Here’s the Zoom link: https://us02web.zoom.us/j/86531496365?pwd=P2REnO1AtSbBv6XWieElXfgq142dUc.1

The Destination Deep Dive is postponed until April because there’s too much for me…

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The good news: I turned the whole session into a full written guide that might be more useful than a replay anyway. You can actually reference it while you’re planning instead of scrubbing through a video looking for what I told you about that Airbnb in Scala you think is a good idea.

This Destination Deep Dive gives you the honest truth about what the Amalfi Coast actually is (and isn’t), so you know exactly how to plan for it and how to avoid being disappointed. I included:

• Town-by-town breakdowns.

• What to eat

• What to skip

• Where to stay, how to get around.

• The tip about not swimming at the beach in Positano that will save you a diesel-scented afternoon. All of it.

Your Amalfi Coast Deep Dive — The Full Notes

The Amalfi Coast is one of the most beautiful places on earth. It’s also been built entirely for tourism since the 1950s. There is no “authentic” fishing village that you can walk to from Positano, no off-the-beaten-path neighborhood where all the locals are sipping wine, no hack that makes it cheap or easy. (Actually, the hack is Cilento, where all of these things are very real and affordable.) The sooner you accept what it is, the more you’ll love it. The people who come back disappointed are the ones who thought they could wing it with Airbnbs, the train, and the bus.

These two things, specifically, will save your trip...

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Did you know the first medical school in the world was on the Amalfi Coast? That Positano was first inhabited by people fleeing mosquitos? That Salerno was a major port for Crusaders leaving for the Middle East? There’s a lot about the Amalfi Coast that will fill you with awe and wonder, while most conventional travel advice will only fill you with froz…

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Paid subscribers can find the full replay below the paywall.

Start with the Flights

When you see an airfare that works for your budget, book it and stop obsessing over “the perfect time.” Airline prices have more to do with fuel and corporate stock than your ability to outsmart the algorithm. Once your dates are confirmed, your trip is real, and you can manage your reservations with clarity. The caveat is that I’m not a points maven or an optimizer. I don’t like feeling paranoid that I missed out on a better deal by not refreshing the browser when Mercury aligned with Pluto. When I find a price that I can afford, I purchase and move on.

Sicily: Train, Plane, or Boat?

We talked about the classic “how do I get to Sicily?” question:

• The train: long, scenic, and a bit of a production. You go all the way down Reggio Calabria, the train car gets rolled onto a ferry, you cross the Strait of Messina, and then keep going in Sicily. Romantic, but it’s your whole day.

• The plane: there are lots of daily flights to Palermo or Catania. You’ll spend half the day between the airport and security, and then 25 minutes in the air.

• The boat: this is the fun one. Overnight ferry from Naples to Palermo. You board around 9–10 pm, have a proper dinner on board, sleep in a cabin, and wake up in Palermo. Very old‑world, very Gen‑X adventure energy. I like to imagine the next installment of the Before Sunrise series taking place on this boat. Jesse and Celine are boarding the boat for their 25th anniversary. A conversation turns into a fight in the middle of the wine-dark sea, which all gets resolved as they pull into Palermo at 6 am.

Renting the Car (and the Boring but Crucial Paperwork)

In places like Tuscany, Puglia, and Sicily, you really do need a car. A guest asked about using Agropoli as a base for exploring Cilento because it has a train, but it’s really for commuters heading into Salerno or Naples, not for people on vacation. All the major rental car companies are in Italy, and you can reserve a car exactly the same as you would anywhere else in the world.

You do need an International Driving Permit. It’s just a piece of paper, hopefully you never need it, but if you get pulled over and the police want to give you a hard time, they can. (One of these days, I’ll tell you the story of my night with the police in Calabria.) It costs $25, and it’s usually free with an AAA membership.

“We Love the Sea, and We’re History People. Now What?”

If you love the sea and you’re traveling with a history buff (or you are the history buff), there’s no better place than Campania.

Naples, Pompeii, Herculaneum, Oplontis, Baia, Paestum, Ischia, and the Cilento. You get ruins, volcanoes, underwater cities, Greek temples, and excellent food, plus the sea. Campania has an embarrassment of riches that are always overlooked in favor of the Amalfi Coast, which, yes, is beautiful, but also not very interesting compared to everything else you can see or do (and eat) within a 2-hour radius of Naples.

Also, a bunch of new discoveries at Oplontis were just announced in late 2025. Archaeologists do most of their digging in the summer when there are students available, so if you can only travel during the scorching months, the upside is that you may see archaeologists at work.

