14-Day Northern Lakes, Tuscany & Riviera Itinerary
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Ahmer Khan
Sacramento, CA Travel Agent· 9 Years of Experience
Hourglass Expeditions, an independent agent with Cruises & Tours, Unlimited, a Travel Leaders Network Affiliate Agency
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COUNTRIES VISITED:Italy
PLACES VISITED:Chianti, Lake Como, Lake Garda, Milan, San Gimignano, Siena, Tuscany
SUGGESTED DURATION:14 Days
Discover the enchanting beauty of Northern Italy and the Italian Riviera with this unforgettable 14-day itinerary. From the tranquil lakes of Como and Garda to the rolling hills of Tuscany, you’ll experience Italy’s most scenic landscapes, charming towns, and rich history. Indulge in the world-renowned wines and cuisine of Tuscany, wander through the medieval streets of Siena and San Gimignano, and unwind on the picturesque shores of the Italian Riviera. This journey is designed to give you a perfect mix of cultural immersion, relaxation, and exploration. Here's a quick overview of the locations and recommended days for each: Milan (1 day), Lake Como (1 day), Lake Garda (2 days), Tuscany (2 days), San Gimignano & Monteriggioni (1 day), Volterra (1 day), Siena (2 days), Italian Riviera (3 days), Milan (1 day).
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DAY1
Milan
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Arrival in Milan – Exploring Italy's Fashion Capital
Arrive in Milan, the heart of Italy’s fashion and design industry. After settling in, begin your exploration with a visit to the iconic Duomo di Milano, a stunning Gothic cathedral with panoramic views from the rooftop. Explore the Galleria Vittorio Emanuele II, a grand shopping gallery known for its high-end boutiques, and spend time strolling through the Brera district, famous for its art galleries and lively cafes. In the evening, enjoy an aperitivo at a traditional Milanese bar, and indulge in a delicious Italian dinner at a local trattoria.
HIGHLIGHTS:
Visit the Duomo di Milano, a Gothic cathedral with rooftop views.
Stroll through Galleria Vittorio Emanuele II, a high-end shopping gallery.
Explore the artistic Brera district with galleries and cafes.
Enjoy an evening aperitivo at a traditional Milanese bar.
Savor a delicious dinner at a local trattoria, experiencing Milanese cuisine.
DAY2
Lake Como
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Discovering Lake Como – A Beautiful Retreat
Take a scenic 1-hour train ride from Milan to Lake Como, known for its picturesque landscapes and luxurious villas. Start with a visit to the charming town of Como, where you can walk along the lakefront promenade or take a funicular ride up to Brunate for sweeping views of the lake. Spend the afternoon visiting the beautiful Villa Carlotta, with its extensive gardens and art collections. Consider taking a private boat tour to explore the lakeside towns of Bellagio and Varenna, known for their vibrant streets and elegant villas.
HIGHLIGHTS:
Take the train to Como and enjoy a lakeside stroll along the promenade.
Ride the funicular to Brunate for panoramic views of Lake Como.
Visit Villa Carlotta’s lush gardens and art collections.
Take a private boat tour of the charming towns of Bellagio and Varenna.
Relax at one of the many lakeside cafes, soaking in the views.
DAY3
Lake Garda
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Exploring Lake Garda – Nature and History Combined
Travel to Lake Garda, Italy’s largest lake, located about 2 hours from Milan. Begin in the town of Sirmione, known for its Roman ruins, including the Grottoes of Catullus, an ancient villa perched on the lake’s edge. Wander through the narrow, medieval streets of the old town and take in the stunning views from the Scaliger Castle. In the afternoon, visit the town of Lazise for its charming lakeside promenade and medieval architecture. Relax by the lake, enjoying the serene surroundings before returning to your accommodation for the night.
HIGHLIGHTS:
Wander through the medieval streets of Sirmione and visit the Grottoes of Catullus.
Tour the Scaliger Castle for beautiful views over Lake Garda.
Visit Lazise for its picturesque lakeside promenade and medieval architecture.
