now just to get some supplies and have a drink. And there we had it for seabbass. Beautifully cooked. What a treat. And just like that, 7 days later, we were back in Polaros.

You look very nice. Thank you. And we had our final meal back in the restaurant where we started. [Music] And that's it. A fantastic week that we had. Slight delay on the plane back. If you've enjoyed our video, then please

like and subscribe. It really helps. Thank you.

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