Top 15 Private Day Trips in Italy

1.Como Private Boat, Bellagio and Lugano Day Trip

★★★★★★★★★★4.8 · 6,271 reviews · 11 hours · from $78Our pick

From Milan Central, you’ll visit Como, cruise Lake Como by private boat to Bellagio, then cross into Swiss Lugano. Expect an 11-hour day, about 78 dollars per person, English commentary, free time in three towns, and guides such as Luca, Amalia, Marina, or Monica depending on the departure.

“Marina and Tadju were fantastic. It was an amazing trip! I highly recommend this - defo worth the value it was a fantastic day!”

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2.Lake Como & Bellagio Day Trip with Private Boat Cruise

★★★★★★★★★★4.0 · 2,587 reviews · 10 hours (approx.) · from $120

Travel from Milan to Lake Como by air-conditioned coach, visit Como and Bellagio, and cruise past villas such as Villa Carlotta and Villa del Balbianello. The private group boat runs from Tremezzina, for one hour in winter and two hours from April to October. Guides such as Anna, Sara, Angelo, and Raffaele have earned praise for keeping the long day lively and organized.

“Very nice trip and overview of this beautiful region in Italy. Everything went smoothly and guides were great.”

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3.Capri & Blue Grotto Semi Private Boat Day Trip from Sorrento

★★★★★★★★★★5.0 · 2,053 reviews · 7 to 8 hours (approx.) · from $216Top rated

Sail from Sorrento toward Capri on a traditional gozzo with a skipper and a maximum of eight people. Expect grottos, Faraglioni rocks, swimming stops, drinks, a Caprese sandwich, and three to five hours on Capri. Guides such as Luca, Anna, Francesco, and Federico are praised for making the day lively and easy to follow.

“Francisco our guide was sensational and our Captain so lovely! We had the best boat tour we've ever had and this came down to Francisco's energy and the extra touch he added to all aspects of the tour. From the wrapped sandwiches, the hotel pick up, the lemoncello spritz and the little farewell treat. Everything was perfect! The island was beautiful and the swimming spot was refreshing. Best tour by far and would highly recommend.”

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4.Ancient Ostia Antica Semi-Private Day Trip from Rome by Train with Guide

★★★★★★★★★★4.5 · 579 reviews · 4 hours (approx.) · from $59Best value

Take a four-hour half-day trip from Rome to Ostia Antica with an English-speaking guide and a group of no more than 12. Ride the train together, then spend about 2.5 hours walking ancient streets, viewing the Baths of Neptune, amphitheater, shops, apartments, and mosaics. Guides such as Alberto, Barbara, Cat, Laura, and Rob have earned particular praise for clear storytelling.

“Outstanding information of all areas by our guide Liv. Her detailed descriptions of everything so absorbing, really brought to our attention the advanced way of life the Roman's led”

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5.Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

★★★★★★★★★★5.0 · 405 reviews · 8 hours (approx.)

Travel from Florence in a private car or minivan with an English-speaking driver such as Marco, Simone, or Massimo. Visit Siena and San Gimignano, stop for Tuscan views, and add a family-run winery lunch with wine tasting. You get hotel pickup, flexible pacing, and time to explore on your own.

“Amazing day touring beautiful Tuscan region with Simon. He was always helpful with ideas for options. Highly recommended.”

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6.Livorno Shore Excursion: Pisa and Florence Private Day Trip

★★★★★★★★★★4.5 · 198 reviews · 9 hours (approx.) · from $546

Travel by private Mercedes from Livorno to Pisa and Florence in about nine hours. See the Leaning Tower, Piazzale Michelangelo, Ponte Vecchio, the Duomo, and Santa Croce. Add a private Florence guide with timed entry to the Accademia or Uffizi. Drivers such as Alessio, Donatello, and Alex are praised for flexible sightseeing and safe returns to the ship.

“Great day in beautiful Tuscany! Our driver was Donatello & our guide in Florence was Silvia. Donatello was there when we exited the ship, so we went right away to Pisa. Since we got there at 8:30am, nothing was open yet & we had the plaza with the leaning tower & church all to ourselves. We got some nice pics without the crowds! Next was the hour drive to Florence to meet our guide. Even though we had skip the line tickets, we still had to wait about 30 minutes to get in to see David. But he is magnificent & worth the wait! Then we did a 2-hour walk…”

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7.Private day trip to Siena, San Gimignano, Chianti and Pisa, from Florence

★★★★★★★★★★5.0 · 104 reviews · 10 hours (approx.) · from $462

Spend about 10 hours touring Tuscany with a private English-speaking driver, stopping in Siena, San Gimignano, Chianti, and Pisa. You set the pace, choose lunch and wine stops, and ride door to door in an air-conditioned Mercedes with Wi-Fi. Drivers such as Mario, Paolo, Donatello, and Giuseppe are praised for local insight and flexibility.

“Fantastic experience ! Highly recommend this tour and our guide was amazing! Guiseppe went above and beyond to make our Tuscan experience memorable. Don’t hesitate to book this tour .”

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8.From Amalfi: Day Trip to Capri Private Boat Tour with Drinks

★★★★★★★★★★4.8 · 82 reviews

Spend six relaxed hours on a private boat from Amalfi, Positano, Praiano, or nearby ports. Your English-speaking skipper guides you past Li Galli, Nerano, Capri’s grottoes, Faraglioni, and Marina Grande, with drinks, swim stops, and an optional seaside lunch. Captains including Luigi and Francesco are praised for local stories and flexible routing.

