11 Private Day Trips in Italy Worth the Early Start

1.From Milan: Como Private Boat, Bellagio and Lugano Day Trip

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

Travel from Milan Central to Como, Bellagio, Lake Como, and Lugano by coach and private boat. Your English-speaking guide, such as Marina, Luca, Amalia, or Monica, handles the timing while you enjoy free time, lake views, shopping, and Como Cathedral.

“I spent a fabulous day, even with a bit of sunshine. Amalia is a very knowledgeable guide, she gaves us a lot of explanations and also some tips for shopping and where to go out in Milano. Manuela drives us smoothly and safely to our destinations. They are both a great team. I recommend this tour !”

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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 by coach to Como, cruise Lake Como by private boat, and spend free time in Bellagio and Como. English service is guaranteed. The boat ride lasts one hour in winter and two hours from April through October. Guides may include Sarah, Anna, or Raffaele.

“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

Join a small group of up to eight for a skipper-led gozzo cruise from Sorrento to Capri. Expect coastal views, grottoes, swimming, drinks, a Caprese sandwich, and four hours to explore Capri. Guides such as Luca, Anna, and Francesco add local tips and lively commentary.

“Capri is a Dream! What better way to see Capri than with a beautiful boat ride with 2 young handsome Italians Carlo and Francisco! Incredible way to see the top with the lift in Anacapri , middle and Marina Granden 3 caves! Beautiful way to relax and enjoy to the fullest! Cheers tutti!”

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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

Ride the train from Piramide to Ostia Antica with an English-speaking guide and a group of no more than 12. Spend about 2.5 hours among the amphitheater, Baths of Neptune, taverns, apartments, and ancient streets. Guides such as Alberto, Cat, Rob, and Laura have earned especially warm praise.

“This was really an insightful tour into a complete Roman city ruin. Provided a very real understanding of how the Romans lived and thought. Our host Alberto provided a clear view of how The Romans lived and the history of this particular city. Highly recommend for anyone who wants to truly explore the Roman day to day experience. Family was initially skeptical of “archaeological” tour (I was quite excited) but they all found the tour enlightening and enjoyable - no regrets at all. If traveling with teenagers - maybe offer them option to continue trek after tour to go to Ostia beaches just 1-2 stops further down rail from Ostia…”

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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 by private luxury car or minivan with an English-speaking driver such as Marco, Simone, or Massimo. Visit Siena and San Gimignano, stop for Chianti views, and add a winery lunch for €50 to €70 per adult. This is a private driving tour, not a guided walking tour.

“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 with an English-speaking driver. See the Leaning Tower, Piazzale Michelangelo, the Duomo, Ponte Vecchio, and more. Add a private Florence guide with timed entry to the Accademia or Uffizi.

“Both Alesseo and Francesco were great hosts and went out of our way to be sure we had a great day. Ale picked us up promptly and on time and took some scenic routes to bring us to Florence. Francesco was extremely knowledgeable about all of the exhibits we visited and it is clear that he has a passion for art. Both of our guides created a wonderful experience and were able to recommend great restaurants as well! It is absolutely worth having a private tour and not getting caught in the huge crowds!!”

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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

Travel from Florence by private Mercedes with an English-speaking driver such as Mario, Paolo, or Donatello. See Siena, San Gimignano, Chianti, and Pisa in one long day, with room to adjust the route, stop for a winery lunch, or swap Pisa for a Tuscan villa.

“What a great day! Giuseppe was excellent and had a great plan for the day, but with some flexibility as well. He had good information on how to maximize our time in each place we stopped and arranged for a fun stop at a winery in the afternoon as well. The A/C in the van was much appreciated as well.”

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

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

Spend about 11 hours traveling from Rome to Pompeii and Positano in a private air-conditioned vehicle. Your English-speaking driver handles the long roads, while you choose self-guided Pompeii or a private guide. Positano may be exchanged for Sorrento before departure.

“Although not cheap, we felt the private tour was worth it. Our ride met us at our hotel in Rome right on time, and was friendly and informative on our ride to Positano. He provided helpful advice and recommendations, then left us to wander about the charming and breathtaking village for a couple of hours, visiting shops, having lunch, hanging out on the beach for a while. waded a little, but the water was too chilly to swim-March--but still a good time to go, as apparently traffic in the summer can be horrendous Then went to Pompeii, where our private tour guide was waiting, and we were able to skip…”

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

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

Start from central Rome and travel by second-class train and vehicle to Florence, then Pisa. Expect a guided walk past the Duomo, Ponte Vecchio, and Piazza della Signoria, followed by free time at the Leaning Tower. Lunch depends on the option you book.

“The biggest problem with this tour was distance. Pisa is about 4 hours from Rome, and Florence 3. So for our nearly 10 hour day was over 8 hours in transit. When we got to Pisa there was no guide. We were on our own, but with barely an hour to explore there was little time to do much beyond look at the tower. This was unfortunate, as the site had multiple other things to see - including a basilica. But each required you to pay (even the restroom), so you didn’t want to gamble on waiting in line for tickets you could not use. I think that between 1/2…”

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

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

Spend about eight hours with a private driver from Tuscany Top Drivers, visiting Siena, San Gimignano, and Chianti from Florence. Guides including Marco, Simone, Tommaso, Martino, Martin, and Paolo offer local stories, flexible stops, scenic detours, and optional winery lunches with wine tastings.

“It was a great day, our driver was very knowledgeable! In hind side, the time in the cities was a-little rushed so next time I would fore go the lunch at the winery and split the time in the two cities. But overall very special day!”

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

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

Leave Rome at 7:30 a.m. in a private Mercedes with an English-speaking driver, then see Pompeii, Sorrento, and Positano in one long day. Pompeii tickets are included, while a local guide costs an extra 170 euros. Drivers such as Mido, Ahmed, and Fabio are noted for safe driving and helpful local advice.

“Excellent trip. Our driver Modi was the best. He made the trip what it was. Really flexible as we didn’t stay in Pompeii for more than an hour. He then drove us to Positano and literally helped the wait staff ready a table by the window for us. And the food was the best we had our entire trip. He then drove us all the way down to a short walk to the beach. If you can request him, I would do so. One of the best guides I’ve had and a great friendly person. Great driver as the roads to Positano are something I wouldn’t want to drive. He…”

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