Possibilities galore for both couples and kids...
We recently spent 4 nights and 5 days at the Caribe. This included my disabled father, my mother, my wife, and my three year old daughter. This hotel, as well as the whole of Puerto Rico (first time) surpassed my expectations. We would love to return.
Rating the Hilton I gave it five stars. There are several pools as well as a beach to use around the hotel. The views are spectacular. There wer many kids that my daughter was able to play with. The staff regularly arrange for bilingual activities such as fish feeding and swimming contests.
There are several restaurants on the hotel grounds. Fair warning - they are expensive, but the quality is generally good to excellent. We ate at the Lemon Grass (Asian-latin fusion) and Mortons (traditional steakhouse) and the food and service were exceptional. These restaurants do not offer a kids menu, but they were willing to accommodate us by permitting us to bring food for our daughter hich they heated up for her. Palmero's is the centralized buffet style restaurant with great ocean views. We mostly ate breakfast there. The staff was friendly and even helped us with some of our excursions outside the hotel.
I would suggest renting a car if possible as the excursions to El Yunque (the rain forest) and the taxis to Old San Juan were overpriced. My whole family managed to see the rain forest on our own time which we needed since I was traveling with child and a disabled adult. The drive with trafiic took about 1.5 hours. But the views and the waterfalls were well worth it.
It is a must to see Old San Juan. From El Morro (the old fort) to the many restaurants along Calle De San Fransicso and Calle de Forteleza, you will feel as if you stepped a few hundred tyears into the past. Parking is easy to find, but the streets can be narrow. If you are used to city driving, it shouldn't be a problem. If you want traditional, inexpensive Puerto Rican food and don't mind a lack of ambience, go for La Bombonera. Arroz y pollo, tostones, frijoles, are the staple items on this menu set in a 1902 diner-esque environment. It was great to have a meal over-hearng all the locals talk about the Wolrd Cup. For something more romantic and trendy, try Marmalade. This restaurtant sets a mood for young couples who are into experimental cuisine. Sushi-style paella bites, Gazpacho with watermelon salad, and prosciutto-wrapped halibut were the dishes that still resonate in our taste-buds. The staff here was very knowledgable and friendly. With a decent bottle of wine, dinner for 2 was $200. But it was worth since it was our anniversary night.
When you return at night to your hotel, expect to find live music and hopping scene just beyond the mian lobby. It's great to see all sorts of people mingle here. Again, staff are always friendly. It's great to have a nightcap and walk along the path overlooking the Atlantic.
Room service was prompt and friendly. Bellhops and valet were also very accommodating.
My criticisms are few. There was some construction at the hotel which made nap time for our daughter a bit difficult. Also, there was a charge for renting rafts at the beach which I found to be ridiculous. I would not recommend lunch at the the beachside bar/grill as it is way overpriced and not worth the trouble. A short trip to town will get you more variety. Also, don't get your gifts at the gift shop. These too are overpriced.
As I mentioned, this place offers many opportunities for young and old to enjoy themselves. If you get a package, avoid flying American. They were four hours late on the return and being over six feet tall, cannot compare to Jet Blue's roomier seating.