But over the years, the San Carlos has fallen out of fashion. Beyond the outdated rooms and amenities, there's been a revolving door of eateries over the past decade, none able to sustain a loyal following.
The hotel is currently under extensive renovation, though, with plans to bring it back to its former vintage glory. And next month, a new restaurant opens, with its owners promising to bring to downtown a hip destination much like Miami's trendy Delano Hotel in South Beach.
"I just love the San Carlos," says partner Stephen D'Amico, who owns another restaurant in Boston. "It's real funky. We want a real cool crowd."
The restaurant, called Prevé, will offer a menu of Italian and Mediterranean cuisines. The decor like both the San Carlos and Delano will be art deco.
D'Amico and partner Andrei Nazarov who plays left wing for the Phoenix Coyotes are also opening an adjacent cafe, offering Italian coffees, pizzas and sandwiches. A third-floor, open-air swimming pool is being turned into a bar.
Check It Out: A friend was cranky the other day, wondering why his takeout order included a 25-cent surcharge per item. Likely it was to cover the cost of the takeout containers, I told him. Sure, it's cheesy, but running a restaurant is a business, after all.
And at least it's not like the creative charges I'd found at many of the restaurants in Cuba. There, it's not uncommon for a visitor to be charged by passers-by on the street just to tell them where the restaurant is (many of Cuba's eateries are paladars, run out of private homes with no signage).
Once inside a cafe, it's not uncommon to be charged extra for rolls, butter, water, salad or vegetables on the side (even if the breadbasket and water arrive unsolicited, and the menu lists an entree as including salad or vegetables). If there's live music playing and usually there is the musicians demand a tariff.
And, if we want to use the rest room, it's free. But there's a charge if we'd like any toilet paper (great fun the first time, when we're already, er, under way, before we learn the drill. We have to buy the paper in advance, outside).
The surprise charges often add about $5 to each bill. Makes that to-go carton charge seem like a bargain.