Santorini with group of 14

With a group that large, a travel agent may be in order. Maybe they could get you some discounts on flights, transportation, etc. with that many people.

With that many people, I'd look for a fabulous vacation rental home. We've had a wonderful time when we've booked a VRBO home for a large group of friends or family traveling together. I did a quick search on VRBO for homes that would accommodate a group your size and found 24 of them. You'll love having common living space to enjoy together, and being able to fix some group meals instead of having to take all your meals in restaurants. Take advantage of the chance to get a stunning place that you couldn't afford if you were traveling with a smaller group!

thank you both for your advice.

We are all coming from different states. I did some initial research on the VRBO and Airbnb. I am not familiar with the area. We are looking to be close to Oia and or Fira. Ideally walking distance. Is that possible? and any suggestions on locations?

I love to organize trips but I am a little nervous with this number of people. I really only need to find the location in Santorini and housing. Everyone will be responsible to get themselves there. We will all be going off to other places from Santorini.

thanks again

I don’t think you will find a house big enough for 14 people in walking distance of Fira or Oia. I organized a trip with my adult children last year and we stayed in an Air BnB in Oia. There were 6 of us not 14 and I didn’t find many options.

The other thing I found were charming caves homes but they don’t allow for much privacy. I knew that would not work for our family.

I would go on booking.com and put in 14 people and 7 rooms and see what comes up. Maybe a hotel with a pool would give you a place to gather.

Without knowing your combined budget it's difficult to know what to suggest. In Oia check Laokasti Villas, Anemomilos Hotel, Olympic Villas, Aethrio Hotel, Old Oia Houses, Rimida Villas, Strogili Houses, Oia's Sunset Hotel and Maryloujohn Villas. Contact them to ask about group rates and availability. Be sure to include a breakdown of how many people will be in each room so you make sure everyone can stay in the same location. Laokasti and Anemomilos both have on-site restaurants, which make dining as a group very convenient. Both are easily within walking distance of everything Oia has to offer.

Fira to Oia is not walking distance, it is a hike.... but if you stay in Oia there is a Windmill airbnb that sleeps over 10 people. We were in Oia last summer and when I was searching for a place on Airbnb that option was popping up every time. it will also depend if you have children, most hotels in Oia will not allow children under 12. With that many people you may need to consider what the budget is for each, as that will make a huge difference.

If your group has many different ages involved, people with this experience tell me that it works best if y ou can find several units in the same hotel, with, as others say, a place where y ou all can also gather. No matter how wonderful a large villa may be, there will shortage of privacy, AND bathrooms. THe grandparents particularly value having a separate unit, to be able to socialize at appropriate times, and yet be away to nap & read at other times, and have early nights if needed.

thank you all for the advice. I have a lot to keep me busy researching. We are a group of siblings and friends, no kids, all adults between 55-65; middle age and fun but well behaved. (smiley face)

Personally, if I was in your shoes I would look for a hotel in Firostefani with a pool or at least a breakfast area where you can gather that can accommodate all of you. We were going to stay in Firostefani but ended up in Oia because we found an Air BnB there that would accommodate all six of us. Oia is lovely but it is less centrally located and restaurants are more expensive (except for gyros). Firostefani is less hectic than Fira but walking distance to Fira which is really the center of the tourist activity. The buses go from Fira.

I am definately open to Fira as well. Can you ar anyone recommend villas, hotels, airbnb’s that would be in or walking distance to the Fira action? And accommodate 14 of us?

Lee from Califorinia thank you for your suggestions I am in email exchange with many on your list. If you know of any in Fira close to the action or in it and can accommodate 14 of us. We are all between the ages of 55-65 just so it gives you and idea of the type of action we can handle.

nmarot, Lee asked you for a price range you would prefer, and y ou never responded ... people cannot help you find lodgings at your price point, if you are comfortable with a €200 per night for a double room, and people keep suggesting hotels @ €500-€1000 per night. Lee is the absolute expert on OIA accommodations, but none of us can read minds. You need to share specifics.

