Italy As You Imagine

Italy As You Imagine Do you dream of Italy? You’re not alone & for good reasons! But you don't know where to start. Well, you're at the right place.

We help bring you Italy As You Imagine, customized to your desires and budget. We only plan in Italy, as it is our passion.

Did you know Milan also has a Grand Canal? And Venice is home to a leaning tower? In the neighborhood of Navigli in Mila...
08/17/2026

Did you know Milan also has a Grand Canal?

And Venice is home to a leaning tower?

In the neighborhood of Navigli in Milan, there’s a grand canal once part of network of waterways engineered by Leonardo da Vinci and others to transport goods—including the marble used to build the Duomo di Milano. Today it hosts one of Milan’s most lively scenes for aperitif, a pre dinner practice that originated in Milan. The area, which features a historic alleyway with a preserved 18th-century open-air washhouse where locals washed clothes for centuries, is also now a must destination for vintage shoppers.

Venice’s Campanile of Santo Stefano (bell tower) leans more than 6 1/2 feet off center thanks to foundation shifting on the soft lagoon soil on which it was built in the mid 15th century. At more than 216-feet tall, the tower can be seen near bustling Campo Sant'Angelo and Campo Santo Stefano.

Both are part of our clients’ itineraries when visiting either city. Each locale visited always includes a section of highlights not to miss. Things that don’t require an advanced ticket or stricter tour but instead our knowledge of when and how to best visit. We love encouraging what we call “structured leisure,” empowering our clients to organically explore cities on their time and based on their interests, armed with the key information we provide.

Tours shouldn’t be the totality of your time in Italy. 🇮🇹




Happy Ferragosto to so many friends and family in Italy. 🇮🇹 Just back, and I miss you so much truly. 😢Tomorrow breaking ...
08/16/2026

Happy Ferragosto to so many friends and family in Italy. 🇮🇹 Just back, and I miss you so much truly. 😢

Tomorrow breaking the 5-day stretch of no clients in Italy, which hasn’t been the case since March.


I’ve shared a lot of beautiful posts along my most recent visit to Italy, this time with my son, a rising senior, in tow...
08/13/2026

I’ve shared a lot of beautiful posts along my most recent visit to Italy, this time with my son, a rising senior, in tow. They are all authentic and unfiltered, as Italy is the most lovely muse. But I’m very much a tell-it-as-is person and wanted to share a not-so-great experience too.

It’s all about people you may spend quite a good deal of time with on your trip - your DRIVERS!

As our Italy As You Imagine drivers were busy with our clients the morning we exited the Amalfi Coast, I thought no biggie, it’s just a transfer from the hotel to the train station and asked the hotel to arrange it.

From the moment the driver was SUPPOSED to pick us up, I realized indeed what a valuable service we provide to our clients at Italy As You Imagine with our trusted drivers across Italy.

First off, he was late. Like really late. The hotel had to call a few times. And it was clear by how long he took to get to us and his appearance (and maybe aroma 🙈 also), that our transfer had been forgotten.

Luckily, as a professional planner in Italy, I know to build in time - usually for traffic and such, not drivers who forget they are driving us. I realized how stressful the same scenario would be for our clients.

But, hey, mistakes happen (to us too). So we thought he’ll probably be extra nice in our 1.5 hours to the train. Absolutely not! We greeted him in Italian, to which his response was “I don’t speak English!” and not in a friendly way.

His gruff response put me immediately in the shoes of our clients and how they’d feel. No English, but more so no desire to try to communicate with us, to make us feel welcomed in his van, which wasn’t particularly clean, by the way. It meant what could have been an enjoyable and interactive time to learn more about this area would instead be highly impersonal, at times uncomfortable…and perhaps even scary, not having a warm feeling about driver we’d learn nothing about, now rushed due to his tardiness along the hairpin, cliff-hanging turns along the Amalfi Coast. Literally entrusting him with our lives. Let’s just say, ZERO stars! Do not recommend!

