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Italy in 2 Weeks

My husband, Matt, and I absolutely know why people go back to Italy year after year – you cannot help but fall in love with the country, the culture, the people, and, well, EVERYTHING! And how has it been almost a month since we have been back home too?

My father-in-law won this trip to Italy, pre-Covid, at an auction and never had the opportunity to use it himself. He gifted it to Matt and I last year for our Wedding, and we only had until November of this year in which to use it. With it being a whirlwind, and a FAST year (seriously, how are we at the end of October), we found this out when we started the planning process in late April, beginning of May. Needless to say, we needed to get this booked ASAP. 

And by plan, I mean contacting the travel group who put the details of the trip together! FYI: If you are interested in offering a travel experience for a local fundraiser or auction, check out AmFund.

It was not until mid-June that our travel was set, and (most) of our flights were booked. This gave us, roughly, 3 months to start really planning and exploring all of our various options. P.S. Yes, we would have started a whole lot earlier!

September was the perfect time for us to go, even if we only had a few months to plan. Not only is it one of the recommended/ideal time’s of year to be in Italy, but we celebrated our 1 year Anniversary (even though it was mostly on a plane) and Matt’s Birthday was a weekend long celebration in Tuscany! 

In front of the iconic Duomo in Milan!

I am much more of a planner than my husband; he prefers to start looking at things a day or two before and, mostly, when we get to our destination. What’s funny is that we end up going with most of the places he scouts out anyway – he picks some amazing places! Maybe I should just focus on what I will be wearing and leave the rest to him!

As much as I could go on and on, let’s get to the fun! Where did we go, what did I pack, some must-knows, and some of the fun places we checked so you can check out the next time in Italy!

First up, where did we go? 5 locations, 2 weeks (September 16th-30th), and 2 countries!

Milan, Maranello, Radda (in Chianti), Rome, & Madrid

Next, some must-knows!

#1: Transportation

This was HUGE! Since we were headed to 4 different areas in Italy, and a quick trip to Madrid, each city presented us with something new and different when it came to transportation. I cannot stress this enough – make sure you are well aware of the transportation options prior to leaving! A lot of the itinerary presented to us from the travel company made it seem that travel to and from was a piece of cake, and everything was easily accessible (and quick for that matter). 

When arriving in Milan after a long day of travel, it would have been lovely to have had a car waiting for us at the airport. In fact, Matt even asked if “a driver with our name written on a sign” would be waiting for us. We ended up getting an Uber – which was totally fine – but it was a little chaotic. Mind you, we were hungry, exhausted, in a new city, and just wanted a shower, cocktail, and something other than plane/airport food. Once in the city, it had lots of available taxis, and most places you went would call one for you upon request. Italians are just the sweetest! 

Here is a “taste” of the 1st of many amazing burrata & pasta dishes during our 2 week trip!

The town of Maranello was a different story. Taxis were few and far between and getting ANYWHERE was a bit of a challenge. We ended up going to the same restaurant two nights in a row because they offered a shuttle service to and from our hotel. Otherwise, we felt a little trapped. When in Maranello, make sure to get your own car. I repeat, when in Maranello, make sure to get your own car. Maybe even a Ferrari.

The quaint village of Radda!

The train ride to Siena – to get to Radda- was relatively easy but the connections made for a LONG trip and the wait for a taxi once there was about 30 minutes. We were told that transportation in Radda was not the easiest; luckily we could walk everywhere but we made sure to hire a driver to get us to the train station upon our departure. Both Rome and Madrid had easy access everywhere but make sure to keep an eye on the meter when you get in the taxi’s, especially in Rome. Some of them started at $15 with no real explanation of why. 

#2: Make Reservations

For the most part, we had absolutely no problem getting into places. There were some we tried that were completely booked which was understandable. If possible, try to map out a plan close to when you arrive or the day when you arrive. There is no harm in booking a reservation and then canceling if needed. Always better to have than not to have. Oh, and always make sure to find a fabulous lounge for aperitifs/cocktails prior to dinner. You get to see some amazing hotels/parts of the city you may not have seen before! Who does not love a rooftop bar? 

Side Note: Most places close in the afternoon before they reopen on the later side – some even at 8:00 pm. Be mindful, especially when traveling to a new city and getting there on the later side. We found ourselves starving upon arrival, and very limited to what we could get past 4:00 pm. 

#3: Clothing

The jury is still out as to whether I would take a carry on again for 2 weeks. I take that back; I would do a carry on if we did another whirlwind trip with many destinations or going to an island where it is bathing suits and CASUAL. I do agree, it does make for easy transportation to and from. 

I, of course, wanted to stay as fashionable as possible while there and started to feel a little wardrobe crazy by the end. I felt I had mixed and matched pretty much everything I brought. We did utilize laundry service at the hotel a few times, and Matt reminded me that we are tourists, not locals. Yeah, yeah! Another thing I was not really expecting was the weather. Janine, when it says it is going to be 85, it does not mean their 85 is cooler than at home. It was HOT, which made for a couple outfit changes everyday and not getting to wear certain pieces multiple times. 