Puglia: The Real Choice You’re Making

In Puglia, don’t agonize over which pretty town is 3% prettier. You’re choosing: interior or sea.

Around Martina Franca and Locorotondo, everything is broadly similar in a good way—whitewashed streets, soft hills, nice food. It’s very easy driving; Puglia is mostly flat, and even the hills aren’t serious hills. The coastline is made of rocks, so I think it’s fine to stay inland and then spend a day at a beach club that makes it possible to enjoy the water without destroying your feet.

If you want the coast, I generally send people to Monopoli instead of Polignano. Polignano is the famous Instagram beach with crowds and “Volare” on repeat all the live long day.

Torcello: Why It’s Worth the Boat Ride

Torcello, an island in the Venetian lagoon, is worth it, but not as a full‑day production. Think of the afternoon into the evening.

You go for the fabulous, unhinged Last Judgment mosaic. You could spend hours staring at this. In particular, on the bottom, there’s a black‑and‑white section of skulls with snakes coming out of their eye sockets. Am I weirdo for loving this so much? Maybe so.

The rhythm is: lunch in Venice, boat out to Torcello, see the mosaics, walk around a bit, maybe a drink, and then head back as the sky turns unicorn pink.

Paid subscribers, the full replay is below.

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The February Ask Me Anything About Italy is happening Thursday, February 12th, at 8 pm ET.

Here is the Zoom link: https://us02web.zoom.us/j/81834755971?pwd=OzVJgpzbayLa7uRmJqvahWubLGa7jx.1

This month’s Destination Deep Dive will cover the Amalfi Coast, about which I have very strong opinions! I guarantee you will get a perspecti…

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Today, Italy is relentlessly marketed as la dolce vita, spritzes at sunset, a Vespa ride with a chestnut-haired hunk, and pasta that doesn’t make you fat. And yes, that Italy is most certainly for sale, but I much prefer the nuanced, complex Italy that is more accurately twenty different countries, each with its own cuisine, history, and even language.

You can see this right now if you’re watching the Winter Olympics coverage from northern Italy, which has Alpine landscapes and lots of boiled meat and dumplings. That’s Italy, every bit as much as Sicily’s black sand beaches, where you can eat razor clams fresh off the boat. Planning a trip without understanding how different Italy is from region to region is setting yourself up for either getting ripped off or being sorely disappointed.

Sometimes you want a trip that’s nearly frictionless: well-organized, easy logistics, clear expectations, maybe even a quasi-resort experience. Other times, you want to explore and have experiences that you couldn’t have anywhere else. Both are valid. What’s hard to know from searching online is which regions, cities, and price points actually align with who you are as a traveler.

So I’m hosting a free live session called The Italy Vibe Check to help you understand what you’re truly signing up for, before you book a trip. I will provide clarity on the most famous places and share the less well-known ones. (That’s what I do best.)

Date: Monday, February 16
Time: 7:00 p.m. Eastern Standard Time

This session is especially for those of you in the early stages of planning an Italy trip whether it’s a once-in-a-lifetime “see all the big sites” journey or your second, third, or fourteenth trip.

I’ll discuss:

• How to think about the “big four” cities—Florence, Venice, Rome, and Naples—honestly: yes, they’re super crowded, but with the right expectations and timing, they can still be extraordinary.

• How to plan your trip to Italy based on your preferences. Do you want coffee and cashmere Italy, or spaghetti and hot springs Italy? Do you want castles and museums or temples and catacombs?

• The “under-the-radar” places that are actually the best.

• I’ll also address pricing, as this is one of the least transparent parts of trip planning. I’ll walk you through what’s realistic across different regions and travel styles, so your budget and expectations don’t contradict reality.

How to join the Italy Vibe Check

To keep things simple, the Zoom link will go out only via this newsletter.

• If you’re already a subscriber (free or paid), you don’t need to do anything right now. On Monday afternoon, I’ll email the Zoom link to all subscribers. Click on it at 7 pm, and I’ll see you there.

• If someone forwarded this post to you, and you’d like to join, please hit Subscribe so the link lands directly in your inbox. Free or paid, either way, you’re invited.

