REQUEST - Insight on trip to Italy - *****Updated with trip results

So, I've got one of those few times in my line of work where I'll be transitioning from one major project to another, which provides an opportunity to take a "significant" (for me, 8-10 day) vacation without having 8-10 days of work pile up while I'm gone.

We're strongly considering Italy.

• Dates of travel are mildly flexible (a couple of days either way). June 1 - June 10.
  
• Departure city: We live in Huntsville, AL, but can easily fly from Huntsville, Nashville, Birmingham, ATL, St. Louis, and Louisville.
  
• Destination: Italy. At this point, we're really that open...details to follow below.
  
• # of people: Me (36) and wife (33).
  
• Budget: $2k-$5k. I've got 149,800 miles on American that are burning a hole in my pocket, so I'm hoping to use those and keep cash cost down.
  
• Activities: Would like to see historical cities, buildings, art, and the like. Nature is good, we're fit enough for hiking, biking, etc. Food. Culture. Beach/sea. Fishing. All of these things are good, so any combination thereof is acceptable.
  

Also, last time I went on a significant vacation, I used a travel agency who was able to get a better deal on the trip I had in mind than I could price, and also offered some valuable insight into were to go and where not to go. That trip, however, is my only experience with travel agencies. Would they be able to (or, open to) helping to plan a trip using airbnb (or some similar set of potential lodging options)?

Lastly, I'm certainly willing to hear any general comments on "do this" or "don't do this".

Thanks, folks.

Edit: Insight on how to get the best bang for my buck on the AA miles is appreciated as well. Best to call AA since I have so many departure options (after I figure out a destination airport or two)?

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Trip Results
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Some asked, so here's where we ended up...

Primarily due to the most effective use of AA miles and in an attempt to have more time in Europe than in airports, we decided to pass on Italy and instead made it from Huntsville to London, Brussels, and Amsterdam.

We flew to London, arriving at 0600. Of course, using AA miles, we got bounced around the county from HSV to ORD to YYZ to LHR. The transatlantic was on British Airways, which was much, much better than AA on almost all fronts. We arrived on Friday, June 1 in London. We were able to leave our bags at our hotel before check-in with no issues. We powered through that first day without a nap to try to shorten the jet lag effect, which was a great thing to do.

We were in London for the 1st, 2nd, and 3rd, leaving on a 8pm flight to BRU, so we basically had 3 full days. The tubes in London were very easy to negotiate, even for people like us with zero public transport experience. We were, by chance, there for the Queen's Jubilee and just prior to the Olympics, so the city was noticeably clean, with lots of police, so we felt safe the entire time.

We got to see all of the "big stuff" in London without too much difficulty, although another day wouldn't have hurt. British food is as bad as you've heard. Other than fish n' chips, we stuck with ethnic foods (Italian, Asian, Greek, etc.).

The British Museum is absolutely ridiculous. Each of the 80 or so rooms had enough significant historical artifacts from around the world to have been a museum of its own. By the end of our four hours there, we were blowing through rooms that were filled with amazing pieces; to be honest, our brains could no longer effectively process the history we were seeing...it was a weird feeling. If you are into world history, plan a full day there.

Westminster Abbey was also very impressive. We did several other walking tours from the TripAdvisor London App (Android). By the way, having a wifi tablet was priceless for the whole trip. Google maps for public transport directions from site to site, Skype-ing the kids back home, TripAdvisor Apps specifically for London and Amsterdam, general TripAdvisor App for restaurant and activity reviews, etc., etc.

We flew to Brussels on the night of the 3rd (Sunday). Contrary to what we read, Brussels is not as English-friendly as we had expected. Many people had passable English, but many did not. Almost all of the public transportation information was in French (thanks, again, Google Maps). Brussels was a nice enough city, but unlike London and Amsterdam, I'm not strongly drawn to return. Speaking in a sweeping generalization, the people in Brussels were not as welcoming as our other two destinations. Food was good; they don't call 'em Belgian Waffles for nothing. Chocolate was delicious, too.

We arrived at 10pm, which was a little too late. Since all of the train/tram info was in French, the public transportation ended at 11pm, we couldn't find anyone who could speak English and wanted to be helpful, and we didn't have WiFi in the airport, we ended up taking a taxi to our hotel, which cost about $60USD. Taxis over there are very different: well-dressed, well-groomed men in Mercedes, driving 60-70 mph down empty downtown streets. It was an adventure.

