Florence (Italy)

90-Day European Schengen Visa Planning

After two fun-filled weeks catching up with the entire extended Oringer clan and friends in Florida, it was time to push forward on our round-the-world journey.

Next stop: Italy.

We are maxing out our time here, staying for the exact 90 days permitted for U.S. passport holders within the Schengen Zone. If you aren’t familiar with it, the Schengen rule means that after 90 days, non-EU nomads have to pack up and completely leave the zone (which covers 27 European nations) for a full 90 days before they can even think about re-entering. Most Americans have no idea this rule even exists because few vacation for three months straight. However, when you live the nomadic lifestyle, it requires some strategic planning.

Shifting to ‘Slow’ Travel

Over the years, our travel style has evolved into true “slow travel.” Through trial and error, we’ve learned that to really sink our teeth into a destination and create lasting memories, we need a minimum of seven nights per stop.

When we first began this RTW journey back in 2015, we were sprinting through Southeast Asia—averaging just three nights per stop across Thailand, Indonesia, Malaysia, Vietnam, Laos, Cambodia, the Philippines, and Singapore. Looking back, that pace was just too fleeting. You don’t retain the soul of a place when you’re constantly packing a bag.

Because of this philosophy, we are keeping our Italy itinerary intentionally streamlined:

The Mainland Lineup: Florence, Lucca, Bologna, and Naples (with day trips to Modena, Parma, Cinque Terre, and Viareggio).
The Main Event: A six-week, slow-paced road trip circling the entire island of Sicily in a rental car, hunting down the best local towns and beaches.

To make this happen, we had to cut a few things. The beach hops through Puglia and the island life of Sardegna will have to wait for our next 90-day stint. They look right up our alley—perfect for avoiding the overcrowded chaos of Rome or the tourist swarms of Venice and the Amalfi Coast.

Florence: Welcome to “Italian America”

Our introduction to Italy began in Florence—a city I have coined “Italian America.”

On most of our RTW journey, we primarily run into European and Aussie travelers. Florence, however, is a different beast as American families and study-abroad college students have inundated Florence. I do not understand this American strange infatuation with life in Florence. The streets in town are also packed with stateside travelers all wanting to do the exact same things.

The formula for the ideal “Italian American” vacation seems to be simple:

Inhale massive amounts of pasta, gelato, and the overstuffed deli-meat sandwiches the city is famous for.
Join the massive, winding queues to get into the endless array of museums, basilicas, and duomos.

The Florence Food Hit-List

We came with a mission to eat, and eat we did. Barbie and I allocated a full 10 nights here just to walk every single neighborhood in the city center and tackle our culinary hit-list. If you’re heading to Florence, the following spots are worthy of a visit:

The Top-Rated Sandwich Shops

All’Antico Vinaio
SandwiChic
Salumeria Verdi – Pino’s
La Schiacciata
Retrobottega
I Fratellini
I’ Girone De Ghiotti
Antica Porchetteria Granieri
Ino
Panini Toscani
Il Cernacchio

**For the Bold: Traditional Lampredotto (Pig/Cow Stomach)**

L’Trippaio Di Sant’Ambrogio
L’Antico Trippaio
Lampredotto Food Cart (Outside Mercato Centrale)
Gusta Trippa
Trippaio del Porcellino

The Best Gelato in Town

Sbrina
Gelateria Santa Trinita
Vivoli
Gelateria dei Neri
Venchi Cioccolato e Gelato
Il Procopio
La Sorbettiera
Gelateria La Carraia
Gelateria della Passera

Surviving the Shoulder-Season Crowd

I thought we were being clever by booking early April to catch the shoulder season. Total illusion. Because of the Easter holiday, the crowds were out in full force.

Coming straight from 2.5 years of living among the wide-open green spaces, deep oceans, and tropical island vibes of Maui and French Polynesia, Florence was a massive culture shock. People in these historic Italian cities literally live on top of each other. Every single activity—whether walking the sidewalk, grabbing an espresso at a coffee shop, or sitting at a bar—means rubbing shoulders in incredibly close quarters. I quickly realized why Covid hit this country so hard initially; one good sneeze in a packed Florentine cafe and your whole row has a positive test result!

Yet, despite the sheer volume of humanity, Florence somehow flows. It’s a vibrant, high-energy crowd rather than a stressful one.

The Big Doug Verdict: Florence is a” must-visit” when you come to Italy as the energy is infectious. However, the food is overrated in our opinion as the menus seamed to be geared to the taste of Americans. However, the sandwich shops are really good. That said, one visit is probably enough—it’s just too touristy and crowded for us islanders to sustain long-term.

It’s time to trade the frantic pace for something a bit more our speed. We’re hopping the Trenitalia train and heading to the significantly more relaxed Tuscan town of Lucca.