Perche

You are going to expensive cities. A reasonable place in Positano is Casa Cosenza. It's a B&B, which saves a bit, compared to a hotel.

If you get one of the rooms with a balcony, you can't get any more romantic than that.
http://www.casacosenza.it/english/Default.htm

The view is twice better than the view at the high end hotels, at least the ones that are walkable to the main area and shops, at half the price. Overlooks the beach, the old town, church, the islands, etc. A hidden gem for the price.

KLouis

To the OP: You are aware of the fact that Pompei is between Naples and Amalfi? If you tell anyone that you spent 4 days in Positano or somewhere closeby and did not see Pompei, they'll think you're nuts!

PWMTrav

Ostia Antica's a pretty interesting day trip from Rome, too. I can't really compare it to Pompeii though, since I've never been to Pompeii - and you're right, they do think I'm nuts.

thebill0322

Looking at some of the other suggestions in posts around flyertalk for a positano hotel and saw some different ones mentioned.

Couple questions:

Is it better to stay on one side of the city vs the other? Like the Villa Rosa side or somewhere closer to your casa concenza side of the city? how easy is it to get down to casa concenza area (at least from google maps it looks further from the road.

Villa Rosa Opinions?
miramare?
Alcione Residence? This one seems interesting at a decent price.

Other around 250-300/night hotel places to look into?

The choices are quite overwhelming when you start looking into it. And everyone has gorgeous views in pictures but its really hard to tell like is that their top of the line suite or something.



I think we would be consider pompei if we were in the area.

Perche

Don't over think it. Almost everyone who goes to Italy, especially where you are going, will have a great time. Just lay your money down, go, and don't look back. Don't over-think. You are on vacation. You already have received a lot of great suggestions. Just do it. You will never know for sure, until you do it on your own. These are just guidelines. Go for it, don't look back, and report your experience to the next traveler.

PWMTrav

thebill0322, I know I'll never convince you of this, but I do promise that if you maybe just planned out 3 cities and just played the rest of the trip by ear, you'd still end up pretty happy What I'm trying to say is, don't sweat it if the plan doesn't come together entirely.

My first trip to Italy was planned to be Rome-Florence-Genova-Venice-Rimini-Alfedena-Rome. In 12 days. We were having fun in Florence so we cut Genova. Then the trains literally caught fire on the day we traveled to Venice, so we lost a day there and decided to make it up by cutting Rimini and Alfedena.

Plan for what you want now, and don't feel bad about making changes on the fly when you're there. Maybe book more flexible hotels - point stays usually are flexible to begin with - and changeable train fares.

The choices are a lot like shopping for a car. You start to split hairs over feature X over feature Y, but then you buy one and the comparisons go out the window, when you'd probably be happy with either one.

sophiesophie

Do not try to do Cinque Terre this trip.

I was in Italy last September. I took a train from Florence to get to Rapallo. On one of the legs, I missed the connecting train by a minute (there was a 7 minute gap which I thought I could make - but it was not enough time!) and had to take a a different route thru La Spezia to get to Rapallo (little farther north of CT) - this detour took me almost 6 hrs to get to the area. My plan was to visit CT the next day. I ended up going to Portofino and Santa Margherita instead. I met a couple from England who had been to CT the day before and they HATED it - it was wall to wall with tourists! They were sorry they went. September is a busy tourist season and quite warm. I would just plan to go back for a second visit (which you will!) - when there are less tourists (early November?)

Lkeade

We are also going to be in Florence and Rome in May, so any restaurant recommendations would be greatly appreciated.

Murphy123

We have stayed at the Metropole - but just for the night of arrival on 4 occasions. The cab fare mid-day from the airport was about 13 euros. If the Hilton Metropole was located in "old" Florence as opposed to "new" Florence, the rate would be much higher. It is not the Excelsior but to classify it as a "basic" hotel is not correct either. Note that there is an "ironing room" in the hotel. We then moved to the small B & B where we normally stay - the innkeepers also own a small B & B in Chianti so we spend half of our time there are well.

