Italy: Cities, Mountains, Canals & One Beautifully Chaotic Road Trip

May 30–31

Empty Middle Seats, Rooftop Spires & Rental Car Chaos

Las Vegas to Milan

Our 9:50 a.m. flight started smoothly: the scheduled Uber arrived, airport security was easy and we had about an hour in the lounge. We even scored the rarest airline luxury—an empty middle seat—to JFK. After McDonald’s and/or Starbucks and a thoroughly “meh” pop-up lounge, we found the free zero-gravity massage chairs at XWELL through Priority Pass. That stop was absolutely worth it.

Our overnight flight appeared on time until someone missed the flight and their luggage had to be removed. A delay of “a few minutes” turned into about an hour on the runway. Milan airport brought passport-kiosk confusion, extra questions and then Avis: we took number 127 while they were still in the 90s. An hour and a half later, our prepaid Jeep/small SUV became a BMW coupe. It did not fit the luggage well, but it had seat massagers, so there was that.

First Look at Milan

After spending more time than we care to admit setting up Apple CarPlay, we drove to B&B HOTEL Milano Sesto Marelli. Parking was easy, but we were racing a timed terrace ticket. The Sesto Marelli M1 station was only a three-to-five-minute walk away, and Milan’s tap-to-pay Metro made everything refreshingly simple.

We reached the Duomo around 5:00 p.m., later than our 4:00–4:30 slot, and it was not a problem. The lift delivered us into a maze of Candoglia-marble spires. Construction began in 1386 and continued for nearly 600 years; the cathedral is famous for thousands of statues, stained glass, archaeological ruins and the golden Madonnina above Milan. The city view was not the most spectacular part—the chance to walk among the architecture was. The skip-the-line lift ticket also covered the cathedral, crypt, archaeological site and museum for the ticket day and the following day.

Galleria, Medieval Milan & Dinner with a View

We walked through Galleria Vittorio Emanuele II, Italy’s oldest shopping gallery, beneath its enormous iron-and-glass roof and past Prada, Gucci and the famous bull mosaic tourists spin on for luck. Piazza Mercanti, tucked behind the Duomo, felt like a little pocket of the Middle Ages left behind among modern storefronts.

Hunger won at Obicà Mozzarella Bar overlooking the Duomo. It may have included a tourist tax, but the boyfriend’s pizza and my beef-cannoli pasta dish hit the spot. We took the M1 back, bought water and morning caffeine at New Alimentari Prodotti Italiani e Stranieri, and I passed out at 8:30 p.m.

June 1 · Milan

Bones, Flamingos & One Very Big Cathedral

Inside, Below & Across from the Duomo

Jet lag woke me at 6:00 a.m. I woke the boyfriend at 7:00, and we walked to Boulangerie Bistrò for three pastries, two espressos and one of the thickest, most delicious hot chocolates I have ever had—all for about €14. By 8:40 we were back at the Duomo, enjoying the rare small crowd before the doors opened promptly at 9:00.

Inside, the cathedral felt less gaudy than expected and simply, absurdly big. Beneath the floor, the archaeological site preserves a fourth-century Christian baptistery, Roman foundations and streets, remains of earlier churches and the Baptistery of San Giovanni alle Fonti, where Saint Ambrose is believed to have baptized Saint Augustine in 387.

At 10:00 the Crypt of Saint Charles Borromeo opened. His preserved body rests in an ornate glass-and-silver shrine beneath the main altar. It was my first crypt directly under a main altar, and the smaller, quieter space felt surprisingly intimate. Across the street, the Museo del Duomo displayed statues, gargoyles, stained glass, tapestries, paintings and wooden architectural models. Some pieces were replicas, but the museum was well designed and flowed efficiently. Overall, the €32 combination ticket felt worthwhile.

A Bone Chapel and Flamingos

Santuario di San Bernardino alle Ossa initially catfished us with a normal church. After exiting, we found the second entrance marked “Ossuary.” Beyond another normal church was exactly the weird, Gothic thing I wanted: skulls stacked in patterns and human bones framing walls, doors, altars and niches beneath elegant Baroque frescoes and chandeliers. The remains came mainly from overcrowded medieval cemeteries and hospitals, yet the chapel was unexpectedly peaceful.

