I love to travel. I also love planning out my version of a perfect trip and had so much fun curating this Italy itinerary. Like a coloring book provides an outline which you fill in, that is how I like to think of my itineraries. I provide a structured outline and during the trip, we color it in with happy accidents, last-minute restaurant reservations, tips from locals and anything else that pops up along the way.
This was my first time back to Europe since I retired from basketball five years ago. I was way overdue for a return trip, and honestly a vacation in general. Since I live in California, my vacations over the past few years have consisted of flying home for weddings, bachelorette parties and bridal and baby showers. I was craving Italy.
I research all aspects of a trip beforehand using Pinterest, Rick Steves, TripAdvisor, Booking.com, and since it was Italy, Reid’s List. I put a 1-10/10 rating system next to each of my recommendations so you have an idea of what to try and what to pass over. You may also notice we visited a grand total of zero museums on this trip. My mom and I have both been to Italy before and had more culturally relevant experiences in the past so if you’re looking for touristy things this is not the itinerary for you. This trip for us was focused on drinking, eating, shopping and living la Bella vita – don’t judge.
I also want to note that this was the first time I have traveled without a set budget – I lived to spend on this trip. I work very hard in a stressful job, saved for this trip for a while and enjoyed splurging on experiences, shopping, fancy restaurants and hotels that are not in everyone’s price range. My mom has carried me in the past while traveling so it was very fun for me to give back to her and not worry about my bank balance. I have traveled before on the cheap plenty of times and included some places I have been to that are more budget friendly. Trust me, you CAN travel abroad on any budget and still have the time of your life.
I included a version of my Italy itinerary here in a downloadable PDF. Please feel free to download and print to take with you on your trip!
“You may have the universe if I may have Italy.”
Italy Itinerary: Venice
Day 1 Venice
I wanted to go back to Venice after an amazing but short trip with my friend and old teammate Christina. We flew into Venice and I gave us three days there, knowing the first day we would be jet lagged and not want to explore too much. You probably don’t need a whole three days to see all of Venice.
We took a private water taxi to the hotel. In the past, I took a bus to the Vaparetto but it is SO SLOW. After an 8 hour flight, the last thing we wanted to do was take another bus, then slow boat even if it is the most cost-effective. One thing I never regret splurging on is transportation and now that I have done it, seeing Venice by private water taxi is the only way to go.
We stayed at the Splendid Venice – Starhotels Collezione (8/10) which I chose based on the great location. Our room and bathroom were exceptionally large for Italy standards, and the staff and amenities beyond accommodating. Warning, you walked out of the hotel and bumped into a million tourists.
We dropped off our bags and hit the streets, forcing ourselves to stay awake and power through. We visited Piazza San Marco and stopped for our first Italian cappuccino at a very overpriced but beautiful Cafe on St. Mark’s Square called Caffe Quadri (8/10) where we were sheltered from the rain but still had a great view and lively waiters.
Then we walked to the Rialto Bridge and wandered the canals without a destination in mind. We ate dinner at Rossopomodoro Venezia (4/10) which I do not recommend even though it has a ton of great reviews online. The service sucked and the food was just okay, and any time there are more Americans than Italians eating at a restaurant you’re in the wrong place.
Since we were tired and jetlagged, we called it an early night.
Day 2 Venice
We slept in a bit this day since it was raining pretty heavily and took our time getting ready.
We had an excellent lunch of beef carpaccio and charcuterie at Osteria San Luca (8/10) before hitting the canals of Venice. The weather was very rainy but luckily the hotel had umbrellas.
We walked towards the Accademia Bridge which I remember the view is better than the Rialto Bridge, and though it was pouring rain we still got some good pictures. Some sights to see on the other side of the Accademia Bridge:
- San Giorgio Maggiore church, Art galleries, Quiet canals with less tourists, Peggy Guggenheim collection if you are into museums
Dinner at Ai Gondolieri (8/10) – this was a recommendation from Rick Steves’ book and it did not disappoint. The service, wine, and food were exceptional. Mom was a little tipsy by this point (we had been drinking all day to be fair), so we just went back to the hotel for another early night.
