Our 10 day Italian Adventure: Tips for having the trip of a lifetime in Italia| PART 1: SORRENTO, CAPRI & POMPEII | Days 1-3

As most of you know Matt and I just WON THE AMAZING RACE… (still hasn’t sunk in) and we used some of the money to  take my parents and one of our best friends on a 10 day vacation to Italy. My parents have gone through a lot in their lives. My father had diabetes and Alopecia Totalis his whole life. Six years ago his one remaining kidney started to fail and he was on dialysis for 6 months before receiving a life changing double transplant (kidney & pancreas.) My mother stood by his side and was his nightly nurse through the whole process. Shortly after he began recovering from his transplant his eyesight started to fail and he’s been going blind ever since. A year ago my mother was diagnosed with stage 2 breast cancer and underwent a double mastectomy. She had ovarian cancer when I was in 3rd grade and had a full hysterectomy so she has lost a lot. Through all these trials they have been the greatest parents to me. They taught me to be strong, independent and always chase my dreams. They gave me the world and made me believe in my ability to actually achieve my goals by loving and supporting me unconditionally. Once we won, I immediately wanted to repay them in some way, to give something back to them. They have always dreamt of seeing Italy, I actually remember my father leaning into my mother right before her surgery last year and promising to take her when she was well again. They always helped me live my dreams and I wanted to help them live one of theirs, so I planned a ten day trip that would satisfy anyone’s need to see the sights, explore Italy and have the trip of a lifetime in one of my favorite places on earth.

Disclaimer: The trip was tight.. It would have been easier/more relaxing with an extra day in each city but we did not have the availability in our schedule to extend it any longer…instead we ran around like crazed, wild, luggage wielding lunatics and still had a blast doing it. Below is our itinerary and links to all the things we loved and enjoyed.


I booked the trip through http://www.virgin-vacations.com. I used their 8 day Rome, Florence and Venice vacation air and land package and I extended it by three days so that I could add in Sorrento  and the Amalfi Coast. They helped me book the extended airfare but I had to book my own travel from Rome to Sorrento and back to Rome (just bought this at the airport) and my own hotel in Sorrento (hotels.com) . Get this.. for all 5 of us it only cost about $8,000.00. $2,000.00 each for all airfare, hotels, first class train tickets… pretty incredible.

Day 1: Arrive in Rome, Naples, Sorrento
After everyone arrived at Rome Fiumicino Airport we hired a driver through welcomepickups.com to take us to Roma termini train station. This service was flawless. I downloaded the app before I left the country and then I got the name and phone number of my specific driver and he showed up holding a sign with our name on it- Easy Peasy. The trip cost about 100 Euro for the 5 of us and all of our luggage. There is an option to take the train from Rome airport to Roma Termini train station. This train is cheaper for sure and since we didn’t take it, I don’t know how easy it is, but I am told pretty easy. Keep in mind we did this trip with my father who is legally blind, so we made some choices based on ease and comfort and not always on budget.

We traveled from Roma Termini to Napoli Centrale train station on a high speed train. The trip was 1 hour and 8 mins and cost about 100 euro per person for a round trip ticket. We could have hopped right on the Circumvesuviana and finished the trip to Sorrento but by this point we had all worked up an appetite and I am a pizza FANATIC. So there was no way I was passing through the birthplace of pizza without stopping for a slice and I can’t tell you how worth it it was. I highly recommend making this pit stop.

We left our luggage in the storage room at Napoli Centrale so that we didn’t have to drag it through Naples to the pizzeria. (To Find the luggage hold: after you get off the train and are facing the exit walk all the way down to the right6 euro per bag or 9 bags for 40 euro). There are two incredible pizza spots in Naples http://damichele.net and http://www.dalpresidentepizzeria.it. We arrived on a  Sunday when Da Michele is closed so our choice was made for us and we hopped in a Taxi toward Dal Presidente.

The pizza at Dal Presidente was out of this world. We were seated outside in the most incredible little courtyard, in front of a beautiful church. It was so old world Italy and we were in love with the whole experience. Every single pie we ordered was the best pizza any of us had ever tasted. We ordered the margherita, con prosciutto and a specialty white pie, we also got some draught beers and had a ball. I highly recommend it!