Take a relaxing boat ride around the lake to explore nearby towns.
Enjoy a lakeside meal with local specialties at a charming restaurant.
DAY4
Lake Garda
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Outdoor Adventures and Historical Sites around Lake Garda
Continue exploring the natural beauty surrounding Lake Garda. Head to the northern part of the lake and explore Riva del Garda, nestled between mountains and the lake. Enjoy a leisurely boat ride or opt for a more active day by hiking in the nearby mountains or visiting the Parco Alto Garda Bresciano, a beautiful nature reserve. For a touch of history, visit the Vittoriale degli Italiani, the former residence of poet Gabriele D'Annunzio, now a museum and memorial. The evening can be spent dining at a lakeside restaurant, sampling local fish dishes.
HIGHLIGHTS:
Explore Riva del Garda, a lakeside town surrounded by mountains.
Go hiking in Parco Alto Garda Bresciano, a stunning nature reserve.
Visit the Vittoriale degli Italiani, the former home of poet Gabriele D'Annunzio.
Enjoy a scenic boat ride or rent a bike to explore more of the lakeside towns.
Dine at a lakeside restaurant, trying fresh fish and local delicacies.
DAY5
Chianti
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Chianti Region – Tuscan Wine and Countryside Charm
Travel south to the Chianti region in Tuscany, renowned for its rolling vineyards and quaint villages. Visit the charming town of Greve in Chianti, the heart of the wine-producing region, and explore its lively piazza and the Wine Museum. Stop by a local winery for a guided tour, followed by a wine tasting of Chianti Classico, accompanied by local cheeses and cured meats. In the afternoon, drive through the scenic countryside to visit smaller towns like Panzano and Radda, where you can explore narrow streets lined with stone houses and olive groves. End your day in a countryside villa for a relaxing evening with a traditional Tuscan meal.
HIGHLIGHTS:
Visit the town of Greve in Chianti, known for its wine museum and piazza.
Take a guided wine tour at a local winery, with tastings of Chianti Classico.
Explore picturesque villages like Panzano and Radda, known for their Tuscan charm.
Drive through scenic rolling hills, dotted with vineyards and olive groves.
End the day with a traditional Tuscan dinner at a countryside villa.
DAY6
Tuscany
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Tuscan Exploration – Vineyards and Villages
Spend the day further immersing yourself in the beauty of Tuscany’s rolling hills and medieval towns. Start with a visit to the charming village of Castellina in Chianti, where you can explore its cobbled streets and picturesque wine shops. Enjoy a tour at a local vineyard to taste the famous Chianti wines and learn about the winemaking process. Afterward, head to the town of Barberino Val d'Elsa, where you can stroll through its historical center and admire the 13th-century architecture. In the afternoon, visit the medieval town of Certaldo, famous for its intact medieval structures and tranquil atmosphere. End your day with a sunset walk through the Tuscan countryside, followed by a delicious local dinner.
HIGHLIGHTS:
Visit the charming village of Castellina in Chianti, famous for its cobbled streets and wine shops.
Take a guided tour at a local vineyard to learn about and taste Chianti wines.
Explore Barberino Val d'Elsa, a 13th-century town with medieval architecture.
Discover Certaldo, a peaceful medieval town with well-preserved structures.
Enjoy a sunset walk through the Tuscan countryside and end the day with a traditional dinner.
DAY7
San Gimignano
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San Gimignano & Monteriggioni – Medieval Magic
Begin your day with a visit to San Gimignano, a UNESCO World Heritage Site known for its medieval towers that once symbolized the wealth and power of local families. Explore its narrow streets lined with charming shops and cafés, and visit the Collegiate Church to admire its stunning frescoes. Then, head to Monteriggioni, a small hilltop town surrounded by medieval walls. Walk along its ramparts and explore the quaint square. In the afternoon, enjoy the surrounding Tuscan countryside, with its olive groves and vineyards, before returning to your accommodation for a peaceful evening.
HIGHLIGHTS:
Visit the UNESCO World Heritage Site of San Gimignano, known for its medieval towers.