There obviously weren't as many great attractions in Brussels as were found in London, so we were able to take a day trip to Brugges, which is a very nice trip. Some good things to see there, and lots of free wifi. We stayed at the Hotel Centrale, which we would not recommend. It wasn't terrible, but left much to be desired, other than location.

We had not prearranged our train travel from Brussels to Amsterdam, but knew we would leave on Wednesday, June 6. We wanted to be able to get a feel for Brussels and decide if we wanted to spend most of the 6th in Brussels or in Amsterdam. As it turned out, we did about 50/50, leaving via train at about 1:30pm.

Amsterdam was great. Everyone, and I mean everyone, is fluent in both Dutch and English, and they are generally welcoming and helpful culture.

One or two folks below had suggested that we look into airbnb.com for lodging for this trip. I was into it, but wife had read some horror story reviews, so she wasn't into it. To avoid the possibility of being one of those horror stories and having to live with the "I told you so" scenario for the next 20 years, I decided to not book anything through airbnb...I let her book all of the rooms. For Amsterdam, she booked an apartment in Leidsplein, which was very nice. After she booked it though TripAdvisor, I subsequently found it on airbnb. After we checked in, and she liked it, I pointed it out on airbnb, so maybe we'll give that a shot next time.

Anyway, lots of cool stuff to do in Amsterdam. We were there from the afternoon of the 6th until our flight out on Monday, the 11th at 6pm. It was our goal to have a longer stay in a relaxing city for the end of the trip, so it didn't feel like an exhausting Amazing Race for the whole trip, and we met that goal with 5 nights in Amsterdam. We bought the Museumkaat (a card that gets you into 400 museums in Holland) and used it quite a bit. This time of year, sunset is at 10pm and it gets dark around 10:45, so we had a lot of daylight hours to walk around. We bought passes for the public transportation which was nice and necessary. It was not as user-friendly as the tubes in London, but after a couple of days with Google Maps helping us out, be got the knack of it.

Lots of old churches to tour, canals to walk down, and museums to see. Windmills were few and far between, but nice little cafes and pubs were plentiful. Although hookers and weed aren't really our thing, a couple of strolls through the Red Light District were enlightening. We did almost everything suggested by the TripAdvisor Amsterdam App over the six days.

We flew from AMS to LHR, then on to Boston. We stayed in the airport overnight in Boston (from 10pm to our 6am departure). It sucked, but was better than shelling out $300 for a hotel near the airport for what would have been four hours of sleep. Went from Boston to ORD, then ORD to Huntsville, arriving yesterday (June 12) at 10pm. A day later, we're still waiting for all of our luggage that somehow got stalled in Chicago.

All-in-all, the flights cost 140k miles + a ridiculous $1425 in taxes/fees.

We were glad to get home to ice (if you get two small cubes over there, you're lucky), American-sized drinks (a "large" coke at McDonald's over there is equivalent to our Medium with no refills), and free toilets (it costs between $0.30 - $0.60 to use a toilet over there, even at McDonald's). In all seriousness, we really had to work to not become dehydrated; drinks are tiny and expensive. We carried a couple of water bottles, but it sucks to pay to pee, so you're in a bit of a Catch-22. We were sure to pound water each night before bed that we could unload for free in our room in the morning.

If we had to do it again, I don't think we'd change much. Maybe be more open to airbnb. Maybe replace Brussels with Luxembourg, which may or may not be an improvement.

Thanks again to those who gave advice below. It really helped to make this a great trip on short notice by a couple of international rookies.

1) Not enough lead time to plan this trip effectively;

2) Not enough time on the ground to make this trip enjoyable;

3) Not enough contributions to this forum over the last 10 years to motivate me to offer additional advice.

You are going to have a hard time finding AA frequent flyer miles seats open for that prime time of year. We are going to Italy in June (from DFW) using AA miles and I booked them back in early August 2011 shortly after June 2012 opened for spending miles and still had a hard time getting seats and the flight on the way back has a long lay over overnight. Better check the miles options quickly to see if it is even possible.

Renting apartments is a great way to go. I have used Homelidays (just Google it, it is a European site so tends to be better deals than some other sites) in the past with good experiences and have used them to book apartments for Italy. Many do have a minimum of 4 or 5 nights though.

Tripadvisor.com forums are good sources of information. Besides that, buy a guidebook such as Rick Steve's for each city you are visiting and pick out what you want to see etc.

