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Recommendations for Itinerary - Two weeks - Group of 9

In June of 2023, we are planning a two week trip to Greece (from Los Angeles) to celebrate my daughters graduation from college and my two nephews high school graduation. There will be four adults and four (adult) children 24, 22, 19 and 18 plus a 13 year old.

We are hoping for recommendations on the best islands to visit for water-sports/daily activities and night time activities (primarily good restaurants and bars - for the older kids), and shopping (small local shops preferred).

We would be flying from LAX to Athens and have 14 nights to work with prior to return. We are hoping to book apartments/AirBnB's that could accommodate our entire group or two smaller apartments near each other....recommendations on where to stay would be appreciated as well.

Thank you in advance!!

Posted by
2891 posts

YOU will be MUCH happier with 2 separate accommodations near each other -- it will giv e you more space, and much needed alone time for the adults... not to mention additional Bathrooms!!! It will make for a more relaxed holiday... and by starting far in advance, you have a good chance to working it out. Incidentally, for booking purposes & room rates in hotels or apartment hotels, your 13 yr old - tho small and winsome - is counted as an adult.

Since fortunately, you have an abundance of time to plan (Very foresighted of you), would you please consider doing a little bit of homework, before coming to us for a Huge Omnibus of ideas. We're alway glad to share our experiences, once people have learn some things on their own, select some islands that appeal -- and check a map to see that their choices are located conveniently for "Hopping" from one to the next. It's easy, really! At your local library you can borrow a whole armful of guides -- LOnely PLanet, Rough GUIde to the Greek Isles, Fodors Greece Guide, etc etc. If print is not your thing, you could start with the one most voluminous online site -- Matt Barrett's encylopedia and its Subset, about the Islands -- - and here's an online map (click to enlarge). ...Why do I suggest actual guide books also, instead of just online sources? Because many internet sources focus mainly on beautiful photos, and glorious sunsets, but don't mention possible drawbacks or downsides (such as... huuuuge crowds in high seasons, not the best beaches, limited transportation, super-high costs, tons of "package tourists"). Guide books have to give both plusses & minusses, or they won't be considered reliable & continue to sell, year after year.

Also, a tip: you are asking for a ton of help -- essentially what you'd expect of a travel agent -- and for a very large group. which is always difficult. But we're not in business, we're all volunteers, and it does make for more enthusiasm if your inquiry shows your group has also done some advance research. Try it, you'll like it... planning is half the fun! ANd get those 20-somethings to do some of the digging... that way they'll be more involved.

Posted by
353 posts

Janet gave you the basics.

With these 14 nights you have enough time to spend a few days inland where there are plenty of things to do and see.

But if your choice is only the islands, know that there are more than 200 inhabited islands in Greece, including at least thirty to visit.

If your choice is concentrated in the islands of the Cyclades, and I know that you will be attracted by certain places, I would add this (it is a subjective opinion which engages only me and is only valid for the high season ):

Santorini is certainly, seen from a drone, one of the most beautiful places in Greece (even in the world).
Unfortunately it has been partly transformed into a kind of mixture of giant blue and white shopping center and Disneyland without Mickey, invaded all summer by thousands of tourists and cruise passengers.

You will find the shopping part there, but for the "local" side you have to be very careful (that said, there are excellent Santorini wines)

Mykonos is the other popular place in the Cyclades for tourists.
Its typical old mills are conscientiously repainted every year, and to accommodate newcomers, year after year more and more white cubes are built there on all the plots of land still available.

What makes Mykonos so successful is rather the lounge bar / giant nightclub side as well as the welcoming aspect for the gay community.

It is your right to choose these islands, but know that you will find what you are looking for in many other Greek islands (including Dodecanese andr Ionian islands), but this is also where you will have to do a lot of research and preparation.

Another website to complete those given to you by Janet:

Posted by
353 posts

About accommodation.

Since you are 9 and will probably need at least 4 bedrooms, in the islands rather than taking 2 apartments you can find many villas.
In general, you have to stay at least 3 to 5 nights to be able to book.
It depends on your budget, but in June the prices are more interesting and from 350€ to 450€ per night you could find something nice with a private swimming pool, nearby beach, minivan transfer service, or rental of car, household, etc.

Here is an example of what you might find:

it's just for example, I have no private or commercial link with this website

Posted by
1780 posts

We went with seven in 2018 and had a wonderful time. I can tell you where we went and you see if something similar might interest you. We had my husband, his brother and me and our twenty something kids plus daughter’s husband. I looked for places that it would make sense to stay three or four nights as moving with a large group is always more challenging.

We stayed 3 nights in Oia, Santorini. We rented an air Bnb. My brother in law stayed nearby in a cave room.

We stayed 4 nights in Naxos at Kymata hotel. We had Suite on top for 3/4 nights. Quickly realized how smart that was. Groups need places to gather.

We stayed 4 nights in Nafplio. Rented a quirky house with six bedrooms. We all stayed together.

We stayed 3 nights in Athens in a three bedroom apartment. My brother in law stayed nearby.

