Livorno is Tuscany’s maritime soul—a Renaissance free port sculpted by the Medici, where sea breezes carry stories of merchants, sailors, and artists. Its checkerboard promenade, the Terrazza Mascagni, frames the Tyrrhenian Sea; its moats and canals thread the Venezia Nuova quarter like a small, practical Venice.

Birthplace of Amedeo Modigliani and composer Pietro Mascagni, Livorno is a city of spirited contrasts: hearty fish stews and elegant liberty-style villas, working quays and languid sunset strolls. Local life revolves around the Mercato Centrale, old fortresses (Fortezza Vecchia and Fortezza Nuova), and cafés where ponce livornese—bracing hot coffee spiked with rum—warms conversation.

Base here for a week and you can sip Super Tuscans in Bolgheri, admire Pisa’s Piazza dei Miracoli, browse Florence’s Renaissance treasures, and hop north to the Cinque Terre. Trains are frequent and affordable; pack comfortable shoes, a light scarf for churches, and bring a hearty appetite for seafood, market snacks, and gelato.

Livorno

Livorno blends port-city grit with seaside glamour. Explore the Venezia Nuova canals by foot or boat, climb the bastions of Fortezza Nuova, and wander the palm-lined Viale Italia to the Terrazza Mascagni and the Acquario di Livorno.

• Top sights: Terrazza Mascagni, Venezia Nuova, Fortezza Vecchia & Nuova, Mercato Centrale (Mercato delle Vettovaglie), Museo Civico Giovanni Fattori (Villa Mimbelli), Santuario di Montenero, Calafuria cliffs.
• Eat & drink: Order cacciucco (Livorno’s iconic fish stew) at traditional trattorie, try a 5 e 5 (chickpea pancake stuffed in bread) from old-school sandwich bars, and finish with a ponce at a historic café.
• Fun fact: The Medici designed Livorno as a tolerant free port; centuries of traders left a cosmopolitan imprint you still taste in the kitchen.

Where to stay (Livorno): Browse apartments and villas on VRBO or hotels on Hotels.com. Consider the grand seafront classic Grand Hotel Palazzo Livorno, the station-adjacent and convenient Hotel Stazione, or the liberty-style villa near the promenade Hotel Gennarino.

Getting to/around Livorno: For flights to or within Europe, compare on Omio (flights). From European gateways, trains to Livorno (via Pisa or Florence) are frequent—check Omio (trains) and Omio (buses). Coming from outside Europe? Search long-haul options on Trip.com (flights) or Kiwi.com. In-region ferries (e.g., to Capraia) can be compared on Omio (ferries).

Pisa

Pisa is far more than a tilted tower. The ivory sweep of the Piazza dei Miracoli—Duomo, Baptistery, Camposanto—has dazzled travelers since the Maritime Republics vied for the seas.

• Highlights: Leaning Tower climb, Baptistery acoustics, Duomo mosaics, strolls along Lungarni, student bars near Borgo Stretto.
• From Livorno: 20–25 minutes by train, ~€3–5 each way via Omio.

Optional stays: If you decide to overnight, see VRBO Pisa or Hotels.com Pisa.

Florence

Renaissance Florence needs no introduction: Brunelleschi’s dome, Botticelli’s Birth of Venus, and the stony span of the Ponte Vecchio are all within a compact historic center.

• Highlights: Duomo complex, Uffizi or Accademia (reserve ahead), Piazza della Signoria, Oltrarno artisans.
• From Livorno: 1h20–1h40 by direct/regional train, ~€12–18 via Omio. Note many museums close Monday.

Optional stays: VRBO Florence and Hotels.com Florence.

Cinque Terre

Five colorful villages cling to Liguria’s cliffs, laced by coastal paths and tiny trains that burrow through headlands. Expect sea views at every turn, pesto, anchovies, and lemon groves.

• From Livorno: Train to La Spezia (1h15–1h35), then local Cinque Terre trains. Budget ~€20–30 total via Omio.

Optional stays: VRBO Cinque Terre and Hotels.com Cinque Terre.

Bolgheri

A cypress-lined avenue leads to tiny, delicious Bolgheri, home to legendary “Super Tuscan” reds like Sassicaia, Ornellaia, and Guado al Tasso. This is wine-country elegance a short hop from the sea.

• From Livorno: Train to Donoratico-Castagneto (50–60 min), short taxi/bus to Bolgheri. Expect ~€8–12 each way via Omio.

Optional stays: VRBO Bolgheri and Hotels.com Bolgheri.

Day 1: Arrival, Seaside Strolls, and Cacciucco

Morning: Fly into Pisa or Florence (compare on Omio; long-haul options via Trip.com or Kiwi.com). Train to Livorno: Pisa Centrale → Livorno Centrale in ~20 minutes, ~€3–5 (Omio).

Afternoon: Check in at the seafront Grand Hotel Palazzo Livorno, the handy Hotel Stazione, or cozy Hotel Gennarino. Ease in with cappuccino and a sfoglia at Pasticceria Cristiani, then walk Viale Italia to the Terrazza Mascagni for sea views and people-watching.

Evening: Kick off with Livorno’s signature dish, cacciucco, at Trattoria Da Galileo (old-school, generous portions) or Osteria del Mare – La Baracchina (on the promenade). Nightcap at historic Bar Civili for a steaming ponce livornese—coffee, rum, and sugar served in a hot glass.