“An orange gem resting on a blue glass plate: it’s Venice seen from above.” – Henry James
Day 3 Venice
We finally had a break in the weather and we got up early to take advantage of the sun. We headed straight for St. Mark’s Square to take in the scene and to eat lunch in the sun on the Grand Canal.
Lunch was at The Hotel Monaco and Grand Canal (9/10) with the most stellar view. There were the gondoliers ferrying passengers by, glamorous Venetians arriving at the hotel to check in or grab lunch, the tourists embarking from the Vaparetto with selfie sticks. In the little oasis, we were separated from them all with the sun shining on the water and an Aperol spritz in hand, nothing could be better.
After lunch, we walked along the Grand Canal to the Bridge of Sighs to see the Doge’s Palace from the outside.
We were supposed to have dinner at Terrazza Danieli (7/10) on our first night, but the weather wasn’t great and we were tired so we canceled. I still wanted to see the view so we headed to the roof for a drink. If you have time, I highly recommend. You can see all of Venice from the rooftop patio, and as Henry James says below, Venice from above is a must-see.
Highest on my list which we saved for the nicest day was a gondola ride. Yes, a gondola ride is super touristy but you have to do it. I didn’t on my first visit because of the cost and regretted it. It is 120 Euros for 40 minutes, and that cost is regulated by the city of Venice.
We stumbled upon Laguna Murano Glass Showroom where we purchased hand-blown Murano glass after a tour of the showroom. Mom and I both bought beautiful champagne flutes and she got a bracelet. Then we asked for a glass-blowing demonstration which they graciously provided which was fascinating.
We then wandered the canals desperate to get away from the crush of tourists until we came to the Castello area of Venice. It was such a refreshing break to see Venezia locals enjoying happy hour, meeting in front of Santi Giovanni e Paolo to watch children play together, and see the real Venice.
We had dinner near the square at Osteria ai do Archi (9/10) which was excellent, probably our favorite meal in Venice. I highly recommend if you want to get away from the touristy area of Venice.
- We had an early train to Florence, so we arranged for a water taxi to pick us up directly from our hotel and leave us at the train station.
- A note on train travel in Italy: I chose the train in between all of our stops instead of flying and think it was the right decision. Between the two of us for 4 different train rides, it was under $400. I would highly recommend upgrading your tickets to first class if you can afford it. First class provides a little more peace of mind that your bags are secure, not as many people getting on and off between destinations, bigger seats with better service, and usually, you have access to a lounge so you don’t have to wait in the train station with all the travelers mulling around. The Naples train station left us the most uneasy with pickpocketers, so as always just keep that head on a swivel and make sure your luggage and belongings are secure.
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Italy Itinerary: Florence
Day 1 Florence
Check in to Hotel Brunelleschi (9/10) – I would highly recommend this hotel. Beautiful amenities, great services, and an unbelievable location. It is literally one street away from the Duomo and we were able to walk everywhere.
We started at the Duomo and walked around the surrounding area, popping in and out of shops and taking in the sights. This was the day we did the most shopping, and I
We walked from the Duomo to Ponte Vecchio just as the sun was really starting to shine, so we sat for a while at a bar overlooking Ponte Vecchio and just enjoyed the sun and people watching.
Dinner reservations were right across the Ponte Vecchio on the other side of the bank at a place that was recommended to me called Golden View (10/10). And oh boy was the view golden. The food and wine were even better than the view, so if you are in Florence this place is a MUST.
We had dinner a bit early so the sun was only just starting to set as we finished our meal, and I had found a rooftop bar where we could enjoy the Firenze sunset. For an amazing rooftop bar in Florence, go to La Terrazza Continentale (9/10). It is definitely a place to see and be seen, with chic Florentines mixing with foreigners as the sun set over the Arno river. It was a magical first night in Firenze.
