Once every year or so I plan a big trip with Best Friend Kaity Kline. We’ve gone road tripping down the California coast, penguin spotting in Argentina and decided it was time for us to go to Italy.

Kaity’s had Italy on her list so when we saw $500, round-trip flights on Scott’s Cheap Flights, we pulled the trigger. Into Naples, out of Florence. The details we’d figure out later.

This post is not another influencer post on how to “do Italy in 2 week” with comp’d hotels and private drivers. This is a travel post for gals in their 30’s who want to travel like normal human beings, but still enjoy the finer things of life.

We learned when to pay 15 euro to have our bags delivered by a porter and when a cheap bus ticket was the best option. A fine line between splurging and savings.

Kaity is a planner and a foodie so MAJOR kudos go to her for finding the best places.

Here’s a brief itinerary and helpful tips we picked up along the way. We called it the trip of a lifetime, but you be the judge.

Quick Itinerary Summary

• Flew into Naples, spent one night there.
• Day trip via train to Pompeii on our way to Sorrento
• Ferry to Positano, 3 days there. Boat trip to Capri + beach time.
• Bus to Sorrento, then train to Rome.
• 3 days in Rome – our favorite city! Vespa tour, Colosseum, Roman Forum, Palatine Hill, Vatican Museums, St. Peter’s Basilica, dome climb.
• Train to Florence, rental car to drive to Tuscany/Montepulciano.
• 3 days in Tuscany – Wine tastings, relaxing and hot springs.
• Drove back to Florence – 3 days there. Free walking tour, Uffizi Museum, Galleria, cooking class, Dumo climb.
• Forece to Home

Travel Tips & Tricks for Italy

• Get a travel pass ($10/day) for your cell phone so you have service
• The best, most authentic restaurants are named for their founders. Da Tonino, da Enzo, etc.
• Always get the house wine
• Tuscan bread is bland since there’s no salt! Legend says it’s because of a long-time rivalry with Pisa
• Sidewalks are uneven, a 15 minute walk with your rollerbag doesn’t sound bad, but it might be worth a cheap taxi to get to your hotel
• While food anywhere in Italy is great, read reviews before sitting down. We avoided bad places a few times when looking for a quick meal.
• Florence is known for its leather, Sorrento for its sandals
• Italy is a no tipping culture
• Make sure you watch Lizzie MacGuire & When in Rome before or during your trip for a truly immersive experience

All the Details: Italia 2019

Day 1 – Flew into Naples. Pizza at L’Antica Pizzeria da Michele. The “best pizza in the world” of Julia Robert’s Eat, Pray, Love fame. We went at 5pm and waited 5 minutes for a table. Heard others who went later that day waited 1 to 2 hours. 5 euro for a pizza (2 options to choose from) and beer or Coke. Best pizza of our trip.

We didn’t love-love Naples and were only there a few hours. Spent the evening catching up on sleep and fighting jet-lag.

Day 2 – Train to Pompeii, then onto Sorrento. A 45 minute train ride from Naples to Pompeii via the Circumvesuviana train from the Naples Centrale station to Pompeii Scavi station. Trains depart every half hour. Bought tickets at the station.

Pompeii is literally right next to the train station. 5 min walk. We chose to store our bags at the train station for 4 euros/bag. Pompeii has free bag storage on a first-come, first-serve basis and probably should have done that. Also bought an unofficial walking tour from the train station. Regrets. Buy a walking tour from the park (8 euros) or go with a tour group.

We spent about 3 hours walking around and exploring areas of the city. Fun to get lost and explore crevices and old brothels in the shadow of Mt. Vesuvius. We had a quick lunch at the Pompeii cafe in the park before heading back to the train station. Opted for the commuter train, should have paid more for the express train to Sorrento. Trains were crowded and delayed, but was a truly local experience.

In Sorrento, we stayed at Hotel Regina. For dinner we walked to Bagni Delfina. Lovely seafood restaurant on the water. Delicious pasta and house wine and amazing views of Sorrento to get there on little footpaths. We called for reseservations ad got there right as they opened.

The quaint little town of Sorrento is known for its sandals. Kaity bought an adorable pair of flip flops and we both got matching straw bags at the market. Cute little town to walk around and sample limoncello.

Day 3 – Took the ferry from Sorrento to Positano. 15 euros/person and took about an hour. Before we left, had lunch by the water and by the ferry depot at Ristorante Bar Ruccio. There’s an elevator from the top of Sorrento to the water for a few euros. We walked down the first time to get ferry tickets, then bought tickets for when we had our bags.