To us, transfers are more than transportation. They are opportunities to learn about the real-life culture of people of the area you’re transferring to and from and the sites along the way. And these pleasantries not only make our clients feel more enriched but also makes the kilometers pass more quickly.

And at very, very minimum, it should not feel cold, frightening, nor rushed because the driver is late.

A sad reality is at the height of peek season, you see endless reports across the travel group pages on social media about how drivers stand travelers up. It’s not because Italy is full of bad drivers, but instead because it’s full of a higher demand of tourists than can sometimes be met. They may have to sacrifice a good review from a single tourists they’ll never see again when things get busy because they have the upper hand in the supply-demand reality.

Taxis randomly strike and with a high frequency and are notorious for unethical pricing. You don’t hail a cab in Italy, but instead have to find lines to queue for them. Uber (and only Uber Black) is not available throughout Italy and is known to cancel out rides at the last second for a quicker euro elsewhere.

But not the case for our clients. Our drivers work with us daily, and will never leave our clients stranded, waiting for them or feeling unwelcome in their vans.

Instead, our clients typically describe our drivers as their bodyguards, lifesavers and buddies when departing Italy. And we are so proud to bring that experience to our clients.

Our drivers know our clients’ itineraries, they know our expectations for the service to our clients but most importantly, we know through years of experience our clients are in exceptional hands.

Our clients’ relationship with our drivers begins before they even depart the States, as we connect them on WhatsApp for a seamless, interactive connection with the people they will trust to safely and efficiently - and also cordially and enthusiastically - transport them through Italy.

With that, we are so very grateful for the splendid services of - - -

🍋 Davide, our longest driving relationship in Italy, and our true friend. He has quite a fan club within our clientele.

🍷 For Massimo, not just a driver but someone when you meet that you immediately feel the kindness and enthusiasm for his region conveyed in his smile and big, bright eyes. We’ve literally had client buy him gifts to give his daughter as they shopped areas he brought them to.

🍝 For “G&G,” the gentleman who keep our guests straight in the chaos of Rome. They’ve used their connections to recover “you’ll never see that again” bags left on trains (also my laptop left on a flight) and been superheros too many times than we can count to the our clients in the eternally hoppin’ city. They are our second longest driving partner.

⛰️ For Daniel, who has taught us so much about the cultural differences in the north and the south of Italy from his northern service area around Milan.

🪷 And Stefanie and her team in Sicily. They handle a region for us that is just now developing a tourist infrastructure, and make transit around the massive, massive island both pleasant and efficient.

And there are many others across the boot that we have so much gratitude for. Grazie Grazie Milleeeeeeeee!




We had the distinct pleasure during this trip of a site inspection and stay at this 17th-century Dominican monastery on ...
08/12/2026

We had the distinct pleasure during this trip of a site inspection and stay at this 17th-century Dominican monastery on the Amalfi Coast, which quite frankly may have been one of my favorite accommodations ever…I just can’t stop dreaming of it!

What repeats in my head is the word spellbinding to describe the views, which each of the 20 rooms share. The floating infinity pool, cantilevered (yes, new word for me) directly over the sheer cliff’s edge blended seamlessly into the horizon and was a magical place to share time with my son (by the way, age 16+ only).

He adored the outdoor gym, also overlooking the sea, as well as the time we spent in the thermal suite of their renowned spa.

We didn’t partake in their Michelin-starred restaurant, but every morsel we ate there was superb, including their Sfogliatella Santa Rosa, a now-iconic, cream-filled pastry that the cloistered nuns invented and still share with guests today, still baked from the original historic recipe.

The views, service and peace offered by the monastery were unparalleled, and one we look forward to sharing with our clients interested in a return to the Amalfi Coast for a more leisurely stay or for a R+R pause in an otherwise active trip.

What may have been our favorite cherry on top is the way they blend the history of the secluded former monastery with the luxury of accommodations they offer today, incorporating in whimsical art of the nuns throughout the property, including the cheeky do not disturb signs. They also maintain an authentic confessional, used now as a suggestion box.

Yet, I have no suggestions…except invite us back!



