If you had to choose between Siena and Lucca to visit which one would you choose?
I want a relaxing place to stay; I've heard that Siena is more like a city? Is that true?

Since I've visited Siena already I would vote for Lucca. Siena is very small and didn't feel like a typical city to me, but I suppose in comparison with Lucca, it would. I think either city would be great.

They are both cities! However, Lucca feels more like a true city because of the enclosed walls, and then the newer city outside the walls. Siena is not that spread out and big. The advantage to Lucca is that it is the flatest of the Tuscan towns, so you can walk around in ease without all the ups and downs of Siena, San Gimignano, etc. While Siena is great to visit, my choice is to stay in Lucca each time!

That's a tough one. I've stayed in both. Siena has more history, more hills and a great place to taste wine, the Enoteca Nationale. Lucca is quieter, smaller easier to get around and has a more small town feel. It does have some great medieval art, as Ruskin noted.
Siena is also more central and a good base for visiting the sights of central Tuscany, like Chianti or San Gim. You pays your money and you takes your choice.

If you are thinking "city" as in New York or Boston or even Rome, then no, neither of them is a "city". They are not small towns in the sense that you can't walk the whole place in 5 minutes, but neither of them is hectic or city like in any way that I think of as a city. They are both extremely historic feeling, relaxed and beautiful. I think Siena does probably get more tourists but maybe for good reason. The duomo and the main piazza are unequaled in Lucca. Lucca had several small squares and a few nice churches but nothing as dramatic as Siena. Siena was definity more hilly, but that was part of it's charm. I preferred Siena, but certainly liked Lucca too. How long will you be there, and do you want to use it for a base for touring other places as well?

This is about as easy a choice as there is. Siena is a beautiful small town with lots to see.It's like a quiet suburb of Florence. Lucca is boring and should simply be avoided. Don't waste any time there.

However, if you are looking for a base for train travel, Lucca's stazione is more convenient to the town. Siena is my favorite of the two for "seeing".

Thanks for the responses.
I need to find a base town. I was thinking of Cortona and from there visiting different towns, like Siena or Lucca. May be both. From Lucca I'd go to cinque terre next.

We've stayed in all three as a "base." You'll be driving, I trust? Cortona is our favorite, but a little out of the way. Siena is more central, but there's a lot of traffic getting in and out of town. Lucca would be easier since more than likely you'd be staying outside the walls and the traffic situation didn't seem so complicated. All in all, I'd choose Siena... stay right in the heart so you can wander around at night after most of the turistas have gone.