Arrive in Lucca and check into your accommodation — opt for a hotel with two rooms near Piazza Napoleone if you want separate spaces, or a two-bedroom apartment inside the city walls for a more local feel; both give easy walking access to sights. Take a relaxed walk along Via Fillungo to orient yourselves, stop for espresso and cornetto at a neighborhood bar such as Pasticceria Taddeucci, and pick up a map and any train/ferry tickets if you’ll head to Cinque Terre later in the trip.
Unpack and breathe — rent bikes and do a gentle loop on Lucca’s famous tree-lined Renaissance walls, stopping at the Torre Guinigi to climb for rooftop garden views and the Duomo di San Martino for a quick look at the Volto Santo. If you prefer a slower pace, browse the antique shops and linen boutiques around Piazza San Michele, and have a light lunch of focaccia and local salumi at a trattoria like Trattoria da Leo.
As evening falls, stroll to Piazza dell'Anfiteatro for the lively atmosphere and aperitivo — try a Spritz at one of the terrace bars while people-watching. For dinner, reserve a table at Buca di Sant'Antonio or Ristorante Giglio to sample Tuscan classics paired with a local Montecarlo or Chianti wine, then enjoy a slow post-dinner walk on the lit walls before turning in, ready for a full day of exploring Lucca tomorrow.
Start your day like a local with breakfast at Pasticceria Taddeucci, then pick up bikes near Piazza San Michele and pedal the full loop of Lucca’s tree-lined Renaissance walls; pause at Torre Guinigi to climb into its rooftop garden for sweeping views of terracotta roofs and the distant Apuan Alps. After the ride, wander to the Duomo di San Martino to glimpse the Volto Santo and the cathedral’s intricate marble façade before a mid-morning espresso at Caffè Di Simo.
For lunch, settle into Trattoria da Leo or Osteria Baralla for hearty tortelli lucchesi and a glass of local Montecarlo wine, then browse the charming boutiques along Via Fillungo and the artisan shops around Piazza Napoleone. In the afternoon visit the Puccini Museum near Piazza Cittadella if you’re curious about the composer’s life, or relax in the botanical corner of the walls and sample regional olive oil and focaccia at a specialty shop such as Forno a Legna.
As evening approaches, head to Piazza dell'Anfiteatro for an aperitivo on a terrace — try a local Vernaccia or a refreshing Spritz — and enjoy the lively square atmosphere. For dinner, reserve a table at Buca di Sant'Antonio or Ristorante Giglio to savor bistecca alla Fiorentina or roasted seasonal vegetables, then take a gentle post-meal stroll along the illuminated walls to cap a perfectly Lucca day.
A private driver collects you from your Lucca accommodation mid-morning for a scenic drive into the Chianti hills — enjoy rolling vineyards and cypress-lined lanes as you head toward a family-run estate such as Castello di Brolio or a smaller biodynamic producer near Greve in Chianti. Begin with a guided cellar tour and tasting of the estate’s Chianti Classico and a Super Tuscan if available, paired with fresh bread and local pecorino to awaken your palate.
Linger on the estate or transfer to a nearby winery for a leisurely vineyard lunch — think panzanella, ribollita, handmade pappardelle with wild boar, and the estate’s riserva wines served al fresco among the vines; many places also include an olive oil tasting and a short walk through the vineyards to learn about grape varieties and cellar techniques. After lunch, stop in the hilltop village of Greve to browse the triangular piazza, visit an enoteca for a regional grappa or Vin Santo, and pick up local cured meats or a bottle of Chianti to take home.
Return to Lucca in time for a relaxed evening — freshen up then head to Piazza dell'Anfiteatro for an easy aperitivo and people-watching, or book a cozy table at Trattoria da Giulio for a light dinner if you’re still sated from lunch. If you prefer a quieter close, walk the illuminated city walls and enjoy a final glass of the Chianti you purchased while the warm Tuscan sunset fades over terracotta roofs.
Catch an early train from Lucca to Florence and start at the Cathedral complex — climb Brunelleschi’s Dome for breathtaking city views, then visit the Baptistery and Giotto’s Campanile; reserve skip-the-line tickets in advance to make the most of your morning. After descending, pause for a mid-morning espresso and a slice of schiacciata at a nearby café such as Caffè Gilli before strolling across to the Piazza della Signoria to soak in the open-air sculptures.
