We decided to book a bareboat charter in Greece, to sail around the Saronic Islands. We ended up booking with Navigare charters via an agent, and this is how the booking process went.

Our requirements were as follows:

• The crew would be me and my wife Jennifer, my brother-in-law Steve and his 2 daughters Brook and Luna, 18 and 16 years old.
• Sailing catamaran with at least 4 cabins, so each person could have their own cabin and me and Jenn would share a cabin.
• 3 Stand-up Paddleboards
• A 40-foot sailing catamaran – big enough to fit crew comfortably but small enough so it’s not too intimidating as a first-time bareboat charterer.
• Hire a skipper for the first 2 days, to give us advice on our itinerary and also to help cach us through the more complicated mooring techniques like stern-to docking in a marina and stern-to anchoring in a bay with running lines to the shore.

Since we were booking only about 10 days prior, our options were limited. In addition, many chartering companies did not offer a 2-day skipper engagement, it was either bareboat or fully skippered for the full 70-day charter.

The best deal came from PlainSailing.com, for a Lagoon 40 or Isla 40—they were able to accommodate our limited time skipper request, and the price was the least expensive. The Isla 40 was the better boat, but it was taken up before we could reserve it—so the Lagoon 40 was our decision.

Here is the price breakdown for the charter:

      Charter fee: xxxx EUR

     Cleaning fee:  xxx EUR

2 Days of skipper:  xxx EUR

          3 SUP’s:  xxx EUR

         Internet:   xx EUR

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            Total: xxxx EUR

There would also be additional costs, such as water taxis, fuel costs, berthing fees and food provisioning costs, as well as figuring the tip for the skipper.

To reserve the Lagoon 40, we needed to first pay 25% of the charter fee to take the boat listing off the calendar, then pay the remaining amount by early the next week.

The Booking Process

Since I had chosen a booking agent and not the charter company directly, I was a bit wary—how do I know that this is a legitimate agent? Sure, there is a web presence and Google Reviews, and even mention of a European service award or two, but surely that kind of thing can be faked. So I did as much research as I could on the company, then pulled the trigger and sent them the first payment via credit card. Boy was I nervous when I did not receive any email confirmation after 10-15 minutes had passed! But after inquiring with the booking agent, the email confirmation soon arrived and I could breathe a bit easier. I then talked over the details of the charter with Steve and Jenn, passing along all inquiries about the boat’s amenities until we were satisfied that the options we chose were all we needed. Finally I sent in the final up-front payment, and the booking was locked in!

Shortly after the final payment was sent in, we got a welcome message from the chartering company, as well as an access to the online portal of the booking agent PlainSailing,com, where you upload crew information (name, DOB, passport number), as well as proof of your sailing qualifications (ASA certifications or International proficiency certificate) and sailing resumé. Once all of that is filled in and you accept the Terms & Conditions of the chartering company, the chartering booking is complete.

Proof of Sailing Competency

My international proficiency certificate (IPC) was expired, but the charterer accepted my ASA 104 and ASA 106 certifications as proof of competency. Which makes sense if you understand how ASA handles the IPC – if you are a paying member of ASA (American Sailing Association), then all you need to do is pay them 40 USD and they will mail you a new IPC. So as the charterer if you understand the ASA scheme, the certifications should indeed be sufficient.

Insurance / Security Deposit

The only other thing to decide on would be the damage waiver / security deposit / insurance option to choose. The options break down as follows:

Option A: Security Deposit

A security deposit of 4000 EUR is paid at check-in time, via credit card.

• This deposit is 100% refunded at the end of the charter if there is no damage to the boat or missing parts or items.
• If there is any damage, the maximum amount you will pay is the entire 4000 security deposit – after that you will not need to pay anything higher.
• In this option you are essentially paying the boat owner’s insurance deductible, after which his/her insurance company pays the rest.

Option B: Damage waiver with reduced Security Deposit

Here, you pay a non-refundable 350 EUR up front, then your security deposit paid a check-in time is reduced to 1250 EUR.

• This 1250 EUR deposit is 100% refunded at the end of the charter if there is no damage to the boat or missing parts or items.
• If there is any damage, the maximum amount you will pay is the entire 1250 security deposit – after that you will not need to pay anything higher.

Option C: Insurance

The insurance option is offered by some booking agents and chartering companies. Here, you still pay the full 4000 EUR security deposit, and there is a non-refundable 360 EUR to pay as well. But the maximum you may pay in case of damage is much lower:

• If the boat is returned damaged, the security deposit will be held up until the insurance claim can be submitted and approved.
• The maximum amount you will pay in case of damage is around 350 EUR.
• This sounds like a good option, but the delays in getting response from the insurance claim make this option less desirable.

The general consensus seems to be that option B is typically the best option, since your security deposit is significantly reduced and there is no delay in the refund. We ended up going with Option A though, as there is no non-refundable portion and the 4000 EUR security deposit amount was not a huge issue.

Charter Timing

In Greece, sailboat charters all follow the same schedule for some reason:

• Charter check-in: Always on a Friday by 5:00 PM.
• The crew is allowed to sleep aboard the boat in the marina for the first evening, if desired.
• Charter check-out: the boat needs to be returned the following Friday by 5:00 PM.
• The crew is allowed to sleep aboard the boat in the marina on Friday evening.
• The boat must be vacated by 9:00 AM on Saturday.

We asked for an early check-in if possible, but we were unable to secure any early check-in.

So we planned to check-in at 5:00 PM, and then quickly leave the marina to get to our first island destination before sunset.

With the charter fully booked, now we just needed to hop on a plane and get to the boat! 

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( Part of series: Bareboat Charter in Greece 2026 )