Stroll through the town's charming streets and visit the Collegiate Church to see frescoes.
Explore Monteriggioni, a hilltop town surrounded by medieval walls.
Walk along the ramparts of Monteriggioni and enjoy the surrounding views.
Relax in the tranquil Tuscan countryside, admiring vineyards and olive groves.
DAY8
Italy
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Volterra – Etruscan Heritage and Scenic Views
Travel to Volterra, a town rich in Etruscan history and perched on a hill with sweeping views of the surrounding countryside. Visit the well-preserved Etruscan Museum and explore the ancient Etruscan walls that encircle the town. Wander through its medieval streets to the impressive Piazza dei Priori, where you can admire the town’s historic architecture. Don’t miss the Roman Theater, a reminder of Volterra’s ancient past. In the afternoon, visit a local alabaster workshop to see how this material is carved into intricate pieces. Enjoy a leisurely evening exploring Volterra’s historic center, followed by dinner in one of the town's rustic trattorias.
HIGHLIGHTS:
Visit the Etruscan Museum in Volterra to learn about the town's ancient history.
Walk through the ancient Etruscan walls that encircle the town.
Explore the Piazza dei Priori, a historic square with stunning medieval architecture.
Visit the Roman Theater, a reminder of Volterra’s ancient past.
Discover local alabaster workshops to see how this material is carved into intricate pieces.
DAY9
Siena
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Siena – Exploring the Heart of Tuscany
Today, immerse yourself in Siena, one of Tuscany’s most enchanting cities, known for its medieval architecture and rich history. Start with the Piazza del Campo, one of Europe’s most beautiful squares, where the famous Palio horse race takes place. Visit the Siena Cathedral, a stunning example of Gothic architecture, and marvel at its intricate facade and beautiful interior. Afterward, wander through the narrow streets of the historic center, stopping at quaint shops and cafés. In the afternoon, explore the Palazzo Pubblico and its frescoes depicting Siena’s history. End your day with a leisurely dinner at a restaurant offering views of the city.
HIGHLIGHTS:
Begin your day at Piazza del Campo, one of Europe’s most beautiful squares.
Visit the Siena Cathedral, a masterpiece of Gothic architecture.
Wander through Siena's narrow streets, stopping at quaint shops and cafés.
Explore the Palazzo Pubblico and its frescoes depicting Siena’s history.
Enjoy a leisurely dinner with views of the city, reflecting on the day’s discoveries.
DAY10
Siena
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Siena – Art, Gardens, and Local Life
Spend another day in Siena, deepening your exploration of this medieval gem. Begin at the Pinacoteca Nazionale, an art gallery housing a collection of Sienese masterpieces from the 12th to 17th centuries. Afterward, visit the beautiful Orto dei Pecci, a medieval garden offering a peaceful escape with views of Siena’s rooftops. Take a leisurely walk through the Contrada neighborhoods to learn about the city's unique Palio traditions. In the afternoon, visit the Basilica of San Domenico and see the relics of Saint Catherine, one of Siena’s patron saints. End the day with a stroll along the city walls, offering panoramic views of the Tuscan landscape.
HIGHLIGHTS:
Visit the Pinacoteca Nazionale to see a collection of Sienese art from the 12th to 17th centuries.
Relax at the Orto dei Pecci, a peaceful medieval garden with views of Siena’s rooftops.
Explore the Contrada neighborhoods to learn about Siena’s Palio traditions.
Visit the Basilica of San Domenico and see the relics of Saint Catherine.
End your day with a walk along the city walls, enjoying panoramic views of the Tuscan landscape.
DAY11
Italy
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Italian Riviera – Coastal Beauty and Charming Villages
Travel to the stunning Italian Riviera, beginning your journey in one of its picturesque coastal towns. Start your day in the charming village of Portofino, known for its colorful buildings, marina, and upscale shops. Wander through its narrow streets, visit the scenic Castello Brown for panoramic views, and enjoy a relaxing coffee by the waterfront. In the afternoon, take a short boat ride to the nearby Santa Margherita Ligure, a town brimming with charm and a beautiful promenade perfect for a leisurely stroll. Conclude your day with a seafood dinner overlooking the Ligurian Sea.