I ♥️ TROPEA!Dear Tropea, You’re savage, less refined than your northern counterparts. You’re a wild, warm, comforting br...
08/11/2026

I ♥️ TROPEA!

Dear Tropea,

You’re savage, less refined than your northern counterparts. You’re a wild, warm, comforting breeze. You’re not there to be fancy or pretentious. You’re there to be beautiful, naturally, effortlessly beautiful.

You’re less used to American tourists. We may have to be more patient with our words. And you take more time to warm up to us, but once you do, you were sad to see us go.

Your food is different, as each region is. But we ♥️ you because you’re known as the spiciest, perhaps the only taste we otherwise miss when visiting Italy. And you know how to embrace your best, putting your native red onions as if a cherry on top of just about everything. We ♥️ your red onions, Tropea. And your peperoncino and 'Nduja too!

Your nightlife was so festive and lively. Where did all those people come from each night? Ah, yes, off the beaches, I suppose.

To those beaches, wow, some of the most crystal clear water we’ve seen since Sardinia. I ♥️ a good sand beach with clear water, not an easy combination to find in Italy.

You’re also not the easiest to get to, Tropea, and you’re gonna steal a good part of our day to get to you so far south. But, you’re worth it. And, the train ride down hugs the coastline, sharing a movie of beaches and ocean as our on-train entertainment.

We think maybe you’re best for those visiting Italy a subsequent time. You offer so much to the seasoned traveler.

But the very best of you, Tropea, I can’t show anyone. Those mental images of all we explored in your coastal caves and under your waters with goggles will be our best and posted only in our treasured memories. They were especially special as seen through the eyes of my son. I ♥️ you for those memories, Tropea. Grazie Mille!

Arrivederci, Tropea. I do indeed ♥️ the wild, spicy side of Italy that you are.

XOXO,
Julie + Jack




I’m an unabashed Kennedy-phile. Jacqueline Kennedy, in particular, has inspired me to visit some of my favorite places o...
08/10/2026

I’m an unabashed Kennedy-phile. Jacqueline Kennedy, in particular, has inspired me to visit some of my favorite places on this earth - from her beloved Martha’s Vineyard to Montecito, CA, where she spent a bit of her honeymoon, to some hidden gems in Italy - from Ravello to Capri.

Here are some items she inspired in my time along the Amalfi Coast this trip - my fourth visit to this INCREDIBLE region in four years.

Let’s start with her story of summer 1962 - - -

Four days after the death of Marilyn Monroe (and it is reported no small coincidence), the First Lady and Caroline departed the States with their entourage and arrived into Italy. She would base in the cliffside village of Ravello for its privacy and its unmatched views. [Sadly, too many unknowing tourists miss Ravello, a true gem of the Amalfi Coast. We recommend time here to all of our clients. As Ravello is on the other end of the Amalfi Coast, it’s yet another reason to stay ON the coast, as it’s a haul for daytrippers staying in Sorrento.]

Her Italian admirers were as plentiful as she experienced domestically - oh just a little local band along with Ravello’s mayor and most of the village’s population were there cheering to greet her upon arrival. It was famously said “In America they admired her husband. In Europe, we admired her.” Villagers hung banners welcoming her with “Ciao, Jacqueline” and phrases of adoration “Italy loves you!” The First Lady seemed at ease soaking up the authentic Italian hospitality of the locals, even with the aggressive Italian paparazzi.

Yet still, the First Lady, her daughter, her sister Lee Radziwill with her husband the Prince and their young son Anthony, for the most part were able to enjoy some privacy on their 23-day Mediterranean holiday due to their remote location along the Amalfi Coast. [For fellow Kennedy-philes, Ravello was suggested by her “ex-step-brother” American writer Gore Vidal, who had earlier visited there alongside playwright Tennessee Williams. Gore later returned to live in Ravello for more than thirty years, where he wrote many of his literary works.]