“Everything about Florence seems to be colored with a mild violet, like diluted wine.” – Henry James
Day 2 Florence
In the morning, we had breakfast at the hotel and decided to follow Rick Steves’ Renaissance Walk. The walk takes you by and gives the history on the Duomo, Campanile, Baptistery, Piazza della Repubblica, Piazza della Signoria, Loggia dei Lanzi, all the way to the Ponte Vecchio.
We crossed the Ponte Vecchio and set our sights on Piazzale Michelangelo, a square overlooking the city which everyone I spoke with about Florence recommended we visit.
On the way, we had lunch at Osteria Antica Mescita San Niccolo (5/10) in the Oltrarno neighborhood. I do not recommend, but this place also has stellar reviews on TripAdvisor. The waitress was so rude and the food just okay. There are plenty of other restaurants around this one though so if you are following in my footsteps, try another place nearby.
The walk up to Piazzale Michelangelo was quite easy and only took about 20 minutes. We were debating about taking a taxi or bus because of mom’s foot but so happy we decided to walk. We came across a beautiful rose garden on the way to the top of the hill which was one of the most serene spots. And Piazzale Michelangelo’s panoramic view did not disappoint.
At Piazzale Michelangelo, mom spotted a church that she wanted to take a look at, so we hopped in a taxi and headed for Santa Croce church. We discovered a beautiful church in a square curiously surrounded by shops selling leather goods. We discovered that in the monastery next to the church is a very old leather school that you can actually get a tour of and see the master artisans working with leather. That is on my list for next time, since we just wanted to get back and ready for dinner.
We had dinner near our hotel at a restaurant called Trattoria dall’Oste (5/10) which also had thousands (literally) of good reviews and which I wouldn’t recommend. It felt very inauthentic and though the food wasn’t bad, it just was not a favorite at all.
After dinner, we headed to the SESTO rooftop at The Westin Excelsior (10/10) because we are here for the views. We loved this place! My mom and I had been fighting off jetlag so hadn’t experienced much nightlife, and there was good music, amazing cocktails, and a cool vibe. I had their mezcal drink which I am still thinking about and very attractive Italian waiters and bartenders whom I am also still thinking about *wink *.
The name of my cocktail for reference is the Aztec Treasure: Inspired by the tales of the infamous pirate Giovanni il Fiorentino, who stole the never-found Montezuma treasure from Cortés and the Spanish crown. It was made of Illegal Mezcal Joven, Ancho Reyes chili liquor, lime, orange marmalade, egg white, Angostura bitters, with a brulé top. 10/10 would recommend!
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Italy Itinerary: Siena and Tuscany
Day 1 Tuscany
I scheduled the train to Siena in the afternoon knowing that our time in Florence was short so that we could have the morning to do a bit more exploring before heading to Siena. We walked around and then stopped to have coffee at Rivoire (9/10) and people watched. It was endlessly entertaining watching the Asian and American tour groups go by, rushing past sites at breakneck paces, selfie sticks waving. I did not envy them as we sipped our cappuccinos in peace.
After our last casual morning in Florence, we went back to the hotel to meet the car who was taking us to the train station for the short train ride to Siena to start our stay in Tuscany.
- A note about Siena: I went back and forth about where to stay in Tuscany for weeks. I researched hill towns, agriturismo spots, luxury resorts in the middle of Tuscany, and on and on. I finally decided to trust Rick Steves and make Siena our home base. Until we arrived at our B&B and I saw the accommodations and the view, I did not know if I had made the right decision. Patting myself on the back here, I did. We fell in love, I mean IN LOVE, with Siena. I promise you I will live there one day. I cannot recommend staying in Siena enough. The people were so kind – the nicest and most helpful we encountered in all of Italy – the food was so fresh, delicious and affordable, the wine was out of this world. 10/10
Stay at B&B La Terrazza Sul Campo (10/10)- if you follow me on social media then you already saw the videos of our huge apartment, the view of the Square, the medieval balcony, the location in the heart of Siena directly on Il Campo. We could not believe how lucky we were and how beautiful this place was.