At Villa Invernizzi, pink flamingos wandered around a private garden pond in one of Milan’s most upscale neighborhoods. You cannot enter, but you can see them through the gate. We passed beneath Porta Venezia and cut through the Giardini Pubblici Indro Montanelli, Milan’s oldest public gardens, on the way to Eataly in the converted Teatro Smeraldo. Lunch upstairs was fresh pasta with shrimp tartare and pesto for me and a calzone that was basically a flatbread sandwich for the boyfriend. You pay by table number, which was new to us.

Castles, Columns, Canals & a €20 Dinner

We walked through the free courtyards of Castello Sforzesco, crossed Parco Sempione and reached Arco della Pace, which was unfortunately under construction. Basilica of Sant’Ambrogio felt much older and quieter than the Duomo, with red brick, rounded arches and a peaceful arcaded courtyard. The nearby Colonne di San Lorenzo date roughly to the second or third century, while the Doll Wall uses dolls, shoes and personal objects as a memorial against violence toward women and femicide.

At the Navigli canal area, the Walrus Pub delivered reasonably priced cold drinks and good service. Dinner at MOI RISTORANTE & LOUNGE BISTROT was a €20 three-course meal: shrimp cocktail, seafood pasta and swordfish gratin. The boyfriend declared his four-cheese pizza the “best pizza of my life.” Milan was still just meh for us. The Metro was wonderful and the city had cool things, but a little over one day felt sufficient. I was glad we were moving on.

June 2 · Lake Garda & Verona

Roman Ruins, Toll-Road Chaos & Gelato in the Rain

Sirmione and the Grotte di Catullo

After the hotel’s €9.90 breakfast buffet, we stopped at Decathlon Lonato del Garda because the boyfriend had discovered the fatal flaw in carrying two backpack-style bags totaling 65–70 pounds. We did not find a replacement, but I did find pants and more of the padded socks I love.

We parked at Parcheggio Monte Baldo (€3.50 per hour) outside Sirmione’s restricted historic center. Scaliger Castle, built in the thirteenth century with moat, towers, drawbridges and a rare fortified harbor, guards the entrance. We wandered past Santa Maria Maggiore, reached the water at Spiaggia, met a cool elephant statue and followed Passeggiata delle Muse around the lake.

An uphill path through Parco Maria Callas led to the Grotte di Catullo, free on the day we visited. The enormous ruins of a Roman villa from around the first century sprawled across the tip of the peninsula. You can walk around and through them and follow a path to a rocky shoreline. By the time we returned, town had become a human funnel. The lanes are about 1.25 cars wide, yet cars still arrive. I do not enjoy shopping in chaos, so we got the hell out of Dodge. The toilets were €0.50, coin only—naturally, we had no coins.

A Road-Trip Detour Worth Taking

Needing both a toilet and food, I happened upon Selva Capuzza, a winery and restaurant with roots said to reach back to the eleventh century and ties to Benedictine monks. Without a reservation, we lucked into a table and had wonderful beef ravioli, rabbit with polenta and a glass of dessert wine. It was the kind of accidental stop that explains why I love road trips.

The toll road then reminded me why I hate road-tripping in foreign countries: wrong direction, traffic, toll, turnaround and another toll. Airporthotel Verona restored the mood with a steal of a price, huge free parking, a spacious clean room, pool and sauna. The shower leaked onto the floor, because Europe.

Verona in the Rain

We parked at Parcheggio Interrato Cittadella, accidentally exited away from the payment machines and learned later that payment must happen on level 0 before leaving. Rain started as we reached the first-century Arena di Verona. From the rear, in rain, it was not very photogenic, so we moved on past San Nicolò all’Arena to Piazza delle Erbe, Verona’s market square since Roman times.

We passed San Giorgetto beside the Arche Scaligere, declined the €4 admission and continued to Ponte Pietra, Verona’s oldest bridge, originally Roman and reconstructed with original stones after World War II. Low visibility killed our plan to climb toward Castel San Pietro. Instead, €3–4 focaccia from Focacceria Genovese and gelato from Gelateria Pellicciai became dinner. We promptly inhaled the gelato like gluttonous pigs.

Via Giuseppe Mazzini returned us to the arena from its photogenic side. After the parking-payment debacle, IperFamila Dossobuono supplied groceries, breakfast, household items and even luggage—but somehow no cold drinking water.

