Off-The-Beaten-Path: 8 Days in Northern Italy

Arrive in Florence, Italy in the morning and check in to your hotel Antica Torre di Via Tournabouni. Settle in and put on those walking shoes!

Explore the Oltrano neighborhood

The Oltrarno neighborhood, located across the Arno River from Florence’s historic center, is a charming and authentic area that offers a glimpse into the city’s artisan traditions and local life. Known for its bohemian vibe, Oltrarno is home to quaint cobblestone streets, independent workshops and historic landmarks like the stunning Palazzo Pitti and the lush Boboli Gardens. This neighborhood is perfect for discovering hidden gems, from antique shops and art studios to cozy trattorias serving authentic Tuscan cuisine. Oltrarno’s relaxed atmosphere and vibrant creative spirit make it a favorite spot for those looking to experience Florence beyond the usual tourist paths.

Get lunch at Osteria Santa Spirito and stop at the famous Babae Wine window for an afternoon spritz.

Spend some more time exploring the neighborhood before you head to Rooftop Loggia for aperitivo. Make sure you make a reservation ahead of time for this charming rooftop bar with a view you can’t beat.

Dinner at La Giostra

After a day of exploring, get ready for an incredible dinner at La Giostra. La Giostra is a beloved and iconic restaurant in Florence, celebrated for its warm, romantic ambiance and exceptional Tuscan cuisine. Located in the heart of the city, this family-run gem is known for its twinkling lights, vaulted ceilings and a welcoming atmosphere steeped in history. Guests rave about signature dishes like pear and pecorino ravioli, bistecca alla Fiorentina and decadent homemade desserts, all crafted with high-quality ingredients and a touch of creativity. With attentive service and an extensive wine list, La Giostra offers a truly memorable dining experience that captures the essence of Florentine hospitality and flavors.

Start off your day with breakfast at the hotel and then get ready for a day of experiencing the art and history of Florence.

Private tour of the Uffizi Gallery

A private tour of the Uffizi Gallery in Florence offers an exclusive and intimate way to experience one of the world's most renowned art museums. With a knowledgeable guide leading the way, you’ll skip the lines and dive deeper into the rich history and masterpieces housed within the gallery. From Botticelli’s The Birth of Venus to Leonardo da Vinci’s Annunciation, your guide will provide fascinating insights into the artists, their works and the significance of each piece. This personalized tour allows you to explore at your own pace, making it an unforgettable cultural experience tailored to your interests.

Lunch with a view

After your tour, head to Angel Rooftop Bar for a lunch overlooking the city.

Explore Florence

Spend the rest of the day hitting some of Florence’s iconic spots. Begin at the Gucci Garden, a stylish museum and boutique showcasing the fashion house’s history and creativity. Next, head to Palazzo Vecchio, a historic palace that offers stunning architecture and views over Piazza della Signoria, home to the replica of Michelangelo’s David. Don’t miss Piazza del Duomo, where Florence’s iconic cathedral and its impressive dome dominate the skyline. For art lovers, a visit to the Galleria dell'Accademia is essential to see the original David—just be sure to book tickets ahead of time to avoid long lines. Indulge in a sweet treat at Caffè Rivoire, one of Florence’s oldest chocolate shops, before stepping into Ospedale degli Innocenti and the Officina Profumo Farmaceutica di Santa Maria Novella, a centuries-old pharmacy where you can explore beautiful perfumes and herbal remedies. Each stop unveils a unique aspect of Florence’s timeless allure.

Dinner at Osteria Pastella

End your Florence adventure with a memorable dinner at Osteria Pastella, a cozy and welcoming restaurant known for its delicious Tuscan cuisine. One of the highlights of the menu is the famous truffle pasta, served in a decadent cheese bowl that enhances the rich flavors of the dish. As the creamy pasta is scooped out of the cheese, it’s a truly indulgent experience. With its inviting atmosphere, excellent service, and authentic flavors, Osteria Pastella provides the perfect ending to your Florence trip, offering a delicious taste of local culinary tradition in a charming setting.

After breakfast at your hotel, take a taxi to the S.M. Novella Rail Station to catch a train to Sestri Levante in the Italian Riviera.

Arrive in Sestri Levante

Check-in at the Hotel Miramare in Sestri Levante. A charming beachfront hotel offering stunning views of the Ligurian Sea. Located just steps from the picturesque Bay of Silence, this elegant hotel combines modern comforts with classic coastal charm.

Explore Sestri Levante

Sestri Levante is a hidden gem on the Italian Riviera, offering a more laid-back and authentic experience compared to the more tourist-heavy spots like Cinque Terre or Portofino. This charming beach town is known for its serene beaches, particularly the beautiful Bay of Silence, framed by colorful buildings and lush hillsides. With its picturesque old town, narrow streets and relaxed atmosphere, Sestri Levante is perfect for travelers seeking a peaceful retreat away from the crowds. The town’s cozy cafes, seafood restaurants and boutique shops make it an ideal destination for those wanting to experience the true essence of the Italian Riviera in a tranquil setting.