We changed and went straight for Piazza del Campo, one of the best squares in Italy. Walking through Siena feels like time traveling to a bygone era, and the city dates back to the Renaissance when they were in constant competition with Florence. The people of Siena are proud, with each section of town having a different Contrada which they support wholeheartedly, all leading up to the Palio races each summer. We sat in the sun at two different bars with outdoor seating at Il Campo, then walked through the medieval streets all the way to a park overlooking all of Siena.
Dinner reservations were at La Taverna di San Giuseppe (10/10) which was the highlight of our trip to Italy and favorite meal. The service was exceptional. Every single waiter bent over backwards to make our dinner the best. We had truffles on just about every dish, and you would think it was outrageously expensive but it was quite reasonable. It is rated in the Michelin Guide as a Bib Gourmand, and it deserves even more. At the end of the meal, we had a tour of their wine cellar which was underneath the city of Siena and used to be a chapel. We finished the meal with Limoncello and the best tiramisu I have ever had in my life. Ugh, I loved this place so much!!!
“Italy, and the spring and first love all together should suffice to make the gloomiest person happy.” – Bertrand Russell
Day 2 Tuscany
Originally, we had planned to arrange a car to take us to see another hill town near Siena like San Gimignano, but when we arrived in Siena we chose to explore more of it on our second day. This was lucky because we were pretty hungover from the night before (too much Italian wine). We slept in late and took our time getting ready, finally venturing out for a Bloody Maria (the Italian version of Bloody Mary) and lunch.
We stumbled upon the beautiful courtyard of a medieval palace – Palazzo Chigi Saracini (6/10)- that literally looked straight out of a fairy tale, and sat down to have lunch there. There was a wishing well and it now houses the Academy of Music and a cute cafe to sit and have a bite.
After that, we headed for the Duomo and purchased tickets to go inside. I highly recommend going in, even if you are not into churches, it was unbelievable. There are frescos on the floors, on the walls, in every nook and cranny. And if it’s not covered in a painting then there is a statue. I had never seen anything like it and I have seen my fair share of churches. It was more elaborate than even St. Peter’s Basilica in Rome.
After the Duomo, we wandered the streets of Siena and went in and out of shops. We purchased some local, handmade, handpainted ceramics from the sweetest little Nonna, and beautiful acrylic bowls and linen scarves at a local shop right next to the Duomo.
We were still fighting our hangovers and the chilly weather, so we stopped for soup and a spritz at the most gorgeous courtyard restaurant called Rosticceria Vitti (6/10). It was a great spot for people watching, lots of young families and kids, Siena is definitely a family-friendly place.
We continued to walk around Siena and wandered into a really cute wine shop called Pizzicheria De Miccoli that also sold meat and cheese. We decided to take advantage of our beautiful apartment that evening, and just have dinner at home. We asked the owner of the shop for a recommendation on a great truffle cheese, Super Tuscan wine, and spicy salami pairing.
As we got back to our apartment for an early night in, we opened the doors to our balcony and heard singing from the square. We were surprised and delighted to see a procession with drummers, flag bearers, and locals parading through Il Campo. We learned later that it was a Contrada practicing for the Palio races, which happen every summer in July and August. Visiting Siena again during the Palio races is very high on my bucket list!
Day 3 Tuscany
This was the day I had planned our wine tour of Tuscany! We had a private driver named Franco in a large comfortable van with wifi from Tours in Tuscany, and they curated an itinerary for us based on what I was looking for. I had always wanted to go to Montalcino and Montepulciano and try the wines there, but Tours of Tuscany has different itineraries for every wine lover.
We set out in the morning for Castello Banfi, a very famous Italian winery near Montalcino. We had a tour of the rooms where they age balsamic, a tour of their wine production area, a tasting, and finally lunch at the fabulous Taverna Banfi (10/10) with wine pairing. The lunch was amazing!
