Late September to Early October | 8 Days on the Ground

Italy has no shortage of bucket list-worthy destinations—but planning the right trip, especially for a milestone like your partner’s 40th birthday, means balancing iconic stops with slower, intentional moments. If you’ve already dipped into Florence, Rome, and Cinque Terre on a cruise, this is your chance to go deeper, slower, and a little more luxuriously.

We’ve designed the perfect semi-luxury Italy itinerary for a couple’s getaway—one that blends the classic charm of Tuscany with a detour that’s either romantic, rustic, or wild (your pick). At Ventana Travel, we love creating handcrafted trips that are equal parts inspiring and relaxing, with room to roam and room to toast.

Days 1–4: Florence & the Tuscan Countryside

Start your journey in Florence. Even if you’ve been before, a few nights here give you time to explore the galleries, sip Negronis, and maybe even zip around the city by scooter. (Pro tip: Read our Scooter Tips for Rome—many of the lessons apply to Florence too.)

• Stay: A boutique hotel like AdAstra, set in Europe’s largest private garden, or Portrait Firenze for riverside views and rooftop drinks.

• Do: Skip the line for the Uffizi and Accademia, but also spend slow afternoons in Oltrarno discovering artisan workshops and tiny wine bars.

• Day Trips: Rent a car or driver for easy vineyard visits in Chianti. Or base yourselves in a romantic agriturismo for 2 nights—think rolling hills, wine harvests, and truffle pasta at sunset.

Days 5–8: Choose Your Next Chapter

Here’s where the magic happens—depending on your style and energy, choose one of the following add-ons:

🌊 Option 1: Amalfi Coast Romance (Positano & Beyond)

If Positano is your partner’s dream, make it happen. The trip from Florence is doable by high-speed train to Naples (3 hours) and then a private car to the coast (1.5 hours). Just note—it’s a long transfer for only 2-3 nights, so go all in.

• Stay: Le Sirenuse if you want iconic luxury. Or Hotel Marincanto for clifftop charm without the five-figure bill.

• Do: Sunset cocktails, boat trips to Capri, long beach lunches, and some gelato-fueled strolling through pastel alleys.

🍇 Option 2: Rustic Road Trip – Umbria & Northern Lazio

Want something a little less “seen-it-on-Instagram”? Drive south from Tuscany through Umbria and into the heart of Lazio. Medieval towns, olive groves, and Etruscan ruins await.

• Stay: Sleep in a 13th-century convent in Perugia or a wine estate near Montepulciano.

• Do: Wander through Siena, Arezzo, Orvieto, Bolsena, or even Viterbo. Think slow food, wine tastings, harvest festivals, and landscapes straight out of Renaissance paintings.

• Bonus: You’ll be back near Rome at the end—making for an easy flight home.

🚤 Option 3: Venice and the Lakes (if You Haven’t Been)

If you’re craving one more bucket-list city, Venice is a strong contender. Just 2 nights is enough to soak in the magic before heading home.

• Stay: Ca’ di Dio or Gritti Palace for an elevated Venetian experience.

• Do: Gondola rides, Murano glass, and wandering until you’re lost (and happy about it).

• Note: You’ll need to train or fly back depending on your departure city.

Final Tips

• Getting Around: High-speed rail (Firenze–Napoli or Firenze–Venezia) is fast, scenic, and stress-free. Comfortable driving unlocks hidden gems—but be mindful of ZTLs (restricted traffic zones).

• Packing: Bring layers. Fall in Italy is crisp in the mornings and warm in the afternoons, and you’ll want comfortable shoes for cobbled streets.

• Travel Style: Think semi-luxury—splurging where it counts (boutique stays, private drivers, unforgettable meals), while still experiencing the real Italy.

Planning a big milestone trip like this should feel like a pleasure—not a chore. Ventana Travel specializes in personalized, culturally rich itineraries that blend style, spontaneity, and substance. Whether you want to toast with Chianti in a stone farmhouse or sip prosecco above the Amalfi Coast, we’ll help make it unforgettable.

Ready to turn this into your trip of a lifetime? Let’s make it happen.