Custom Italian Travel Planning for Unforgettable Moments
Through the Arch
Ciao!
It's September, and while I will stubbornly hold on to summer until it's official end on the 21st, I am deep in the throes of that “new school year” positive energy and life chaos.
The girls are getting used to new classes and homework again, and I'm juggling color-coded carpool schedules and new routines that are a little hard to adjust to. Also in the mix - our 22nd wedding anniversary and my youngest turning 13 yesterday.
At the same time, September almost always feels like a sort of fresh start for setting healthy habits and positive intentions, and I am HERE FOR IT. I'm not the only one though.
My inbox is proof that y'all are too: spring break 2027 requests are rolling in (yay for the planning ahead people), summer 2027 is getting booked (yay for the REALLY planning ahead people), and I'm fielding Thanksgiving getaway requests too. If holiday travel is even a passing though for you too, reach out now. It might feel early. It's not. It's already late.
And where are my skiers at? If a Dolomites ski trip has been living in your head as a “someday” idea, there's no time like the present! Let's turn the idea into an actual 2027 trip. Let's get it on the calendar.
On my end, I'm gearing up for some travel too. In just 2 weeks, Jason and I are off to California to attend the wedding of one of my bestest friends who I am trauma bonded with thanks to the newborn baby years (ha!). In October I'm heading to Rome and Puglia with another advisor to scout properties and experiences. I'm always refreshing my Italy knowledge so I can keep sending you to the right places, and I'm especially excited for Puglia. I haven't been to the mainland part of the region since before my girls were born, so it's overdue in the best way. I can't wait to report back on new favorites and overall impressions. And then in November, I'm off to Miami for a travel conference. Phew! It's gonna be a fun and busy fall y'all.
Let's get into it!
Discover: Sicily
Capital: Palermo
Known for: Being its own universe with Italy: Greek Temples, Arab-Norman architecture, an active volcano and a food culture shaped by every civilization that's ever invaded (a lot of them). Also - cannoli and the motherland of many Italian-Americans. Consider visiting: April-June or September-October. Summer works if you're beach-focused and can handle the heat, but shoulder season gives you comfortable temperatures for exploring ruins and hiking Etna without melting.
Stay
Monaci delle Terre Nere is a former monastery turned boutique hotel set in the black volcanic soil on Etna's eastern slopes, surrounded by citrus groves, vineyards and pistachio trees. The rooms are simple and elegant, and there's a spa, an infinity pool with Etna views and a restaurant serving food grown almost entirely on property.
The whole property really leans into its setting rather than trying to compete with it ie. the volcano in the background is a pretty backdrop instead of a scary threat. Wake up, see Etna smoking gently in the distance and go about your very relaxed day.
Visit
One of the largest and best preserved collections of Greek temples outside of Greece is here in Sicily. This archaeological park near Agrigento has seven temples standing in various states of preservation in the Sicilian countryside.
The Temple of Concordia is the showstopper. Very much intact and absolutely stunning during the golden hour and at sunset (see evidence above). Go early morning or late afternoon like we did to try to avoid the heat and crowds, wear comfy shoes and give yourself a few hours with a guide. There's a lot to learn.
Experience
I'm tempted to say BOAT DAY! again because Sicily is an island after all, but let's switch suggestions to another of my favorite activities in Italy - wine tasting.
Etna's volcanic soil makes Sicily one of Italy's most exciting wine regions. Some vineyards sit high on the slopes with black volcanic rock underfoot while others are on the lower, more gentle slopes. Regardless, Etna makes herself clearly visible in the background.
Book tastings at a few different producers to see how the wine changes depending on which side of the mountain the grapes are grown on.
Taste
An eggplant dish that's part relish, part vegetable stew and part dip. It's made with eggplant, celery, tomatoes, olives, capers and a vinegar-sugar combo that gives it that very distinctive agrodolce Sicilian flavor. Every family and restaurant has their own versions. It's served at room temperature usually as an appetizer with bread for scooping, and it's BOMB.
Drink
Sicily's answer to summer AND breakfast, essentially a coffee slushie topped with whipped cream. The correct way to eat it is with a warm brioche used for dunking. It's part drink, part dessert and entirely acceptable at 8am. Do as the Sicilians do and have it for breakfast at least once, but it can be enjoyed all day for a refreshing pick-me-up.
book your own
Like doing your own hotel research or just need a quick hotel room that you don't want to “bother me with”?
Our new client booking portal puts the search in your hands. Compare rates, browse properties, and book it yourself, all in one place.
Once it's booked, it's treated exactly as if we'd booked it ourselves: we'll confirm directly with the hotel, flag your upcoming arrival, and confirm any perks attached to your rate.