- This is just a review of the Banfi tour – I have been to Napa a million times and don’t really care about seeing how a big production winery operates, so I was very cranky and did not enjoy this part. We were stuck with tourists who asked the most inane questions, one couple who brought their toddler (???) and a couple who was pregnant. Why someone would come to a winery while pregnant is beyond me. If you go to Banfi, do not do the full tour. I would recommend just lunch with the wine pairing at Taverna Banfi and see the tasting room and grounds.
Our Tours of Tuscany trip continued as we headed through the Val d’Orcia, a UNESCO world heritage site and something I had high on my list for this trip. The Tuscan countryside zoomed by in a prismatic swirl of shapes and colors. Green grass and trees blended with blue sky, red and yellow wildflowers, peachy-orange villas, brown-and-gray farmhouses, and the occasional olive and cypress trees lining the roads. Franco, our driver, recommended a pit stop in Pienza for the view, and I am so pleased he did.
Pienza is halfway between Montalcino and Montepulciano where our next winery was located, and I wish we had more time there. It is the most picturesque hill town, with winding cobblestone roads, ivy-lined stone houses, and a market selling fresh flowers and lemons. I felt like we walked into a dream. Pienza, I will be back!
Our last stop for the day was de’ Ricci winery in Montepulciano. I 10/10 recommend the wines, the tour, and the location. It was amazing! Debbie showed us through their medieval wine caves under the city of Montepulciano, with some of the caves dating back to the Etruscan period. Debbie gave us the whole history of Montepulciano, the Etruscans, and the de’ Ricci family, and then lead us up to the tasting room for our pours.
- We met the owner of de Ricci who was celebrating because his wine had just made it into a Michelin Star restaurant and he could not have been nicer. He sat and talked to us for a while, gave us extra pours and grappa to celebrate with him. I bought a case of wine (I regret nothing) and I ended the day flirting with the sommelier who spoke zero English through google translate (again I regret nothing).
We were sad to leave Montepulciano, but we had an hour ride back to Siena. Thank you so much to Franco and Tours in Tuscany for the wonderful experience!
Dinner was at La Campane restaurant (10/10)- one we just happened upon near our apartment which was exceptional. I had steak with truffles and mom had the fresh fish of the day. I think I became a truffle after this trip because they were so cheap and delicious. It was a very quaint restaurant with excellent service and such delicious food that rivaled our dinner at Taverna di Guiseppe. Neither my mom nor I wanted our time in Siena to end, so we went to Il Campo for another glass of wine to put off packing.
Italy Itinerary: Positano
Day 1 Positano
Our train to Naples this morning was pretty early, and we had a short stopover where we had to change trains in Florence. The train from Siena to Florence was delayed which we were stressed about, but ItaliaRail was great and just booked us on the next train out.
We arrived in Naples around 2 pm and hired a taxi to take us to Positano. It was about an hour and a half trip with no traffic, and as we got closer to the coast we were white-knuckled as the roads wound around the cliffs. I truly do not know how people drive on the Amalfi and Sorrento Coasts! There are tour buses, Vespas, cyclists, people walking, small cars, big cars, all clinging to a cliffside road that with one wrong move goes straight down to the Bay of Naples.
As we arrived in Positano, we couldn’t believe our eyes. It is the most enchanting place I have ever been in my life.
- We checked into our favorite hotel of the trip, Hotel Buca di Bacco (10/10).
- I did so much research on where to stay in Positano and again wasn’t sure if I made the right decision until we arrived. Positano is built vertically, and our hotel was at the bottom of Positano near the beach. I selected this for our Italy itinerary because I knew we wouldn’t want to deal with walking up loads of stairs just to get back to our room every day. We had an ocean view (I think every room does), complimentary breakfast every morning, access to their exceptional restaurant with a discount, and the most accommodating front desk of any hotel I have ever stayed in. As we checked in, we asked for recommendations on dinner, and I mentioned I had tried fruitlessly to get reservations at La Sponda, a Michelin Star and very famous restaurant located in the Le Sirenuse hotel. The front desk staff said that they would try to get us in, and they ended up securing reservations for what would be the meal of a lifetime. I cannot thank the staff at Bucca di Baco enough!
