Positano or Orbetello

Positano is very chic and on the amazing Amalfi Coast. Lots of opportunity to shop, sightsee, etc.

Orbetello is more quaint, not exactly on the sea. Porto Santo Stefano is the best coastal town nearby. This is the Italy less-traveled by foreigners. Not so many shops or sights, very laid back.

Are you planning on spending the entire two weeks in one spot?

Yes, we were planning to stay two weeks. Orbetello has an Italian school where we could take classes. We were planning to go to the beach in the afternoon. However, there is a lot to be in Positano. My daughter might not want to spend her vacation in school. Any suggestions? Thank you for your reply.

It just depends on what you want. I have been to the Amalfi coast but did not make it to Positano. I just spent four days in Orbetello so of course I am really high on it right now (loved the entire area). I don't know how long the classes are each day, but you do need a little break from the sun, so why not learn some Italian on vacation?--it will certainly be nice to have that skill on future visits! I actually stayed near the language school.

Both will be very crowded in August. The Amalfi coast has more of a problem dealing with this because of the transport logistics and large numbers of foreign tourists, while Orbetello is still more of an Italian vacation spot. There are some great beaches nearby. Many on the Monte Argentario promontory are rocky (as are most Amalfi coast beaches), but on the mainland and on the two other isthmuses (the proper term?) there are fantastic sandy beaches. We loved Feniglia--very natural. I am certain Orbetello would win on the affordability side, and safety is not of concern. Feel free to ask more about the region. You really can't go wrong, but they are two very different trips I think.

Thank you for your reply. I was wondering if I need a car in Orbetello? I will arrive at the Rome airport and found a route the requires taking two buses. I will be staying near the school. Is it near the beach? Thanks again!

I think you would enjoy staying in Porto Santo Stefano more than in Orbetello. You can take a bus between the two.

Re transport--I don't think getting there would be terribly onerous--train plus bus or two buses. But for getting around you may prefer to have one. You would want a parking spot with your apartment. We stayed just outside of the old town, so walking in was a couple minutes, but driving out was easy.
You could reach the sandy beaches I referred to without one, though you may want bikes on the flat isthmus side (on the Monte Argentario side, it is much more hilly, but there are buses). For trips to the mainland, you would probably be better off with a car--and there are many day trips within a couple hours.

If you decide on Orbetello, or Porto Santo Stefano or anywhere in the area, I would rent a car. There are a lot of great towns to visit nearby, and national parks like the Uccellina both on and off the coast, in Maremma. The Mt Argentario peninsula (which was an island once) has some great beaches like here or here. Most of those spots require a car to reach.

I thought of another thing to consider--Orbetello is on a lagoon, so you may not get sufficient breezes to be without air conditioning. Just something to consider. We were there in May, so open windows were fine, but August would be tough. I'd look for something with air-conditioning or inquire into whether the towns on the promontory (or close by hill towns on the mainland like Capalbio) are more pleasant at night if no air conditioning is to be had. We stayed outside the old town because we wanted outdoor space like a terrace, which was in short supply in the old town.
The apartment blocks just outside the old town (where the language school is--literally a two minute walk to the old town gate) don't look like much from outside, but the inside of ours was fabulous and it had a panoramic lagoon view.
Definitely start looking now, because places probably book well in advance for August.