TRAVEL
The Tuscany Travel Guide
July 21, 2026
We’re all about making bucket lists and finding the fun. Here’s where to stay, eat, sip, and explore in Tuscany, according to Tuckernuck.
The Tuscan Look
When escaping to the country, your style should feel feminine and relaxed. Wear linens, breathable cottons, and not so tailored styles. For accessories, think timeless raffia hats or bags, and simple gold jewelry with a head scarf. When you’re not barefoot at home, wear espadrilles and sandals for cobblestone and dirt roads.
Getting There
Fly into Florence or Pisa if you’re starting in northern or central Tuscany, or Rome if you’re heading toward Porto Ercole, Bolgheri, or the Maremma coast. Once there, Tuscany is best explored by rental car, especially if you’re planning to hop between the coast, countryside, vineyards, and hill towns.
Coast First
Start by the sea in Porto Ercole or Forte dei Marmi. Swim, stroll, order seafood, and ease into vacation mode before heading inland.
Wine Country Ways
Make time for vineyard hopping. Whether you’re sipping Chianti, Brunello, or a Bolgheri red, the views are half the experience.
Still Life
Pack a sketchbook, a disposable camera, or both. Between the fruit stands, flower-filled terraces, and rolling hills, inspiration is everywhere.
Visit Pienza
Plan a day trip to the magical little town of Pienza. Visit the Palazzo Piccolomini and the cathedral overlooking the idyllic countryside of the Val d'Orcia.
From seaside icons to countryside estates, these stays capture the essence of Tuscany.
Hotel Il Pellicano
Casual coastal elegance at its best. Start your mornings with a brisk walk up the Argentario hillside for views of the Tuscan Archipelago, then fill the day with tennis, long lunches, and pool time.
Borgo San Felice
A true countryside escape in Chianti. Borgo San Felice feels like stepping into a beautifully restored Tuscan village, complete with vineyard views, stone lanes, a spa, and amazing restaurants.
Castiglion del Bosco
A dream stay for Brunello lovers, this Rosewood property sits on a historic estate in Montalcino, surrounded by vineyards and rolling Val d’Orcia views. Come for the wine tastings, stay for the suites, spa, and next-level luxury.
Agriturismo La Casa by Caparzo
For those who prefer a house stay, this charming farmhouse has apartment-style accommodations, a beautiful pool, and sweeping views of the Val d’Orcia. We love it as a home base for picnics by the Abbey of Sant’Antimo and walks along the Via Francigena.
Pensione America
Your home base for exploring Forte dei Marmi, aka the Palm Beach of Tuscany. This boutique hotel is polished, nostalgic, and full of Italian seaside charm, with luxurious rooms, lemon trees, and an incredible pool.
Monteverdi Tuscany
A hilltop hideaway in the Val d’Orcia, Monteverdi is set within a restored medieval village with beautifully designed rooms, a spa, and a dreamy pool. Stay here for the artful interiors and some of the best views in Tuscany.
Unforgettable food, great wine, amazing views. This is what Tuscany does best.
Isolotto Beach Club
Stop here on your drive from Rome to Tuscany for seafood and a spritz on the water. Located at La Roqqa hotel in Porto Ercole (near Hotel Il Pellicano)—we love Isolotto for its cool atmosphere and local Italian feel.
Sette di Vino
Tucked into the historic town center, Sette di Vino is the place to eat in Pienza between shops and strolls—casual, charming, and the place to sample the town's famous pecorino.
Dopolavoro La Foce
A casual, homey spot near the famous La Foce gardens, with great indoor and outdoor seating and a modern barnhouse feel. Book a tour to see the spectacular English gardens, then come here for lunch afterwards.
La Sosta Montalcino
A good lunch stop when you’re visiting Brunello producers near Montalcino. Part restaurant, part shop, La Sosta is perfect for a midday break, a glass of something local, and a few souvenirs to take home.
Ristorante Daniela
In San Casciano dei Bagni, the little town just over the Lazio border, Ristorante Daniela is the spot for aperitivo, a bite, and people-watching from the main square.
Build an itinerary around the must-dos: wine, pasta, and market finds.
Go Wine Tasting in Chianti
Plan a wine tasting at Castello di Meleto, a beautifully preserved medieval estate in the heart of Chianti known for its Sangiovese wines and sweeping vineyard views. Don’t miss the guided cellar tour and a peek inside the castle’s theater.
Go Truffle Hunting
Head to Castello di Bossi for a truffle hunting experience that feels straight out of a movie. Set out with an expert guide and trained dogs through the wooded hills, then return to the castle for a meal prepared with your finds.
Take a Cooking Class
Whether it’s an afternoon pasta class with wine pairings or a week-long course at an Italian villa, cooking in Tuscany is the best way to experience the local culture. Book through Tuscookany, our favorite local cooking school.
Shop the Market
The Forte dei Marmi market is a must for anyone who loves a good find. Look for linens, ceramics, leather accessories, cashmere, and gifts that feel more special than souvenirs. Arrive early and beat the crowds for the best experience.
We hope this inspires you to book a trip,
pack your bags, and plan your itinerary!