Romantic 11-Day Italian Journey: History, Cuisine, Nightlife & Hidden Gems

Day 1: Arrival & Ancient Rome

Rome, Italy on September 1, 2025

9:00am

Colosseum and Roman Forum Tour

Explore the iconic Colosseum and adjacent Roman Forum to immerse yourself in the heart of ancient Roman civilization. Book a guided tour to avoid lines and understand its rich history.
EUR16, 3h0m

12:30pm

Lunch at Trattoria Da Enzo al 29

Enjoy traditional Roman dishes like carbonara in this cozy, authentic trattoria located in Trastevere, perfect for local ambiance and mid-range budget.
EUR30, 1h0m

2:00pm

Pantheon and Piazza Navona Walk

Stroll the charming streets to visit the Pantheon, one of the best-preserved ancient Roman buildings, then relax at the Baroque fountain-filled Piazza Navona.
Free, 2h0m

6:00pm

Aperitivo at Freni e Frizioni

Experience a vibrant Roman aperitivo culture in Trastevere with cocktails and complimentary snacks, ideal for couples before dinner.
EUR15, 1h30m

8:00pm

Dinner at Roscioli

Dine on exquisite Italian charcuterie, cheeses, and creative pasta in a refined yet romantic setting near Campo de’ Fiori.
EUR50, 2h0m

10:30pm

Night Stroll to Trevi Fountain

Visit the illuminated Trevi Fountain, an enchanting spot to make a wish and enjoy the lively Roman nightlife ambiance.
Free, 1h0m
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Day 2: Vatican & Local Flavors

Rome, Italy on September 2, 2025

8:30am

Vatican Museums & Sistine Chapel

Start early with skip-the-line tickets for a self-guided or audio tour to the Vatican Museums and Sistine Chapel, marveling at Renaissance masterpieces.
EUR30, 3h30m

12:30pm

Lunch at Pizzarium Bonci

Grab some of Rome's best gourmet pizza al taglio from acclaimed chef Gabriele Bonci, perfect for a quick and delicious lunch.
EUR15, 1h0m

2:00pm

Borghese Gardens & Galleria Borghese

Reserve a timed ticket to visit the Galleria Borghese, home to Bernini sculptures and Caravaggio's art. Then enjoy a peaceful walk in the expansive gardens.
EUR20, 3h0m

6:00pm

Gelato at Giolitti

Taste authentic artisanal gelato at this historic Roman gelateria near the Pantheon for a sweet treat.
EUR6, 30m

8:00pm

Dinner at Osteria dell’Ingegno

Enjoy refined Roman cuisine with a modern twist paired with regional wines in a stylish setting near Piazza Navona.
EUR45, 2h0m

10:30pm

Night Out at Shari Vari Playhouse

Experience Rome’s popular nightclub offering live DJ sets and cocktails for a fun and lively night.
EUR20, 2h0m
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Day 3: Florence Art & Architecture

Florence, Italy on September 3, 2025

9:00am

Train to Florence

Take an early 1.5-hour high-speed train from Rome to Florence for convenience and comfort.
EUR45, 1h30m

11:00am

Duomo Complex

Climb the dome of Florence Cathedral for panoramic city views and visit the Baptistery and Giotto’s Campanile nearby.
EUR20 (combined ticket), 3h0m

2:00pm

Lunch at Trattoria Mario

Savor traditional Tuscan dishes in this lively spot known for authentic cuisine and local atmosphere.
EUR25, 1h0m

3:30pm

Uffizi Gallery

Pre-book skip-the-line tickets to see Renaissance masterpieces by Botticelli, Michelangelo, and Leonardo da Vinci.
EUR25, 3h0m

7:00pm

Sunset Walk at Piazzale Michelangelo

Enjoy breathtaking sunset views of Florence's skyline, a romantic spot overlooking the Arno River.
Free, 1h0m

8:30pm

Dinner at La Giostra

Experience refined Tuscan dining with a romantic ambiance in the city center.
EUR50, 2h0m
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Day 4: Medieval Siena & Wine

