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  • Writer's pictureKatie Wright

Italy Trip Itinerary: Rome & Positano Guide

Who doesn’t have Italy on their travel bucket list?

Hand-made pasta, exquisite wine and cheese, pizza from the original land of pizza (!), history at every turn… not to mention the shopping — leather goods, shoes, handbags! — beaches, lakes, mountains. This little country has it all. My first trip to Italy is one that I will remember for the rest of my life and I can’t wait to share it with you!


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Italy was a super spontaneous trip for my mom and I. Lewis and I had to cut our Australia trip short for personal reasons and head back to England. But just because our time in the Southern hemisphere was coming to a close I wasn’t ready to stop traveling. I called my mom up and completely out of the blue asked her if she wanted to come to Italy with me. She said she couldn’t possibly go on such short notice and I said alright, I’m going anyway. Two hours later she called back to say she had booked her flights haha.

I love a travel challenge… and planning a week-long Italian vacation during high season only a few weeks before we were due to get there was my perfect puzzle. I’ll be honest with you, a good trip to Italy takes a lot of planning and research since there is so much to see, eat and do! As usual, the Lonely Planet guidebook was my bible.

Side notes:

Like I said, we planned this trip only a few weeks before going. A lot of hotels were booked up which is why we had to change hotels so frequently and I am sure we didn’t get the most competitive pricing. 

We went at the end of May and had PERFECT weather. We didn’t have a single day of rain and it was really hot and summery in Rome and fantastic beach weather in Positano.

Day 1

Since I was flying from London and Mom was coming in from Boston, we booked our flights to land within 5 minutes of each other at FCO Rome airport which worked out really well!

Once we found each other and our luggage we searched for the airport shuttle bus that we had prebooked. It cost USD $33 which seemed like too good of a price to be true… and it was. I definitely would NOT recommend the shuttle bus. We waited FOREVER and would’ve been much better off just sucking it up and taking a taxi.

We got to our hotel at about noon on the first day. We had booked two nights at the Hotel Degli Artisi. Located in the center of Rome, right by the Spanish Steps (Via degli Artisti 18, Rome, 00187 Italy), Hotel Degli stands as one of the top 5 nicest hotels I’ve ever stayed at.

What are the best areas of Rome to stay in?

I’m no expert, but our hotel in Rome, Hotel Degli Artisi, was conveniently situated in the neighborhood of the Ludovisi district on the Pincian Hill. It was walking distance to some of the best sights in Rome such as the Spanish Steps, Villa Borghese (the heart shaped public park of the city) the Fontana di Trevi, and Fontana del Tritone as well as the historic shopping streets of Rome’s Via Condotti and the famous and luxurious Via Veneto. We loved being able to walk most places in Rome and it felt safe and friendly.

It was a smaller hotel that was just so beautiful, sunny and comfortable. It was a place you wanted to come back to and just relax after long days spent exploring Rome.

The coolest part of the hotel was that they gave you a smart phone  preloaded with everything you could possibly need: Free phone calls back to some countries of Europe, USA and Canada, tourist maps and guides, information on public transport, events and museums, translator, currency exchange and many other services. This was such an AWESOME service and I hope more hotels start to catch on to how fantastic this is!

After unpacking a little we grabbed some pizza across the street from our hotel and let it soak in that we were really here! In Italy!

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Then we hit the ground running on our ‘Best of Rome Walking Tour’ that we booked via Viator. It basically just got us acclimated with the area and the history of some of the major landmarks and neighborhoods of Rome.

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We had dinner at Piccolo Arancio which was just about a block over from the Trevi Fountain.


It was so cute because we wanted to sit outside but all of the tables they had set up outside were taken, so instead they just grabbed another table, carried it out to the sidewalk and set it up for us! Only in Italy!

If you see ‘carciofi alla giudia’ (crispy artichokes) on a menu in Italy, order them! They are so delicious! Crispy, flaky, nutty… yum. The recipe for carciofi alla giudia date back to the Roman Empire, when the Roman Jewish community numbered about 50,000. I saw this dish featured on the Food Network (my fav channel) before coming to Italy so when I saw it on the menu at Piccolo Arancio we ordered it straight away! So good!

Day 2

I wish we had had more time at the Villa Borghese gardens. They were absolutely stunning!


The next day we woke up early for a private tour of the Vatican.


Did you know that Vatican City is the smallest country in the world? Another country to add to the list.

We had an hour to rest in the hotel room and get changed before leaving off on yet another tour: Secret Food Tour – Rome. We met our group at 5pm at the Piazza Navona and for the next three hours we sampled all of Italy’s must eat foods: pizza, cheeses, wine, gelato, pasta and so much more…  as well as exploring some of Rome’s most famous areas: Campo dei Fiori Market, the Jewish Ghetto and more.


Read my full review of the food tour here. 

After  the food tour we met up my friend Mackenzie and her sister Maddie who were spending a few weeks backpacking around Europe. We ended up going back to our hotel where they had left us a bottle of champagne! (Have I mentioned how amazing this hotel was?!)


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We took the bottle up to the hotel’s private roof deck and sipped champagne while taking in the stunning Roman views.

Day 3

The next day we had to move hotels just around the corner to Hotel Barocco. (Piazza Barberini, 9, Rome, RM, 00187). We accidentally booked a room in the hotel’s annex which we didn’t like at all. But I think if we had had a room in the normal part of the hotel our experience would’ve been totally different. This hotel did have a pretty spectacular breakfast included.

Colosseum tour


We spent the day shopping and exploring.

