Roman Wonders to Amalfi Dreams: A Journey Through Italy

Rome (based in Trastevere)

Walk into Basilica di Santa Maria in Trastevere with no plan and no ticket—ancient artifacts sit outside and the gold mosaics inside are breathtaking, yet somehow crowd-free. Each evening, we drifted between Piazza Santa Maria and Piazza Trilussa, where live music, street performers, and families created the most joyful energy.

One night, we rented e-scooters and rode along the river all the way to Stadio Olimpico, stopping at historic landmarks with almost no one around—my 13-year-old still says this was his favorite memory of Rome. When we wanted quiet, we packed a picnic and walked 30 minutes uphill to Colle del Gianicolo for sweeping views and total calm.

Book the underground, all-levels tour of the Colosseum to walk beneath the arena floor where gladiators once stood—it makes Ancient Rome feel real. Then climb the dome at St. Peter’s Basilica (€12) for a tight, winding stair climb that opens to one of the best views in the city.

When it was time to leave Rome, we took the high-speed train to Naples and hired a private driver to Positano—the coastal drive is so stunning it feels like part of the vacation.

Positano

We pre-booked loungers at Spiaggia Grande and spent the day swimming with Aperol spritzes and food delivered right to our chairs. Positano is vertical, so wandering the stair streets between boutiques, lemon stands, and sea views becomes the activity itself.

Hiking Path of the Gods was unforgettable because we researched it first: private driver to Bomerano, a 3.5-mile cliffside hike to Nocelle, then 1,700+ steps down into Positano (bring lots of water, real shoes, a hat, and sunscreen). The lemon granita (lemon slushy drink) at the end tasted like a reward.

At La Tagliata, we took a cooking class, picked vegetables from their garden, made lemon pasta with pesto, and danced while we cooked—then returned later in the week for their endless family-style feast with unlimited wine. Shopping at Luisa Positano for dresses and designing custom sandals at Artigianato Rallo made for the most fun souvenirs. We also wore these dresses with our matching sandals to dinner and drinks at Drinks at Franco’s Bar and La Tagliata—both places had stunning views of Positano.

One night, we joined the teens and danced at Music on the Rocks carved into the cliff above the beach. When we were ready to move on, we pre-booked a one-way ferry to Capri—arriving by water is unforgettable.

Capri & Anacapri

Right off the ferry, we jumped into an open-air taxi up to Anacapri—such a fun first impression. The single-seater Monte Solaro Chairlift (€14) floats you to panoramic views over Capri and Naples; we celebrated at the summit bar with an aperitivo and chips.

We spent slow afternoons poolside at Hotel San Michele with Caprese salad (when in Capri) and limoncello spritzes, then wandered to Villa San Michele for gardens and views. From Marina Grande, we pre-booked a boat to the Blue Grotto, transferring into a tiny rowboat, ducking low into the cave, and watching the water glow electric blue. Absolutely stunning! Then dinner at Capri Rooftop.

In Capri Town, the two-minute Funicolare di Capri lifts you from the marina to shopping streets and gardens in minutes. When it was time to go, we took a one-way ferry back to Naples and the train to Rome—simple logistics that made this multi-stop trip feel seamless.

Rome

• La Tabenetta 29 di Tony e Andrea
  In Trastevere, dinner felt like an event every single night. At La Tavernetta 29 di Tony e Andrea, Tony welcomed us like family and served homemade Roman dishes that made this our favorite restaurant in the neighborhood. We ordered carbonara, shared chicken parm, and were surprised with complimentary tiramisu and limoncello shots at the end of our meals.

• Suppli (Trastevere)
  One night, we grabbed fried rice balls (ragù and cacio e pepe), took them to Piazza Trilussa, and ate while a street musician played to the crowd.

• Aroma
  For a completely different vibe, Aroma gave us front-row views of the Colosseum glowing at night as we shared amatriciana and carbonara between six of us and lingered over the moment.

• Caffé del Cinque
  In the morning, we would enjoy a pistachio croissant and cappuccinos, while in the evening, we would enjoy the nightlife with live music and wine, within walking distance of our hotel. I even bought the T-shirt since it was our first and last stop each day in Rome!

Positano

• Chez Black
  Lunch at Chez Black put us oceanfront in the main square where we all ordered seafood pasta and watched the beach buzz around us.

• Da Adolfo
  Getting to Da Adolfo was part of the fun—their small boat picks you up (call for reservations), and we spent hours eating grilled fish, fresh seafood, and fruit pies, and relaxing on their beach chairs before heading back.

• Franco’s Bar
  Before dinner one night, we went to Franco’s Bar for a bottle of prosecco with sweeping views.

• La Tagliata
  We had a family-style feast of garden salads, cheeses, charcuterie, Roman artichokes, pastas, steaks, sausage, pork, fish, desserts, and unlimited wine—Italians fully expect you to try everything.

Capri

• Da Paolino
  At Da Paolino, we dined under a canopy of lemon trees; I ordered the lemon ricotta ravioli and we visited the dessert room after espresso martinis at the bar.

• Il Riccio
  Near the Blue Grotto, Il Riccio wowed us with sea views and the famous “Room of Temptation” filled with sfogliatelle, torta caprese, and the best cannoli I’ve ever had.

• Capri Rooftop
  On our last night, we splurged at Capri Rooftop for Caprese ravioli, eggplant parmigiana, and a bottle of prosecco overlooking Capri Town, the perfect ending to the trip.