June 3 · Dolomites

Snowy Summits, Sardine Gondolas & One Beautiful Wrong Turn

Seceda: Spectacular and Much Colder Than Expected

We woke early to no power; it had gone out shortly after I went to bed. Daylight arrived around 5:30, so we ate our market breakfast and packed. The power returned five minutes before departure, saving us from hauling luggage down the stairs. The apologetic front desk comped our €4 minibar charge and offered breakfast.

The drive from Verona changed from vineyards to mountains and produced postcard moments everywhere. At Seceda, we arrived around 9:30 with only 16 parking spaces left. Parking cost about €5 per hour, and the round-trip cable cars were €148 for two. A six-seater lift reached the first summit; a sardine-packed gondola went to the top.

We were not ready for cold, slush and ice. In June, bring warm layers, hats, gloves and waterproof footwear with traction if you want to explore the highest point. After about 20 minutes, we retreated to the warmer lower summit and hiked to a stream where clear and brown water met. By departure the lot was full and cars were waiting. Go early.

Postcard Views, an Excellent Lunch and a Castle Detour

At Santa Maddalena Panorama Viewpoint, a short walk ended with the iconic little church, green fields and jagged Odle peaks. We skipped the church interior and found Salty Dog Fish Restaurant for pasta with langoustines and grilled salmon. It was fantastic and I cannot recommend it enough.

We detoured up a cliff toward Trostburg Castle, one of South Tyrol’s best-preserved castles, built in the 1100s and filled with creaky medieval charm. The winding road and valley views made the detour worthwhile even before the castle.

Gardena, Sella and Pordoi

Passo Gardena wound through towering cliffs like a stone amphitheater. Sella Pass, beneath the massive Sella Group, was even better—the highlight of the two and completely cinematic. Passo Pordoi added a €68 round-trip cable car for two to Sass Pordoi. This gondola was less crowded than Seceda, with two viewing decks, but the snow was deeper and anything beyond the decks required actual snow gear. Parking was €2.50 per hour; shops and restaurants operated at both top and bottom.

We accidentally drove the wrong direction and completed the pass before backtracking. Oops. There are worse mistakes; it was beautiful. Hotel Rododendro Val di Fassa had free parking, immaculate Alpine-style rooms and amazing views. We chose the set four-course dinner at 7:30, selected our courses at check-in, restocked water at a bougie little Coop and finally slowed down.

June 4 · Dolomites

Closed Cable Cars, WWI Tunnels & Emerald Lakes

When the Plan Falls Apart

Passo Giau started the day with 360-degree views and a spectacular winding road. It delivered us to Funivia Lagazuoi and its World War I tunnels, where suspiciously free parking revealed the cable car was closed. Hiking to the tunnels was possible, but I rerouted. Cinque Torri also disappeared from the plan because the chairlifts would not open until June 6.

Cortina d’Ampezzo was the largest Dolomite town we encountered, but it was busy, parking felt complicated and leaving luggage in the car did not feel safe. We skipped eating and shopping there. With most of the morning turning sour, we moved on annoyed.

Emerald Lakes and a Battlefield in the Clouds

Lago di Misurina, the “Pearl of the Dolomites,” improved things immediately with reflections, mountain views, parking, a store/café and the Italian rarity of free bathrooms. To replace Lagazuoi, I added the Monte Piana Jeep Shuttle and open-air World War I museum.

Monte Piana is where Italian and Austro-Hungarian forces fought a deadly two-year mountain war and roughly 14,000 soldiers died. The €25 round-trip Jeep reaches original trenches, tunnels and uneven hiking trails with views toward Tre Cime. It is not accessible, but you can enter tunnels and climb into caves. When enough visitors gather at the drop-off, the Jeeps return downhill. It was unique, moving and genuinely cool—I was almost glad the cable car had been closed. Although the area normally requires a parking reservation, requesting the shuttle allowed entry and included parking.

Antorno, Landro and the Tre Cime Workaround

Lago d’Antorno offered free lakeside parking and another reflection stop beneath Tre Cime. At Ristorante Lago Antorno, a late lunch of pizza and a sandwich was good, reasonably priced for the location and served well. Lago di Landro followed with emerald water and Monte Cristallo reflections. Paid roadside parking was inexpensive, but the machine was far away, so we grabbed a couple of photos and continued.

