First Time to Greece - Any & All Advice Welcome!

Wherever you decide as your destinations, do Athens at the end to simplify your flight back to the US.

Have nothing to offer on how to do Greece with a 20 month old.

Those famous islands are super expensive-scary in high season.

We stayed about a mile north of the Acropolis on a city square and were happy with the good price and low cost restaurants.

Down by the big museum there were restaurants claiming to be RS approved and getting 22 eu for a whole fish dinner. But we were paying 7 eu for same meal up by the hotel.

I would wait a few years until your child is older and more appreciative of the experience. Most of your time and attention will be on him and his needs and not the beautiful country.

A logical order for your itinerary would be Santorini, Naxos, and Athens.

Fly to Santorini
Take the Blue Star Ferry from Santorini to Naxos - takes 2 hours
Fly from Naxos to Athens Airport.
Take taxi to your hotel.

Santorini doesn’t have to be super expensive. We stayed in Firostefani at the Blue Dolphins Suites. We had a lovely room overlooking the caldera for about $230 per night. This was in May 2022. Not sure what prices would be like in September. Had a delicious meal at Aktaion. Decent prices. Love the food. Must make reservations in advance.

There are beaches on Santorini such as red sand beach and black sand beach. You would need to rent a car for the day to drive to these beaches.

On Naxos stay on St. George’s Beach. Short walk to the old town. We stayed at Hotel Palatia on the beach. Price was about $70 per night in May.

I endorse kmkwoos suggestions. Many transatlantic flights arrive mid day in Athens. That will give you lots of time to take a connecting flight to Santorini. We always get out to our first island on day of arrival. Getting over jet lag on an island is way easier than doing it in Athens
You could do a connection to Naxos on day of arrival but there are lots of flight options to Santorini while there are fewer flights daily to Naxos.

You might want to consider staying at a beach village on Santorini and do a day visit to the famous Caldera view areas. I only suggest that because its a flat area compared to all the up and downs in Fira and Oia.

Naxos is a great companion to pair with Santorini. You will get a more realistic Greek experience there. I would suggest you find a hotel on St George beach. Its a good sand beach and is full of little kids. It is also very shallow. It is a 15 minute stroll along the oceanside headland into Naxos town so you get the benefits of a beach and all the activities of the town.

Fly or ferry back to Athens so you are on the mainland at least the day before your return flight.

Here is Naxos
Around Naxos town 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299959098
Back to Naxos 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299940917
Naxos sunsets https://www.flickr.com/photos/stanbr54/albums/72157700728046481

Thank you so much for the excellent feedback!

We are considering the following:
1. Santorini (3 nights)
2. Naxos (5 nights), Maybe a day trip to Paros from Naxos
3. Athens (2 nights)

Does this seem like an appropriate itinerary with a toddler in tow? Should we spend one less night in Santorini? I understand that Santorini is not toddler friendly (lots of steps, dangerous in some areas, rocky beaches, etc.) but we are hoping to at least see the island. Also, do you think a day trip to Paros from Naxos is a good idea?

Stanbr, You suggested a beach village on Santorini - Do you have anything specific in mind?
Kmkwoo, Thank you for the lodging recommendations, we will be sure to check them out!

You suggested a beach village on Santorini - Do you have anything
specific in mind?

On the East coast of Santorini, in the villages of Perissa and Kamari there are beaches suitable for toddlers, but this side of the island is not really "Santoriniesque", these are places like you can see on all European coasts.

do you think a day trip to Paros from Naxos is a good idea?

I don't think it's a good idea because Paros is like Naxos, you need at least 4 or 5 full days to get a glimpse of it, just like you won't see much of Naxos if you stay in Naxos Town every day, so going there for a few hours is not worth the trip.

However, if you really want to, don't do it with the usual ferries. There is a boat operated by Kerras Cruises which travels twice a day between the small port of Agia Anna and Naxos

https://maps.app.goo.gl/qhGeuYfvjNN8kQXN7

and the village of Piso Livadi on the east coast of Paros.

https://kerrascruises.com/

It’s €15 per passenger

Michelle, I'm going to beat my friend stanbr to the punch and say YES, cut a night from Santorini and add it to Naxos ..,. Naxos is the deal for families like yours, whereas Santorini is Not. Awful getting around... he's going to be too heavy to carry, and it's a nightmare for strollers (tho do bring a cheap foldable "cane" stroller for Naxos & Athens). The beach towns are on East side of Santorini, black grit beaches, not good for tots ... and pools r no answer for that age. The Famous Caldera View which is the Main THing about santorini is on the West Side requiring tedious (and sometimes crowded) bus ride to access... and if u wd rent car, no place to park!

Your best solution (which vets recommend over & over) is to book a transatlantic nonstop that leaves from East Coast US/Canadian airports, shortest airtime, all arriving (99.9% on time) between 9 - noon... so u can allow 2-hr layover, & catch 1st available domestic flight (Aegean or Sky Express) to Santorini. W luck, u can be in hotel in time to wander a bit & enjoy 7 pm sunset 1st night. Do your main sight-seeing and Caldera-Gazing day 2, and on Day 3 take a ferry to Naxos. There's an AM "rserved-seat" ferry (faster but pricier) arrives Noon-ish at Naxos. At 3:15 pm the BIG Blue Star Conventional ferry (llike small ocean ship - 1200-1800 psgr). It has open rear decks to sit on... arrives 5:30. But can be a hassle going up/down stairs, etc.

For Santorini, think about Hotel near view... but away from hubbub of OIA or FIRA. I favor Firostephani... on N. Fringe of FIra but bypassed by cruise crowds/bus tours. Try to avoid anything w steps DOWN cliff, or UP to higher floors. Sunset Hotel has entry direct off main N-S street, and has large common terrace for sunset views... my own Fave budget pllace, Villa Fotini, has one mainlevel unit w separate bedroom... also check booking.com. W toddler, u will really have to strategize to see stuff!! I advise early on Day #2 book taxi to OIA by 8 am -- you get 2 hrs to wander & take pix before cruise & bus-tour throngs invade.. then you leave, can catch bus to FIRA town for museum, lunch etc. Good Firostephani lunch/dining - Taverna Aktaion, Cafe Remvi/Remvi hotel (great sunset views no crowds sane prices).

I stumbled across this thread because I am thinking about a Greece trip so I do not have any specific input on the country. However, do not pay attend to the poster who says not to travel with a 20 month old. I have taken my four kids abroad every year since the first one was born 12 years ago. We started when he was an infant and just kept going. Yeah, maybe they don't remember much but you'll make great memories and you won't regret it.

I have been to the places you are going. Naxos is best for a child. Santorini requires a lot of strategizing because there are steps everywhere. I would definitely arrange for a car service to take you to your hotel. If you want to see the famous view, I think Janet has the best advice. If your child can be carried in a back pack, I would suggest that.

Otherwise, you could skip Santorini and focus on much more child friendly Naxos. When we were on Naxos, there were lots of small children at St George beach. Our children were in their twenties by then but I remember thinking it would be a good place to bring kids.

In Athens, you can’t take a stroller easily up to the Acropolis. Maybe find a hotel with a view if it. There are other sites you can walk to and a couple great museums which would be stroller friendly. I would go to Athens last and I would spend three nights. That would give you two days. But you could spend two nights if you want to spend minimal time in Athens.

JoLui, Janet, BethFL - Thank you for taking the time to respond, I really appreciate it! This information has been extremely helpful!

And thank you for your comment, mr_henderson7! We have taken our son on many trips with great success so far. This will be our first time taking him overseas, and of course we are anticipating some hiccups along the way, but we are looking forward to making memories with him!