As you might expect, planning a trip through most of Italy required more planning and preparation than any of our trips throughout the U.S. (especially with kids in tow). Therefore, we thought it might be helpful to others to share some of the tips, products, pre-planning and websites we found helpful.
By the time we typed up our notes, it ended up being over nine pages. However, we wanted it to be a comprehensive list, so we broke it into four categories – Planning (this page); Getting Around or Driving; Preparing and Packing; and Once You Arrive. So here we go…
Passports, Global Entry
Obviously, you’ll want to be sure you have your passports renewed – and, if you want, apply for Global Entry well in advance of your trip. There are several credit cards which now reimburse you for one Global Entry application fee per card; and it can take well over four months to get through the entire application/approval process. So, you may want to start the process as soon as you begin planning.
It is also a good idea to keep photocopies of your passports in a second secure place when traveling, as well as emailing yourself digital scanned copies. It is much better to have backups if needed.
Please note, Italy also requires copies of your passports when checking into hotels so don’t be unnerved when they take your passports and walk away for a few minutes. Plus, according to Italian law, you should always have your passports on you. It’s unlikely you will be asked by a police officer, but you are always supposed to have them and can get a ticket if you do not.
Airfare and Points
Travel is different for everyone. However, we get asked a lot how we maximize the use of points, so we will share what we found worked best – especially if you want to fly business class.
Our primary card is the Chase Sapphire Reserve as we get 3X points on travel and dining – and the points can be transferred to either Southwest Airlines (works great in the U.S.) or United Airlines or British Airways (for overseas travel). After a lot of research (and seeing others come to the same conclusion), if you want to get business class tickets overseas for a family of four – United Airlines and the Star Alliance are your best options for using points.
Tip 1 – Business Class Award Tickets are very scarce – especially if you’re trying to book for four people. What worked best was to determine our travel dates and then start to watch as United posted the business class award tickets on their site (months in advance). We then figured out what day they would be posting the ones we wanted over six months in advance and logged on that morning to grab all four. This requires some dedication but if you want to get over $10K in round-trip, business class tickets for free, it’s going to require some work.
Tip 2 – Don’t try to find business class tickets from your hometown to a city like Milan or Naples. You’re not going to find options from Cleveland to Milan or Nashville to Florence. Focus on the major airports that fly to Italy which are Chicago, New York and Washington D.C. You will find more options using those airports. Then, you will have to determine how you want to get from your hometown to those airports using points and miles (typically Southwest is a good option).
For us, it required 140K per person (70K each way) for a total of 560K points. We had quite a bit saved but needed a few more, so we signed up for two United Explorer Cards (netting us 100K more United points). With all our combined points, we were able to book business class tickets through Chicago/Vienna/Naples and back from Milan/Vienna/New York. And then we used points to get to/from Chicago and New York on Southwest Airlines. Our international flights were booked through United on Austrian Airlines – which we will say has earned its reputation for having some of the best meals you can find in business class. Truly a five-star meal and a great way to sleep on your flight there.
Special Note – Lufthansa. Lufthansa is part of the Star Alliance and may be your only option for travel. However, you can Google “Lufthansa Airline Strike” and see how often the airline has flight disruptions due to employee strikes. It may not change your plans, but it is something to consider if you feel strongly that you must be at your destinations at certain times and dates. This is another reason we wanted to find something through Austrian Airlines for our trip (plus the food!).
Hotels
Planning a trip to Italy will be completely different for every family or traveler depending upon budget, location, kids, etc. Our trip was focused on more upscale locations while accommodating our family (including two kids). However, for those without kids, we met a number of couples staying in Airbnb lodging.
Please note, Italy is not designed for families so finding lodging in Venice or Positano can be quite an adventure. If you are traveling with kids (or even not), we found the website below to be the most useful for searching for hotels in an entire area – versus city by city; which can be quite daunting in a region like Tuscany. We also appreciated the filters for type of accommodation, locations, etc.
