A Summer Family Vacation in Italy

Regina and her family were overwhelmed with planning a summer getaway to Italy. With three kids (ranging in age from 10 to 18) and a very limited window of opportunity to get everyone together in one place, they needed to make the most of their time, without overdoing it. They wanted to see as much as they could, experience the art and history but also have some relaxing time by the sea to really feel that summer vacation vibe. We put together an adventure in Italy with spectacular views and a little bit of everything! Here is their report of the adventure:


We had many many highlights and favorite moments! Florence was literally steaming hot, but the kids surprised us by totally loving the two tours we had — the walking tour which ended at the Accademia, and then a short but awesome whirlwind into the Uffizi!

They are old enough and curious enough to have been utterly wowed by the history — and both guides we had were AWESOME! It was too hot to climb the Duomo, but no matter, we walked and walked and felt always in the orbit of that amazing dome. Of course, beautiful food and endless gelato helped keep spirits up too!

view from the florence rooftop

Plaza Lucchesi was fantastic — can’t tell you how much fun that rooftop pool was at the end of a dripping hot day, before heading out for dinner! 


We loved Sorrento. As you predicted, the location of the apartment was perfect. And we all enjoyed having a little more room to spread out. (you cannot overestimate how amazing it was to have a washing machine to deal with our very very sweaty clothes!)

We had some of our very best days in the orbit of Sorrento. The amazing joyful cooking class at Villa Pane, the drive through the Amalfi Coast with Carmine (who works with Fabrizio — we totally loved both of them).

I would say the boat ride — which we were able to salvage after the initial cancellation — was quite simply one of the most wonderful days we’ve had in recent memory.

So much fun! Such a great way to get glimpses of the gorgeous coastal towns without having to spend too much time amidst the crowds. I would recommend this small boat trip to EVERYONE!


But as amazing as all this was — our favorite 2 days of the trip were on Ischia! Seriously, we didn’t want to leave! I briefly pitched the idea to Jim that we could retire there! We loved the hotel (the Continental Mare) — here was the view from our balcony:

We had the most amazing experience at a hydrothermal park/beach – Negombo Thermal Park and Preserve. So so incredible.

We got there when it opened at 9, and stayed until 7pm. The first half of the day was spent going from one thermal pool to the next

… and the afternoon was spent floating in San Montana Bay. The kids made us promise to return — and truthfully, we could have stayed several more days there happily.


So by the time we got to Rome, we were wiped out! After Ischia, we didn’t have a lot of tolerance for the 100+ heat. But — we had dear friends from White Plains (one of whom was Roman born) who coincidentally were there the exact time we were. So we canceled our tours and spent the time with them roaming around Italy, having great food, and getting some wonderful views. Such a beautiful city — we will return some November! (We would totally return as well to our awesome Hotel Dei Mellini!)

Really, for us, it was more spectacular than we could have imagined. You took what could have been a chaotic and unwieldy trip to Italy and made it as smooth as it possibly could have been! And we are so grateful!!!!

A Honeymoon in Paris & Italy

Kelly and Chris were looking for an October honeymoon in Europe. Someplace romantic, with plenty of food, museums, and opportunities to explore on their own. The perfect combination of these? Florence, Rome, the Amalfi Coast, and Paris! Here is their feedback on their European Honeymoon:

We had such a great time on our trip! Everything turned out amazing! The transfers you set up for us were very helpful. The cars were all on time and it was nice to not have to worry about finding transportation. All of the flights and trains were on time and easy to navigate.

The Highlights

We loved all of the hotels but we especially loved Hotel Le Littre in Paris and Hotel Berchielli in Florence (the views and the locations)! All of the tours were great. The guides were all very knowledgeable and helped us see the main attractions in a short amount of time.

One of the highlights of our trip was the Semi-private wine-making experience and gourmet dinner. The vineyard in Tuscany was beautiful and we had fun at the wine and olive oil tasting. We also loved getting to blend our own wine to take home.

The Sorrento Farm Experience was another activity we really enjoyed. It was nice being able to try their different olive oils and cheeses and even watch them make fresh cheese in front of us! 

Good to Note

We just had a few things to note: When we landed at the Paris airport it took us over an hour to get through customs. Luckily the driver was still there when we got through so it wasn’t a problem. The other thing was the private tour of the Amalfi Coast. The driver was so great and he recommended an excellent place to eat.