Jackie and crew stayed in Ravello’s villa Palazzo Episcopio, a 900-year-old former Bishop’s Palace and then royal residence that the First Lady described in letters as "the loveliest house with the most staggering view in the world." She was informally hosted and often escorted by Gianni Agnelli, the ultra-wealthy, impeccably styled heir to the Fiat automotive empire. Gianni made a few of his open-air Fiat cars and even his yacht, the Agneta, available to the First Lady on the coast. The yacht enabled them to escape the eyes of welcoming locals and more so the lenses of the paparazzi to swim and waterski more freely.

During her holiday, Jackie came down daily from the villa she was staying perched high in Ravello to practice her waterskiing in the bay off Conca dei Marini. She had learned the sport early into her time with the now-president to keep up with the active Kennedy lifestyle off the shores of Cape Cod and West Palm. Afterwards, she would then return to the secluded beach of Conca dei Marini to enjoy the privacy it offered. Some of my personal favorite pictures of the First Lady are taken as she sat incredibly relaxed on the ground barefooted, make-up free with hair still wet from her skiing and swimming.

On that secluded beach was a small restaurant, Ristorante La Tonnarella. It became one of her absolute favorites and put the beachside eatery on the global map. [I was so happy to finally make it here, after being on my list for a while - accessible only by 300 steep cliffside steps or by boat. We opted for the latter. And I now recommend it for lunch for our clients on full-day boat adventures along the coast.]

I was shocked and have to say, La Tonnarella served quite literally one of the most delicious meals I’ve EVER had in Italy. And, of course, I had Jackie’s favorite dish, made specifically for her combining the sweet crunch of pan-fried local zucchini (courgettes) with the savory, smoky depth of speck, all bound together by a velvety emulsion of melted butter, starchy pasta water and plenty of sharp Parmigiano-Reggiano cheese. It is said that the First Lady requested this specific combination of ingredients, prompting the chef and original owner, Umberto Lauretano, to whip up a customized pasta dish for her. Today, you can order Spaghetti alla Jacqueline from one Umberto’s sons, Franco and Angelo (the former pictured below).

The tuna net storage room turned local eatery in the 60’s does not look to have changed too much in the more than 60 years since it hosted the First Lady. And it’s a real treat, complete with locals bathing and rock jumping on the small area of beach in front of the historic restaurant.

Each morning before her daily waterskiing, Jackie was treated to a breakfast of Sfogliatella Santa Rosa, a sweet creation of the nuns of the Conca dei Marini, reportedly with a cold coffee to combat the high August Mediterranean temps. The Dominican nuns’ version of the local delicacy from the 17th or 18th century is considered the sacred ancestor of the modern Neapolitan Sfogliatella. [I had the distinct pleasure of enjoying one during my stay at the monastery turned luxury hotel where they were invented, Monastero Santa Rosa Hotel in Conca dei Marini. What an amazing location I look forward to sharing with clients! 16+ years only.]

Jackie enjoyed gelato at Caffè Calce, still open in the beautiful Duomo square of Ravello. She also ate frequently at Garden Ravello Restaurant, where I ate with my family in 2022. Today the restaurant proudly displays a plaque - one in English and another in Italian - commemorating her stay as well as the “Jacqueline's Bar" in her honor. The cocktail menu says today “In the summer of 1962, Jacqueline Kennedy came to Ravello for peace, poetry, and perhaps a little mischief. She found all three just steps from where you sit now. This bar is her story retold in sips, bites, and soft whispers.” Cocktails include Angnelli’s Affair, J.K. Was Here and Sumner of ‘62.

Jackie joined the ranks of many previous famous dinner guests at Trattoria Cumpà Cosimo, a rustic neighborhood trattoria famous for its family-style traditional Neapolitan home cooking. [Also still open and on my list for my return next year, God willing.] She also regularly ate meals prepared by local culinary legend Mamma Agata, who worked as a private chef. Jackie famously fell in love with Mamma Agata's simple “Spaghetti del Contadino” (farmer's spaghetti), a recipe still taught today at the family's renowned Ravello cooking school [also on my next to-do list.]