Ciao Bambino – Hotels, Lodging
Meals and Wine
You can plan your entire trip to dine at Michelin-rated restaurants and elaborate five course meals. But the food in Italy is simply good… almost anywhere. So while you may want to splurge on an amazing meal at Club Del Doge on the Grand Canal (and it is worth it), some of the best meals we had were also those enjoyed easily by locals – pizza in the street (Antico Forno Roscioli in Rome); fresh salads and sandwiches (Casa e Bottega in Positano) or sitting on the steps with arancino rice balls with meat (Bellavita in Bellagio).
The same goes for wine. We did find some bottles of wine that were amazing (I’m looking at you Grattamacco Bolgheri Superiore!). But we also loved trying all the other wines as well – which are often much less expensive than wines in the U.S. At one point, we found we could buy bottles of wine in Lake Como for less than water at our hotel. So, we enjoyed mixing in a few nice meals along with local, less expensive meals and wines.
Breakfast
Be sure to check all your hotels for an inclusive breakfast. We found breakfast was included at every hotel we booked – which saves a lot of money and planning for 1/3 of your meals. Besides, breakfast is not usually the highlight of your day when dining in Italy so it’s best to focus on where to have lunch and dinner.
Skip the Line or “Skip the Line!” Tours
There appears to be three levels of access to the most popular attractions. The first is the normal entrance which is the longest line and might take up half of your day.
The second are Skip the Line passes which are only a few euro more and can cut your wait down by hours. If you can, you want to pre-purchase these passes at a minimum.
And then there is the third which we will call the more awkward, “Skip the Line!” passes. Many of the private guides are residents who know the staff working the entrances to the most popular places. After a few minutes of impassioned Italian dialogue back and forth – many times, they can cut in front of the rest of the line.
The first time, this “cutting the line” felt very awkward as you can feel the eyes in the back of your head and almost hear people thinking “who do you think you are?”. However, after seeing this from four different guides in four different places, it truly is more of a sense of a cultural birthright. In other words, the guides strongly believe this is their home (in many cases, going back four or five generations) – and they have the right or let’s say, belonging to the area, to bring their guests in through these relationships. After the second or third time, it begins to feel very Italian in nature and much less odd like it would in the U.S. You almost get the rebuttal in your head of “oh yeah, well she ACTUALLY LIVES here and that’s why she can get us in faster”.
Lounges
We are not usually big fans of airport lounges; as we are often just traveling between one city and another. But when going overseas, there are likely going to be several lay overs – and getting a free meal, clean restroom and some water is a welcomed perk.
If you booked your ticket as we noted above in Business Class, you should be sure to check for business class lounges in each city you visit. Not only can you get a chance to rest a bit, but many of these lounges will help to verify your documents (versus standing in line at the counters) and/or track your luggage to be sure it is still with you at each stop.
If you are not flying business class, be sure to check to see if any of your credit cards offer the Priority Pass benefit. Many of the top travel credit cards include this pass. You will need to sign up a few weeks prior to leaving to get your card in time. This pass will give you access to several lounges at no charge. One we found particularly unique was the new Gameway lounge at the DFW airport which provided bottled drinks, snacks and a few hours of playing video games (Soccer and Mortal Combat) up until our flight time.
If you are a planner, researching the lounges you have available and where they are in each airport is worth a few minutes.
For notes on our entire trip to Italy, here is our two-week Itinerary. And, if you are just starting to plan your trip, we have created four “how to” guides – Planning, Preparing and Packing, Getting Around and Driving and finally Once You Arrive.
We also have detailed notes for each individual destination for Positano, the Amalfi Coast and Capri; Rome and Pompeii; Tuscany, Siena and Florence; the Palio di Siena; Venice and Lake Como. We would love to hear if you found any of these pages and notes helpful – or if you have any feedback you would recommend for other travelers.