We got to visit Positano and Ravello which were beautiful but we spent almost 2 hours in traffic and were not able to stop at Amalfi due to crowds and timing. Totally understand that traffic can’t be predicted and we had a great time at the stops we did get to make! That is really the only feedback we have!

We had an incredible honeymoon thanks to you! Your planning was a great help and took a lot of stress off of our plate and the Pocket Travel app made everything so easy and accessible. We will definitely use your services again when we plan another big trip.

Ann’s Tuscany Adventure

I’ve been to Tuscany before, but always with Florence as my home base. Doing day trips to Siena or Lucca, or heading out into the countryside for a day of winetasting before retreating back to the city. When the opportunity arose to spend a whole week in Tuscany, I jumped at it! 

The focus for this trip was romance travel (destination weddings and honeymoons). We had the opportunity to tour some gorgeous properties and meet some fantastic local business owners (florists, caterers, event planners, and photographers). And, of course, eat and drink some amazing local food and wine.

If you’ve ever dreamed of getting married in Tuscany, we can absolutely hook you up!

[Photo: The dining hall of Corte dei Papi villa in Cortona]

But I am really excited about Tuscany in general, and what a different experience it offers vacationers when compared to the big cities.  


We stayed at the Buccelletti Casali and Cantina, in Castiglion Fiorentina. It’s a charming property that has been in the Buccelletti family since 1625. They’ve been growing olives and making olive oil for generations, and they now make wine as well.

They have converted the old farm workers’ houses into clusters of villas and apartments. Plus, they’ve turned the olive oil mill into a stunning event space. It was the perfect home base for a week spent exploring the surrounding countryside.

[Photo: Buccelletti Casale and Cantina]

The accommodations themselves were the first big difference from previous trips to Italy. I was in a cute little house with two bedrooms and bathrooms, a living/dining area and small kitchen, and a private yard/garden.

We could prepare our own breakfasts of farm-fresh eggs, homemade bread, and locally produced yogurt, jams, honey, and fruit. We had bottles of wine and olive oil produced right there on site. And the cuisine could not have been more “farm to table”. So different from staying in a hotel! 

When you’re out in the country at an agriturismo like this, it does help to have a car, so that you can get out to the local shops and markets. But at the Buccelletti Casali, we had a basket of provisions (replenished mid-week) and it was more than enough for breakfasts and snacks.  

The Countryside

We were a group, with a very organized itinerary (and drivers/guides), but I would highly encourage clients to rent a car and enjoy a more independent stay in Tuscany. The roads are great, the traffic is light, and they drive on the right side of the road. It’s very manageable for American drivers.

[Photo Credit: MIP Studios via Shared Adventures – a road in Cortona]

While we were there, we had a busy itinerary filled with site inspections at hotels/inns/B&Bs, guided tours of Tuscan hill towns, tastings at local vineyards, and many lengthy multi-course meals with wine pairings. Brutal, I know.

We learned how cheese is made. We met mayors, hoteliers, restauranteurs, and the fascinating couple who purchased and renovated the villa featured in “Under the Tuscan Sun”.

[Photo: Ann & Kristy at Villa Laura]


Some of the highlights, for me, included: 

  • Cortona – a town of steep streets, gorgeous views, Etruscan history, and tempting shops.
  •  Pici – traditional hand-rolled Tuscan pasta, made from just the “poorest” of ingredients (flour and water).  
  • Podere il Casale – a pecorino cheese producer, organic farm, and farm-to-table restaurant outside of Pienza, where we enjoyed a fabulous meal completely sourced from right there onsite. (So delicious that I purchased and carried home their very heavy hardbound cookbook in the hopes of recreating that magic
  • Brunello di Montalcino wines – made with 100% Sangiovese, bold and fruity, one of the best Italian reds!

The Tuscany Takeaway

Tuscany is all about the slow food movement, slowing down to take it all in, and enjoying the views.

There’s no long list of “must-sees”. You can while away an afternoon (guilt-free) sitting by the pool sipping wine and snacking on prosciutto. Or riding an e-bike through the countryside. Or rolling up your sleeves for a cooking class.  

I realize now that I was doing it all wrong when I visited Tuscany as a quick side trip from Florence. Tuscany invites you to stop, linger, indulge, experience, and enjoy. And I can’t wait to come back and do it all again! 