When arriving in Positano, we planned to walk to our Air BnB. Thankfully there were guys at the ferry depot in blue shirts shouting, “70 steps to the top, log walk”. We later realized they were ANGELS. The Positano Porters would deliver our suitcases for 15 euro/bag to our place. We hadn’t planned on using them, but my goodness, we would have paid double. Turns out it was 200 steps to our place and we would have probably actually died if we did it ourselves. For us normal people who aren’t staying in 5-star resorts, pay to have your bags delivered.

Days 4 & 5 – Positano. Positano is everything you’ve heard. Beautiful, one million steps everywhere and overpriced. But dang, it’s worth it. This part of our trip was everything beach, sun and water-related.

Private boat tour around Capri – Gianni’s Boats. 180 euros cash for 4 hours for the 4 of us. We ferried from Positano to Capri (20 euro/person; 40 mins) where we met our captain, Luca. BYOB.

Luca toured us around stunning grottos where we could swim in the Mediterranean.

We went to the Blue Grotto because you have to when you’re that close. Lots of tour boats waiting to get in. We somehow cut the line and paid the 14 euro entrance fee + a hefty tip to the row boat that let us go in ahead of others. Fine and you have to do it, but wouldn’t recommend if you’re tight on time since there are so many other beautiful grottos and places to boat. One of our favorite excursions. You truly feel like queens.

Restaurant La Tagliata – Recommended by a few friends and totally worth it! Set menu of 45 euros/person since “we’re all family here”. 6 courses of food that just kept coming – veggies, meat plates, pastas, desserts and unlimited wine. Made a reservation in advance and they picked us up at a hotel in town. 25 minute ride to the restaurant up the hill to a quiet little enclave outside of downtown.

Beach Chairs + Umbrellas – We’d had every intention of hiking the Path of the Gods, but instead opted to rent beach chairs and an umbrella and spent the day sipping pina coladas and reading. 20 euros/person for front-row seats (17 euro for second row). You’re in Positano, get the front row.

Day 6 – Bus to Sorrento, then train to Rome. Big travel day to get up to Rome. Took the SITA bus from Positano to Sorrento. Bought bus tickets at the Tobacci shop at the top of the hill in Positano for a few euros. Sat with the locals on the 45 minute, turny ride. Convinced my best friend not to throw up.

Once in Sorrento, we took the Circumvesuviana train from Sorrento to the Naples Centrale station (trains depart every half hour). Lovely trains with reserved seats. Bought our tickets a few days before at the train station when we first arrived in Sorreto.

Private Vespa Tour in Rome – Another one of our favorite activities that we splurged on. Referred to Valerio of Dearoma Tours from a coworker.

Booked a 3 hour vespa tour of Rome and got to feel like a local while seeing more remote spots of the city. Great intro on our first day!

For hotels in Rome, we stayed at a boutique near the Trevi Fountain. Great location, good price and central to most things. The Trevi Fountain was always, always crowded. We liked going there best at night when it was all lit up. Don’t forget to throw a coin (or two or three!) into the water.

Days 7 & 8 – Rome

Rome was our favorite city and we’re so glad we booked three days there. It’s historic and beautiful and larger than life. Something ancient on literally every corner, you can turn around and see something new. No joke, we accidentally walked by the Pantheon one night – oh surprise! Look at that.

We booked two big tours in Rome: one to see the Colosseum and one to see the Vatican.

For the Colosseum we booked a “skip the, skip the line tour” through Viator. There’s a 3,000 person capacity for the Colosseum and our 7-person group walked right past people who had been standing in line for hours.

One thousand percent worth it, especially because of our fantastic tour guide, Erturk. He also does private tours around Rome – highly recommend! He was our favorite guide of our trip. The afternoon Viator tour included the Roman Forum and Palatine Hill. (Morning tours went to see the Pantheon which we were disappointed at first to miss, but Palatine Hill was so much cooler).

We also booked a skip the line tour for the Vatican Museums, Sistine Chapel and St. Peters Basilica. Worth doing since you’re there, but not one of our highlights. The tour group let us walk right in without waiting, but the place was crowded, despite our tour guide being pleased how un-crowded it was.

It was cool to see the School of Athens and the Sistine Chapel ceiling. We weren’t that into St. Peter’s Cathedral. We climbed the cathedral Dome (8 euros to climb the stairs). Tight little steps that start to slant when you get to the top. Great views of Rome and worth the exertion.

Kaity found a cool pizza place a 20 min walk from the Vatican that had traditional square Roman-style pizza called Pizzarium. Place wasn’t crowded when we got there at 4pm, but we could only imagine how busy it would get. They cut pizza by the slice with scissors and weigh it. Very rushed ordering, but got to enjoy it at the standing counters outside.

We walked around the Spanish Steps and Borghese Gardens on our own. The Orange Garden is serene and has great views of the Vatican.