HIGHLIGHTS:
Start your day in Portofino, exploring its colorful buildings and marina.
Visit Castello Brown for panoramic views of Portofino and the Ligurian coastline.
Enjoy a relaxing coffee by the waterfront in Portofino's charming village.
Take a boat ride to Santa Margherita Ligure, a picturesque seaside town.
End your day with a seafood dinner overlooking the Ligurian Sea.
DAY12
Italy
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Italian Riviera – Cinque Terre Exploration
Dedicate today to discovering the breathtaking beauty of the Cinque Terre, a UNESCO World Heritage Site made up of five stunning seaside villages. Start in Monterosso al Mare, the largest of the five, and explore its old town and beach. Take the scenic coastal train or hike the rugged trails that connect the villages, enjoying spectacular views of the cliffs and turquoise waters. Continue to Vernazza, where you can explore the colorful harbor and climb to the medieval castle for stunning vistas. In the afternoon, visit Corniglia, perched high above the sea, before returning to your base for a relaxing evening. Enjoy a traditional Ligurian dinner, such as pesto pasta, to cap off your day.
HIGHLIGHTS:
Begin your Cinque Terre adventure in Monterosso al Mare, exploring its old town and beach.
Take the scenic coastal train or hike the rugged trails between the villages.
Explore Vernazza’s colorful harbor and climb to its medieval castle for stunning views.
Visit Corniglia, perched high above the sea, for breathtaking vistas.
End the day with a traditional Ligurian pesto pasta dinner in one of the coastal villages.
DAY13
Italy
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Italian Riviera – Relaxation and Local Culture
After a few days of exploration, spend today unwinding along the Italian Riviera. Start with a visit to Rapallo, a picturesque town known for its long promenade, charming harbor, and the 16th-century Castello sul Mare. Stroll through its historic center and stop at a café for a refreshing aperitivo. In the afternoon, head to the seaside town of Camogli, where colorful buildings line the beach and the peaceful atmosphere invites relaxation. Take a boat ride along the coast, enjoying the serene beauty of the Mediterranean, and then savor a delicious seafood dinner by the shore.
HIGHLIGHTS:
Visit Rapallo, known for its long promenade, charming harbor, and Castello sul Mare.
Take a leisurely stroll through Rapallo’s historic center and enjoy an aperitivo at a café.
Head to Camogli, a serene town with colorful buildings lining the beach.
Enjoy a relaxing boat ride along the coastline, soaking in the Mediterranean beauty.
Conclude with a delicious seafood dinner by the shore in Camogli.
DAY14
Milan
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Milan – Farewell to Italy
Travel back to Milan, where you’ll spend your final day before departing. After checking in to your accommodation, take time to explore any last-minute sights in the city. Visit the iconic Duomo di Milano, the stunning cathedral that dominates the city’s skyline, or walk through the elegant Galleria Vittorio Emanuele II for shopping and a café stop. If time allows, take a stroll through Sforza Castle and its surrounding park or visit Leonardo da Vinci’s “The Last Supper” at the Convent of Santa Maria delle Grazie. End your time in Milan with a memorable dinner at a local restaurant before heading to the airport for your departure.
HIGHLIGHTS:
Spend your final day in Milan by visiting the iconic Duomo di Milano, a Gothic masterpiece.
Shop or enjoy a café break in the elegant Galleria Vittorio Emanuele II.
Visit Sforza Castle and its surrounding park for a glimpse into Milan’s history.
If time permits, see Leonardo da Vinci’s "The Last Supper" at Santa Maria delle Grazie.
End your Italian adventure with a memorable dinner in Milan before heading to the airport.
FINAL THOUGHTS
Maximize your 14-day Northern Lakes, Tuscany & Riviera trip by planning key stops while leaving space for spontaneous adventures. Savor Italy’s beauty, from views to local flavors, and let each day offer a perfect mix of exploration and relaxation.