Side by side Hotel Cipriani, A Belmond Hotel, Venice vs Villa San Michele, A Belmond Hotel, Florence

The case for the Cipriani starts with the pool. It's the largest in Venice, set inside gardens people describe as immaculate, and it turns a city built entirely of stone and canals into somewhere you can actually spend a lazy afternoon. Add the private boat that gets you into San Marco in about ten minutes and back out again before the crowds peak, and you have a genuine strategy for doing Venice without Venice wearing you down. The breakfast terrace earns its reputation too, right down to the trained hawk that keeps pigeons off the tables while you eat.

The trade-offs are real and worth pricing in before you book. Restaurant costs run well ahead of what the food and service deliver, by more than one account, and the poolside restaurant in particular has drawn complaints about slow, inattentive waitstaff and a strict dress code enforced without much grace. One long-time family flagged a genuinely ugly encounter with the pool bar manager and event security that soured a tradition spanning three generations. Rooms have improved a great deal with the recent renovation, but at least one guest found the air conditioning couldn't keep up on a hot night, which is not a small thing at these prices. The new Dior spa, opened this year, is the freshest addition and by early accounts a legitimate reason to book, though it's too new for a real track record.

None of this cancels the pull of the place. This is for people who want a resort that happens to be in Venice rather than a city hotel with a view of it, and who'd rather deal with occasional restaurant friction than give up the pool, the gardens, and that boat ride. Couples and honeymooners get the most out of it; families with young kids may find Airelles or a quieter alternative fits better. Book it for the grounds, the pool, and that breakfast terrace.

A restored fifteenth-century monastery on a hill above Florence, its facade traditionally attributed to Michelangelo, is not a normal hotel pitch, and the reviews back it up: people describe walking the cypress-lined grounds before dinner and forgetting they're 20 minutes from a city. The 2026 renovation refreshed junior suites and public rooms without stripping the monastic bones, and the *thing* people actually book it for is dinner on the loggia as the sun goes down over the Duomo. One couple got a jazz set on the terrace they hadn't asked for; a birthday guest got a staff member offering to help with a personal errand before their flight, on his own time. That's the register here: specific, staff-driven generosity rather than generic five-star polish.

The catch is real and worth pricing in before you book. You are up a hill in Fiesole, and the shuttle into Florence runs on its own schedule, fine if you want a slower trip, annoying if you're planning museum mornings and dinner reservations around it. One dinner review flagged a training gap in the restaurant staff, and a separate visitor described a genuinely unpleasant front-desk reception before they'd even checked in. A solo traveller also noted the staff kept treating a party of one as an oversight rather than a norm. None of this is the median experience, but it happens often enough that the location and the front door are the two places this can wobble.

Book a Garden Room in the main monastery, or the Limonaia Suite if the budget stretches, and treat Florence as a day trip rather than the point of the visit; some travelers even split their stay with a Four Seasons or Portrait property in the old town for exactly this reason. If you want to be walking distance from the Uffizi, stay in the city. If you want a week where the hotel itself is the destination, this is one of the two properties in Florence that people put in that category, and the dinner on the loggia alone justifies the drive up the hill.