After we checked in and changed, we were hungry so we wandered to the beach and grabbed a spritz and a quick bite at Ristorante la Pergola (8/10). With the sounds of the waves breaking on the Spiaggia Grande, soft Italian music playing, and the sun shining through the clouds to reflect off the deep blue water, we finally felt like we were on vacation.
After lunch, mom walked to the church and did some shopping, and I went for a walk to check out the beach club, La Scoliera. Even though the host warned me that the weather might not be great the next day, I decided to take a chance and booked two private lounge chairs with the best view of Positano for our second day.
Since it was Mother’s Day, I wanted to treat mom to somewhere nice and we had heard great things about the restaurant located in our hotel (10/10). We headed down for dinner just as the sun was setting, and had the best seat in the house and the patio almost to ourselves. Our waiter was very attentive and recommended a delicious local wine from Furore (see wine recs at the bottom of Italy itinerary).
Since we had a long day of travel and excitement, we called it an early night and headed back to our room to read our books in bed and listen to the sound of the sea from our room.
Day 2 Positano
We woke up early to grab breakfast and do some shopping before heading to the beach club La Scoliera while the sun was still shining.
- A note about shopping in Positano: I could not believe how affordable things were. Mom and I bought about 20 scarves, all in the most beautiful fabrics and colors, I got an amazing hat and an investment piece ring that was worth every penny; limoncello, candles, and any ceramic or bag with a lemon on it. The locals definitely were very obliging, kind, and welcoming and I heard so many personal stories about their families, where they live, and how much pride they have in their shop and the region. Definitely visit The Lemon Lady – she was literally sewing scarves and linens in the back of her shop – and Antica Sartoria for scarves and dresses.
We arrived at La Scoliera Beach Club (10/10) around 11 am to the sun glistening off the water, and basically had the club to ourselves the whole day.
- Our waiter at the beach club was a tanned, handsome version of Harry Potter named Francesco. We read our books and enjoyed the sun and view of Positano as Francesco served us drinks against the sound of the waves breaking against the rocks. Francesco recommended an absurdly good amber-colored Pinot Grigio, which we sipped on the sun-bleached cliffs. We came to learn that “bad weather” in Positano meant a few fluffy white clouds covering the sun here and there, and although the weather report promised rain we were visited by Fortuna.
We had great weather until about 3 pm when Francesco escorted us to a late lunch at L’Incanto (10/10). I had the best clams with spaghetti ever and mom had prawns with salad. The storm clouds rolled in just as we were finishing our lunch and heading back to the hotel for a nap before dinner.
I saw pictures of Villa Treville (10/10) on Instagram while planning this trip and put it high on my list for places to visit. When we told people we were going there, everyone commented on how excellent of a restaurant Mastro’s was.
- It truly was the most amazing place I have been as we ate under a vine-covered terrace lit by custom Morrocan lamps, perched high on the cliffs overlooking Positano. We arrived a bit before our reservation, so we were welcome to enjoy the patio with champagne and light snacks before being seated. Dinner was incredible, truly one of the best meals of my life. The dessert was our personal favorite, it looked exactly like a whole lemon. The wine, the view, the stemware (I have such a love affair for great stemware), the peacefulness, the high level of food: everything was out of this world. It is definitely a bit pricey, but if you are going to splurge, do it here!
“Positano bites deep. It is a dream place that isn’t quite real when you are there and becomes beckoningly real after you have gone.” – John Steinbeck
Day 3 Positano
We slept in a bit and headed for breakfast as the sun poked in and out of the clouds. The weather wasn’t too bad, and we wanted another relaxing beach day, so we decided to try the beach on the other side of Positano called Spiaggia del Fornillo (8/10).
It is a bit of a walk to get here along the cliffs overlooking the sea, and we relaxed on the rocky beach with our books until heading up for lunch at Hotel Pupetto (8/10). This restaurant was adorable as you are basically eating under the vines of lemon trees with a view all the way to Praiano. We had a long lunch in the sun of aperol spritzes, freshly caught grilled octopus and lightly fried fish, with jovial and experienced service. The clouds started rolling in just as we were finishing, and again the locals warned of rain which never came but scared us enough to head back near our hotel.
