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Josh Flagg Ranks The Best Hotel Pools in Italy

Where: Italy
May 29, 2012 at 4:43 PM | by | ()

Our resident celebrity hotel hopper, Josh Flagg is about to invade your living rooms again when the fifth season of Million Dollar Listing premieres on Bravo on June 6. But life isn't all "house" work for Josh. As soon as filming finished, he packed up and resumed his whirlwind travels. Now Josh is telling us the Top 10 Hotel Pools in Italy. As you can imagine, each night will cost you at least five hundred Euros. After you decide on a bathing suit, best ring up your favorite sugar daddy.

I just got back from a three and a half week trip to Italy and after staying in 20 different hotels and swimming in 20 different pools, I sat down and compiled a Top 10 List.

I visited all the top locations so I am sure I did not miss any. Below in the following order is my list of the top ten hotel pools in Italy, some of which are among the best in all of Europe

10. Coming in at number ten is Hotel Quisisana in Capri (pictured above). The tiny island of Capri is a 45-minute hydrofoil ride away from the port of Naples (a place which unless there is a gun put to your head, I would recommend you never visit... This wouldn't be so difficult because during the short time I stayed in Napes, I met two people that were held up at gunpoint and one that was run over by a motorcycle. I digress.)

Capri has been known as a jet set location for years and is evident by the number of designer stores located within a three block radius. In fact they have an Hermes store which is the size of a good walk in closet. At the end of the shopping street is the famous Quisisana hotel. The round pool with it's mosaic tile work that reads "I heart Quissi" is a staple of the Italian pool scene.

Be very careful in the rooms however, as the floors are all made of porcelain tile and very easy to slip on (which is evident by the fact that my grandmother slipped and broke her right hip, thus putting an end to our lovely trip and causing her to stay in a hospital on the mainland for two weeks.)

9. Le Sirenuse was made famous when it was featured in "Only You" with Marisa Tomei. Prior to that however it has always been known as a place for the rich and famous to be seen. Book way in advance though as it is a very small hotel. My father gave my mother her wedding ring while staying at this hotel in 1982, only three months after knowing each other, so this place must have a special effect on people.

8. If you like looking at big flashy boats and big flashy people, then you will surely like the scene at Cala di Volpe in Porto Cervo, Sardinia which feels like a scene out of a movie. Just think the Italian version of St Tropez. If you really want to have a look at unpretentious people, visit "The Billionaire Club" while you are there.

7. The Grand Hotel Timeo is on the Mafia-infested island of Sicily, but don't worry you won't get killed here. The hotel guards will protect you. This Orient-Express property is magnificent and so is its pool. Sicily is a lot less pretentious than neighboring Sardinia and in my opinion, much more beautiful. Try them both though. They are very close to each other so it's doable.

6. Hotel Splendido in Portofino is a class act. This hotel just oozes sophistication. The pool overlooks the bay of Portofino and is one of the most magnificent sights you will ever see. The hotel's restaurant is exceptionally good and the service is excellent. I would not expect anything less from an Orient Express hotel.

Make sure to get to the pool early though as their are few seats and a lot of demand. By the way, the hotel has two properties, the Splendido Mare which is in the town of Portofino and the Splendido which is on the hill. I stayed in both because I am just strange like that. My recommendation although they are both lovely is to stay on the hill. You will never forget it.

5. Coming in at number 5 is probably number one on the list of most beautiful hotels, but since we are just going by pools, I would put it at number 5. Set on multiple acres in the center of Florence, The Four Seasons which was a private villa, is truly amazing. The pool is set in the middle of a lush garden and while sitting by or in the pool, you totally forget you are in Florence. Check out the hotel interiors. Pierre Yves Rochon, who did the George V in Paris and the gorgeous luxury suites at the Danieli (where I also stayed this trip and was highly impressed by their renovations), did the Four Seasons Florence.

4. At number 4 is the world famous Villa d'Este. If you have never seen a floating pool than I highly suggest you come here. Set in famous Lake Como, the outdoor pool actually floats on the lake. If you like to sun and you want to be seen, then this is the place for you. Don't forget to book way in advance though, as this place fills up during the summer in a heart beat. Equally as impressive as the pools are the magnificent gardens. I highly suggest you take one of their boats out for the day with or without a captain (without is more fun) and coast through Lake Como.

3. (It's no surprise that numbers three two and one are all Orient-Express hotels. ) Coming in at number three is the Villa San Michele in Florence. Located in the town of Fiesole (a five minute drive from Florence) the Villa San Michele is a magnificent property. In fact the hotel's facade was designed by Michelangelo himself when it was built as a monastery. The grounds are exquisite and the dining room is unreal. The pool however is a sight to see.

Overlooking all of Florence and the hills of Tuscany, it is one of the most beautiful views I have ever seen. The pool restaurant which is located right next to the pool will bring whatever you want to your chaise lounge and the service is beyond excellent!

Some people like pools to be cold, but I am like an old Jewish woman from Florida and there is nothing I like more than a pool that is eighty degrees. Although not in the center of Florence, if you are returning to Florence for a second time or you don't mind the ride into town every time, this is an exquisite European property and I highly recommend it.

2. Number two is a close tie with number one and even now I really have a hard time deciding which I liked better. Number two is one of the most beautiful hotels I have ever stayed in--Hotel Caruso in Ravello, Italy.

Set on the hillside town of Ravello on the Amalfi Coast, this hotel has stunning views, and not just from the rooms. Jump into the infinity pool and float on over to the edge where you will not believe the sight you see. Set up thousands of feet above the sea, you really feel like you are swimming in the clouds. I have never seen anything like it. The restaurant at the pool is wonderful and the scene is so much fun. This truly is an incredible property with an equally incredible pool.

1. The number one pool award goes to The Cipriani Hotel in Venice. Set on a small island across the grand canal from San Marcos Piazza, take a private boat to Cipriani and immediately forget all your worries at home. Aside from the world famous cuisine, the pool and the pool scene at Cipriani Venice is simply put, heaven. Surrounded by dozens of white umbrellas and chaise lounges, the Olympic sized tile pool--yes, Olympic sized--is that much more massive once you get in it.

The pool looks like a giant bathtub as it is not recessed into the ground like most pools but rather pops up out of it. If you like a warm pool on a warm day, you will want to fall asleep in it and it is heated to 87 degrees! Have a snack or a glass of wine at the pool and you will never forget it. This was my grandfather's favorite pool to swim in and I now I know why.

If you like old world charm, incredible food, gorgeous gardens and wonderfully done rooms, then this is the hotel for you. Go to Venice in the morning, take the five minute boat ride back across the grand canal and just veg at this private oasis.

[Photos: Josh Flagg]

Archived Comments:


Been to Le Sirenuse. Always thought the pool a little small, but being on a cliff, what can you do? Always dudes in teeny tiny speedos there.

Capri Palace

The hotel at Capri Palace is nicer IMO. Big pool with ample seating areas. When I was there Cristiano Ronaldo and his crew stopped by for a visit.