8 Questions to Ask Before Booking a Charter

You've picked your dates, chosen between Croatia and Greece, and narrowed your search to a 40-footer that sleeps your crew of six. Now comes the decision that will shape the entire week more than any of those choices: which charter company gets your money.

A well-maintained 2019 yacht from a responsive operator will outperform a brand-new hull from a company that ghosts your emails and skimps on maintenance. I've chartered with more than a dozen companies across the Med since 2016. The difference between the best and worst wasn't the yacht. It was the organisation behind it.

Here are the eight questions that separate a good charter week from a regrettable one. Ask every single one before you pay a deposit.

Question 1 , How Old Is the Fleet?

Fleet age is the single most reliable indicator of comfort, safety, and how many things will break mid-week. Ask the company for the model year of the specific yacht you'll board, not the average age of their fleet. A company advertising "yachts from 2022" may still assign you a 2017 hull if that's what's available on your dates.

Yachts between one and five years old typically have current electronics, functional winches, and rigging that hasn't yet fatigued. Once a charter yacht passes seven years and roughly 40 weeks of charter use, wear accelerates sharply: gel coat crazing, tired upholstery, galley appliances on their last legs. That doesn't mean an older boat can't be excellent. A well-maintained 2018 Jeanneau will outsail a neglected 2023 Bavaria. But the burden of proof shifts to the operator.

What to do: Ask for the hull's commissioning year and last refit date. If the company can't answer both within 48 hours, move on. For a detailed comparison of popular 40-footers and what to expect from each generation, see our guide to the best 40-foot charter yachts in the Med.

Question 2 , What's Included in the Price?

A headline price of €2,800 per week means nothing until you know what's inside it. Two companies quoting the same number can differ by €600–€1,000 once you add extras. The items that catch people out most often: end cleaning (€150–€300), outboard engine for the dinghy (€80–€150 per week), bed linen and towels (€15–€25 per person), and transit log fees (€50–€100 in Croatia).

For a full breakdown of every line item, check our real cost of a week in Croatia or the Greece sailing price index. Both list actual 2026 prices so you can cross-check what a company charges against the market rate.

What to do: Request a written quote that separates base price from mandatory extras. Build your own total using the table below, then compare like for like.

Question 3 , What's the Cancellation Policy?

COVID taught the charter industry a hard lesson about rigid cancellation terms, and most reputable companies now offer tiered refund schedules. But "most" isn't "all." Some smaller operators still enforce a no-refund policy once 50% of the deposit has been paid, sometimes as early as six months before departure.

The industry standard for mid-range companies in 2025–2026 looks like this: full refund (minus a €100–€200 admin fee) if cancelled more than 90 days out, 50% refund between 60 and 90 days, and no refund within 60 days. Better operators offer a rebooking option that lets you shift dates within 12 months instead of losing money outright.

What to do: Read the cancellation clause before you sign, not after. Ask specifically: "If I cancel 45 days before, what do I get back?" If the answer is vague, ask for the clause in writing. Also consider trip cancellation insurance, typically €80–€150 per booking, which covers illness, injury, and sometimes weather-related cancellations. Our charter yacht insurance guide explains what policies actually cover.

Question 4 , How Fast Do They Respond to Emails?

This sounds trivial. It isn't. A company's email response time before booking is a near-perfect predictor of how they'll handle problems during your charter: a fouled anchor at 18:00 on a Saturday, a jammed toilet, a VHF radio that won't transmit.

Send your first enquiry and start the clock. If you don't have a substantive reply within 24 hours on a working day, that's a data point. Follow up and wait another 48 hours, and you have your verdict. The best companies, Navigare, Sunsail's direct booking team, well-run independents, typically respond in 2–8 hours with specific answers, not templates.

What to do: Ask a question that requires a human, not a bot: "Can you confirm the exact model year and last survey date for yacht X on these dates?" A generic response pasted from a FAQ page tells you the company either doesn't have the staff or doesn't prioritise individual bookings. Either way, your week will reflect that.

Question 5 , What Insurance and Deposit?

The security deposit is the single largest hidden variable in charter pricing. It ranges from €1,500 for a 35-foot monohull to €4,000 or more for a 45-foot catamaran. That money is frozen on your credit card at check-in and released 7–14 days after you return the yacht, assuming no damage.