Siena, Italy on September 4, 2025

8:30am

Bus to Siena

Take a 1.5-hour bus ride from Florence to Siena, enjoying scenic Tuscan landscapes en route.
EUR15, 1h30m

10:30am

Piazza del Campo & Torre del Mangia

Explore Siena’s historic central square and climb the Torre del Mangia for spectacular city views.
EUR10, 2h0m

12:30pm

Lunch at Osteria La Chiacchera

Taste hearty, traditional Sienese cuisine in an intimate setting with seasonal ingredients.
EUR30, 1h0m

2:00pm

Siena Cathedral (Duomo di Siena)

Visit this Romanesque-Gothic masterpiece with stunning mosaics, sculptures, and frescoes.
EUR8, 1h0m

3:30pm

Chianti Wine Tour

Join a half-day wine tour through the Chianti countryside, tasting local wines and learning about winemaking traditions.
EUR50, 4h0m

8:00pm

Dinner at La Taverna di San Giuseppe

Enjoy authentic Tuscan dishes paired with regional wines in a charming medieval cellar restaurant.
EUR45, 2h0m
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Day 5: Coastal Charm in Cinque Terre

Cinque Terre, Italy on September 5, 2025

7:30am

Train to Cinque Terre

Take an early 2.5-hour train from Siena to La Spezia, then connect to Cinque Terre villages by local train.
EUR40, 3h0m

11:00am

Explore Vernazza

Visit the charming fishing village with colorful houses and a stunning harbor, perfect for romantic photos.
Free, 2h0m

1:00pm

Lunch at Ristorante Belforte

Dine on fresh seafood with spectacular cliffside views in Vernazza's well-regarded restaurant.
EUR40, 1h30m

3:00pm

Hike to Corniglia

Walk the scenic coastal trail (Sentiero Azzurro) to the next village, taking about 1.5-2 hours, enjoying stunning sea views.
Free (Park ticket EUR7.50 if required), 2h0m

6:00pm

Sunset Aperitivo in Corniglia

Relax with a glass of local white wine at a terrace bar overlooking the Ligurian Sea.
EUR15, 1h30m

8:00pm

Dinner at Osteria a Cantina de Mananan

Enjoy local Ligurian specialties in a cozy, family-run osteria in Corniglia.
EUR35, 2h0m
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Day 6: Hidden Gems of Cinque Terre

Cinque Terre, Italy on September 6, 2025

9:00am

Boat Tour of Cinque Terre

Take a scenic boat ride along the coast to appreciate the villages from the sea and discover hidden coves.
EUR40, 2h0m

12:00pm

Lunch at Ristorante Miky

Savor Michelin-recommended Ligurian dishes in Monterosso al Mare by the beach.
EUR45, 1h30m

2:00pm

Visit Monterosso’s Hidden Beaches

Relax and swim at less crowded parts of Monterosso’s coastline, perfect for couples seeking tranquility.
Free, 3h0m

6:00pm

Sunset from Sanctuary of Soviore

Take a short hike or taxi up to this peaceful sanctuary with stunning panoramic views at sunset.
Free, 2h0m

8:00pm

Dinner at Belforte Restaurant

Dine once more in Vernazza if desired, or choose a romantic dinner spot in your village for local specialties.
EUR40, 2h0m
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Day 7: Venetian Splendor

Venice, Italy on September 7, 2025

8:00am

Train to Venice

Take a 4-hour train from Cinque Terre to Venice, relaxing and enjoying scenic views.
EUR60, 4h0m

12:30pm

Lunch at Osteria alle Testiere

Enjoy fresh seafood and Venetian dishes in an intimate, charming osteria popular with locals.
EUR50, 1h30m

2:00pm

Explore St. Mark’s Basilica & Doge’s Palace

Visit the iconic basilica with its golden mosaics and tour the historic Doge’s Palace, booking skip-the-line tickets.
EUR25, 3h0m