[Photo: Villa Le Prata in Montalcino]

Florence vs Rome

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These two famous Italian cities are incredible, unforgettable destinations that everyone should visit at least once. But sometimes, depending on what else you’re hoping to do and see in Italy, you have to choose between Rome and Florence, and can’t do both in one trip. Whichever one you choose, you’ll find incredible food, plenty of history, and some famous sites paired with classic Italian dolce vita. But how do you decide? If you can only fit one into your trip here’s a little guide to help you find the perfect fit. 


Let’s face it, neither of these cities can be fully experienced in just one day. You could spend weeks or even months in them and keep finding new amazing discoveries. But what is the minimum amount of time you need to enjoy the city and see the most famous sites? 

Depending on how long you have to dedicate to your city, it may determine which one you visit. 

In such a big city, it’s best to spend 4-5 days. Ideally, you’ll have 3 full days dedicated to Rome in addition to your arrival & departure half days.

To see the top tourist sites you need a minimum of 2 days, though 3 days is more ideal. Florence is a much smaller and more walkable city so if you’re short on time you’re more likely to “see it all” in Florence. 

Best Time of Year

Another external factor is seasonality. What time of year are you planning on going? Depending on the weather, you may want to skew your trip further south or north. 


Best Time: Late Spring
Winter: Average: 47°F – cold winds and occasional rains
Spring: Average: 67°F – warmer, a mixture of sunny & rainy
Summer: Average: 87°F- very hot and dry, lots of sun.
Fall: Average: 70°F – the wettest season, starting in Mid-October.


Best Time: Early-Mid Fall
Winter: Average: 45°F- cold & cloudy with high humidity
Spring: Average: 59° F – sunny with chilly evenings
Summer: Average: 80°F- sunny, hot and humid
Fall: Average: 66°F – brisk and cool until November when the chill starts to set in and the rainfall increases.

Overall Vibes

an aerial view of the piazza in Rome

Rome– The capital and largest city in Italy, it is a sprawling megalopolis. Even with its ancient ruins, impressive architecture, and historical sites on every corner, it feels like a city. You’ll have to use the metro, bus, or taxi to make your way around. But it’s still a city with a clear Italian feel. Rome is famous for street food, slow espresso mornings, and late evenings. Rome has a vibrant nightlife and because of its size, there’s a huge variety. If you’re traveling with a group, you are sure to find a little something for everyone, from top fashion, to tourism, cuisine, and cinema. You’ll find everything a modern city has to offer, in addition to the ancient ruins.

[Photo Credit: Caleb Miller via Unsplash]

Florence Duomo and the city behind it

Florence- The cradle of the Renaissance, Florence is a large but very walkable city that has managed to keep its medieval and Renaissance feel. With winding streets, elegant palaces, and lots of beautiful Renaissance architecture, it’s a very cultural city with some of the most famous artworks in the world. Every corner of Florence oozes that old-world charm and you won’t have to worry about taking public transport. Florence gives you the quintessential Italian city feel, plus those Under the Tuscan Sun vibes. You won’t find as much variety in the nightlife or activities, but whichever corner you turn down, you’ll feel as if you’ve stepped into a romantic Italian film.

[Photo Credit: Herr Bohn via Unsplash]

Amazing Foods

If you’re a foodie, deciding between Rome and Florence is entirely down to personal preference. Both of these cities have incredible local/regional food, quality ingredients, and innovative chefs. Rome will have a bit more variety and more street food. You’ll find simple but delicious dishes like cacio e pepe, pizza, pastas, and stews. Florence has embraced the slow food movement, with tiny cafes and earthy restaurants. You’ll find pappardelle with wild boar sauce, tripe, gelato, and of course Bistecca Fiorentina! 

Must-try Dishes in Rome

Suppli- rice croquettes
Trapizzino- stuffed pizzas
Jewish-style fried artichokes
Cacio e pepe- pasta with a creamy cheese sauce
Allesso di bollito – simmered beef
Saltimbocca –veal wrapped in prosciutto and marinated in wine
Maritozzi –candied buns filled with lightly sweetened whipped cream
Torta Ricotta e Visciole –sour cherry cheesecake

