Free your heels Todd, there's tourism for all tastes here, it's hard to describe shortly, to me the most interesting part is in the south, starting at the lakes district, from Temuco to the south. Then way south Torres del Paine is an amazing place, I'm sure there's a lot of it in google. in betwen there's ice fields, forest, mountains and lots of amazing natural and unpopulated landscapes. I don't like the beach as much as the lakes, so I'm probably biased, but despite our long coast, the beaches we have are not what best defines our tourism. Viña del Mar is a crowdy place in summer, with very limited chances to launch a sailboat. But some party and casino stuff that could be interesting. There are marinas in the popular places but more like private clubs, no idea what they might charge for launching if they even allow it. Maybe Algarrobo is an interesting place to sail a boat, that's close to Santiago. My cat is south, I store it at my in laws, in Concepción, there's a small lagoon by the house where I can sail daily or the beach nearby, but mostly I go to the lakes in the South. Pucón is probably the most touristic place at Lake Villarrica. Then of course we have mountains and skiing, Pucón itself is a place where you can do both, not the best skiing compared to Chillán and Santiago, but worth a visit. I general, I would say our tourism is not as developed as it could be and unfortunately it's not easy to find useful info like to book a cabin or hotel. I'd be glad to help if you consider a visit.
Lake Rapel is where most of the cat sailing happen here, it's about 250km from Santiago, nice lake for sailing, but not really a destination you'd fly thousands of miles to, just for sailing. The wine zone is mostly in the center of the country, mainly at Los Andes and Casablanca valleys, north of Santiago, then Maipo, Colchagua, Cachapoal, among other valleys from Santiago to the south. Then if you go way north, you get the deserts, some interesting spots like San Pedro de Atacama and lake Chungara (not for sailing but rather see flamingos and very high volcanoes.
Well, that was a rough and disorganized and limited description of our tourism. Worth a visit anyway.
Saludos!