Grabbing a taxi  in Naples isn’t the easiest so ask for a card from the taxi that drops you off and hold on to it to call another taxi to return to the train station. We took the taxi back to Napoli Centrale to retrieve our bags and then headed downstairs into the circumvesuviana train station. Circumvesuviana means “Around Vesuvius” and its the special train that takes you down to the south of Italy and circles the incredible volcano.

We had absolutely no idea what we were getting ourselves into with this train… literally none. This train is insane. Its packed, its rickety, rocky, wild and at some point I am pretty sure we traveled at light speed. In retrospect it was not the best idea for us with my disabled dad and 7 pieces of massive luggage but it was definitely unforgettable and we made it. The train is by far the cheapest way, we paid under 5 Euro per person. The other option would have been a taxi which would have run us upwards of 150 Euro. The train took about an hour and was a lot of fun, it’s the method I would recommend.


Once we arrived in Sorrento we walked out of the circumvesuviana and I didn’t have any idea what to do. I didn’t look into how to get from the train station to the hotel, which was a rookie mistake- but hey, it happens lol. We were able to take a taxi but it was ridiculously expensive; It cost us 50 Euro to go about 15 minutes up a hill. Most of the hotels have shuttles that go to the hotel from the main square so its worth it to look that up with your hotel and be aware of the best and cheapest way to get to your hotel before you arrive. (my bad)

After a beautiful ride up a very large hill we arrived at our gorgeous hotel, Le Terrazzehttp://residenceleterrazze.it/. I cant rave about this hotel enough. It was breathtaking, with panoramic vistas from every angle that you almost cant believe are real. On top of that the staff took the most exceptional care of us, especially Vincenzo.  The breakfast buffet was delicious and included!

We arrived late at night after many of the local restaurants had closed and he made a call to his friend Pasquale who owns the most unreal restaurant up the street called Le Grotelle http://www.agriturismo.it/en/farmhouse/campania/naples/LeGrottelleSorrento-7280558/index.html. He picked us up in his car and drove us over there after they had closed. They grow 90 % of their ingredients on the premises and the food was probably the best I have every eaten anywhere on earth. The restaurant had such a fun old world vibe too- a must if you visit Sorrento.

TIP: Le Terrazze has a LOT of stairs. It’s carved into the side of a cliff which is why it is so incredible and has such beautiful views- but make sure to let the desk know if you are traveling with anyone disabled or elderly. The steps are treacherous.

Day 2: Capri by private boat

This was everyone’s favorite day of the whole trip, by far. We rented a private boat through Capitano Ago boat rental http://www.capitanoago.com/ and it was flawless. It was 800 Euro for the whole day up to 8 people and it included soda, beer, wine and limoncello and caprese sandwiches (pretty cutesy since we were in Capri). They also picked us up at our hotel in the morning and dropped us off at the end of the day.

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We had Capitano Agostino and he was so much fun! He started the day by bringing us to an ancient roman aqueduct and driving the boat right underneath it. It was soooo cold! He took us to see all the grottoes, the Faraglioni rocks and then brought us to a beautiful spot to jump off the boat and swim and snorkel. He played music for us and we had the time of our lives relaxing on the boat, drinking wine and swimming in the Mediterranean.

To  visit the Blue Grotto you must wait in line, when you have a private boat the line is considerably shorter. We waited about 10 minutes while others waited upwards of an hour. We were transferred from our boat into a small rowboat (pictured below), taken to the ticket booth to pay and then brought into the grotto. It really is a spectacular sight unlike anything I have ever seen. The cave is pitch black and the water literally glows. The trip into the grotto is short, maybe 5 minutes long and your rowboat driver will pester you beyond belief about being tipped- that’s just the way it is so don’t get upset. Make sure you have cash to pay the entrance fee which I believe is 13 euro per person and some tip for your rowboat driver.

blue grottorowboat

Once we finally arrived in Capri we were let off the boat to explore for a few hours. We took a Funicular (old school cable car) up to the top of the hill and had lunch at a charming little restaurant nearby the square called Isidoro. I had the pasta with clams and that was a hit with everyone lol. We shopped, grabbed some gelato and headed  back down to our boat. We went for another swim and then finished the trip back to our hotel.