We wandered in and out of stores, I bought a painting from the adorable Nonno named Francesco who told me about his life and that the colors of Positano matched my soul. Couldn’t have agreed with him more!
The restaurant had secured us a 9 pm reservation at my dream restaurant, La Sponda at the Sirenuse Hotel, and I wanted to catch the sunset at their popular champagne and oyster bar, Franco’s Bar (10/10). If you can’t get a rez at La Sponda, I highly recommend visiting Franco’s for the ambiance. It is definitely a place to see and be seen!
Dinner at La Sponda (10/10)- I do not know if I can do justice to our unforgettable experience.
- It has to be the most romantic restaurant in the world. You are seated under 400 candles that are illuminated by hand nightly, with the white columns wrapped in vines and the blue tiled floors matching the colors of the sea beyond. It’s the most whimsical and dream-like place with perfectly balanced service (not standoffish but friendly and charming and all of the waiters seem to be witty and knowledgable. The food is incredible and full of flavors from the Amalfi Coast. We chose the chefs tasting menu with wine pairing, and every dish with accompanying wine was an explosion of flavor. Not to mention the two musicians who walk around the restaurant and serenade each table with music, with the waiters joining in on Volare and That’s Amore. I wanted to cry with how lucky we were to be there together in that moment. It deserves much, much more than just one Michelin Star.
Day 4 Capri
The weather was not good at all on this day, and I had booked us a boat tour of the coast and Capri on Lucibello.
- If you are going to Positano, use Lucibello and mention my name for 10% off!
Our knowledgeable and charming captain Dario turned bad weather into an amazing day. We learned legends and history of the Amalfi Coast. We got up close and personal with the dolphin-shaped Li Galli Islands which can be rented for a cool $150k a week (Lebron vacationed there last summer). As we approached Capri, Dario was able to fit our boat inside even the smallest caves, telling us the legends about the ancient Romans who vacationed on the island of Capri, where to go and what to see.
We disembarked after 3 joyous hours at sea and caught a taxi to Piazza Umberto, the main square of Capri. We walked around through the narrow streets avoiding the crush of tourists until we were ready for lunch.
Lunch was at La Capannina (7/10) which came highly recommended from Dario and our taxi driver as an authentic local spot serving seafood and fresh fish.
After lunch, we really got into the shopping scene which rivals Rodeo Drive in Beverly Hills. I really wanted custom leather sandals, which are handmade in Capri, but once I saw how much cheaper the sandals were in Valentino, I couldn’t resist.
We stopped for drinks as it started to rain at the stately Grand Hotel Quisisana. The Quisisana opened its doors in 1845 and is one of Capri’s most historic hotels, counting Ernest Hemingway and Jean-Paul Sartre among its guests.
The weather continued to get worse, and we figured we should head back to Positano before the ferry stopped running. I highly recommend the ferry by the way! It shuttled us back to Positano in a half hour.
Dinner was room service in bed while we rested and talked about how wonderful Positano had been, and how we couldn’t wait to come back one day.
Italy Itinerary: Rome
This was my third time in Rome and my mom’s second, so we really didn’t do much touristy stuff. I will work on finding my full Rome Italy itinerary that I curated in the past and publish it on my blog at a later date!
Day 1 Rome
The hotel arranged for us to have a car to take us to Naples where we were catching our last train of the trip to Rome.
Rome was not our friend on our first day. It figured that after experience until Rome went off without a hitch, we were destined for at least one bad day. All we could do was laugh though and chalk it up to the travel gods.
Check in to The Pantheon Iconic Rome Hotel, Autograph Collection (0/10). – DO NOT STAY HERE. The worst hotel ever, so much went wrong I won’t even go into it. Just know that Marriott refunded our points and more because of how terrible our experience was. The rooftop bar and location are the only redeeming qualities.