Make sure to bring some athleisure for morning breakfasts. I tend to only pack my nice pieces and that was always fun when your husband wanted to go eat as soon as we got up. My routine is a bit different but I was a team player. One morning I threw on my jacket over my pajamas and called it a morning. The lady at the table next to us made sure to tell me I looked “tired.” What does one say to that comment? Thank you?

As for pieces, my Misa and Ramy Brook dresses and separates I packed worked/traveled beautifully, and I would certainly have done a few more. Cotton dresses that can be layered and dressed up, as well as more casual tees, would have been great. The lady jacket I purchased from J.Crew was only worn one night and was not even really needed. But, it is a lady jacket and you just never know when it would be needed! Here is a “brief” rundown of everything I took with me:

Jenni Kayne Cashmere Everyday Sweater & Bevy Flogs (Travel): This sweater will pill initially but it came out beautiful once I took to the dry cleaners post return home. 

White Denim Jean

Cropped Boot Denim

Faux Leather Shorts 

Chambray Shorts

Vintage Tee

Dressy Tee

Fun Sleeved Tee

Light Sweater

Cotton Blouse

Silk Blouse

Evening Dressmy recommendation is to pick one with a fabric that travels well (and pack 2)

Skirt & Blouse Combo that can be worn 3 different ways!


Rain Jacket

Lady Jacket


A handful of jewelry pieces that could go with everything

Casual yet fashion forward (and comfortable) sneakers

The “go with anything” heel

Classic flip flops

Go to sandal

Underwear for 12 days – my go-to is Hanky Panky

3 bras – my go-to is Natori

5 pairs of socks – my go-to is Ondo

Carry-on expandable spinner

Carry on bag

#4: Toiletries

Most of the hotels had lovely shampoo & conditioner, body wash, lotion, and various other amenities. Our hotel in Rome, Italy had all ACQUA Di PARMA products too- AMAZING. While there are some things that are a must, a lot of what I brought I didn’t really need since it was provided by the hotel. Plus, when we got to London, my fabulous face cleanser was taken since it was .5 oz more than I was able. Note to self – London only allows for 3 or less ounces. 

Where Would We Go Back from this Trip

  • Milan – we fell in love with the city; where high end met laid back
  • Rome – you just need to see it
  • Tuscany – so many places to see
  • Madrid – another city we fell in love with

A perfect selfie in front of the Royal Palace of Madrid!

Where We Would Like to Go

  • Amalfi Coast
  • Positano
  • Naples
  • Sicily
  • Venice

We loved being in Italy for 2 weeks, and could have even stayed longer. While we did enjoy seeing all different cities/towns, we do like the idea of staying in 1 or 2 spots and taking day trips. An AirBNB in Italy just sounds lovely too! Oh, and I, DEFINITELY, want to do some cooking classes & more wineries!


There is not a whole lot more than I can say other than  – WOW, WOW, and MORE WOW!

Favorite Cocktail: Yes, my martini and wine were always a go-to but it was the Aperol Spritz that stole my heart! I was surprised how much I loved it too! 

Where to Stay, Where to Eat, & What to Do: While it would be easy to simply tell you to go everywhere, here were some of the standouts (at least we thought):


  • Osteria da Fortunata – The pasta and tiramisu were out of this world
  • Cantine Milano – A fabulous upscale Italian restaurant with an emphasis on amazing wine and culinary creations
  • White Rabbit – A throwback to traditional speakeasies during the prohibition; oh, and you need to go online to request the password they ask you when you enter!
  • The Armani Hotel – If money was no object, this would be an amazing place to stay! The Bamboo Bar was so swanky and elegant – a definite must!
  • Grand Hotel et de Milan – An iconic hotel that represented class, sophistication, and history
  • Don Carlos Restaurant – A perfect date night spot and the Veal Milanese was out of this world
  • Hotel Cavour – Although this was part of our trip, it really was a super cute boutique style hotel in a fantastic location
  • The Duomo of Milan – Absolutely breathtaking! Italy’s largest church right in the heart of the city
  • The Last Supper Museum – Unfortunately, we did not get tickets early enough so this will be a must next time! If you want to see, it is highly recommended to get tickets 2-3 months before your visit.


  • La Gazzella Maranello – As mentioned before, we went to this spot 2 nights in a row because it had a shuttle service to and from the hotel. The food and wine – no cocktails unless you wanted an Aperol Spritz or Gin & Tonic – were solid. You can never go wrong with a meet and cheese board!
  • Antica Acetaia Cavedoni Balsamic Vinegar Tour – The area of Modena is known for its balsamic vinegar, and this family owned vineyard was a perfect place to learn about the process and sample what seemed like delicacies! And the food pairing was simple yet incredible.
  • Museo Ferrari – If you are a car fanatic, then Maranello is where you want to go and you can do it in a day. The town is mostly built around Ferrari; car fan or not, it is a very cool experience to check out. Part of our itinerary included 2, 10 minute test drives which was a lot of fun! Although we did not walk away with one, it can still be a pipe dream!