We had dinner at what immediately became our favorite restaurant in Rome: That’s Amore. I don’t remember how we even found this place but WOW am I glad we did. Don’t be put off by the cheesy sounding name—this place is AMAZING. That’s Amore is cozy and adorable and you’ll definitely want to make reservations ahead of time. It’s one of those places that with every steaming dish that is paraded past your table you have to wave your waiter down to say ‘what was that?!’ Someone once told me that to find the good restaurants in Italy look for happy people celebrating and toasting and thats what you’re surrounded by at That’s Amore.

Both nights we went here mom and I ordered the Tagliolini with fresh sea bass, grape tomatoes, olives from the Cinque Terre and capers from Sicily.



Followed by the home-made Millefoglie cake which is light pastry layers with Chantilly cream and flakes of chocolate. Simply amazing.


Conveniently located just a a few steps from the Trevi Fountain, That’s Amore is the cozy Roman trattoria you are looking for.

Day 4

We woke up early to indulge in the delicious breakfast at the hotel and pack up our things to get on the train to our next destination — Positano!


We took a cab from the Hotel Barocco to Rome Termini Station and took the train from there to Salerno. Read my full post about Getting From Rome to the Amalfi Coast here!

We spent the journey splitting out time between reading our books and gazing out the window  as the olive groves and green pastures blurred by.

From Salerno we had about 20 minutes to cross a few blocks over to the ferry station to get on a ferry to Positano.

The views from the boat as we travelled from town to town along the Amalfi Coast was an experience in itself!

Immediately upon arriving in Positano you’ll find that it’s extremely unique in that while there are roads, the majority of the town is made up of narrow, winding paths and lots and LOTS of stairs. And I really mean a TON of stairs. You need to make sure bring comfortable walking shoes and maybe do some stair master workouts at the gym before your trip. Our hotel, the Pensione Maria Luisa was slightly on the outskirts of the town center. We walked with our suitcases up what honestly may have been 3,000 stairs and in retrospect I really wish we had tried to find a taxi or something but it’s all part of the adventure, right?


I found Pensione Maria Luisa (Via Fornillo 42, 84017 Positano SA, Italy) from the Lonely Planet guidebook. We loved our room’s private balcony overlooking the sparkling mediterranean sea. The decor was definitely true to the guide’s ‘no frills’ description. All in all Pensione Maria Luisa was good but not luxury and we much preferred our next hotel in Positano.

After taking photos off of our balcony we set off into town to hit the many (!) beautiful shopping boutiques!


Pro-tip: If you’re going to Positano, SAVE ROOM IN YOUR SUITCASE! The shopping is AMAZING. We actually had to buy a whole new suitcase in Rome for all of our purchases for mom to fly back home with.

To top off our luxurious day we had a very lux dinner at Covo dei Saraceni.


This was our ‘fancy meal’ of the trip and it was really special. Definitely make reservations in advance, and try to schedule your dinner around sunset. We sat outside on the front terrace with a beautiful vista of the beach and harbor.


We asked our waiter what the fish of the day was and he smiled a little smile and told us to wait one moment. This is what he returned with.


We couldn’t believe it! So we selected our new friend to be prepared our new favorite Italian way — with tomatoes and fresh capers and local olives and garlic— YUM.


The fish is cooked and they wheel a cart up to your table where they prepare the full fish right in front of you. Amazing.

Day 5

The next morning we woke up bright and early and packed up our sunscreen, swimsuits and sun hats for our day trip to Capri.

We had booked a semi-private wooden motor boat to take us cruising along the Mediterranean sea for a trip to the famous island of Capri. Our tour was organized with Blue Star Positano and it was hands down one of the best days of the trip FOR SURE. Highly recommend this company! Read my full review of the experience here.


We were pretty wiped out from our day of sun and sea, so we decided to have dinner at a restaurant slightly closer to our hotel. Saraceno d’Oro was so classically Italian in that half of the tables were across the winding road from the restaurant, so the waiters had to dodge vespas and dart across the while street balancing glasses of wine and plates of spaghetti piled high in order to serve their guests. It was quite the balancing act! Our food was tasty and we were serenaded by a band of Italian street musicians.

Day 6

The next morning we again had to check-out from Pensione Maria Luisa by 11:00am and move to our new hotel: Hotel Savoia which was in a much more of a central area of Positano (Parco Regionale dei Monti Lattari, Via Cristoforo Colombo, 73, 84017). We much preferred this hotel for it’s luxury feel, central location, and DELICIOUS included breakfast. AND HOW ABOUT THIS VIEW??!


The tile flooring was stunning, wasn’t it?


As recommended by the hotel’s concierge we booked a water taxi to take us to the Bagni d’Arienzo Beach Club where we had booked two day beds and made lunch reservations.


I loved this beach club. I felt like a 1970s celebrity being delivered by boat to a private beach club and sipping cocktails under the striped umbrellas.

After a day being pampered in the sun we went home for a shower and change of clothes before looking a restaurant for our last dinner in Positano.

We ended up at Chez Black for dinner and had heart shaped pizza! Chez Black is right on the beach and has a quirky fun nautical-boat theme and it was ALWAYS packed every time we walked past.


Day 7 

The next morning we checked out of Hotel Savoia and started our journey back to Rome. We took the exact same Travelmar ferry to Salerno, train back to Rome, cab back to Hotel Degli where we would spend our last night in Rome.

Our last dinner HAD to be at That’s Amore. Make reservations in advance, this place gets busy!

Day 8

On our final morning together we took a cab to the airport and went our separate ways. Mom was flying back to the states and I was off to Venice to meet up with Mackenzie and Maddie!

Check out my Photo Diary from my Trip to Venice!

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As always, if you LIKE this post, please SHARE it! Leave me a comment if you visit Italy and get a chance to try any of my suggestions!

What did I miss? What should I add to my itinerary next time I am in Italy? 

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