Must-try Dishes in Florence

Pappardelle al cinghiale- pasta with wild boar
Tagliatelle Porcini e Tartufo- porcini and truffle pasta
Pici- dense hand-rolled pasta
Ribollita- vegetable soup
Coniglio con umido- rabbit stew
Bistecca Fiorentina
Lampredotto- a street food sandwich made with thinly sliced tripe.
Schiacciata Fiorentina- a soft sponge cake covered with powdered sugar
Panforte- a thick florentine containing fruits and nuts

Rome is Perfect for…

History Buffs

a couple in front of ancient roman ruins in italy

Both cities have deep historical roots on display around every corner. But for history buffs, Rome comes out ahead. Florence’s history is undeniably concentrated in the Renaissance. In Rome, you’ll find everything from ancient Roman ruins to the Medieval period, the Renaissance, and a modern city. Rome is full of ruins, churches, and museums from every era that might interest. It’s also just a day trip away from archaeological wonders like Pompeii.

[Photo Credit: Dana via Shared Adventures Travel – read all about her anniversary trip to Rome here! ]

Top Historical Sites in Rome:

Roman Forum
St. Peter’s Basilica
Castel Sant’Angelo

Fashionistas & Shopaholics

Being a big city, Rome offers numerous shopping opportunities. With huge brands, big fashion centers, and lots of shops this is a shopaholic’s paradise. While Florence is known for some key shopping opportunities (leather, hand-made paper), Rome offers everything from top luxury designers to incredible vintage shops to stunning antique markets. Some of the famous shopping streets are like an art gallery of fashion – perfect for a day of window shopping!

Bucket-listers & First Timers

trevi fountain rome italy

Florence does boast some incredibly famous sites, like Michelangelo’s David and the impressively huge Duomo. But if you’re the type of person who likes to see the most famous and well-known sites in a destination, or it’s your first time in Italy, Rome has more bang for your buck. So many of the most famous Italian sites are located in and around Rome. You can see the places that spring to everyone’s mind when they picture an Italian vacation.

[Photo Credit: Dana via Shared Adventures Travel – read all about her anniversary trip to Rome here! ]

Top Bucket-List Sites:

Sistine Chapel
Trevi Fountain
Spanish Steps

Piazza del Popolo
The Mouth of Truth
Vatican Museums

Florence is Best for…

Art Lovers

a panel of the Gates of Paradise on the Baptistery in Florence Italy

Being the cradle of the Renaissance, Florence is the best place for art lovers. With famous works from Michelangelo, Donatello, Boticelli, and Leonardo Da Vinci, Florence has incredible galleries and art museums! You could easily spend entire days taking in all the amazing works of art around the city. While Rome has plenty of galleries, Florence can’t be beaten in this respect.

[Photo Credit: Liz via Shared Adventures Travel – read about her trip to Florence here!]

Top Sites for Art Lovers:

Michaelangelo’s David at Galleria Academia
The Uffizi Gallery
Boticelli’s Birth of Venus
Ghiberti’s Gates of Paradise

Taking it Slow

If you only have three days to see all of Florence, you will have some very full days fitting everything in. But once you pass the three-day mark there’s a feeling of being able to slow down. From hidden side streets and gelaterias to the extremely popular slow flood movement, Florence encourages taking your time to enjoy its wonders. Because the city is so walkable, the more time you have to spend here the more you feel like you can relax into enjoying the city at a slow and mindful pace. You get a chance to enjoy the little details without feeling like you’re missing out on the “big sites”. Taste your way through the Mercato Centrale, wander through the Boboli Gardens, and catch the sunset from Piazzale Michelangelo.

Top Hidden Gems:

San Marco Museum
Todo Modo Bookstore
Oltrarno Neighborhood
Torrigiani Gardens

Santa Maria Novella Pharmacy
Via Toscanella Street Art

Day Trips

a smiling honeymooner on a wall with beautiful rolling Italian hills

If you like to get out of the city or are keen to spend some time in the incredible Italian countryside, Florence is the best city for you. With the beautiful Tuscan rolling hills just outside the city, taking day trips is extremely easy. Visit nearby towns like Siena, Pisa, and Lucca; hop on a train to Bologna; book a cooking class in Chianti; or you can even head to a country villa or farmhouse to see how they make wine and olive oil!

[Photo Credit: Jamie & Matt via Shared Adventures — read about their Italian adventure here!]

So which city is perfect for you? The best part of custom travel planning is being able to pick the perfect experiences for your interest and your style of travel. Inspired to visit Florence or Rome? Or do you have time to see both? Let us know and we can start planning!

You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)