The drop-dead gorgeous lair of artist Jan D'Esopo, this centuries-old mansion looms over city, and boasts spectacular views from its rooftop wine deck of the steep Atlantic coast on one side and across Old San Juan rooftop to the bay and beyond, on the other side. Jan's fine clay and bronze sculptures, paintings and prints adorn this highly bohemian, character-filled house, with its interior gardens and patios, fountains and tropical birds and a small waterfall pool. Guests are free to ramble through the 50-plus room inn, which spirals up seven levels. Much of the owner’s work is on exhibit in the guest rooms. Yes, some of the bathrooms are dated and you’ll see a scruff mark every once in a while on a wall. But most overlook those flaws (which don’t show that the place isn’t clean, it is—very!) because they feel privileged to be staying in such a unique environment.