Be careful with your room assignment at the Metropole. My husband was Gold on our last stay 2 years ago - and trust me, it was our last stay. We will now drag ourselves directly to the known B & B. It was just nice originally to have the first night in a North American style hotel.

There is a shuttle that runs from the train station (I know the location of the shuttle changed I think last year) to the hotel and back. But note that it is first come, first served and it does not run during the siesta period and stops running at a certain time of night. It does not service the airport.

The HGI does not have a shuttle and the cab fare would probably be about 30 euros from the airport. It is a more basic hotel with laundry facilities. There is a local bus that runs downtown.

I do think that you are trying to squeeze too many places into your trip - but to each his own. We prefer the Tuscany area so now limit ourselves to that area - we have been north and south in the past.

Re food - avoid any place that has pictures of food outside or the words "menu turistico".

dkelly1110

As stated upthread, my wife and I love to eat and drink great wine. Italy was a home run for us in that sense (and many others). We did extensive research on Chowhound and used both Katie Parla and Elizabeth Minchilli's iPhone apps both before and during our trip. Except for where starred below, I would make reservations at these restaurants (we used the Amex Plat concierge service to do this for us well ahead of time). Be careful, as some restaurants are closed on days you may not expect, particularly Mondays and some on Tuesdays, so you will have to jigsaw some in. Prices vary here - some were inexpensive, some were moderate, and some were splurges. However, the Euro will very likely be more in your favor than it was in May 2014 (approx 1.40 USD - now trading closer to 1.18-1.20 USD).

If you made me choose one or two from this list for the best experiences .. Cesare al Casaletto in Rome (bit of a trip from the city center but fabulous) and either Sostanza or Il Santo Bevitore in Florence.

I really owe Chowhound a huge review post that maybe I will attempt this weekend. If so, I will link it here.

Venice
Osteria Alle Testiere
Bancogiro
Al Covo

Florence
Lunch
Nerbone at Central Market *
Ino *
Trattoria La Casalinga

Dinner
Sostanza
Osteria De' Benci
Buca dell' Orafo
Cibreo Trattoria
Il Santo Bevitore

Rome
Lunch
Armando al Pantheon
Nerone
La Campana
Pizzarium *

Dinner
Salumeria Roscioli
Sora Margherita
Cesare al Casaletto
Pizzeria da Remo *(believe reserverations not accepted)

apagan4182

I'm certainly no expert on Italy, but I've started researching too as my wife and I are going there in August. Our itineraries seem pretty similar, and for the Naples/Amalfi Coast area, I think we have decided to stay in Sorrento. From what I've read, it's a great location logistically for what we want to go do (Day trips to Naples, Positano, Pompei). They have a Hilton there as well, if you're looking at a points redemption.

Perche

I would agree that staying in Sorrento is OK if it is free on points, but as for visiting Italy, it is not a good choice in my opinion.

It would be hard to find a place more touristy. Almost all of the shore in southern Italy is beautiful, including Sorrento. Of course, there are a lot of touristy areas in Rome, Florence and Venice, but at least you can walk away from them if you know where to go. In Sorrento you cannot. It is like going to Olive Garden - there is almost nothing authentic about it left. It's OK for a night or two to use as a jump off to other places, but as far as Italy goes, it is tourism central.

Expensive trinket shops selling jewelry and fake handbags, gelato advertised as fresh that is made in a factory somewhere, full of artificial ingredients; tour buses, and cruise ships. It is unlikely that that you will hear the one Italian word spoken, it is that touristy. It's sunny and pretty, but it's also as if you never left the USA except that with very few exceptions, the food costs twice as much and is worse in Sorrento (No one is going to serve a top notch meal to tourists they will never see again, and who will think that it is divine no matter what.).

