The Greece Booking Checklist: The Exact Order to Book So You Don’t Lose Your Dream Hotel

A short, honest checklist from someone who planned this trip the hard way and now does it in the right order every time.

Most people booking a Greek island trip do it backwards. They lock in their flights first because flights feel like the big, scary purchase, then discover the hotel they wanted is gone and the ferry they needed only sails twice a week.

It’s not carelessness. Nobody tells you the order matters until you’ve learned it the expensive way. So here’s the order I actually use, the routes are worth checking before anything else and the questions I email a hotel before I hand over a deposit.

Work through it top to bottom. Don’t skip ahead.

Step 1: Hotels first

The good small ones go first, not last.

The intimate, 10-to-15-room places that are the whole reason you’re going boutique rather than booking a big chain sell out months ahead for peak summer. There are only so many rooms and they don’t come back. This is the part of the trip with the least flexibility, so it’s the part you book first.

• Make a shortlist of two or three hotels per island, a first choice and a backup, because your first choice may already be gone.
• Check real availability for your exact dates today, before you do anything else. Even if you’re not ready to book, you need to know where you stand.
• Book the moment a room you love is available for your dates. Look for a free-cancellation rate so you can hold it while you finalise the rest.

You can compare and hold most boutique stays with free cancellation on Booking.com. I use it to lock a room while I sort the ferries, then confirm once the route is set.

Not sure which hotel on which island? My area-by-area hotel picks for Paros are here: Where to stay in Paros.

Step 2: Ferries second

Once your hotels are held, build the ferries around them and never the other way around.

Greek island ferries in shoulder season (June and September into October) don’t run as often as they do in peak July and August. Routes that look obvious on a map sometimes only sail a few times a week, and the fast boats sell out first.

• Map your islands in the order you’ll actually visit them, then check the real schedule for your dates.
• Confirm the route exists on the days you need it, don’t assume two islands that look close are well connected. Some aren’t.
• Book the fast ferries early; they sell out before the slow ones.
• Give yourself a buffer between your last ferry and your flight home, never connect a ferry to a same-day departure flight if you can help it.

Check live routes and timetables for your dates on Omio. It’s the clearest way to see what actually sails when and you can book the tickets in the same place.

Step 3: Flights last

Flights are the most flexible part of the whole trip, so they come last.

There are dozens a day in and out of Athens and you can build them around the hotels and ferries you’ve already secured. Booking them first is what traps people and it’s the one piece you can’t undo, locking in dates before you know whether the rest of the trip fits them.

• Book flights only once your hotels are confirmed and your ferry route works on those exact dates.
• Fly into Athens and home from your last island where you can, it usually saves a long backtrack at the end.
• Leave a full day between your final ferry and your flight out.

The shoulder-season question almost nobody asks

Late September into early October is my favourite time to be in the islands. Warm sea, thinner crowds, lower prices, a table without booking three days ahead.

The catch: that’s also when a lot of the smaller, family-run hotels and tavernas start closing for the season. Arrive in the first week of October and you can find half a village shuttered.

• If you’re travelling late in the season, email the hotel one question before you book: “Will you, and the restaurants nearby, still be open during my dates?”

Most won’t volunteer it. All of them will answer honestly if you ask.

A quick gut-check on timing

• July-August: Hot, busy, everything open but everything booked out. Fine if you have no choice, but you’ll feel rushed and pay the most.
• Early-to-mid September: The sweet spot. Warm, calmer, everything still running.
• Late September-early October: My personal favourite for price and peace, as long as you’ve checked what’s still open.

If you can move your dates even a week or two out of peak, it’s almost always worth it. Read my full guide on best time to visit the Cyclades with the full month-by-month breakdown on what to expect.

The short version

1. Hotels first: Shortlist, check availability today, book with free cancellation.
2. Ferries second: Confirm the route runs on your dates, book the fast boats early.
3. Flights last: Build them around what you’ve already secured.
4. Ask: If you’re late in the season, check that the hotel and tavernas are still open.

That’s the whole thing. Follow it in order and you won’t end up redesigning a trip around two flights you already paid for.