Through the Arch: to Marche

Custom Italian Travel Planning for Unforgettable Moments

Through the Arch

Ciao and Happy New Year!

January hits and suddenly everyone's talking about their goals, their word of the year, their vision boards. I'm doing all of that too, but I'm ALSO over here like... have you booked your Italy trip yet? Because that's a goal I can actually help you achieve.

Here's the thing about planning Italian travel: timing matters. A lot. And I'm not just talking about when you want to go. I'm talking about when you need to reach out to make it happen.

So let's talk calendar strategy.

If You're Traveling This Year

Spring Break & Summer 2026: We need to talk yesterday. Seriously, close this email and send me a message right now. Prime accommodations are filling up fast, especially in popular spots like Rome, Florence, and the Amalfi Coast. Tours are booking out. The good stuff goes first, and we're already playing catch-up.

Fall 2026: You've got a tiny bit more breathing room, but not much. Reach out by end of February, early March at the latest. September and October are Italy's sweet spot – amazing weather, slightly fewer crowds, kids are back at school. Everyone else has figured this out too though, so don't delay.

Winter 2026: Reach out this summer. Do your September self a favor and have a Dolomites ski trip already booked to look forward too. Rome and Florence are also practically empty in January. Besides, what better way to beat the heat than reviewing a cold-weather itinerary?

Looking Ahead to 2027

This is where you've got options:

Spring Break 2027: Start conversations with me this summer for the best availability.

Summer 2027: Reach out this fall.

Fall 2027: Connect with me towards the end of this year.

Winter 2027/28: I'll be going on a skiing work trip in March. Let's chat after you've been inspired by following along with me on Instagram!

See the pattern? Six to nine months out is the sweet spot. It gives us time to design something really special, snag the best properties, secure private guides, and generally make sure your trip isn't just good – it's exactly what you've been imagining.

So whether you're dreaming about spring in Tuscany or fall in the Dolomites, the time to start planning is probably right now.

Ready to make 2026 the year you have an Italy trip to look forward to?

Let's talk.

Discover: Marche

Capital: Ancona

Known for: Pretty much the same things as Tuscany but without the name recognition (who cares) and the crowds (now we're talking). Located in the middle of the country to the east of Tuscany and Umbria.
Consider visiting: May-June or September-October. Summer's great for beach time, but it gets HOT. Fall is truffle season, which should really be reason enough.

Stay

Filodivino is a contemporary wine resort that sits smack in the middle of vineyards with views that stretch to the Adriatic.

The property is modern and design-forward (think clean lines and big windows), which is a nice change from the usual converted monastery situation. There's a wine bar that takes its job very seriously, a restaurant showcasing local ingredients, and a spa where you can get wine-based treatments because apparently that's a thing now🤔.

There are only seven suites on the entire property, each with a private patio perfect for grabbing a bottle of the house Verdicchio and watching the sunset over the vines.

I'm not saying this is on my list for my next milestone birthday with a bunch of friends, but I'm also not saying it isn't.

Visit

This UNESCO World Heritage town is a Renaissance fever dream perched on two hills.

It's Raphael's birthplace, home to one of Italy's oldest universities, and still feels like a functioning town instead of a museum. The Ducal Palace is absurdly beautiful, the streets are steep enough to count as cardio, and the views make you understand why artists have been setting up easels here for centuries.

Wear good walking shoes. Those cobblestones weren't designed with your cute shoes in mind.

Experience

Acqualagna calls itself the truffle capital of Italy, and they're not messing around. Truffles can be found nearly all year here.

When you visit, go truffle hunting with a local guide and their very serious, and usually very cute, truffle dog. You'll tromp through the woods, learn why truffles cost more than your mortgage, and then feast.

Eat them on pasta, on eggs, on things you didn't even know could handle truffles.

Taste

Olive all'Ascolana are criminally underrated: giant green olives, pitted, stuffed with a meat mixture, breaded, and fried until golden and crispy.

They're served as an appetizer, but you'll want to make them your entire meal. Crunchy, savory, bite-sized perfection.

This is the kind of thing that is WAY too labor intensive to make at home, but is also inclusive of all the major food groups, so don't hold back - order them whenever you see them!

Drink

This crisp white wine can often be found in an amphora-shaped bottle that looks like it belongs in a museum, but don't let that intimidate you. It's fresh, minerally, pairs with literally everything (especially seafood), and won't wreck your wallet. What a combo.

The Castelli di Jesi wine area has been making this delicious, drinkable stuff since forever, and they've gotten really, really good at it. Drink it cold. Drink it often. Let's drink it together.

Ciao for now!

Ashley

Don’t just dream about it.

Reply now! Let’s design the Italian trip you've always imagined!

Feel free to forward this newsletter to another travel enthusiast too!

Not Italy
Glen Ridge, NJ 07028, United States