6:00pm

Gondola Ride at Sunset

Experience a romantic gondola ride through Venice’s canals during sunset, creating unforgettable memories.
EUR80, 0h30m

8:00pm

Dinner at Antiche Carampane

Known for authentic Venetian cuisine away from tourist crowds, perfect for a mid-range, intimate dinner.
EUR50, 2h0m
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Day 8: Venice & Nightlife

Venice, Italy on September 8, 2025

9:00am

Peggy Guggenheim Collection

Visit this modern art museum showcasing works by Picasso, Pollock, and Dalí, open from 10am.
EUR15, 2h0m

11:30am

Walk the Hidden alleys & Libreria Acqua Alta

Discover lesser-known lanes, picturesque bridges, and visit the quirky Acqua Alta bookstore for unique souvenirs.
Free, 1h30m

1:00pm

Lunch at Enoteca Al Volto

Taste cicchetti (Venetian tapas) and local wines in this cozy wine bar favored by locals.
EUR30, 1h0m

3:00pm

Relax at Lido Beach

Take a vaporetto to Lido for a few hours of beach leisure and peaceful surroundings.
EUR15, 3h0m

7:00pm

Aperitivo at Skyline Rooftop Bar

Enjoy panoramic Venetian sunset views paired with cocktails, perfect for couples.
EUR20, 1h30m

9:00pm

Night Out at Venice Jazz Club

Enjoy live jazz music in an intimate setting, capturing Venice’s sophisticated nightlife vibe.
EUR25, 2h0m
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Day 9: Amalfi Coast Scenic Drive

Positano, Italy on September 9, 2025

7:00am

Flight & Transfer to Amalfi Coast

Fly from Venice to Naples (~1.5 hours), then private transfer or rental car (1.5 hours) to Positano for comfort and convenience.
EUR120 (flight + transfer), 4h0m

12:00pm

Lunch at Chez Black

Enjoy fresh seafood and stunning beachside views at one of Positano’s most famous eateries.
EUR40, 1h30m

2:00pm

Explore Positano Village

Wander narrow streets lined with boutiques and cafes, discover hidden staircases and scenic vistas.
Free, 3h0m

6:00pm

Sunset at Spiaggia Grande

Relax on the main beach at sunset, enjoying the colors and romantic atmosphere.
Free, 1h0m

8:00pm

Dinner at La Sponda

Experience Michelin-starred dining with candlelight in a setting overlooking the sea, perfect for a special romantic evening.
EUR100, 2h0m
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Day 10: Ravello & Amalfi Coast Beauty

Ravello, Italy on September 10, 2025

9:00am

Transfer to Ravello

Short scenic drive or bus ride along the coast to charming Ravello, famous for its gardens and views.
EUR10, 1h0m

10:00am

Villa Rufolo & Villa Cimbrone Gardens

Visit these stunning historic villas with terraced gardens overlooking the Amalfi coastline, ideal for romantic exploration.
EUR10, 3h0m

1:00pm

Lunch at Ristorante Pizzeria Vittoria

Enjoy fresh Mediterranean dishes in a relaxed atmosphere in Ravello's town center.
EUR30, 1h0m

2:30pm

Relax & Explore Ravello

Wander through narrow lanes, boutique shops, and cafes to discover hidden gems in this peaceful town.
Free, 3h0m

6:30pm

Dinner at Rossellinis Restaurant

Indulge in refined Mediterranean cuisine at this Michelin-starred establishment in Ravello, ideal for celebrating your trip.
EUR90, 2h0m
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Day 11: Departure Day

Naples, Italy on September 11, 2025

8:00am

Transfer to Naples Airport

Private transfer back to Naples airport (1.5 hours) for your return flight, allowing ample time for check-in.
EUR50, 1h30m

10:00am

Breakfast Near Airport

Enjoy an Italian breakfast with espresso and pastries at a cafe in Naples airport before departure.
EUR10, 30m
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