The first thing we did after finally checking in was head for Piazza Navona. Mom and I stayed at a small B&B on the Piazza during our first time in Rome years ago, and we had so many good memories from that area. We sat at Caffe Barocco (3/10) and people-watched while enjoying a spritz in the sun.
Next, we decided to do the Rick Steves’ Heart of Rome Walk which took us past all of the major sites like the Spanish Steps and the Trevi Fountain all the way back to the Pantheon. At this point though, we were so sick of tourists, and just wanted to enjoy the sunset on our rooftop, so we went back to the hotel for a nightcap.
Dinner was another place I researched well which was a miss Osteria del Sostegno (5/10)- not because the food wasn’t great but because the service was laughably atrocious. It took two hours to get us our two plates of pasta, they were so disorganized and chaotic, and they were still seating people for dinner at 11:30 pm.
We went to a nearby wine bar (Collegio 10/10) after dinner to chuckle about how Rome did not like us anymore and prayed that tomorrow would be a better day.
Day 2 Rome
Our second day in Rome and last of the trip proved much better thankfully.
We spent the morning and afternoon in the Trastevere neighborhood – my favorite. Picture old crooked buildings, winding alleyways, bougainvillea and vines climbing the houses, and students from the nearby university milling around in between class. If you are in Rome, definitely plan on spending time here. Start at Piazza di Santa Maria, the heart of this labyrinthine district; take Via del Moro, with its many shops and cafes, then divert into the quiet cobblestoned side streets lined with crumbling buildings with faded paintwork.
Lunch was at Tonnarello (10/10) – highly recommend the carbonara and spaghetti and meatballs. Arancini (rice balls stuffed with mozzarella and then deep-fried #cleaneating) is always a must when in Rome, and they were excellent here.
After lunch, we hopped in a taxi and headed for the Vatican. As Catholics, it is always overwhelming to see St. Peter’s Square and think about the history of the area. We had seen the Sistine Chapel and St. Peter’s Basilica on our last trip, so we didn’t go inside. We just said some prayers before we walked from the Vatican to Castel Sant’Angelo and across the Tiber.
We found ourselves back at Piazza Navona, and as we crossed the square the craziest thing happened. We were approached by a painter who recognized us from our last trip to Rome!
- We had purchased art from Roberto five years prior, and we couldn’t believe he remembered us. He said – yes you were the basketball player right! We chatted with Roberto and found out that he and his brother Massimiliano also offer walking tours of Rome. Roberto could not be nicer, and although I didn’t have time to take a walking tour with him this time, it is high on my list for next time. We bought more art from Roberto and were so touched that an artist cares about his customers to remember them after all those years.
- Check out his Facebook page here.
We went back to the hotel to get ready for our last night in Italy, dinner at Dal Bolognese.
- Dal Bolognese is a special place where the beautiful and moneyed Romans go to see and be seen. It is located on the corner of Piazza del Popolo and is a great place to get some fancy pasta. The dining room and service were elegant yet comfortable, with red leather chairs and couches punctuating the brightly lit space. Kim and Kanye ate here before so I knew it had to be good and was shocked the prices weren’t exorbitant. Highly recommend for the namesake bolognese pasta, people-watching, and wine list.
After dinner, we had one more glass of wine at a bar with a view of the Pantheon, and we cheersed to the trip of a lifetime.
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I would like to thank my mom for coming with me on this trip. I am so lucky to have you in my life, and that we could go on this trip together. Thank you for trusting me implicitly with the planning and recommendations, and thank you for the memories we created in Italy! Sposami Italia!!!!
No good Italy itinerary is complete without some wine recs. Before visiting Italy this go-around, I didn’t have an affinity for or know much about Italian wine. I have been to Napa more times than I can count so I love California wines, as well as Oregon Pinot Noirs, but was not too familiar with the wine regions in Italy or what to look for when ordering an Italian wine. We had so much good wine on this trip, learned what we liked and didn’t care for, and I tried to take a picture of every bottle so I could remember which I loved and wanted to buy again. Here are my wine recommendations:
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