If you can do it on points there is never anything wrong with something that is free, and Sorrento in August is sunny and pretty. However, it is not a good place in and of itself, compared to other places in the region.

thebill0322

I really considered the Sorrento hotel when I first looked because of points. They even have 24,000 + 90 USD rooms which is a steal for a redemption.

With deciding to do the free nights in florence at not the greatest location hotel frees my budget up to spend a little more to stay in a nice B&B in positano, which in my wife's eyes is a dream. I think just visiting Positano while home basing in sorrento won't feel as authentic to her. Sort of Peche's argument (which I agree with) about staying at the Hilton in Florence, not really being inside the city to get the culture. Unfortunately budget must make this decision for that portion. We will still do our best to enjoy the city though I am sure! Plus we are in great shape for location on Venice and Rome.

Narrowed our Positano choice to the Villa Rosa or the Alcione Residence. Any last comments about the two before we decide tonight I am all ears! I like the location of both being pretty close to bus stops. Seem to have decent views and a good compromise on location close to restaurants, shops, etc.

PWMTrav

Hey, you gotta do what the wife wants too - and quite honestly, a B&B in Positano will be a great experience. Are you considering Casa Cosenza? I've never been, but it's on my list based on Perche's recommendation.

Out of curiosity, is there a cash rate in Florence that you would be comfortable with in the budget? I'd be willing to poke around and see if I can find something decent in that price range for you. If it's gotta be points, I understand that too. I'd rather you blow the money on food and wine

Perche

Your wife is right. You cannot day trip Positano. It's about sitting there on the beach, or up on the side of the hill for days, languidly soaking up the beauty, until the culture gets so under your skin that you never want to leave. You will have to leave, but if you stay in one spot long enough you will be able to carry a piece of that culture back home with you, and it will change you. It will make you part Italian, regardless of where you are from.

It's not about getting on the bus or the train to get to the next spot on a TripAdvisor list.

It's like Venice. If you only have one or two days, you might as well skip it, because you won't understand it. At Boscolo, a hotel I don't know, but in a neighborhood I know very well, the location will help make up for the short stay, at least in part. Great neighborhood to stay at. It is at least a 20-25 minute walk to San Marco, not counting time getting lost.

A lot of gondoliers live in that neighborhood. It is one of the few places that has the same rhythm and feeling that Venice has had for centuries. The sheet thread count, the breakfast, the friendliness of the guy at the front desk, his ability to speak english, that I don't know. I am just saying that you will be in a great neighborhood.

Go out and get lost. The church Madonna dell'Ortho is almost right behind you. It was a neighborhood church well before Columbus discovered America. I'm more into music than paintings, but Tintoretto lived in that neighborhood. He did a lot of great paintings in Venice, they are hanging in San Marco and in other neighborhoods, but his best work is there. I'm not an art expert, but this is a church where the beauty can knock anyone into submission. It's dark. You put a euro into the slot next to any of the altars and it will wake up an old man who will come out and turn on the lights so you can see, but if you try to take a photo he will chase you out.

Staying in Sorrento, and taking a bus back and forth to Positano, would be downright ugly, so obey your wife.

Go to Positano, near, but not on the beach, and don't look back. Don't question yourself. It's hard to screw up Italy in September. The only possible mistake is trying to cram the whole country down your throat in two weeks. You are doing fine so far. Keep trimming. You and your wife, sitting on the beach in Positano in September is going to be pretty hard to beat for a lifetime of memories, barring something strange like an earthquake or a freak storm. Relax and go for it, it doesn't have to be perfect. You will make it perfect.

Dall'Ortho neighborhood in Venice, ICH in Rome, stay out of Sorrento and go to Positano, this is what dreams are made of. I'll leave Florence out of my comments, because others are better able to comment on that than me, except to say that location is everything. You don't want to walk out of your hotel and find out that you are standing next to a highway. Even though it was on points, you won't be happy. So far, except for Florence, you are doing pretty well.