Dinner on the beach

Enjoy dinner on the beach at Portobello, a delightful seafood restaurant in Sestri Levante, offering a refined yet cozy dining experience with stunning views of the Ligurian Sea.

Start your morning relaxing in the beach chairs at the hotel after enjoying your free hotel breakfast.

Cinque Terre from the sea | Private boat tour

At mid-morning take the train to Monterosso Al Mare (one of the Cinque Terre Villages). Get off the train and take in the views of the iconic beach chairs in Monterosso.

Meet your private boat captain in the bay on the Old Town Monterosso side and embark on a private tour of the Cinque Terre Villages from the sea. This was one of the highlights of our trip and I highly recommend spending the extra money on it. Our captain was a local from Riomaggiore (another Cinque Terre village) and was extremely knowledgeable. He also brought us some of his mom’s homemade pesto to enjoy on the boat along with some local Lingurian wine.

Monterosso lunch with a view

After your boat excursion, walk up the sidewalk to the incredible Torre Aurora for lunch with an incredible view of Monterosso Al Mare.

Return to Sestri Levante

After your lunch, take the train back to Sestri Levante for an evening at your leisure exploring the beautiful city on the water.

Start your morning with breakfast at the hotel and then head back to the train station for another day of sightseeing.

Cinque Terre from the land

Explore the charming fishing villages of Cinque Terre, wander through quaint squares and hidden alleys and delve into the region’s rich winemaking heritage—all while enjoying stunning, postcard-worthy views. All villages are accessible by train!

If you’re a wine enthusiast, it’s impossible to overlook the incredible effort that went into creating the terraced vineyards that define this breathtaking landscape. Book a private tour visiting these vineyards perched above the sea offers a glimpse into the true heart of Cinque Terre. A renowned local winemaker will welcome you into their vineyard, sharing the fascinating story behind their "heroic wine."
Return to Sestri Levante.

After your day of exploring, take the train back to Sestri Levante for an evening at your leisure. Reserve a table at La Locanda, a cozy, family-run restaurant in Sestri Levante, offering delicious traditional Ligurian cuisine with a focus on fresh seafood and locally sourced ingredients, all served in a warm and inviting atmosphere.

Head back to the train station to travel to your last stop on the trip, Lake Maggiore. This travel day does require a stop in Milan

Day at leisure in Stresa

Arrive in Stresa, check-in at the newly renovated Sempione Boutique Hotel and explore. Stres is a picturesque lakeside town on the shores of Lake Maggiore, known for its stunning views, charming streets and elegant villas.Stroll along the lakefront promenade, enjoy a scenic ride on the cable car to Mount Mottarone for panoramic views or relax in one of the town’s cozy cafes. With its blend of natural beauty and cultural attractions, Stresa offers something for every traveler.

Dinner at Taverna Del Pappagallo

Taverna del Pappagallo is a charming and cozy restaurant known for its warm ambiance and delicious Italian cuisine. Specializing in traditional dishes made with fresh, local ingredients, the restaurant offers a menu that includes hearty pastas, perfectly prepared meats and flavorful risottos.

Its inviting atmosphere, attentive service and excellent wine selection make Taverna del Pappagallo a favorite spot for both locals and visitors seeking an authentic dining experience in the heart of Stresa. This was one of our favorite meals of the trip. Be sure to try the pear pasta dish.

The Borromean Islands on Lake Maggiore are a trio of stunning islands rich in history, art and natural beauty. Isola Bella features an opulent Baroque palace and exquisite terraced gardens; Isola Madre is a tranquil retreat with lush botanical gardens and exotic plants and Isola dei Pescatori, the only inhabited island, is a quaint fishing village with narrow streets and charming restaurants. Traveling between the islands is easy and scenic, with regular ferries and private boat services connecting them. Exploring these islands offers a perfect blend of culture, relaxation and breathtaking lake views.

Dinner with a view

Enjoy a panoramic view of Lake Maggiore with dinner at Ristorante Cardini. Make sure to arrange a taxi with your hotel concierge ahead of time to get there. The restaurant is slightly outside of the city up on a hill.

Spend your final day in Stresa embracing the town's serene beauty and laid-back charm. Relax at one of the lakeside beach clubs (or lidos), where you can lounge by the water with breathtaking views of Lake Maggiore. For a touch of history and elegance, visit Villa Pallavicino, known for its beautiful gardens, parkland and small zoo. Alternatively, explore the quaint streets of Stresa, enjoy local shops and cafes or take a leisurely stroll along the scenic promenade. Whether you choose to unwind or explore, Stresa provides a perfect ending to your Italian adventure.

Apertivo on a rooftop

Enjoying an aperitivo at one of Stresa’s rooftop bars is a perfect way to soak in the beauty of Lake Maggiore while savoring a pre-dinner drink. The La Palma Sky Bar is a standout spot, offering stunning panoramic views of the lake and surrounding mountains.