My little sister lives in London and her #1 travel goal (despite having seen most of the world already) was to get a group of her favorite girls together and do a dedicated wine tour vacation, with some good food & hiking mixed in. For her bachelorette, I planned a trip to Tuscany but of course book-ended it with other travel. First, I spent a few days relaxing with my mom at Villa Lena and exploring nearby tiny towns, then headed to Lucca & stayed at a Lucca Villa for the big event, and finally relaxed with some solo travel in Florence.

ADVENTURES:

📷 Villa Residence: Villa Lena is an artists’ retreat and guest hotel in one, which makes for a beautiful and creative space. Spend time by the pool, enjoy live music at sunset with wine, go on a nearby hike or bike ride (beware it is on a hill!), or take one of many artists-in-residence classes. We did flower pottery, morning yoga, and still life painting.

📷 Village Trips: About an hour from Villa Lena is a tiny town called Peccioli that we ended up in by accident but later learned it is the home of a modern art revitalization. During COVID, to revive the town, they installed modern art among the historic monuments and created a tour that you can pick up at the cultural center which is attached to the gorgeous Terrazza Panoramica with views of the whole valley. Grab pizza and a beer, and find somewhere to sit by the square.

📷 Wine tasting: Too many vineyards to pick from, but we ended up in Castelfalfi and got a wine tasting from the resident sommelier in this absolutely tiny but picturesque village very close to Toaiano, which is another tiny and adorably walkable village with nothing more than a fairly good bakery and an ok pub and a hill with great views. Once in Lucca, it was a bit. more organized and we visited the following 3 vineyards: Fattoria Sardi (high end, great port); Cantina Biagiotti (cavern style, family owned and small, but fantastic wine); Valle del Sol (expensive and a bit overpriced for what the experience was).

📷 Hiking: The northern Tuscan mountains are known as the “Apuan Alps” and have many reknown hikes including Monte Matanna, up the coast to Cinque Terre, Camaiore hillsides, and more.

EAT & DRINK:

🥂 Lucca: After climbing the Guinigi Tower for sunset (worth it, but be prepared for heights), walk around to taste & shop at the local square markets. Some later night evening spots we enjoyed for dinner and drinks were Trattoria da Giulio (get pasta dishes to share & sit outside under the bridge), Ristorante Cocktail Bar San Colombano on the port, and small wineries/ristorantes down alleys off the main plazas.

🥂 Florence: I could wander this city forever, and that is my favorite way to explore. It is large but walkable, and the best way to explore is by seeing the main sites in Piazza della Republica by morning and Piazzale Michelangelo – the panoramic viewpoint over the city accessible either by bus or a couple miles of staircases from downtown. No matter which plaza you visit, be sure to get gelato. The best gnocchi is a solo date with a giant plate and a single glass of white wine at Osteria Santo Spirito. It is worth the wait, or go across to Hotel Palazzo Guadagni and get a drink on the roof while you wait (if they will let you leave the queue!) While in Florence, worth noting that I found a great deal at The Moon Boutique and felt completely safe beyond its secure doors and five-star desk given I was a solo traveler, plus it was on the train line to the airport and walkable to most things in town. It also offers solo appointments to the spa, sauna, and hot tub for guests which was a great way to unwind after traveling and before exploring.