Trains for travel between major cities is good. Mass transport is good in the big cities. Seems public bus is big there with metros (subways) being more limited in say Rome.

For 8-10 days, I would not do more than 2 cities so you can see them good and keep in mind travel time between cities.

Hope this helps a little.

solley said:   Very helpful, davido. Thank you.

I was checking AA this morning and 60k miles seats were available for every day around my dates. There was one leg (home) to one airport that was only 20k, which was a real surprise. So, at best, it looks like I should be able to get at least one of us there on miles. I agree that we'll need to pull the airfare trigger quickly, so we're narrowing down cities quickly.

Thanks again for the insight.

Sounds like your search is pretty fruitful for 40 days out. I just did a quick search ATL-LON, and if you're willing to do a LGA-JFK transfer in New York, you can get on 60K seats (RT, 30K per direction). From London, you can get to most of Europe on cheap airlines (Easyjet, Ryanair, etc), but I know taxes on BA to London can be outrageous, so be watchful of that on AA.

solley said:   dukerau said:   solley said:   Very helpful, davido. Thank you.

I was checking AA this morning and 60k miles seats were available for every day around my dates. There was one leg (home) to one airport that was only 20k, which was a real surprise. So, at best, it looks like I should be able to get at least one of us there on miles. I agree that we'll need to pull the airfare trigger quickly, so we're narrowing down cities quickly.

Thanks again for the insight.

Sounds like your search is pretty fruitful for 40 days out. I just did a quick search ATL-LON, and if you're willing to do a LGA-JFK transfer in New York, you can get on 60K seats (RT, 30K per direction). From London, you can get to most of Europe on cheap airlines (Easyjet, Ryanair, etc), but I know taxes on BA to London can be outrageous, so be watchful of that on AA.

Now that's what I'm talking about. Didn't know to consider just getting to Europe and then hopping to where we need to go. Will add that option to the mix. Thanks again!

Admittedly, when I looked at getting from London to Italy for your time period, it was pretty expensive. In my experience, it's worth looking into flying into London, Dublin, Madrid, Rome, Paris, Brussels, and Frankfurt.

solley said:   Having never flown in Europe, what is pretty expensive? First place I looked had options around $230/pp RT from London to Rome. I would not have expected "way" cheaper than that...

That's not too bad - I was seeing more like $400pp RT. If you're looking at a multi-city trip (and with such a short time frame I would limit to 2 cities max), make sure you price out doing London-one city and then return other city-London. One-way pricing is not marked up on the European airlines I'm familiar with.

ETA - I've never flown London-Rome. $230 could be a great price. For reference, I booked an Easyjet one-way flight for my wife and I for 6/1, Amsterdam-Edinburgh for $60pp. Back in 2007, I flew Santander (Spain)-Rome RT for 69 euros on Ryanair.

We flew into Dublin, last year and then flew Ryanair into Italy. You might consider a B&B also.

stevie123 said:   I kinda agree with DSJ.. Not to sound discouraging, but from your initial post, you (and wife) doesn't sound like experienced international travellers, and you want to plan an ambitious trip to Italy with about a month's time... anyway, some FW advice:

- Your "plan" (more like an idea) is definitely doable, but you have some work to do now.
- Your biggest cost will be airfare. If you can get your tickets with miles, get them now! Note any strings (cancellation policy, change policy, trip insurance incase you get sick last minute, etc..)
- You don't need to fly into Rome. You can fly into any of the major EU cities and then take another low cost carrier or a train there.
- Time constraint/realities: 10 days is barely enough to see Rome AND do the other stuff you describe (relax in some small costal town). Remember that your travel to/from Europe will take a day each. Travel time from Rome to/from the small towns will take a day each (so thats roughly 4 days wasted on "traveling"), leaving you with 6 days of real sightseeing and fun.
- Energy constraint: Remember that you have to account for jetlag, unfamilar climate (air),language, food, water, foreign bed, etc. Just because you and the wife is "fit enough for hiking and biking", you are looking at 10 continuous days of activities.(both you and your wife). You want a relaxing vacation, or to play "The Amazing Race"?
-There will be A LOT of planning - flights, train schedules, lodging at 2 different locations, and then what to see/do when you get there.
- Do you and your wife have a valid passport? Get it now!
- Will you be comfortable driving in Italy? Everyone in the city (and highway=autostrada) drive like they're Mario Andretti. Don't rent a car in Italy... Driving is very different there compared to where you currently live. You don't want the hassle of a fender bender.
- June is hot and humid in Italy, but then again, you live in Huntsville, AL, so you'll be fine.
- June is tourist season. Its not as bad as July/August, but expect crowds and high prices.
- In my very personal opinion, forget the fishing/hiking/beach things. Italy is not famous for those....Concentrate on the pretty buildings, old cities, the food, and the people. (culture) You can get better fishing/hiking/outdoor stuff in USA! (think California, Utah, Alaska! just to name 3 states out of 50)
- AirBnB, in a nutshell is like Craigslist for lodging. Are you comfortable with staying in someone's home? Sharing the bathroom/shower/kitchen with other people? (often other tourist) (Its not very different from living in a Hostel...) Some people like the social aspect... some do not.

