Choosing where to stay in Toscana is one of the most important decisions you’ll make when planning a romantic trip. It shapes how your days feel, how relaxed you are, and how deeply you experience the region.

As a local guide working in Florence and across Tuscany, I’ve seen many couples make the same mistake: trying to stay everywhere instead of choosing one or two bases that truly fit their travel style.

Here’s a helpful guide to choose the right place for your needs in order to enjoy Tuscany the way it’s meant to be experienced.

1. Countryside villa or Boutique hotel

If romance is your priority, staying in the Tuscan countryside is unbeatable.  just immagine: vineyards outside your window, quiet mornings, organic breakfasts, long lunches, and golden sunsets.

Why couples love it:

– Privacy and tranquility.
– Panoramic views and outdoor spaces.
– Excellent wine and food on-site (if you’re in a villa you can hire a private cook).
– Slower pace, fewer tourists.

The best areas to look for countryside stays could be Chianti hills near Florence or Val d’Orcia area around Montalcino or Montepulciano

If you stay in the countryside, plan at least one guided day for wine regions or villages. It lets you relax fully without worrying about driving or logistics.

2. Hill towns for views and evening strolls

For couples who enjoy exploring on foot and dining out in the evening, small Tuscan hill towns offer the perfect balance.

Why they work well:

– Romantic historic centers
– Excellent local restaurants
– Easy walks and beautiful viewpoints
– A lively atmosphere without big-city chaos

Some ideas of great hill towns for couples are: Pienza, Cortona, Volterra, Montepulciano

Guide insight:
Hill towns are ideal if you don’t want to drive every day but still want a strong sense of place.

3. Florence (if chosen wisely)

Even if it seems imposible to imagine, Florence can be romantic if you avoid the busiest areas.

If you’re a couple who looks for art, culture, and fine dining, sleeping in boutique hotels and historic palazzi and guided experiences with deeper context you have to consider the following neighborhoods:

– Oltrarno
– San Niccolò
– Santa Croce area (away from the main streets)

My honest advice:

Florence is best enjoyed with a private guided tour, especially in peak season, to avoid crowds and make the experience personal.

4. One Base or Two?

For a first trip, I usually recommend 4–5 nights in one place, or a split stay: Florence + countryside.

This avoids packing and unpacking and keeps your trip relaxed.

Example romantic itinerary:

– Florence (art, food, private walking tour)
– Countryside base (wine, villages, slow days)

This combination works beautifully for couples.

What I DON’T recommend is:

– Changing hotels every night
– Staying too far from where you want to explore.
– Relying only on public transport for rural areas.
– Overbooking activities.

Tuscany rewards slowness.

Final thoughts from Lucy, your local guide

There’s no single “best” place to stay in Tuscany — only the right place for your idea of romance.

Whether that’s a vineyard-view hotel, a medieval hill town, or a refined stay in Florence, the key is choosing a base that lets you enjoy the region without stress.

👉 Let’s plan your perfect adventure —  Send me a message HERE if you’d like help planning experiences around where you stay — wine days, countryside tours, or private guided walks — I’m happy to help you build something truly personal.