We had dinner in Sorrento in Piazza Tasso (pictured below) at Bar Faunohttp://www.faunobar.it/en/index.php. I ordered the ravioli sorrentina, which was fabulous.

piazza tasso


Day 3 Pompeii and Mount Vesuvius

We took our hotel shuttle down to the square and caught the Circumvesuviana to  the Pompeii Scavi stop, which takes about 30 minutes. I opted to buy tickets outside the train station in Sorrento before we departed, from tiempo travel, which is in an office to the right hand side if you are facing the train station. I purchased train tickets(2.20 per person), bus tickets to the top of Vesuvius( 22 per person) , and skip the line tickets and guided tour for Pompeii (12 euro per person- not including 13 euro pp entrance fee which we paid at the gate).

The tour we purchased for Pompeii was picked up outside the Pompeii Scavi train station. They walk you over to the entrance and help you purchase your tickets and then walk you through the whole area of Pompeii. This could be a good option because Pompeii is expansive and very confusing. However, due to my dads blindness we were a slower group. In all honesty though we were way happier to walk around on our own and really only bought tickets so we could “skip the line.” The tours are very in depth, even at our slow pace we blew passed them- long windedness is just not really our style. We did a short loop, started by turning right after the entrance square, through piccolo teatro and then  turned left up the ramp. We then made the first left, checked out the bath house, forum and hall with the pottery – I was really most interested to see the plaster casts of the bodies so we asked around and made a bee line for that. We followed that around past the basilica of justice and out the exit toward the Circumvesuviana. That exit brought us right back to the train station– which is where you pick up the bus for mount Vesuvius.

This took us about an hour and was plenty of Pompeii for us but depending on your level of history buffness, you might opt to follow a tour for a longer (2.5 hour) more in depth look at the ancient city.

pompeiipompeii bodypompeii body 2

Because of the weather (it was raining and lightening) we ended up not being able to take the tour we purchased to Mount Vesuvius. The busses were not driving up because of the rain and at first we were super bummed. Then the same company we purchased the bus tickets from sold us a private tour in a taxi for 25 euro per person (10 euro per person entrance fee not included.) It turned out this was a way superior option and we got so lucky. The taxi was going up even when the busses weren’t, we had no one else with us (we would have been with a group of 20 or so if we had gone with the bus group) and we got to be on our own time. The cab ride took about 30 minutes.

Mount Vesuvius was so bad ass, excuse my french, but theres no other way to say it. We were all stunned and beyond obsessed. It was pretty much one of the coolest things I have ever seen and definitely was worth the hike. The hike was moderate intensity on a well worn path and took us about 20 minutes. The rain made it so creepy and epic- most blogs say don’t go up to the top in bad weather because it does compromise the view outward, but it made the volcano so much cooler to us. Make sure to bring a sweater no matter what the weather because of the altitude it does get colder at the top.

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We ended up taking a taxi back from Pompeii to our hotel in Sorrento. It cost about 80 Euro. We could have returned on the train but we were all tired and it was raining and we knew my dad needed a break lol.

We had dinner that evening at a restaurant called Fattoria Terranova- Fattoria means farm in italian, but it may as well mean place that makes you fat. The ambience at this restaurant is to die for and the food is excellent. We hear the bread is a stone wheat (inside joke…) http://fattoriaterranova.it/ but seriously, definitely a spot to check out- just be careful for the per person appetizer because that can get pricey 🙂



One thought on “Our 10 day Italian Adventure: Tips for having the trip of a lifetime in Italia| PART 1: SORRENTO, CAPRI & POMPEII | Days 1-3

  1. I love you Dana. The choice is yours is another work of art. Thank you my darling. I feel every emotion so crisply when I read your inspired words. You are my angel.
    Love your auntie & 2nd mama

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