- Instead of reading a guidebook, visit tripadvisor.com for some general ideas/review on popular tourist sites. flyertalk.com will have invaluable advice on the logistics (flights/train). Other notable sites include lonelyplanet, Frommers, etc.
- you may have hotel points. Use them to your advantage (in Rome, or another big city)... In fact, it is not too late to go apply for a Marriot or Priority Club credit card now for some extra points. The Priority Club credit card has no foreign currency fees, so that will be good for your trip. (Otherwise, expect 2-3% added to your Italian credit card expenses) The Marriott card will give you free hotel night immediately AND 70K points. If you apply today, you'll get the credit card and points before the end of May.
- Like most cities hosting the Olympics, it will be expensive/chaotic. Don't go to London this summer.
- There is an android app from Traveladvisor for Rome. It list the most popular sites and locations. What I find the most useful is that it will "point you there", with a compass and map. This is extremely beneficial since the data/map is already downloaded on your phone, so you won't be eating roaming data charges on your smart phone!
Regarding your question about AA: Go the the flyertalk forum for AA, and you'll get 100x better advice then you will here. (Flyertalk is the world's biggest/best english forum for these topics), but from what you already wrote, i think you know enough to book the lowest cost award ticket. My only advice is not to be greedy and pack too many destination/acitivities in your trip...flying is a hassle any way you look at it (checked luggage, security, etc.) Italy is small (compared to USA), and taking the train is better and not difficult.

Good luck, and let us know how your trip plans end up.

Wow. Great post. I really appreciate your time.

We're making great progress, thanks to posts like yours and some others above!

See the update in the OP with the end results of our trip. Thanks again for the helpful insight.

Airline miles usage was driver #1 and lodging cost was #2. We tried to get to Paris initially, but we couldn't find a good way to use miles to get there, without having to spend many, many days there (6+, as I recall), which would cut us from three different cities to only two (due to length of time we had available), and lodging in Paris was more than double (closer to triple) all of the other cities (LON, BRU, and AMS).

We opted to save the lodging money we would've had to spend, so that we could treat the rest of the cities as essentially "all-inclusive". In other words, with the $1,500 or so that we saved by not being in Paris for 6 nights, we were able to eat/drink/visit/do pretty much anything we felt like in the other cities. Had we gone to Paris instead, I think we would've had to be much more cost conscience while we were there, which makes vacations much less enjoyable for us.

After Paris was eliminated, we were pushed to Brussels in an attempt to try to get a 3rd cultural experience into the trip (vs LON and AMS), which we were successful at...it just wasn't an overly enjoyable cultural experience. We liked it and we're glad we went, but as I said before, it won't be high on the list for our "return to Europe" trip that we'll get to take in about 50 years when all the kiddos are out of school.

weblogger said:   your update was great solley, thanks for a good read.
pay money for a toilet?
wow.Fairly common in parts of Europe, we saw that a lot in Croatia, Solvenia, etc. - it was like $0.10 or so and they were very clean public restrooms.

You must be young, not that long ago that pay toilets were common in the U.S.

jfdhdh said:   Very beneficial, davido. Thank you.

I was verifying AA today and 60k kilometers carseats were available for every day around my times. There was one leg (home) to one terminal that was only 20k, which was a actual shock. So, at best, it looks like I should be able to get at least one of us there on kilometers. I acknowledge that we'll need to take the air travel induce easily, so we're consolidating down places easily.

What's your story, guy? Repeating my post and swapping kilometers for miles, etc.? I see you've done this type of thing on several other threads. What gives?