Things I learned. 1) important to have place to gather as a group. 2) very difficult to find big enough places for six in apartments so can’t imagine you can do 9 in very many places. Also many larger places are located places on islands that are not central. We did not want to have to drive to do things automatically. Greece historically has not been wealthy and thus does not have many large accommodations (unlike Italy in contrast). 3) going out to eat all the time gets old. We ordered food in about 1/2 the time. It was cheaper and made going out when we did more fun. But you have to have a place to eat. 4) somebody needs to plan activities or you will spend half the time figuring out what to do (at least my family would). That was me. But anyone could do something else if they wanted but usually did not. And sometimes someone had an idea we did instead.

We had so much fun we went to Italy last summer with a slightly different group of seven.

Posted by
2891 posts

Beth that is SUCH wonderful and practical advice, I wish I could post it at the TOP of the Rick Steves Greece forum, with the notice "Required Reading FOr all large groups planning Greece visit"

Posted by
5 posts

I appreciate all the suggestions, thank you! I actually just returned from a northern Italy with my husband and daughter where I did all the planning - made me excited to dig into planning for this trip with my sister and her family. However, I find Greece much more challenging/confusing-- so many islands -- so appreciate the input.

Posted by
2891 posts

MIChelle we have SO MAny people coming to Greece after a N Italy experience and being frustrated because they cannot apply their N Italy-trip experience to Greece. So I'm saving u time and saying; don't try. 2 VERY different countries, i.e.:

ITALY -N Italy lots of wealth 1600-20th C - so lots of Villas in scenic sorroundings, now available for big-group rentals. Extensive Rail network. Varied landscape & highlights in All directions. Thus on day #1 - drive/rail 20 M North to charming new villlage, spend day, return @night, Day #2, drive E 20mi to different lively town, return to villa for dinner - Day #3/4 etc. Then get on train & in 2 hours, get to whole different area, New Villa. Repeat as above.

GREECE - NO wealth (due to centuries of occupation by oppressors) from 800?AD - 20th Century. Thus NO big villas on scenic mountains. Also NO Rail network. If on island, and you want to drive 20 miles for the day, you may fall in sea & drown. Thus, you have to pack, leave, spend half-day-plus getting to new isle. When Greece first started having postwar tourism (1960s) it was for modest-income visitors, so most beach areas built up with small family-run places, 10-30 rooms. When "upmarket" people finally discovered greece, all best locations were built-on, so the new (luxe) villas, with granite counters & pools, had to be built in more remote locations, thus rental car required to do beach or even grocery-shop. Thus our advice, smaller units = better locations.

Of course, with all that Greece has to offer, it's worth every bit of effort & planning required -- breathtaking scenery, wonderful welcoming people, food that's not fancy or "gourmet" but SO rewarding because of fresh amazing tastes (I've been handed apricots right from the tree, given my morning eggs still warm from the hen). A wonderful adventure awaits.

Posted by
1780 posts

If you are feeling overwhelmed, let me give you some advice that is not specific to large groups.
1. Pick one island group to visit. The ferries do not often go between island groups and flights all go through Athens. I would suggest Cyclades as the White Houses are what everyone thinks of when they think of Greece.
2. You probably have only heard of Santorini and Mykonos. Their fame makes them the most expensive and crowded islands. We went to Santorini because we all had seen the photos and am glad we did. It is a great soft landing into Greece. Everyone speaks English and everything caters to the tourist. But it is not very authentically Greek any more. So if you go to santorini, I would go to at least one more island in the Cyclades. We went to Naxos but Paros is another good choice. There are of course others.
3. Fly to your first on island on arrival day if possible and save Athens for last. In 2018 we bought separate tickets on Aegean air for several hours after our arrival. Last month we went to Crete on one ticket. It allowed us to have a much tighter connection in Athens. This year the price was no higher than separately, which was not true earlier. Use goggle flights to find out options. You want to go to Athens last because it is about an hour to it from the airport and you will need to be near the airport to depart (so don’t waste time going to Athens twice).
4. The bus service in Greece is excellent but can rent cars as well. If you explore mainland, rent from the airport. You do not want to drive in Athens.

And once you understand how Greece works, it is easy. You will love it and want to come back!

Posted by
353 posts

Janet, dear Janet, I would like to know where this statement "smaller units = better locations" comes from.
As if it were a rule!

Moreover, the fact of saying that these luxury villas are only built in isolated places is totally false.

If there have actually been real estate programs for 10 to 15 years that tend to build more or less luxury villas in remote places on certain Greek islands (and give the impression of a large holiday camp for wealthy people, it should not be made a general rule.

Just like those who built sets of ten or more rooms or studios in the 70s, 80s, taking advantage of the boom in tourism, a large number of these villas were built at this time and also by local landowners, (this was often for their personal use by the way)
These villas, houses are located close to all facilities, even beaches and the smartest have been able to install a swimming pool.

Now, having the experience of staying with 8 or 10 people in several Greek islands, I could list the advantages and disadvantages of "multiple accommodations" vs "one villa"

And I too could speak not "history" but in this case "history and real estate", by addressing the subject of the Greek cadastral system and the tax advantages obtained thanks to certain rules of the Orthodox Church.

