I'm planning to holiday in the Greek islands (Cyclades) in early July 2011 with my wife and two kids, aged 17 and 18.

My wife and I have island hopped a few times years ago (pre-kids) and so we'd consider ourselves reasonably experienced in taking the 'spontaneous' approach to holidaying/exploring. We've always enjoyed getting away from the crowds, and treasure the memories that came about by mixing with the locals. However, our experience was based on the Greece of nearly 20 years ago. And, though we're all decided that we'd like to travel to Greece to have what might be our last 'family holiday' together, its clear that we have somewhat conflicting needs, and balancing them could prove difficult. For example;
Kids: They want sea and sand, and a lively nightlife. They're not excited by the prospect of ruins/exploring etc, although when we've done stuff like this with them in the past it showed that they got a kick out of it when there's 'nothing else' to do...
Wife: She wants the comfort of having pre-booked accommodation (for the duration), and would enjoy anything that Greece throws at her (lively or chilled),
Me: I love exploring, soaking up the culture in a relaxed, chilled environment and would usually choose to stay in a quieter part of an island.

Besides the four of us going ahead and having separate holidays(!), the way I see it is that we have two options;

1. Book a two centre package deal (one week on a lively island, one week on a quiet one), with a tour operator (expected cost £2,000-£2,500 plus spending), even though it goes against our sensibilities, or

2. Book separate flight, travel and accommodation in advance independently.

The second would be the preferred option and I'm sure we'd all be able to make the required compromises. However, I'm wondering if you can offer some suggestions, or feedback, as this option throws up a number of questions;

Budget: Initial research suggests we can get to Athens for c.£800. Any ideas what we should allow for travel to and from, and accommodation on the likes of Paros/Anti-Paros / Ios / Mykonos / Sifnos? We're not expecting 'luxury', but clean, private facilities with two twin rooms for 13 or 14 nights.

Booking accommodation in advance: Never having done this before, any suggestions for how to go about it? Is duration an issue (i.e. do some places insist on minimum stays)? How should I research and qualify the options?

The idea in principle: My take on island hopping has always been about the spontaneity. Pre-booking accommodation (certainly pre-booking +all+ of it) seems to go against the principle of what makes island hopping so special. Would we be just as well to go with a tour operator (and suffer all that goes with it)?

Any help is gratefully received...

Travel in Greece in 2011 is nothing like it was 20 years ago. Prices have quadrupled. Many of the small, mom-n-pop accomodations on the more popular islands have been absorbed and combined with neighboring properties to form small hotels, meaning those that are actually left are in high demand and the competition for booking them is stiff. Yes, you will still find locals meeting the ferries with offers of basic rooms to let. Yes, there are still bargains to be found, but in July even these will be relatively expensive. Thousands of visitors still do this every year and are satisfied with what they get. Just be aware that if you're not familiar with the islands in question you need to do some research so you know in advance where on an island you want to stay as well as where to avoid. As ever, you are not obligated to stay with someone who picks you up at a ferry port and takes you to their rental, but neither are they obligated to return you to 'civilization' if you don't like the accomodation and you happen to find yourself out in the middle of nowhere.

All that being said, I still recommend the do-it-yourself approach. Google is your friend. You can find whatever it is you want online these days, including discounted airfares and cheap hotels. Based on your price quotes in £ I'm assuming you're in the UK. Easyjet offers very cheap flights to Athens and several Greek islands. That might be the best way to save money and kick off your family adventure.

TripAdvisor.com can provide you with excellent hotel reviews and advice from designated experts for every island and mainland destination.

You don't actually have to book in advance if you want to play it by ear. Just compile a list of possibilities on each island you want to visit, start with your first choice and call ahead from wherever you are to check up on last-minute availability. If you don't travel with a mobile phone you can do this with a pre-paid OTE phone card available just about everywhere. You will have to include the island code for wherever it is you want to call. If all else fails just wait until you get there and let the hunt begin. Keep in mind that there are usually room-finder businesses within easy walking distance to the ferry ports.

Tour operators can help make your holiday pleasant as long as you feel the need to have everything taken care of in advance, but I do suggest you deal with one working in Greece instead of in the UK so you have a local contact in case of problems. Do some price comparisons and check out the websites for Dolphin-Hellas Travel and Fantasy Travel, both in Athens and both excellent and reliable providers of services for visitors to Greece.

A copy of T. Cook's "Greek Island Hopping" might go a long way to helping you decide which islands to visit.

Happy planning and have a great holiday.

You'll get all sorts of different suggestions. It's very easy to book accommodation on the Greek Islands, and early July is still outside the peak period. My first thoughts for locations that will please everyone are Fira on Santorini and Naoussa on Paros. My favorite island, Antiparos, is also a possibility for a (slightly) quieter island, although it gets very busy in high season.

Wherever you go on the Greek Islands, lively nightlife begins at midnight and goes on until dawn. Don't wait up for your teenagers! ;-)

Hi Tiffer, Four years ago we took our daughter and her friend with us to Greece. (at the time they were 17 and 18). They LOVED the trip and talk and dream of it still. They aren't into nightlife so much so I can't help you with that part but, I'll give you a list of the things they especially loved.

On Mykonos - we stayed outside of town on Platy Gialos. We would take the bus or a taxi into town each night and they loved being able to go off on their own, have dinner, shop, etc. They also loved Delos. They like that they could wander the island at will and how the entire island is an ancient site.

On Santorini - They absolutely loved sitting on the terrace of our cave house overlooking the caldera in Oia. They would sit out there and talk and just look at the view. I think that was their favorite place of all. They also enjoyed doing the hike along the rim of the caldera between Oia and Fira, and the trip to the wineries.

On Naxos - they also enjoyed wandering the main town in the evenings without us. Visiting the Citron Distillery, seeing the 100+ old distiller and learning about how they make it. They also loved the beaches on Naxos.

On Antiparos - we did a kayaking trip here. It was just us and we spent pretty much the entire day kayaking, stopping at small beaches, etc. It was an incredible day and they still talk about it.

These are the things that stick out in my mind because they are the things they still talk about. They both are dreaming of going back some day and hopefully they will.

I hope that helps a little.