During their stay, Jackie and her crew were treated to traditional folk dance and singing performances and custom fireworks. They even awarded her honorary citizenship during the stay. Jackie was so captivated by the hospitality of song and dance that she had four-year-old Caroline and her young nephew, Anthony Radziwill, dress up in traditional regional Tarantella clothing. Caroline joined the local children in the square, learning the energetic tarantella dance steps right in front of her mother. The memory of her legendary visit remains a foundational part of Ravello's modern identity as the "City of Music". Today, Ravello hosts a summer music festival on the iconic open-air stage at the Belvedere of Villa Rufolo, offering panoramic views of Italy's Amalfi Coast. [I was so honored to attend this event last week and will most definitely recommend to clients desiring a unique, authentic and STUNNING music experience during the months of July, August and very early September. The performances range from orchestral symphonies and opera to early baroque and jazz genres in the evenings with one special sunrise performance, called Concerto all'alba, which will actually be held tomorrow starting at 5:30AM! The sole morning performance will feature, as it often does, The Orchestra Filarmonica “Giuseppe Verdi” di Salerno.]

The world-wide press coverage of a tanned, relaxed Jackie alongside Italy’s most famous pl***oy, Gianni Agnelli prompted President Kennedy to famously send his wife a brief, direct cablegram reading: "More Caroline, less Gianni," urging her to protect Camelot's domestic image by posing for more photos with her daughter instead of the reportedly undeniable “electric" chemistry between the two as they walked down cobblestone streets and swam off his yacht. While married, Gianni was also known for his high-profile affairs with the likes of Anita Ekberg and Rita Hayworth. That all said, Gianni’s wife Marella was present and pictured with Jackie for portions of her trip. Still the First Lady’s “Dolce Vita" lifestyle ended a few days later when Jackie and Caroline returned to the U.S. to meet the President in Rhode Island after a brief meeting with Italy’s Prime Minister in Rome.

There are some conflicting reports, including some of the literature included in the pictures below, as to whether John Jr. joined the First Lady and his older sister in Italy, but pictures misattributed as John John are instead of his cousin of the same age Tony. And the First Lady’s secret service agent’s account of the trip in his book “My Travels With Mrs. Kennedy” by Clint Hill only mention Caroline in tow.

Many of the pictures of the First Lady below are actually taken by Agent Hill and others on her protection duty and not the paparazzi.

Thank you again, Mrs. Kennedy, for your incomparable travel tastes and where they have led me to great joy! You simply never disappoint!





Let’s chat T•A•🌸•R•M•I•N•A (Sicily) while I’m here again. The coastal town on the eastern/boot-side of Sicily is dramati...
08/09/2026

Let’s chat T•A•🌸•R•M•I•N•A (Sicily) while I’m here again.

The coastal town on the eastern/boot-side of Sicily is dramatically perched on Mount Ta**us overlooking the Ionian Sea and Mount Etna, an active volcano.🌋

Taormina is really 3 levels.

LEVEL 1️⃣ / ON THE WATER - We prefer clients to stay ON the water, where they can enjoy all Taormina has to offer, especially the sea. This is vital in the summer when Taormina bakes in the sun (we’ve been in Taormina in late October when the water is still welcoming). As beaches are accessed via your hotel stay (or purchasing a beach club day pass), we love to share two lovely resorts hotels right on the beach.

🚠🚠🚠 There is a quick, super scenic funicular to take you from the beach level up to…

LEVEL 2️⃣ / TOWN CENTER - This is the historical center offering panoramic views over the sea. Since HBO’s inaugural season of the White Lotus, this level has experienced an astronomical increase in tourism. And accordingly, also prices. The charming streets of the town are now a wave of tourists. It’s a must to visit, including the Greek amphitheater, but we prefer our clients return to the retreat of the beach level.

LEVEL 3️⃣ | UP IN THE CLOUDS. Well, really up the mountain. With views of Etna, it’s the spot we like to share with clients over dinner.

Taormina is not a budget destination, but it pays back in its beauty.

