Italy - La Dolce Escape (The Sweet Life)
March 5 - 11, 2026
Indulge in a beautifully curated Italian escape, for the incredible price of $3,750 Price Reduction ($3,265). Wander romantic streets, sip your way through sun-kissed vineyards, and lose yourself in the charm of Italy’s timeless villages. This journey isn’t just about seeing Italy — it’s about savoring it, feeling it, and sharing unforgettable moments together.
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7-Day Italy Itinerary (March 5–11, 2026)
Cities: Milan → Florence
Trip Style: Couples / Small Group / Boutique Travel
Flights (Airport): Milan Malpensa (MXP)
Day 1 – March 5: Arrive in Milan
Upon your arrival at Milan Malpensa Airport (MXP), you will be greeted with a private transfer to your hotel for an easy, stress-free check-in. After a little time to unwind, head out for a relaxed stroll through the iconic Galleria Vittorio Emanuele II—because Milan just hits different in person. If you’re in the mood, enjoy an optional aperitivo with skyline views at Terrazza Aperol, then we’ll come together for a beautiful welcome dinner to kick off the trip in style.
Day 2 - The Milan Glow-Up — Duomo Sights, Designer Streets & Navigli Nights
We will enjoy a private, guided Milan experience with an expert host, designed to show you the city’s icons with ease and style. You’ll be picked up right at your hotel, then spend four hours with your own private English-speaking driver at your disposal as you cruise through Milan’s most memorable sights—think the Duomo, Sforza Castle, Colonne di San Lorenzo, and the legendary La Scala Opera House. Along the way, you’ll have time to soak in the with local restaurant and café suggestions from your driver based on what you’re craving. And if you want to end the day the Milan way, an aperitivo in the glamorous Navigli district is the move—lively, sparkling, and unforgettable.
Day 3 - Florence Unlocked — High-Speed Arrival, David’s Big Moment & Uffizi Legends
We will check out of Milan and take the train to Florence—this is where the magic really starts. After you check into your new hotel, we’re heading straight into your Renaissance era, beginning at the Accademia for that “I can’t believe I’m seeing this” moment with Michelangelo’s David (plus incredible works like I Prigioni, San Matteo, and the Palestrina Pietà). Then we’ll make our way to the iconic Uffizi Gallery, where you’ll get to soak in masterpieces by Botticelli, Leonardo da Vinci, Michelangelo, Raphael, and more—especially Primavera and Birth of Venus, which always feel unreal in person. We’ll wrap up on the Uffizi Terrace with a gorgeous view over Florence, and if you’re in your element, you can stay in the museum afterward and keep wandering as long as you want.
Day 4 - Tuscany Temptations — Leaning Tower Moments, a 4-Wine Lunch & Siena Magic
We will start in Pisa to soak in the iconic “Field of Miracles” and grab those must-have Leaning Tower photos, then it’s off through the rolling Tuscan countryside to San Gimignano—where the real treat begins. You’ll sit down for a traditional Tuscan lunch paired with a tasting of four local wines (the kind of slow, flavorful moment you’ll talk about all trip), then enjoy free time to wander the cobblestone streets and artisan shops. We’ll end in Siena with a guided walk through its medieval heart—Piazza del Campo and the stunning cathedral—plus a little time to explore on your own before we head back.
Day 5 - Cinque Terre Dreams — Cliffside Villages, Boat Views & Coastal Lunch
On this day we will spend the day traveling through the storybook villages of the Cinque Terre—one of the most breathtaking stretches of coastline on the Italian Riviera. This protected UNESCO World Heritage Site (and National Park) is made up of five colorful fishing towns tucked between steep mountains and the sea, which is exactly why it still feels so untouched and special.
With a knowledgeable guide leading the way, you’ll explore the coastline and visit several villages using quick train rides—Vernazza, Manarola, and Riomaggiore—plus a scenic boat ride to Monterosso (weather permitting). You’ll have free time in Vernazza to relax at a cheerful café, time in Riomaggiore to browse charming little shops, and in Monterosso you’ll enjoy a delicious local lunch before taking the train back to meet the bus and wrap up an unforgettable day.
Day 6 - The Grand Finale — Milan on Your Terms & a Farewell Dinner Celebration
We will travel by train back to Milan and check into the hotel for our final night together. The day is yours to enjoy however you want—shopping, sightseeing, or simply relaxing—then we’ll come back together for a beautiful farewell dinner to toast an unforgettable trip.
Day 7 – March 11: Departure
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Hotel check out (light Breakfast)
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Private transfer to Florence Airport (Amerigo Vespucci Airport)
What's included (Trip price: $3,750)
PRICE SLASH:$3,265.00
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Six nights of boutique, 4- to 5-star accommodations (luxury-boutique hotels or historic palazzos) in Milan and Florence.
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Daily breakfast, plus 3 gourmet dinners (one in Milan, one in Florence, one countryside wine-estate dinner) & welcome cocktail reception.
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Private airport transfers (arrival in Milan & departure from Florence).
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High-speed train transfer (business-class) between Milan and Florence.
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Private guided tours in each city: Milan – Duomo, Galleria & fashion district; Florence – Duomo, Uffizi gallery, Ponte Vecchio.
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Day-trip excursions: – Charming day in the Chianti wine region (luxury wine estate, tasting + lunch) – Scenic visit to the shores of Lake Como (boat ride, villa gardens)
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Spa & wellness session: one afternoon dedicated to a curated spa experience (inclusion of steam/sauna or aromatherapy massage) for each guest.
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Luxury small-group size (maximum 12 travelers), ensuring intimate, personalized service.
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Dedicated travel specialist & concierge support from booking through return.
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Pre-departure travel guide pack, and in-destination welcome packet (local SIM/data options, curated restaurant list, spa & shopping map).
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All local taxes, hotel service charges, and porterage at the hotels.
What's not included
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International flights from the United States to Italy
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Meals or beverages other than those listed above.
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Personal travel insurance (strongly recommended).
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Gratuities/tips for guides, drivers, hotel staff (we can provide suggested amounts).
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Optional excursions or free time activities not listed above.
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Visa fees or documentation costs (if applicable).