Tre Cime itself required advance, timed parking; nothing was available until after 7:00 p.m., and the lot cost €40. Our workaround was Punto Panoramico Dolomiti, said to be the only viewpoint showing Tre Cime and Cadini di Misurina together. The large lot cost €1 per 30 minutes. Poor service prevented the machine from taking our card, so our lucky €2 coin saved us.

The drive south to HOTIDAY Hotel Conegliano became an easy toll-road run once we left the mountains. The room had hot water, a mini fridge and air-conditioning. Breakfast was only €8, but we had to leave by 7:30 and a group of 50 was scheduled to eat at 7:00, so we skipped it.

June 5 · Venice

Colorful Islands, Tourist Chaos & a Mad Dash Through Venice

Murano and Burano

Our Venice base was hu Venezia Camping in Town. Staff had been super chill about leaving the car and sent a shuttle-ticket link. We arrived at 8:20, skipped the chaotic breakfast and jumped onto the earlier 8:25 shuttle because it had space. In Tronchetto, we bought a €25 day pass for the vaporetto and connected to line 12.

Murano’s glass furnaces were moved from Venice in 1291 to reduce fire risk, and the island’s artisans built a world-famous craft from there. We admired canals and church exteriors, skipped paid church admission and I bought glass-bead art shaped like a ghost voodoo doll.

Burano delivered brilliant houses, lace history and the leaning bell tower of San Martino, tilted by the soft lagoon soil. Lunch at Ristorante Pizzeria Principe—lasagne and gnocchi—was good, well priced for the island and accompanied by excellent service.

Weird Statues, Too Many Bookstore Tourists and Grand Venice

Back at Fondamente Nove, we trekked to Campo dei Mori and its odd stone merchants. The legend says the Mastelli brothers were turned to stone after cheating a customer. The payoff may not satisfy a normal tourist, but if you like weird, it is for you.

Libreria Acqua Alta stores books in gondolas, bathtubs and boats to survive high water. I wanted to love it, especially as physical bookstores disappear, but it felt more like a tourist attraction. The narrow aisles were so crowded that stopping to browse made you the asshole. Ninety percent of visitors seemed there for photos. It had interesting books, but I could not browse freely enough to add to my weird-book collection.

San Zaccaria brought a Gothic-Renaissance façade, Bellini altarpiece and flooded crypt. A short walk led to the Bridge of Sighs, Doge’s Palace and Piazza San Marco. We only saw the palace exterior; timed entry required advance booking and was not how we wanted to spend the money. St. Mark’s Basilica, though, is my one regret. The Byzantine domes and gold mosaics looked unreal from outside—possibly one of the most impressive church exteriors I have ever seen. Buy that timed ticket in advance.

San Giorgio, Rialto and the Run for the Shuttle

Across the water, San Giorgio Maggiore displayed free 3D-printed art like little Easter eggs throughout Palladio’s church. We cruised the Grand Canal to the Rialto Bridge, where both bridge approaches, shops and streets were chaotic. We fought to the middle, passed San Giacomo di Rialto and continued to Palazzo Contarini del Bovolo’s “snail” staircase.

A closing church and directions requiring a water taxi killed our final mission. Food nearby was overpriced, so I booked the 6:30 shuttle. Then the vaporetto line went insane. We boarded the third boat, stepped off with seven minutes remaining and literally ran to the pickup, arriving with three minutes to spare.

Our bungalow was spacious. The hotel restaurant’s seafood-and-asparagus risotto and service were merely okay, but prices were reasonable and convenience won. After 10.5 hours of walking and exploring, we were done. Venice had postcard moments and discoveries around every corner.

June 6 · Bologna & Florence

Medieval Towers, Squid-Ink Lasagne & Falling for Florence

A Quick Tour of Bologna

Because Bologna has many ZTLs—camera-enforced limited-traffic zones—we parked at Parcheggio Piazza VIII Agosto without driving into restricted streets. The Two Towers were closed, but Asinelli and dramatically leaning Garisenda still showed why Bologna once looked like a medieval Manhattan. Nearby Palazzo della Mercanzia recalled the city’s fourteenth-century merchant power.

