Jena Sims’s Tuscany Travel Guide Is the Ultimate Wine Lovers Escape

The SI Swimsuit model spent four weeks in five European countries with her husband and son this summer.

Jena Sims | Aug 6, 2025

Jena Sims / Shaun Egan/Getty Images

Below, SI Swimsuit model Jena Sims shares her ultimate travel guide for wine lovers in Italy.

This summer, I spent four weeks visiting five countries for the ultimate European summer vacation. Full disclosure: two of those weeks were supporting my husband, Brooks Koepka’s, golf tournaments, but still, I made the most of it. I saved the best for last, staying at the No. 1 hotel in Italy (and No. 2 best hotel in Europe), Castelfalfi in Tuscany, Italy. Some of my favorite wines in the world are from this region, so I was in heaven!

Jena Sims / Courtesy of Jena Sims

One thing I particularly loved about Castelfalfi is how many smaller towns are nearby. For dinner, we had a short 30-minute drive to Casa Masi, arguably the best meal of the trip. The owner of the restaurant was our server, and he had the best recommendations. We felt like family by the end of the night and the views, ambiance and vibes were chef’s kiss.

Below are a few highlights of our time in Italy.

Casa Masi / Courtesy of Jena Sims

Day one: Wine tastings and a romantic lunch

On the first day, we traveled to Bolgheri, Italy, the birthplace of the first Super Tuscan wine. We were lucky enough to score a private tasting at Ca’Marcanda winery, with wines curated by the Gaja family. This was my personal Disney World. We concluded our visit with a romantic lunch at Osteria del Tasso, which was the most picturesque meal of the trip. This was also peak sunflower season in Tuscany, so we convinced our driver to stop in one of the many sunflower fields on the way home and capture some content for us!

Sunflower fields / Courtesy of Jena Sims

Day two: Truffle hunting

On our second day, we were the most excited about truffle hunting. It was prime black truffle hunting season in the area, and I knew this was the perfect excursion for my 2-year-old, Crew. He loved petting the dogs and the “treasure hunting” adventure we went on. He kept sniffing the truffles the dogs dug up, and at one point, tried to eat one straight from the ground! After this, the chefs back at the hotel prepared a pasta lunch complete with our findings from the day.

Jena Sims and her son, Crew / Courtesy of Jena Sims

Day three: More wine tastings

The next day, it was time for another wine and olive oil tasting. Our hotel had its own winery and olive oil mill. We toured the vineyards on the property and we got to taste the first grapes of the season. I shipped so much wine and olive oil home after this.

Wine tasting with Jena Sims / Courtesy of Jena Sims

That night, we took Crew to “Medieval Manhattan,” a nearby town called San Gimignano. It is a picturesque town known for its skyline of medieval towers. We grabbed some Vermentino and stood in line for half an hour for Italy’s best gelato and took in the sights.

Day four: Custom bikinis and a concert

We ended our vacation with a road trip over to Forte dei Marmi, a beach town about an hour and a half from Tuscany. Sadly, we were rained out, so we cancelled our beach club plans and hit the town for some shopping. We stumbled upon Glamour in Rose, this amazing shop that had a build your own bikini bar, so we loaded up on some unique swimsuits!

Build your own bikini bar / Courtesy of Jena Sims

Andrea Bocelli is from an area nearby, so we concluded the trip with a 20th anniversary concert and charity event for his foundation. This isn’t something I would usually seek out, but it felt like a once-in-a-lifetime opportunity, and we were so moved by his performance.

Since we flew in and out of Pisa, Italy, we absolutely had to stop by the Leaning Tower of Pisa before heading home. Seeing it in person was so surreal, as it felt like my grade school textbooks coming to life. Totally worth the detour, and the perfect little ending to such a magical trip.