For paid subscribers

For those of you already supporting this work as paid subscribers (thank you!), we also have our regular sessions this month:

• Monthly Q&A on Zoom

  • Date: Thursday, February 12

  • Time: 8:00 p.m. Eastern Time

• Destination Deep Dive: Amalfi Coast

  • Date: Thursday, February 26

  • Time: 8:00 p.m. Eastern Time

    Subscribe now

Here’s the replay: https://us02web.zoom.us/rec/share/2Edsd8JBfhiGrtDQpt7Pf1Plhu8-rp-S2SWCAtvrzCiyCoNJ-Zyx-0e34RXNRjA.RA2tPsQtuvD9bbxy

Passcode: f9&YonB.

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On a map, Venice is in Italy. Historically, it’s a city of merchants, sex workers, and gangsters, and understanding that will transform your experience.

For about a thousand years, Venice was its own republic, an independent maritime power looking toward the Adriatic and the eastern Mediterranean rather than toward the Italian countryside. Its incredible wealth came from ships, trade, and colonies, not from fields or vineyards. Venice didn’t grow atop a Roman grid; it emerged from muddy, useless islands, settled by people fleeing for their lives.

Venetians were gangsters. They quite literally stole the remains of Saint Mark in 828, when two merchants smuggled his body out of Egypt by hiding it under slabs of pork so that Muslim customs officials wouldn’t search the cargo too closely. They were also trying to steal the relics of San Nicola (yes, Santa Claus) from Turkey, but gangster sailors from Bari got there first. Venice has its own language, customs, and cuisine, all unique.

Why does this matter?

One of the big themes of the Destination Deep Dives is orientation: how to “tune your dial” to each city instead of treating Italy as one big, interchangeable menu with endless breadsticks.

Food might be the easiest way to explain it. When most people say they love “Italian food,” they’re usually thinking of the pizza and pasta of southern Italy, whether they realize it or not. Venice is bigoli in salsa: thick, rough buckwheat noodles with onions and anchovies. It’s risotto because northern Italy has abundant rice paddies, with sauces of squid ink, or in the spring, with pancetta and peas. Venice is whipped codfish on bread, or sardines, eaten standing up at a bar with a little glass of wine.

Tonight, I will walk you through five days in Venice, unfolding the history, art, neighborhoods, and food with enough context to make your next trip feel like a second visit, not a first.

Afterward, each Deep Dive is turned into a kind of Masterclass-style video series with:

• Edited video modules you can watch (and rewatch) at your own pace.

• A very detailed, practically usable itinerary built from everything covered in the session. It includes restaurants, specific tours I recommend, day trips, and shopping tips.

  

  Right now:

• Naples and Rome are already available in that polished video + itinerary format.

• Florence is with the video editor right now.

• Venice will go to her next month, once tonight’s premiere is done, and I re-record it with much better lighting and a fresh blow-out.

Next month’s Deep Dive goes to the Amalfi Coast

You already know the Amalfi Coast brings out the saltiest of my opinions. But my Amalfi Deep Dive will anchor in Salerno, home to the world’s first medical school, and

• Introduce you to Trota, a medieval female physician who was very famous, and take you to a medicinal garden with the most amazing views.

• Take you into the building where ships were built to sail to Jerusalem, laden with crusaders and luxury goods like the Salerno Ivories.

• Show you the Roman villa beneath the cathedral in Positano, which has only been open to the public since 2019.

Take you to Vietri sul Mare, where the ceramics are made, and walk through its residential alleys, where you’ll find this window where poor people would leave their children to be raised by nuns.

If you’re reading this on the free side and want to get my best stuff, this is your nudge. Right below this line is the link for tonight’s Venice Deep Dive, as well as a code to get 50% off the Naples and Rome Deep Dives.

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We had another fun session, not just of Q&A but also of discussion and follow-up on trips recently taken. The questions submitted via email happen at 46 minutes.

Watch the recording here: https://us02web.zoom.us/rec/share/p0rReM-kDvmc…

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Join me this evening at 8 pm ET for the January Ask Me Anything About Italy. If you can’t join us live, send your question to danielle@danielleoteri.…

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Italy may be geographically tiny, but every region and city has its own cuisine, its own history, wildly different landscapes, and even its own language.

Here’s a quick Italian vibe check to help you choose the version of Italy that actually fits you.

Venice is a fever dream.

I mean, what else looks like this? The streets are made of water, everything is the color of candy, and the insides of the churches are covered with small chunks of gold and colored glass. But if you go to Venice for just one day or stay over for just one jet‑lagged night, you’ll only see pigeons and pickpockets. You’ll miss the Venice that was once the most powerful city in the world and became so glamorous thanks to the trade in treasures from across Asia and the Middle East.