The free Basilica di Santo Stefano, Bologna’s interconnected “Seven Churches,” had long corridors, 1,500 years of history and a farmers market in the entrance courtyard. Piazza Maggiore was partly obscured by stage construction, but massive San Petronio still delivered soaring ceilings and one of the world’s longest indoor meridian lines. Neptune Fountain stood at the corner.

On the way south, Sanctuary of the Madonna di San Luca offered free entry, city views and the famous 666-arch portico. The road was wild—curvy, narrow and terrifying at one blind arch where two-way traffic shares one lane.

Florence Had Me at Squid-Ink Lasagne

At hu Firenze Certosa, our small but clean luxury tent was ready early and included a mini fridge, air-conditioning, bathroom and assigned parking. We drove to Parcheggio Sotterraneo Sant’Ambrogio and walked through the indoor market.

Cru – Cucina Rustica Urbana seated us in a secret back garden. My squid-ink seafood lasagne looked as if it had been served straight from hell but tasted heavenly. The boyfriend’s salami spread and crud sandwich and our salted-caramel pastry were also outstanding. Highly recommended.

We paid €10 for Santa Croce to see the tombs of Michelangelo, Galileo and Machiavelli, plus chapels, halls and courtyard. Piazza della Signoria became a free open-air museum with Loggia dei Lanzi, Perseus with the Head of Medusa, Neptune Fountain and a replica David. Ponte Vecchio crossed the Arno in its familiar rows of jewelry shops.

Florence’s Duomo and Brunelleschi’s dome dominated the skyline, while the neighboring Baptistery and its bronze Gates of Paradise reached back to the 1000s. Our 5:00 p.m. Accademia reservation had sold out directly, so Headout cost about €40 each versus €24 face value. Inside was aggressive-crowd territory, but Michelangelo’s David was larger and more detailed than expected. The galleries also held wall-to-wall sculpture and a small musical-instrument museum.

On the walk back, Caffè Michelangelo served an excellent chicken Caesar salad, quiche and five or six pastries; our lovely server added extras. Piazzale Michelangelo ended the day with the city’s defining panorama. Florence was our favorite city so far—beautiful, more compact, more laid-back and the first place where I wanted more time.

June 7 · Pisa & Lerici

Leaning Towers, Thin Walls & the Great Italian Ice Hunt

Pisa Beyond the Leaning Tower

After our free 7:30 breakfast, we reached Pisa and parked free at Parcheggio Via Pietrasantina. It is farther out, but easy to access with an obvious walking route. The €11 Complete Monument pass covered the principal museums and monuments in Piazza dei Miracoli; climbing the tower costs more.

Camposanto Monumentale was my favorite stop, with Gothic cloisters, enormous dark frescoes, sarcophagi, elaborate floor tombs and a courtyard. Sunday Mass limited our view of Pisa Cathedral to the back, but its scale still made us tiny. The Baptistery—the largest in Italy—allowed us upstairs to an excellent cathedral view.

The Museum of the Sinopias displayed planning sketches discovered beneath Camposanto frescoes. Best of all were small nineteenth-century father-and-son drawings recording the murals before many details were lost. Outside, people-watching at the Leaning Tower was nearly an attraction itself; visitors can no longer step onto the grass for photos.

Lunch, the Arno and One More Tower View

At Trattoria Toscana dal 1976, we had buffalo-cheese bruschetta, meat-sauce pasta and steak with salad. A photo menu made ordering easy. Along the Arno, tiny Santa Maria della Spina showed off an absurdly ornate Gothic marble exterior. Borgo Stretto’s arcades led us to excellent gelato from La Bottega del Gelato and the small, free Chiesa di Sant’Anna.

The Duomo Museum held cathedral treasures and, more importantly, a less-crowded tower view plus a second-floor café overlooking it. Mass blocked the cathedral again, the historic cemetery closed for lunch, and we skipped climbing the city walls after already earning an aerial view.

Lerici: Beautiful Views and Questionable Walls

Albergo Serena sat above Lerici with a nice view, but it was our worst hotel: thin walls announced a neighbor in the throes of passion, the room and shower were tiny, and check-in had a strict 1:00–7:00 p.m. window reinforced by many messages. It did have air-conditioning and a small lot that filled overnight.