But my dear Janet, I stop here

BTW I didn't undersrtand the " If on island, and you want to drive 20 miles for the day, you may fall in sea & drown"

I guess this is a scare joke?

Posted by
1780 posts


Could you share the islands that in your experience have well located accommodations for large groups? I admit I have limited experience but found few options when I looked. I am sure the information would be helpful for the OP as well as for others.


Posted by
353 posts

Of course Beth but sorry it won't be in Naxos, it was in Paros (Drios and Krios) and Serifos (karavi). 2 with Airbnb and 1 in direct contact. details in private to those interested

Posted by
2891 posts

JoLui, glad to hear your searches are bearing fruit. From experience on both islands (PAros 5+ times, Serifos 3), I'd recommend Paros since u are planning to stay quite a while; Serifos, while enchanting, is small, not as much scope for activities/discoveries. Paros has added plus of Antiparos a few minutes away... and fun adventures such as Capt Ben's Lazy Day boat-circle of island, with bbq's & swims & archeology.

Posted by
1780 posts

Thanks JoLui. I will make a note of this for future reference. Perhaps OP might look at possibilities in Paros.

Posted by
353 posts

Let's talk about Paros. (in case someone who stays there more than 4 days is interested)

Indeed Paros is full of villas for rent, unfortunately more and more of these new complexes are being built there, bringing together 6 or 8 villas with pretty names "Blue something...", "Luxury Sunrise thing..." in relatively isolated places (the ones you were talking about janet).
There are more and more of these complexes east of Naoussa.

Naoussa, which I already didn't like very much and which tries more and more to imitate Mykonos (but more chic) ​​with its pseudo-designer shops, its restaurants where you don't go to eat but to experience " Greek fooding" by getting ripped off with a €12 Greek salad.

Last week I stopped for an hour in Naoussa and a glass of "56 Isles" cost me €5.50. It's twice the price compared to other places in Paros.
There are also some recent villas to the west of Naoussa, going towards the lighthouse, but there at least there is nature and beaches that are quite nice in my opinion (Molos and Kolympethres).

Nice old houses in authentic places with real inhabitants, bakeries, butchers and taverns, you will find them near Prodomos, Marmara, even Lefkes or Drios.
I am not objective concerning Drios it is the fault of Anna, the "Eugénie Brazier" of Paros.
On the entire South-South East part between Drios and Aliki there is also a lot of accommodation, new and not new, small houses or large villas, and vice versa.

In short, even at 9, it's not very complicated to find accommodation in Paros if you plan ahead.
Some links:


Excellent organic wine from Paros:

The same thing in beer version

A nice bar in Parikia



Rent a car (Not recommended for procedural people.
No deposit, payment in cash, cars sometimes damaged but not expensive, minimal formalities, optional driver's license verification..).

Posted by
2891 posts

JoLui, that is a Fabulous roundup of info on Paros ... I misspoke above, I got confused above, answering the wrong query (from someone who wanted to choose between Paros & Serifos for a long stay). I see we were both right about villas (desirable & not). I'm bookmarking this thread for my PAROS folder! THANKS!

Posted by
353 posts

Since I forgot Serifos

Serifos has the advantage of being close to Piraeus, but it is very different from Paros, it is smaller, wilder, more mountainous and the architectural style is not the classic "white-blue" of the Cyclades.

Much of Serifos is not accessible by car and is more for non-beginner hikers.

Outside of Livadi (the port) there are few accommodation options. Many of the houses are actually Greek-owned vacation homes.

With the exception of the far south which is relatively flat, travel by car can be difficult for those unaccustomed to narrow mountain roads (and goats walking on the road).
The 4 km road that leads to Chora the capital of the island is a good example.
The more adventurous can go explore the island by car and go for example to the very small and charming village of Panagia with a pretty little church.
It's not that abandoned since I met an American couple there who lived in a small house opposite the church.

From Panagia you can go to the beach of Sikamia in the North West.
It is a narrow and winding dirt road and once you take it you have to go all the way because a U-turn is almost impossible.

The seafront of Livadi is full of restaurants (for tourists), the beach of Livadakia right next to it is nice. Continuing west, a 5 minute walk is Karavi Beach which is much quieter (but no shade)

In the south of the island, on the east side, there are superb isolated beaches Ganema and Vagia. The road to get there is good (the last hundred meters can be dirt).

There are surely good places to eat near Chora, but I have no particular recommendation since we cook ourselves in those famous villas we were talking about.

Oh yes!! I ate a great chicken sandwich at Captain' Serifos while waiting for the ferry.
In Livadi we also went to the Marina tavern which is located at the end of the port outside the row of restaurants. It's very simple, family but ultimately not recommended even for lovers of authenticity.

BTW. For people interested in an example of visits to the Cyclades by organizing their own trips and accommodations, there is a video made by an American couple that I find useful to have an overview.
It's about Mykonos, Naxos, Paros, Milos and Santorini.

It is a bit long (1h20) and far from describing everything, but it gives advice and interesting examples on ferry crossings, restaurants and accommodation.