Florence is nerd paradise.

Florence is a city of the mind. It makes you want to think and learn, which is why it’s such an enduring center for study abroad. Florence feels like stepping into the past because its architecture was so well designed, so rational, so considered, that it still stands intact. Florence was a power center, and its citizens today are very proud of the city’s intellectual and artisan traditions and have always been eager to share them. And that’s why everyone I know who lives in Florence despises the sandwiches and wine windows. Go to Florence with an open mind.

Rome has seen it all.

Nothing is ever thrown away; it’s just used again and again, because the classics never go out of style. The ancient world bursts from the seams of modern Italy’s capital. Step out of the Roma Termini train station to wait in the taxi line, and you’re already looking at a chunk of the Aurelian Wall. Romans are sarcastic and cynical because they’ve seen it all. Their favorite food is tripe. They know that Rome is a pilgrimage city, and that religion is both faith and commerce. And Rome, for better or worse, is eternal.

Naples is your entry into the Mediterranean world.

Naples has more in common with Athens or Alexandria than with Venice, Florence, or Rome. It’s loud and ancient, and its original name was Parthenope, named for a mermaid who cried so much over a sailor who ignored her that her tears formed the Bay of Naples, and then she drowned in them. Naples is drama and passionate chaos. Neapolitans invented pizza. It used to be super wealthy, and now it’s not, but it still holds on to its best jewelry. Oh, and if you have ideas for making it more organized or for cleaning up the graffiti, my dear, please do not share them. Go to Naples with an open heart.

If you want help figuring out which experience is best for you, join us tonight for the December 18th Ask Me Anything About Italy call. If you can’t join me live, email your question to danielle@danielleoteri.com, and you’ll hear the answer when I send out the replay tomorrow.

Please find the Zoom Link below:

Here’s the link: https://us02web.zoom.us/j/83538567219?pwd=2p3fng23bnVkU7nUl8JVeUM4qyQJE0.1

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Mark your calendars for December 17th at 8 pm ET for the Venice Destination Deep Dive.

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In the last few years, the city was trash-strewn, and nature seemed to be reclaiming the architecture. Then, suddenly, it was covered in scaffolding as Rome prepared for the 2025 Papal Jubilee. But on both visits this year, I found Rome renewed, full of fresh energy and great vibes as people seem genuinely happy about the new American Pope Leo. I just spent five days in Rome, walking 18,000 steps a day and testing the best (and worst) of what the city has to offer, both to prepare for tonight’s Deep Dive and for my off-season tour in Rome next November.

Though editing down Rome’s infinite wonders is an absurd exercise for a history nerd such as myself, I’ve designed a five-day itinerary that does the city justice: you’ll see the essentials, plus get a feel for ancient Rome, early Christian Rome, and baroque Rome. Naturally, there will be plenty of talk about food because, honestly, for every perfect veal saltimbocca (my favorite Roman dish), there are twenty tourist traps that will make you think the food in Italy is meh at best.

And just a few minutes ago, I added a “bonus round” to the presentation: a slide with random tips like “Don’t wear a sundress” and the name of my favorite vintage jewelry shop near Campo de’ Fiori.

If you’re a free subscriber and want to join the full session (with replay access for two weeks), consider upgrading to a paid membership. The link is below:

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We had an especially fun conversation last night! If you couldn’t join us, you can watch the full replay here:

https://us02web.zoom.us/rec/share/8705YkB4JJ8HbYedOUuBt2IKHf876BTncIG_ep9YtE426bXer2s-fPc308ya85Ya.GOFDfSH8YzmPErBN

Passcode: 8=…

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I’m freshly back from a research trip where I tested out a few new things and road-tested some of my regular recommendations.

First, I am staunch on my position that you absolutely must make reservations if you want to eat well in Rome. Even though there seems to be a restaurant on every corner with plenty of people who seem to be enjoying what they’re eating, Rome is a landmine of meh to bad food.

Second, I think I’ve truly nailed my Italy capsule wardrobe. I went with just a carry-on and a backpack and had plenty of room to spare. Should I do a podcast episode about packing?

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If you’d like to go deeper on Naples, I have several lectures available to watch right now via Context Travel.

For fans of Elena Ferrante’s My Brilliant…

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For years, I’ve found it hard to design tours that aren’t really “tours” because I’m not that into organized fun. Even though I plan trips for a living, I often prefer my independence and the freedom to be spontaneous. At the same time, there’s no denying how much better travel is when you have a…

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