The 3 levels are labeled on each picture below. ⬇️




I’m fortunate enough with my business to be in Italy 4-6 weeks a year. It’s a huge perk but still part of the job, nonet...
08/08/2026

I’m fortunate enough with my business to be in Italy 4-6 weeks a year. It’s a huge perk but still part of the job, nonetheless. This trip is different.

No laptop (a first in 4 years since starting the company). Less pictures and extremely few “because I need to see it for work” activities.

Instead, it’s the way European summering should be done (after you’ve visited all the core sites prior, of course). Leisurely. Strolling. Floating. Boating. Talking to locals and all the Europeans holidaying. Mid-day napping to avoid the heat. A lot of eating and drinking. Slow meals and talking to each other (I’m here with my son, a rising senior in high school).

At the very same time, I’ve checked a lot of boxes -

✔️ Added the region of Calabria finally to my offering. I’ve now visited 2/3rd’s of Italy’s 20 distinct regions. The few left you’ve likely never heard of but will be thoroughly explored April 2027.

✔️ Attended a concert of the internationally famous Ravello Music Festival at Villa Rufolo.

✔️ Fallen absolutely in love with Conca dei Marini. Perfect for a second trip to the Amalfi Coast or when clients have extended time there as a second location on the coast.

✔️ Got to know Praiano better, also on the Amalfi Coast. Absolutely the best sunset on the coastline. Thanks again, CM, for the nudge to another great place. Fair to say, I’m not just a specialist in Italy but also with an intimate connection to/knowledge of the Amalfi Coast, where relationships still matter and opinions online and Google Maps don’t!

✔️ Finally made it to a small seaside restaurant, primarily only accessible by boat, that I’ve longed to visit a while now. One of the most authentic and tasty meals I’ve ever had in Italy - their Spaghetti alla Nerano. It’s now named for the late First Lady Jacqueline Kennedy due to her time on their beaches, eating the same. (Yes, Jackie once again led me to great places.)

✔️ Swam among the yachts of Capri.

✔️ Visited colleagues-now-friends all along the Amalfi Coast. It’s hands down my second favorite place in Italy. Even got a birthday party invitation for next year!

✔️ Had one of THE BEST boating experiences I’ve ever had off Tropea. Ate raw sea urchin my son caught off the boat.

✔️ Trained/ferried over to Sicily (prior times I’ve flown from the boot).

✔️ In Taormina as Etna erupted.

✔️ Revisted one of my hotel partners there to see their incredible renovation.

✔️ AND TO MY SHEER SHOCK, Kinda fell madly in love with Sicily. It took me a few times, but she got me! Added the new area of Syracusa/Ortigia to my offering and already thinking about my next visit to Sicily. I do still think Sicily is a second-timer destination. And I’m still learning to love the food off the boot, truth be told.

✔️ Survived the heat. I think we’ll make it, but it is indeed no joke (and I grew up in the south!) Florida you got nothing on this humidity!

…and all with my son in tow, who asked by day 3 if I’m famous or something here 😂😂😂

I think the gift of travel and time together is better than anything material.

Will share more of each later. Back to mum/son time.


🔥 We made a decision to accept less clients in 2026 so we could make some system upgrades, including authoring almost 20...
08/04/2026

🔥 We made a decision to accept less clients in 2026 so we could make some system upgrades, including authoring almost 200 new pages from our own travels that we can draw upon to enhance our clients’ itineraries.

But there is one page we think we may delete for 2027.

We currently add average daily temperatures based on our clients’ travel dates to their itineraries. And, while accurate, we feel this may be a tad misleading.

We have visited Italy all months except February and November. In each month, the temperature differs greatly from the feel like temperatures. Greatly!

Here are some examples from this week. See the number in red. The feel like is HOT. 🔥



I swore I’d document this trip more real-time here, but we’ve been too busy being present. So before I catch up (likely ...
08/03/2026

I swore I’d document this trip more real-time here, but we’ve been too busy being present. So before I catch up (likely on a train in a few days), here’s Jack living his best life…with mum.

Don’t miss the video in the first comment.



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