Also, you seem to want to be "close to the action" but not in the middle of hubbub -- and if your days in Santorini are M-T-W-TH, you certainly WILL be in the cram-jam center in Fira Town, because those are the days with 4-5 huge monster cruiise ships docking. On the other hand, Beth from experience highly recommended Firostephani... which is just on the north fringe of Fira town, maybe a 15 - 20 minute stroll to cafes, shops, nightlife etc, but bypassed by cruisers or bus-group tours, and thus is serene day & night. You did not respond to her either.

Have you tried doing some research on your own? Booking.com/firostephani can give you a good idea --- it would be too early to get a good "read" on what's available in June 2020 -- but you could "simulate" the availability of lodgings in the shoulder season, by searching with a "dummy Date" of , say, Sept 15 - 20, 2019. WHen a list comes up, on the top RH corner is a box called "map view" and when you click on this, you see blue "baloons" representing all available hotels, exact location on the caldera edge, and the rate per night. If not enough show up, pick a later September date. Rates may be similar to June 2020.

In my 12 trips to greece, and counseling probably scores of Santorini newbies, I have located numerous good-value Firostephani hotels that have 7 rooms available, and common areas to gather .. some with pools, others not, all with caldera views. But not inclined to list them unless you indicate what your budget range is. wasted time/effort.

I would ditto the recommendations from upthread (Janet & BethFl). We were very pleased to stay in Firostephani for 4 nights. We were looking for an area that was less touristy, the same Caldera view as Oia, walking distance to Fira, restaurants and public transportation just steps away. Booking.com is an excellent resource for accommodations that might meet your needs.

thank you Janet for calling me out. Not my intention to not answer questions. I am so appreciative of you and everyone else's help.
My group is now 16. I need 8 bedrooms with at least double beds. The group are all adults and mostly couples. We have 2 singles.
I am looking for 4 nights in Santorini. I am fine with either Fira or Oia villages. Ultimately it would be fabulous to put us all in the same house or hotel. We want to be close to the action. We don't have to be in the thick of it. I do not want to worry about anyone driving home after they have a drink or two (if that makes sense). I personally am a walker and the walking path between Fira and Oia looks terrific to me personally and would like to have access to that.

Does this help better clarify what we are looking for?

In Oia Laokasti Villas, Anemomilos Hotel and Aethrio Hotel are still your best chance for all of you to be staying in the same location. What is your combined maximum daily room budget? You might have to contact these hotels directly to get all the information you need to make an informed decision and to make sure they will book a year in advance. Be prepared to put down a hefty deposit NOW or take a chance on losing some of these rooms LATER

thank you Lee, I am thinking the room rate would be like 100-150 per day. do you think that is doable? I would like to set expectations for my group. If I could get something decent for less that would be preferred. I will check into the locations. I did reach out to the locations recommended for Fira. all the locations have responded they will not have 2020 rates until september. At this point I want to find locations that meet the budget give or take and more importantly can accommodate us for June of next year.

just to be clear 100-150 per room, per night, for 4 nights. So if I am looking for 8 bedrooms then I would be paying around 5k. I can see where there would be a hefty down payment

Unfortunately your budget will not get you what you want. It will take at least €200-250 to accomplish your goal, and even then the pickings are slim. Unless you can come up with more money you will have to settle for rooms away from the caldera view. There's just no way around it. I did find one x-large villa in Imerovigli on the VRBO website that's just under your budget and it has an east-facing view of the Aegean Sea. Still quite beautiful, just not into the caldera. Looks quite nice and has a pool. Look here: https://tinyurl.com/y6coj88s

This is between Oia and Fira. We walked by this area when trekking from Oia to Fira. It is higher than surrounding area and has beautiful views.

We are staying in Fira at a place recommended by Rick —— Sricocco Apts. Less than 200 euro per night. On the caldera. It would be so fun to have several rooms for family members.

There are tour groups that you and your cohort of 14 could join. Why are you struggling to plan this? It is madness with a a group of that size, many of whom will be dissatIsfied, no matter how hard you try to please.