Day 2: Markets, Canals, and Street Food

Morning: Breakfast grazing at the Mercato Centrale—order a warm 5 e 5 (chickpea pancake in a bun) from a market counter and sample pecorino and seasonal fruit. Then join this delicious guided wander: Livorno Street Food Tour: A Tasty Local Adventure.

Afternoon: Explore the Venezia Nuova quarter: bridges over quiet canals, artisan workshops, and the red-brick Fortezza Nuova. If timing allows, take a short canal boat tour to see the Medici “fossi” from the water. Coffee with sea breeze at Surfer Joe by the aquarium.

Evening: Aperitivo canalside, then dinner at Osteria La Barrocciaia (standing counters, Tuscan small plates) or Il Sottomarino (seafood in a cozy nautical dining room). Finish with local craft beer at Piccolo Birrificio Clandestino’s brewpub.

Day 3: Pisa’s Piazza dei Miracoli

Morning: Train to Pisa (20–25 minutes; buy on Omio). To simplify logistics, consider this half-day: Half Day Shore Excursion: Pisa And The Leaning Tower From Livorno—ideal if you want transport and a guide.

Afternoon: Marvel at the Leaning Tower, step into the echoing Baptistery, and peek into the Duomo’s gold-and-mosaic interior. Wander Borgo Stretto’s arcades; grab a simple Tuscan lunch at Osteria dei Cavalieri or a modern espresso at Filter Coffee Lab.

Evening: Return to Livorno for a clifftop sunset at Il Romito over the Calafuria coast, or a relaxed seafood supper at La Baracchina Bianca on Viale Italia. Stroll the Terrazza Mascagni under lamplight.

Day 4: Bolgheri and Super Tuscan Wines

Morning: Ride the regional train to Donoratico-Castagneto (50–60 min; Omio), then taxi or bus to Bolgheri. Book this intimate tasting: Bolgheri: Classic Wine Tasting with Winery Tour—learn how Cabernet and Merlot on Tuscan soil sparked the “Super Tuscan” revolution.

Afternoon: Lunch at Enoteca Tognoni (walls of bottles, platters of salumi and local cheeses) and stroll the cypress-lined Viale dei Cipressi, celebrated by poet Giosuè Carducci. If it’s warm, detour to Marina di Castagneto for a quick beach walk.

Evening: Back in Livorno, keep it casual with wood-fired pizza at O’ Vesuvio or seafood spaghetti at a neighborhood trattoria. Nighttime spritz back on the promenade if the breeze is kind.

Day 5: Florence in a Day

Morning: Early train to Firenze S.M.N. (about 1h20–1h40; Omio). Start at the Duomo complex—admire the facade and Baptistery doors—then walk to Piazza della Signoria and the outdoor sculpture gallery at the Loggia dei Lanzi. If art is priority, prebook Uffizi or Accademia (note Monday closures).

Afternoon: Refuel at Mercato Centrale’s upstairs food hall (fresh pasta, truffle sandwiches, gelato) and cross the Ponte Vecchio into the artisan-filled Oltrarno. Browse small workshops for leather goods, marbled paper, and jewelry.

Evening: Return to Livorno for dinner at Il Sottomarino (try grilled catch of the day) or Osteria del Mare – La Baracchina. Gelato and a slow walk along the seawall to close.

Day 6: Cinque Terre Views (Full-Day)

Make it effortless with a private driver and local timing: Cinque Terre Private Tour from Livorno. You’ll weave between villages like Manarola, Vernazza, and Monterosso, mixing short walks, train hops, and sea views; lunch on pesto trofie or lemon-scented anchovies.

If you prefer DIY: train to La Spezia then buy the Cinque Terre train pass on arrival (budget ~€20–30 total; plan 2–3 villages well). Return to Livorno by early evening for a laid-back dinner at La Baracchina Bianca and an after-dinner amaro.

Day 7: Montenero Sanctuary, Cliffs, and Departure

Morning: Ride up to the hilltop Santuario di Montenero by funicular for sweeping views over the Tuscan coast and votive folk art inside the sanctuary. Back in town, pick up edible souvenirs at the Mercato (bottarga, olive oil, cantucci) and grab a final 5 e 5 from an old-school counter.

Afternoon: If time allows, stop by the Calafuria cliffs or Tre Ponti beach for a salt-air farewell. Depart via Pisa or Florence; trains run throughout the day (Omio). For flights within/to Europe, check Omio; for intercontinental legs, compare on Trip.com or Kiwi.com.

Evening: In transit.

Practical Tips

• Timing: Spring and early fall bring mild weather and fewer crowds. Summer is lively and hot; bring sun protection.
• Local transit: Validate regional train tickets before boarding; watch for ZTL (limited-traffic) zones if you rent a car.
• Food notes: Cacciucco is traditionally spicy and served over toasted bread; “5 e 5” is perfect for quick, budget-friendly bites; try the local hot rum coffee, ponce.

This week balances seaside living in Livorno with world-class day trips—easy trains, big tastes, and unforgettable views. You’ll return home with salt in your hair, art in your camera roll, and Super Tuscan notes in your notebook.