Most companies offer a deposit waiver (sometimes called CDW or Collision Damage Waiver) for €150–€400 per week. This reduces your liability to zero or a smaller excess of €300–€500. Whether it's worth it depends on your experience and risk tolerance, but first-time charterers should almost always take it. One botched stern-to mooring can cost €2,000 in gel coat repair.

What to do: Ask three things: (1) What is the deposit amount? (2) Is a deposit waiver available, and what does it cost? (3) What is the excess after the waiver? Get the answers in writing. For the full picture on what charter insurance actually covers, including the exclusions that catch people out, read our dedicated insurance article.

Question 6 , Where Exactly Is the Base?

"Athens" can mean Alimos Marina (12 km from the airport, taxi €25–€35), Lavrion (60 km away, taxi €70–€90), or Kalamaki (15 km, taxi €30–€40). "Split" can mean ACI Marina Split in the city centre or Kaštela Marina 20 minutes away by car. The difference affects your first and last day entirely: transfer costs, provisioning access, and how quickly you get sailing.

Base location also shapes your cruising options. A base in Lavrion puts you 25 NM closer to the Cyclades than Alimos, which matters if you're heading toward Kea or Kythnos. A base in Trogir instead of Split cuts your first-day hop to the Kornati archipelago by about 15 NM.

What to do: Ask for the exact marina name and GPS coordinates, not just the city. Check it on Google Maps for proximity to the airport, supermarkets (you'll want to provision before departure), and the open water. Our marina guides for Greece and Croatia include facility ratings and real costs for the most popular bases.

Question 7 , Can I See Real Photos?

Stock photos of a Lagoon 42 tell you what a Lagoon 42 looks like fresh from the factory. They tell you nothing about hull #347 after three seasons of Adriatic salt, sun, and 30 crews who didn't wipe down the teak. The gap between marketing photos and reality is the subject of our entire article on what charter listing photos hide, and it's substantial.

Legitimate operators are happy to send dated photos of the actual yacht. Some maintain galleries updated each season. Others will send a 60-second walkthrough video shot on a phone: rough production quality, but infinitely more informative than a glossy brochure shot. If a company says "we don't have photos of that specific yacht," treat it as a yellow flag.

What to do: Email this exact request: "Can you send 3–4 recent photos of the actual yacht I'll be chartering, including the cockpit, saloon, and one cabin?" If they respond with a manufacturer's PDF, push back once. If they can't produce real images, consider a different operator.

Question 8 , What Do Reviews Say?

A charter company's own website will never feature the review that says "the heads blocked on day two and nobody answered the phone." You need to triangulate across at least three sources: Google Reviews, Trustpilot, and one sailing-specific platform such as Click&Boat, Yachtcharter.com, or the fleet-level reviews on SailChecker.

Don't fixate on the overall star rating. A company at 4.2 stars with 300 reviews is far more trustworthy than one at 4.9 with 18 reviews. Read the 2-star and 3-star reviews specifically. They contain the most operational detail. Look for patterns: if three separate reviewers mention poor check-in organisation, that's a systemic issue, not bad luck.

What to do: Search "[company name] + review" and "[company name] + complaint." Spend 20 minutes reading. It will save you seven days of frustration. Also check how the company responds to negative reviews. A professional, specific reply indicates a team that cares about resolution.

Green Flags and Red Flags

After asking all eight questions, you'll have a clear picture. Here's what to look for, and what should make you walk away.

Putting It All Together

Build a simple spreadsheet with your shortlisted companies across the top and these eight questions down the side. Score each answer 1–3, then total them. You'll almost certainly find a clear winner, and the process takes about two hours spread over a few days of email exchanges.

If you're booking for the first time, our step-by-step booking guide walks through the entire process from initial search to handover day. Once you've signed the contract, don't skip the handover checklist. It covers 47 items, takes 45 minutes, and can save you thousands in disputed deposits.

The yacht itself matters, of course. A well-designed catamaran or a responsive monohull will shape your experience. But the company behind the boat determines whether the sails are in good trim, the engine starts reliably, and someone picks up the phone when you need help at 20:00 in a marina you've never visited. Choose the operator first. The right yacht follows.