Let me start out by saying that I had two connecting rooms for eight nights all on Hilton points so my view is partly clouded by what I was paying (zero!). That being said, I stayed at the Cancun Hilton last year (paid retail prices) and Barbados Hilton two years ago (also all points) and the Caribe is very comparable and a great stay.
This is a really big hotel and service is predictably middling. In addiition I understand there is great variability to the rooms. We were given a "garden wing" pair of rooms which we entered with trepidation thinking they were out of the way (they are not), that they would have a terrible view (mostly true) and that they might not be up to par (completely not true - in fact they had very recently been beautifully renovated - would make a W proud). In addition, my kids two double bed room connected to my king room which really was itself a suite - it had a living room with a pullout and a second larger flat screen. I got over the view (partly a roof and its equipment and partly the lovely garden) and really liked the rooms (443 and 444). I would actually ask to stay in the Garden Wing again. The in-room coffee is really great too. No wife in rooms though.
Aside from the rooms, the lobby is big, dramatic and open air and has wifi. The pool and beach area is the hotels biggest plus. The pool is pretty big, multi-levels, has a swim up bar, two large working hot tubs of varying heat levels and has a fantastic water temperature in the main pool. The beach is private (the only one Puerto Rico) and had a really neat lagoon since a breakwater shields the beach from all waves (both a plus and minus). On the plus side, their are fish everywhere. The hotel gives out the old bread from breakfast for people to stand on their fish feeding pier and feed the fish - the number of fish is really not to be believed. Their is nothing from stopping you though from walking around the lagoon feeding the fish by tossing little pieces of bread in the water and watching them feed around you - really cool. I brought snorkels and masks from home and thus snorkled right in the lagoon most days - I thin they are available for rent at typically high prices.
They have free float hour every day where you can borrow an inner tube or float for free for an hour, they have a free exercise class every day, free (virgin) pina colada tasting every day from 1 to 1:30, free bingo with nice prizes (like free drink tickets) every day at 2 - lots to do.
The gym is fantastic, perhaps the best I have been to in a hotel. The hotel is also nicely suited for runners, there is a very scenic twenty five minute round trip run from the hotel to the edges of old san juan.
Some might not like the location (older or less active people) since it is between condado and old san juan but in neither. It is an easy although 15 minute walk to Condado - I did the walk to Condado for dinner three times and home from dinner one night (took taxis the other two nights) and felt completely safe. I didn't walk to Old San Juan but the bus is literally a block away and fifty cents each to Old San Juan. I took the bus every time I went to Old San Juan and took taxis back each nigh - again felt totally safe. Some complain about the cost of taxis here but they are far less than in places like Barbados. Also all the tourst taxis are very large SUV's or minivans and easily accomodate famillies of five like mine (in Cancun I think we wedged into a Corolla taxi).
Breakfast for Hilton Honors Gold members was include via tickets which can be exchanged for one of (i) five dollars worth of food at the onsite Starbucks - don't believe the ticket which says Tall drip and danish, SBux will give you anything you want provided it doesnt cost more than five dollars); (ii) the full buffet in the main restauarant with a sixteeen (yes $16) co-pay; (iii) continental breakfast in Il Giardino - wasn't bad, we had this almost every day or (iv) the smaller buffet in Il Giardino for a six dollar co-pay - we had this a few days and it was good but basic.
Drinks are quite expensive at the hotel, $12 for a mojito, $7 for a mediocre local beer, plus tax and tip. Get the refillable drink "shaker" your first day for $22 - they sold out easter weekend before I could get my hands on one.
The pool grill is pretty terrible. Completely unimagintive menu - how can you not have fish tacos, chicken wings or a cuban sandwich on an island menu? It is pretty basic and boring food with truly slow service. After the first day, we just skipped it and I walked one block to Subway and brought back lunch for the family. It is hard to say this I pretty much never eat at one of the nine Subways within walking distance of my NYC office, but the Subway was a lifesaver for lunch. The pool food is probably the weakest part of the Caribe.
All in all, really pretty happy - nice family resort - would definitely consider staying again although would also consider the cool looking Conrad across the way in Condado (we walked through to check it out).
Choose the "garden wing" for no views but really nicely, recently refurbished rooms.
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.