“We had an amazing time on our boating trip on the Amalfi Coast! Flora was very organized and checked in with us a few days before by WhatsApp to make sure we had all the information that we needed. She had wonderful recommendations for our trip itinerary. Luigi was our guide and picked us up in Cetera at the dock. It was very easy to locate him and he sent us a WhatsApp message upon his arrival with a location pin. We then spent the day out along the coast line. Luigi was a fantastic guide and knew all of the best spots to stop for a swim and view…”

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9.Private Tour: Pompeii and Positano Day Trip from Rome

★★★★★★★★★★4.5 · 74 reviews · 11 hours (approx.) · from $550

Travel from Rome by private air-conditioned car or minivan to Pompeii and Positano, with hotel pickup, an English-speaking driver, and optional Pompeii guide. Expect about 11 hours, long drives, two hours at each main stop, and flexibility to swap Positano for Sorrento.

“We met our guide-Ida- who was very fantastic! Excellent English and very nice.She did a great job of working us through the crowd. Being a group of just 4, she got us into areas large tours cannot. Definitely go in the morning if going in the summer. This was worth every penny just to skip the lines”

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10.Private Tour: Day Trip to Florence and Pisa from Rome with Lunch

★★★★★★★★★★4.0 · 65 reviews · 12 hours (approx.) · from $481

Start early from Rome and reach Florence for guided visits to Piazzale Michelangelo, Ponte Vecchio, the Duomo, Piazza della Signoria, and Giotto’s bell tower. Continue to Pisa for the Cathedral Square and Leaning Tower. Expect a very long day, limited free time, and a tour style that may vary between a private vehicle and a small group.

“Driver was the guide. He was helpful and I could understand him to talk to. Showed us interesting information in Florence and also Pisa. Was a very long day and he even showed us some of the sights of Rome when taking us back to the hotel. The reason I would not recommend to a freind is that for Elderly it is a very long way. For younger people ,no worries.”

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11.Private Tuscany Tour: Siena, San Gimignano and Chianti Day Trip

★★★★★★★★★★5.0 · 64 reviews · 8 hours (approx.) · from $422

Travel from Florence in a private, air-conditioned minivan with a driver-guide such as Marco, Simone, Tommaso, or Martino. Visit Siena and San Gimignano, pause at Piazzale Michelangelo, and add a winery lunch with tastings if you want a longer Tuscan meal. Hotel pickup and drop-off are included.

“Best tour ever!! Marco was amazing and totally treated us like royalty! We had the best lunch at Marronaia!! Thank you!!”

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12.Private Day Trip Rome to Pompeii & Amalfi Coast tickets included

★★★★★★★★★★5.0 · 61 reviews · 12 hours (approx.) · from $639

Leave Rome at 7:30 am in a private Mercedes with an English-speaking driver such as Mido, Ahmed, or Fabio. Visit Pompeii with skip-the-line entry, then enjoy scenic stops in Sorrento and Positano. A private Pompeii guide costs an additional 170 euros, and lunch is extra.

“Had a wonderful day with Ahmed traveling from Rome to Positano and Pompeii. He is pleasant, a great driver, knowledgeable and very attentive. Everything went smoothly & I’m very pleased with the whole trip. Would book this tour again. This is the perfect way to travel for a family or small group.”

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13.From Positano: Private Day Trip to Capri by Boat w/ Skipper

★★★★★★★★★★4.3 · 40 reviews

Spend 7 to 7.5 hours on a private boat from Positano to Capri with an English or Italian-speaking skipper. See the White Grotto, Red Grotto, and Faraglioni, swim with provided gear, enjoy snacks and drinks, then spend 3 to 4 hours exploring Capri. Skippers such as Giuseppe, Mattia, and Gianluigi are praised for safe, personal service.

“Giuseppe was amazing and so friendly! Had an amazing time🙌🏼”

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14.Amalfi Coast Private Day Trip

★★★★★★★★★★5.0 · 29 reviews · from $267

You’ll travel by private minibus or minivan from Naples to Ravello, Amalfi, and Positano, with an English- or Italian-speaking driver. Expect grand villas, cliff roads, citrus fields, photo stops, and time for lunch in Positano. Drivers such as Michele, Ciro, Stefano, and Fabio have made the day personal and flexible for private groups.

“Marco was an excellent guide. There was good communication in the days prior to our shore excursion. He tailored our tour to what we wanted. There were roads closing on Amalfi coast that day due to rock falls and he planned the drive so we were not stuck in traffic. We went to Amalfi and Positano and then stopped for olive oil tasting. After that we went to lovely winery for lunch. He had us back at the ship with plenty of time to spare. Highly recommend this private tour.”

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15.Cinque Terre Private Day Trip from Florence

★★★★★★★★★★5.0 · 27 reviews · 10 hours

Spend 10 hours exploring Riomaggiore, Manarola, Vernazza, and Corniglia with a private English, Spanish, or Italian-speaking guide. Your driver handles the difficult roads and village transfers while you walk colorful lanes, take a seasonal boat from Manarola to Vernazza, and find lunch with a sea view. Guides have included Nunzio, Lucca, Marco, and Adriano.

“We learned things we never would have learned on our own.”

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