I'm brainstorming a 3 week-ish trip to Europe in September with my husband and our son who will be 15 months old then, and I'm trying to decide where to go.

Some places that are on our radar are Portugal, Croatia, Montenegro, Prague (with a day trip to Budapest), Slovenia, Bosnia. Open to other suggestions! (I think the Azores will be a future trip.)

What combination of these countries/places would be on your itinerary? And what cities? How much time would you spend in each? Are there any other countries/cities that you think we would like?
We love food and wine/cocktails, beautiful sights, history, sightseeing tours, food tours, cooking classes, fun tours like ghost tours, etc, beach days. A combination of cities and towns or islands for beach days mixed in to relax especially since we will want to take breaks and a slower pace with our baby/toddler. We will have a baby carrier for baby wearing and a stroller and we would be totally comfortable renting a car.

We've been to and *loved* Paris, San Sebastian, Naxos, Santorini, the Scottish highlands/Isle of Skye, Granada, and Venice. Our favorite trip pre-baby was a combo trip of Scotland & Greece, two totally different but beautiful places in one trip.

We've also been to but didn't necessarily love (for various reasons) Athens, Tuscany (we were a bit bored with the hilltowns), Amsterdam, Nafplio, Seville, Barcelona, Rome, Edinburgh. We would love to explore more of Greece, Italy, and France but would like to visit new countries first. London & England is in mind for a future trip when our son is older and can handle a busier trip.

If you have any suggestions I'd love to hear them!

I don't think it matters the destination so much as how you structure the visit--longer stays, working around nap time, not doing "amazing race" style itineraries, etc. That said, Portugal would appeal greatly for the shorter flight (assuming you are coming from US). You could stay a week in Lisbon and a week in Porto, then choose a smaller town for the other week.
(Prague to Budapest is several hours--not day trip distance)
Croatia would be great--I've always wanted to go in September for the warm seas, etc.--it just can be a pain to get there.
If you could get a good flight, how about Crete?

thanks for your response Yorkshire. Prague and Budapest may be better in a Germany/Austria trip. Crete was on my list, I've heard great things, but was thinking since our last trip was to Greece that we should visit a new country.

Gotcha, Puglia was another thought. But really, the potential of a short or even direct journey would be hard to pass up. All of the countries that you listed adjacent to Croatia par well, but I'd choose either north or south (Slovenia and Croatia or Croatia, Bosnia, Montenegro).

When we did this, we focused on renting gites in France. They rent by the week, usually Saturday to Saturday. The prices are often surprisingly low.

Of course, the gites concept does exist in other countries as well, though the program in France is so extensive and well supported that it is unequaled.

other countries with good gites systems include Greece, Spain, Latvia, Slovenia, and Bulgaria.

For other places agriturism includes houses for rent, usually in the countryside.

This trip with a little one you might want to move around less - one or two destinations, maybe a gite (France) or an agriturismo (Italy). Does bub travel well in the car? Our daughter could only last 2 hours in the car seat before there were tears. We knew about it so we could work with it, but it does make it tricky. At that age we had an apartment which we stayed in for 2 weeks but took lots of day trips out from there. Not having to pack and unpack, and having a high chair and cot for the baby was very civilised.

Lavandula

thank you for those ideas! so, after thinking more about it we actually decided to go to Germany/Vienna/Prague instead so I guess I will be heading over to the Germany forum for some ideas!