Hello, we are planning for a one week trip in Greece this May. We will fly into Athens and take a ferry to Santorini next day and stay there for the rest of our trip for 5-6 days.
My open questions are:
1. Is May a good time to visit Athens/Sanotirni
2. Are 5-6 days too long for Santorini. We can make it shorter or add another destination if advised
3. What should be considerations while travelling with the baby. We would normally have a stroller with us. Will there be a problem walking with it? Or any other consideration while choosing hotel etc
4. Should we consider hiring a car for a part of staying in Santorini?
5. We are also hoping to make a trip to Volcano. Is it possible/advisable with the baby?

Thanks!
Regards,
Daven

Santorini is one of my favourite places in the world, but it is one of those places (along with Venice) where a stroller is just not practical, and it is a tough place to visit with a 2.5 year old. The beautiful towns along the caldera where most people want to base themselves are essentially towns built on the edge of a cliff, with steps and cobblestones everywhere, and lots of walls and precipices for a toddler to fall over. 2 and a half is a tricky age for Santorini as they are too old to be carried in a sling and will really have to walk in most places, or you will have to struggle with the stroller.

You might let us know what town are you planning to stay in, and we can recommend hotels then. Were you planning on a place with a pool, or by a beach? Many of the kid-friendly, flatter, locations are by the beach whereas the picture-postcard views of Santorini are on the caldera / cliff side of the island. If you are planning to stay on the caldera side then I would go for a hotel right in the middle of either Fira or Oia town so that you can come back to the hotel during the day for rests, and so that you are near a (semi) flat main street and can occasionally take the stroller with you.

You can certainly take the boat trip out to the hot springs with a toddler, you will just need to be vigilant while on the boat. He/she should be able to swim in the sea there with you - it is not so hot, and you can paddle away from the springs to the cooler part - so bring whatever life vests / buoyancy aids you will need for him to swim. Otherwise one of you will have to stay on the boat at a time, and take it in turns to swim in the hot springs. There are trips of varying lengths so take one of the shorter ones to avoid boredom.

May is a lovely time to visit Santorini. There are good bus services between Fira and Oia so you can stay in one and visit the other quite easily by bus or taxi. With 5-6 days I would recommend a car for one or two days so that you can see the rest of the island as there are some sights well worth seeing outisde of the caldera e.g. Akrotiri, the red beach, the black beach, ancient Thira.

Of course people who live there have babies, but they are not all over sightseeing.

IMHO, it seems a difficult place to visit with a toddler who wants to be running around. You have to be very watchful.

As Littlejane suggested, take a life jacket, not just one of those play things.
I would also buy one of those very good quality child harnesses that you can hold onto firmly. Have thicker fabric on little one's knees to protect from scrapping if they stumble on the cobbles.

You would be MUCH happier if instead of Santorini, you would head straight for NAXOS for y our stay, and do a day-excursion (on a special excursion vessel, HM Alexander), to see Santorini. If your purpose is mainly to see the Famous Santorini View, the caldera & cliff, with the cube-like white houses ... that can be done nicely in a day trip, and BTW, are you aware that all 20+ islands in the Cycladic Group have those same beautiful white houses with blue shuttters, red flowers etc. Some people are brainwashed by cruise brochures to think the "look" exists only on Santorini.

Naxos is deservedly known as THE most family-friendly Cycladic isle for those with toddlers & pre-schoolers. Right adjacent to Naxos' port town is St. George beach (also called Ag. Giorgios), a sandy shallow beach where toddlers safely play at waters edge all day long. In May Scandinavians are 99% of St. George vacationers with their cute blond babies & sandpails. If you stay here, you need NO car, It's a short 10-15 minute LEVEL walk with your stroller in to the town's cafes, shops, museums etc. If you want to explore the whole island (it has dramatic mountain scenery, hillside villages, marble quarries, ancient ruins & statues), you can either rent a car for a day, take a tour, or just use the excellent island bus network.

You are very late looking for accommodations on or near beach but you can make a start by looking at booking.com specifying st. George beach & putting in your dates. Many units here are called "studio units" or "1 BR Studio Units" which mean they have a kitchenette ell w. table/chairs -- very handy with a 2 year old whom you must feed on HER schedule. Even w.o. that, almost all Rooms in Greek isles have fridges & small tables. The closer you are to the beach the better -- some well-situated places at Ag. Giorgios include Studios Thomais, Studios Kalergis, Sun Beach, Studios Naxos, SIgma Studios, Hotel Kymata, Hotel Akrogiali, Naxos Dream Studios. If you find any with vacancies for your dates, I suggest you contact all of them simultaneously & see who answers first.

All of this unrequested advice of course is irrelevant if you have your heart set on a full week on Santorini ... but you haven't shared why that island is your #1 destination, when you haven't been there before and from your queries, do not seem to know much about it yet. It's Honeymoon Central, and is visited on weekdays by up to 3 Giant Cruise ships daily, which can disgorge up to 9,000 passengers onto the busy lanes of Fira and Oia, not to mention the many other package-holiday groups. Even in May the crowds are major. Its Caldera is a justly famous View, but is it right for you at this stage in your life? Just wondering.

Just another voice to the chorus, Santorini is spectacular but it is not stroller friendly as the alleys are all paved with one inch round pumice stones thus bumpy. Also there are stairs everywhere. You will end up carrying your child the whole time you are there.

Jan is providing you with a good option. Find a hotel at Naxos St George beach which gives you a beach experience plus all the activities of stroller friendly Naxos town.

St George is the favourite place for people with kids as it is shallow and has lots of beachside hotels so you can get back to the room in a hurry when the child needs it.
Lastly it will be half the price of Santorini.

St George Beach Naxos http://www.flickr.com/photos/stanbr5...7632113170279/
Naxos Town http://www.flickr.com/photos/stanbr5...7632094558042/

There are two excursion boats to Santorini each does that excursion twice a week so there is an opportunity to see Santoirni from Naxos. Best of both worlds.

I would never take a toddler to Santorini. The caldera side is a steep cliff. If you must go there, two days maximum then head to Naxos or Paros with their nice beaches and a much more Greek experience.

So glad more posters have emphasized the same problem with a toddler on Santorini. So often posters get reprimanded for being "negative" about a proposed itinerary, I try to be light with suggestions, but too gentle and the OP ignores it.

Santorini - lovely place to relax as a couple when toddler can be left with GPs.

Santorini will be difficult with a stroller due to steps, cobbles, uneven pavements and crowds of people around the most picturesque sights. Also, be aware that many hotels on the caldera side do not allow babies - make sure you read the small print before booking!