Spend the afternoon at the Uffizi Gallery with a pre-booked timed entry to see Botticelli’s Birth of Venus and masterpieces by Leonardo and Michelangelo, then cross the Arno to the Accademia to behold Michelangelo’s David—if time is tight, prioritize the Uffizi and book a shorter Accademia visit or audio highlights. Break for lunch at Trattoria ZaZa or La Giostra for classic Florentine dishes, and wander the artisan workshops on the Oltrarno side afterward to discover leather goods, ceramics and perhaps a family-run gelateria for an afternoon gelato.
As the light softens, head up to a rooftop bar such as La Terrazza Rooftop Bar at the Hotel Continentale or SE·STO on Arno for a sunset aperitivo with views of Ponte Vecchio and the Duomo; sip a Negroni or local Vernaccia while watching the city glow. For dinner, reserve a table at a trattoria like Trattoria Sostanza or Osteria del Cinghiale Bianco to sample bistecca alla Fiorentina or seasonal fare before catching a late train back to Lucca, arriving in time for a relaxed stroll on the walls and a nightcap.
Catch an early train from Lucca to La Spezia and continue to Monterosso al Mare to maximize daylight — drop your luggage at a sea-view B&B or small hotel, then head straight for the soft sand of Fegina beach for a refreshing swim and a coffee at Bar Ristorante L’Ancora della Tortuga. If you prefer active mornings, take the scenic, stair-filled hike from Monterosso toward Vernazza (the Monterosso → Vernazza stretch is about 5-6 miles with spectacular coastal viewpoints) and pause at panoramic ledges to photograph the colorful villages tumbling into the sea.
Arrive in Vernazza in time for a leisurely seafood lunch at Belforte Restaurant perched above the harbor, sampling anchovies, fresh linguine alle vongole and a local white wine before exploring the tiny streets and the Doria Castle tower for sweeping views. In the afternoon, either hop a short ferry (seasonal) or take the train down to Manarola to stroll the famous Lovers’ Lane, sip a Sciacchetrà or a glass of Cinque Terre DOC white at Nessun Dorma bar, and wander the terraced vineyards above the village if you’d like a quieter panorama.
If you’re staying overnight, settle into your accommodation in Manarola or Monterosso and enjoy a sunset aperitivo on a terrace — try a chilled Vermentino with focaccia at Trattoria dal Billy in Manarola or Ristorante Miky in Monterosso for a refined dinner of catch-of-the-day and pesto-tossed pasta. Finish the evening with a moonlit stroll along the waterfront, or for a memorable treat join a short night-walk down to the harbor to watch the village lights reflect on the Mediterranean before turning in for a restful night.
If you stayed overnight in Cinque Terre, take an early regional train from Manarola or Monterosso back to La Spezia and then to Lucca, arriving mid-morning; drop luggage at your Lucca accommodation or a left-luggage service and enjoy a relaxed breakfast of schiacciata and cappuccino at Pasticceria Taddeucci. If you’re already in Lucca, linger with a slow walk on the tree-lined walls or visit a quiet corner café near Piazza Napoleone to savor the morning light over terracotta roofs.
Spend your final afternoon according to your departure schedule: squeeze in a last paseo through Via Fillungo for souvenirs like local olive oil or artisanal linen, or choose a short detour to Bagni di Lucca (if time allows) for a restorative soak or riverside lunch at a trattoria. Alternatively, if your flight or train is later, relax with a light seaside return to Fegina beach in Monterosso (train ~40-60 min) for one last swim and seafood risotto, easily timed with a direct transfer back to your departure point.
For early-evening departures, enjoy a final aperitivo in Piazza dell'Anfiteatro—sip a Montecarlo or Vernaccia and nibble on focaccia while watching Lucca’s evening rhythms—then collect your bags and head to the station or airport. If you have a later night, savor a leisurely farewell dinner at Ristorante Giglio or Buca di Sant'Antonio and take one last moonlit stroll on the walls before transferring to your onward train or flight.