Sunday crowds eliminated every Tellaro parking space, so we continued to Parcheggio Lerici Centro. At the harbor, the rocky Frangiflutti strip reached into the sea beneath Castello San Giorgio. We skipped the castle climb and chose cocktails, complimentary snacks and views at Corona Boat Club. Bar Colibrì’s enormous €8–9 focaccia sandwiches were a better value; mine combined smoked fish, shrimp and cocktail sauce.

After Via Roma, the boyfriend resumed the ice hunt he had conducted basically our entire stay. ChatGPT led us to SIGMA Superstore, where we finally asked and discovered bags hidden at the back of an apparently empty freezer section. Ice is hard to find in Italy. Be warned.

June 8 · Cinque Terre, Parma & MXP

Stairway Suffering, Parma Perfection & One Well-Earned Hotel Upgrade

Riomaggiore to Manarola

Parcheggio Riomaggiore had perhaps ten public spaces; only three remained when we arrived. A man was directing traffic, so another lot may exist, but arrive early. Manarola can be a backup, and the two villages can be done in reverse. Parking ran about €3–4 per hour, followed by a ten-minute downhill walk.

Our 9:00–9:30 Via dell’Amore ticket cost €10 per person. The walk to Manarola took only 10–15 minutes and had gorgeous views, though I am not fully convinced it justified the cost. At Manarola Punto Panoramico, pastel houses and terraced vineyards stacked above the Ligurian Sea.

Google Maps sent us up a punishment staircase to San Lorenzo when a graded road also reaches the church. We took that sensible route down. The train back to Riomaggiore cost €8 per person for a three-minute tunnel ride with no views—also a bit of a rip-off. Our Via dell’Amore ticket included Castello di Riomaggiore, so we climbed more stairs for village and sea views, then passed San Giovanni Battista on the final ascent to the car.

Both churches were modest inside. Riomaggiore had the prettier façade; Manarola had the better adjacent clock tower. This was our roughest incline day, layered over a trip already averaging 8–12 walking miles daily. We survived, though I may have left a small part of myself behind. Dramatic, I know. The payoff was beautiful villages from above.

Parma Perfection

We parked at Parcheggio Toschi and passed the massive sixteenth-century Palazzo della Pilotta, grateful for its shade. Trattoria Corrieri became one of the trip’s best meals. My Tris di Tortelli included ricotta-spinach, pumpkin and salami fillings; the boyfriend chose gnocchi and vegetables cooked in vodka. Even the dense bread was amazing.

The pink Verona-marble Baptistery and Romanesque Parma Cathedral frame Piazza Duomo. Both charged admission, and I have issues with churches charging when the interiors are not must-sees for us, so we admired them outside. Silvano Romani | Casa del Parmigiano Reggiano supplied cheese and salami for the road.

One Well-Earned Hotel Upgrade

We dropped optional stops and drove two hours toward the airport. Points booked DoubleTree by Hilton Milan Malpensa Solbiate Olona, where private parking and an upgrade produced a huge room, large bed, bathtub/shower, mini fridge and all the whistles.

The hotel restaurant did not appeal and nearby options were limited, so Deliveroo won. An appetizer, two entrées, two desserts, fees and tip still cost less than two hotel entrées. The pasta and calzone were mid, but the desserts were epic. Eventually I passed out and woke several hours later. Oops. Long trip.

June 9 · Homeward

Delays, Random Screenings & 27 Hours Awake

The day began with a text saying my flight was delayed an hour, so I left 30 minutes later than planned. The boyfriend dropped me at Malpensa. Check-in and security were efficient, although I was randomly selected for hand swabs. Passport control involved a kiosk and then a long line; roughly an hour after arrival, I finally reached the other side.

The flight was uneventful beyond the delay. Atlanta Global Entry was quick, but the baggage wait was not. A customs dog caught a few people, which provided entertainment. After collecting my bag, an agent randomly selected me for questions, mostly about THC products. I had none and was released.

Back through security, I was randomly selected yet again—this time for a body scan. My onward flight started on time and gradually became an hour late because two flight attendants had landed elsewhere and needed to travel from A to E. An upgrade to Comfort+ with an open middle seat helped.

I landed in Las Vegas, found my pre-booked Uber without trouble and reached home after 23.5 hours of travel and 27 hours awake. Two days later, I was sick. Yay!