  • Casa Del Chianti Classico – Although we just had wine, the view is just gorgeous, and a great starting off point to celebrating Matt’s birthday.
  • Le Forchette Del Chianti – Watching them put together the most gorgeous cheese and charcuterie board was so cool! And their Nicoise salad was so incredibly tasty too!
  • Il Barlettaio – Since we did not have a car, and a lot of the wineries required one to get to, we found this highly recommended spot within walking distance from the town and our hotel. The wine was phenomenal and the husband/wife duo were so nice too! 
  • Palazzo San Niccolo – Again, another hotel that was part of our trip but simply perfect. You felt like you were part of a movie – old world charm meets Tuscany!


  • Anantara Palazzo Naidi Hotel – If you are looking for a splurge, I highly recommend you check out this hotel! Simply stunning, with gorgeous rooms, bars (and rooftop bars), marble and chandeliers, and well, I think you get my drift. Their lobby bar not only does amazing drinks – they serve complimentary sushi – but their cappuccinos/lattes are perfect for post dinner!
  • Osteria 44 – Italian elegance in a super intimate setting
  • Colosseum – Because you cannot go to Rome, Italy and not see this historical amphitheater!
  • Vatican Museum & St. Peter’s Basilica – It is just an absolute must see, and to my point in the above comment.


  • Only You Hotel – For the money, this was a perfect spot (and we were lucky to get a room upgrade too). Super trendy and FUN! Their restaurant was on the top floor and had the most beautiful views of their ever bustling city!
  • Hotel Urban – Their rooftop bar was awesome; laid back meets city life!
  • Aarde – The hotel concierge made us a reservation since we could not get into Ten Con Ten until our last night. Beautiful setting, high energy, and the food was outstanding! The setting and decor was so unique too!
  • La Mi Venta – When in Madrid, you have to try the paella! Plus, the bistro tables and chairs were calling my name too!
  • Hotel Fenix Gran Melia – Another hotel that was just stunning! Enjoyed our final pre-dinner cocktails in their gorgeous bat!
  • Ten Con Ten – Fast paced, lively music, and one of the yummiest burrata with fig salads we have ever had! Since we had been to its sister restaurant – Aarde– the night before, we did see some crossover of entrees on the list. 
  • Royal Palace of Madrid – The official residence of the Spanish Royal Family, and quite an unbelievable self-guided tour! While every room brought something new and exciting, the dining which appeared to seat 50 was just exquisite.
  • Museo Nacional del Prado – Whether you are into art or not, this is a must see national art museum!

The Culture: We loved how every meal is a ritual and experience; it is how it should be! I am an early to bed kind of gal but it was fun starting the night out at 7:00 pm with cocktails, and getting seated for dinner late. On our first night in Milan, we were blown away that people were still being seated at 11:00 pm. 

I think we ate pasta and bread for 12 days straight while in Italy, and it was glorious! And I was happy. This is coming from someone who does not usually participate in the bread/pasta cuisine. I, definitely, have a new appreciation! I told Matt he was going to see a different side of me – one that wanted to enjoy every minute of the trip. One of satisfaction, fulfillment, and enjoyment. Did I ever! 

And everyone is so right – the food is just different in Italy!

Two New Appreciations: Parma Ham and Balsamic Vinegar; as I mentioned earlier we did a balsamic vinegar tasting in Maranello and it was amazing! We got to try one of their 100 year old bottles – and so much more – and learn about the incredible process they go through. 

The Number of Courses: Every night we started with an antipasto, then our first course was always pasta, our second course was our main protein dish, and then dessert if feeling up to it. The cappuccinos were simply divine too! The coffee does taste better in Italy.


Yes, I could have gone wild in Milan but it was more fun showing Matt the items I have on my Birthday & Christmas list. Plus, we are spoiled because all of these high end stores are, basically, down the street from where we live. If you are into stores such as Prada (the first ever is located in the Galleria Vittorio Emanuele II), Gucci, Louis Vuitton, etc., then you will just love it! I will say that I like to buy things that I cannot get at home too. This picture represents Matt’s goals for wardrobe and travel!

I did manage to find a gorgeous magenta pleated skirt from a boutique in Radda, along with a gorgeous ivory colored pashmina. We bought lovely wine from this incredible vineyard – the owners were just delightful. Oh, and some cute tea towels with Roosters that signify the Chianti logo. 

Something really fun we did do was attend the Ryder Cup which was being held in Rome, Italy. The club where we belong is getting this (fun) golf tournament – between the US and Europe – in the next 10-15+ years. It was quite the coincidence that it was happening in Rome…the very same time we would be there. Although it was just the practice round – and very quick – we managed to get up close and personal with the players and snag some awesome memorabilia. 

Finally, I like to try and get a Christmas ornament everywhere we go. We found a beautifully hand painted one of the Vatican that was such a unique shape too. It was a must for the tree! 

All in all, our real “shopping”- and our Honeymoon for that matter – was visiting some amazing historical landmarks, churches, museums, and going to some of the best places for lunches, cocktails, and dinners in both Italy and Spain. Definitely, a trip of a lifetime!

Now, a serious question, when can we go back?