For food in Rome, our vespa guide gave us a hot tip: the best, most traditional restaurants in Rome have their owner’s name. We ate at da Enzo and da Tonino, both excellent. We loved da Tonino – cheap, delicious pasta in the Trastevere district. No reservation, went at 8pm and got a table in 5 mins. The Trastevere was a quieter neighborhood with local places. Da Enzo only takes reservations for 7:30. We couldn’t get one so lined up with the rest of the peasants and waited 90 mins for a table. There were 3 parties seated at our table and it was tight and busy, but food was good.

Days 9, 10 & 11 – Train to Florence, rented a car and drove to Tuscany. From Rome, we hoped back on the train and went to Florence. We walked 5 mins from the train station to the Hertz to get our rental car. We also met back up with our two friends and the four of us piled in and headed for wine.

Tour & Wine Tasting at Castello di Verrazzano – We visited this rustic winery from the 16th Century. Bigger production, but the best dang balsamic we had. Planned to bring some home before we saw the 48 euro/3 ounce price tag.

Had a tour, tasting and light lunch at Capannelle. One of our tour highlights! Staff was lovely, place was small, quiet and remote. We had the entire space to ourselves. Juliana, the 75-year old Italian cook, made us one of the best meals we had. Pastas, leek souffles and desserts to die for. Wine was also good. Reservations required, highly, highly recommend for a top-tier experience. 50 euro/person.

We stayed in a very remote villa in Montepulciano we booked through Air BnB. Lots of steep hills and blind turns to get there.

One day, we booked a wine tour through Tours of Tuscany Montepulciano/Montalcino. They picked us up at 9am and our party of four joined two others as we visited 3 wineries and had lunch. They dropped us back at our Air BnB around 4:30pm.

Motepulciano is know for “vino nobile”, a delicious, medium-bodied red wine made from Sangiovese grapes. loyal red drinkers, Kaity and I were in heaven.

Had dinner at Ristorante la Grotta and one of our favorites! Classy/casual place – welcome wine + appetizers from the kitchen. Homemade pastas and delicious wines. Made a reservation the day before, but you may be able to walk in if you get there early enough.

Kaity and I had an extra day in Tuscany. We slept in til noon, then went to the Gattavecchi Winery in Montepulciano for lunch and a tasting. Love, love! Ate on the terrace and enjoyed the best service and perfectly made pasta. Got the potatoes with cheese and regret nothing. Ended up buying a bottle there, the place was so darling and welcoming.

That evening, we drove to the hot springs, Bagni San Filippo. You park on the side of the road and hike maybe 10 minutes until you find an open spring. It was dark when we were there so we were hilariously stumbling over everything. Almost sat down in a lukewarm pool before we found truly hot, shallow water and shared a space with a German couple. Hug out maybe an hour before we were done and tired of smelling like sulfur.

Driving in Florence, Montepulciano and Tuscany was no joke. It was quick and tight and you’re surrounded by sneaky vespas! Kaity got her international driver’s license through AAA so we kept it legal.

Days 12, 13 and 14 – Drove from Tuscany to Florence. Woke up and made the 2 hour drive back to the city. Stayed in a darling Air BnB 3 minutes away from the Ponte Veccio and the downtown area.

Did one of our favorite things to do and booked a free walking tour of Florence at 10:30am on Day 1. We’re a fan of Reign (the Mary Queen of Scots teen drama) and were enamored with the de Medic family and how they influenced the city.

Tour-wise, we hit the Uffizi and Galleria dell’Accademia, booking normal tickets on the museum websites for both. The Uffizi we walked through in about 1.5 hours and the Galleria we spent 20 minutes in since it was built solely to house Michelangelo’s David.

We reserved tickets ahead of time online to climb up the dome of the Duomo, one of the most unique buildings we saw. Tickets sell out so reserve your spot before you go.

Our tickets to climb the dome also got us into the museums where the original Gates of Paradise are. Very cool to see the bronze doors.

We took cooking classes and made pasta and tiramisu after having a market tour. Very fun, especially since we met some cool people and the wine was flowing very liberally.

At the market, we got to sample cheeses, meats and chutney and some of the best sweet hot pepper jam.

Diner highlight in Florence was 4 Leoni – I splurged and got the bistecca Fiorentina, the famously huge steak from Florence. Cuts start at 55 euro for 1 kilo. *gulp*. Kaity had the best eggplant parm of her life.

The best gelato in Florence we found at Sbrino. All locally made and delicious sorbets, too. Tip from our tour guide from the walking tour.

He also told us to try lampredotto, which is a traditional Florentine dish made from a cow’s stomach.

Kaity and I could’t stomach the stomach and nearly threw up. I repeat, do not try lampredotto.

From Florence, we took a taxi to the airport where we had 20 long hours of traveling ahead of us. Italy, you were bellissima. Thank you for delicious food, savory wine and too many memories (some of which we’ll never share). We will be back!