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Sun, sea and dolce vita – extend your summer with a trip to Tuscany

Tuscany is a coveted destination not just for wine lovers, culture buffs and connoisseurs of Italian cuisine. September is also a great time of year for sun worshippers to visit. The sea retains a pleasant warmth from the summer months, and you don’t need to make reservations weeks in advance to lounge in your favourite front-row “bagno.” 

A wonderfully elegant thing to do is to travel in a vintage Fiat 500 from Florence all the way to the Mediterranean via Arezzo, Montepulciano and Siena, and to explore the beauty of Tuscany on the way. Follow us, the turquoise Fiat 500, to Tuscany. From our experience, we know Tuscany offers countless opportunities for exploration and relaxation.  Here, we reveal our ten favourite destinations. 

10 tips for a Tuscan break:

Tip no. 1: Relais Borgo Santo Pietro – a destination for aesthetes

Behind the historic villa lies one of the most beautiful hotel gardens in Tuscany. Just the thing for nature lovers! The extensive garden at Relais Borgo Santo Pietro has 250,000 trees and shrubs, offering plenty of space to relax among lavender, English roses and rosemary – there is an ideal spot for everyone.


Tip no. 2: Il Pellicano – a dream villa by the sea

Marine blue seas as far as the eye can see. A breath-taking view over the sea to the Isola del Giglio. Il Pellicano is a hidden gem on the peninsula of Monte Argentario, nestled behind a terraced garden with direct access to the sea. The hotel consists of six villas connected by numerous staircases and walkways.


Tip no. 3: Locanda al Colle – a stylish hideaway

If you love individuality, this is the place for you. No reception, no concierge, no room numbers. At Locanda al Colle, the 12 stylishly furnished rooms and suites speak for themselves. The interior design captivates guests with its closely coordinated arrangement of contemporary sculptures, lamps, retro-chic furniture and sensuous home fragrances by Diptyque. 


Tip no. 4: Villa Grey – 50 shades of grey design

If you’re looking for a stylish location to take in the sun and sea breeze, look no further than Villa Grey. The villa is located directly on the beach promenade of Italy’s fashionable seaside resort of Forte dei Marmi and showcases elegant shades of grey in its up-to-date rooms. Just a short walk across the road and you’ll be relaxing under your own beach gazebo with a wonderful view of the sea. 


Tip no. 5: Poggio al Casone – life at a winery

Roaming the vineyard and wine cellar, you may find yourself dreaming about buying a piece of land in this idyllic region, and becoming a vintner in your own right. The Poggio al Casone villa, with its 10 apartments and organic wines, is a real gem at the heart on the eponymous vineyard (30 hectares). 


Tip no. 6: Relais Sant’Elena – a little jewel in Bolgheri

This lovingly converted Tuscan country house is a testament to charm and originality. Each room has been uniquely designed by interior designer Mariquita Papi. Relais Sant’Elena is just 8 km from the world-renowned wine village of Bolgheri, home of the Super Tuscans. 


Tip no. 7: Like Italy in the 1960s: La Pineta di Zazzeri

Fish, fish and more fish! A place to warm the heart of any fisherman and leave no wish unfulfilled. From the outside, the venue is an inconspicuous wooden hut on the beach, while inside, elegantly decked tables await seafood lovers. Pineta di Zazzeri is a charming mix of bathing resort, fish stall and gourmet restaurant, and is run by brothers Andrea and Daniele, the third generation of the Zazzeri family. 


Tip no. 8: Villa Bordoni – rooms to fall in love with

A stylishly renovated villa with cheerful cosiness in the heart of the Chianti hills. At Villa Bordoni, it’s hard to get enough of the bold mix of styles from Tuscany, southern England and Provence. Here, the motto “country house style” is exemplified to its fullest and underpinned with loving details. A real paradise for interior design fans – from the open-air gym to the foliage-covered shower by the pool and bathrooms with hand-painted antique tiles. 


Tip no. 9: La Perla del Mare – a beachside destination for lunch or dinner

The “bagno” or lido is an Italian institution. Every Italian has a favourite “bagno” and remain loyal over years or even decades. If you buy a season ticket, you can use the same “tenda” (beach gazebo), and many of the regulars will wear matching bathing accessories they picked in the colours of “their bagno” in order to cut a dashing figure or “bella figura”. We, on the other hand, are curious people and test a different “bagno” each day. For us, the winner of 2022 was: La Perla del Mare. We love its pleasant ambience and Deborah Corsi’s fantastic cuisine. The light and fluffy “gnocchi soffiati”, which Deborah prepares without any flour, is an absolute must. 


Tip no. 10: Osteria Le Logge – a Siena institution

It resembles the set of a Fellini film: tables with white tablecloths set out on the street, while inside you overlook the open kitchen from the elegantly rustic room with its ancient chemist cupboards. The delicious traditional cuisine with Tuscan specialties is the ideal way to indulge after exploring the alleys of Siena. And the wine list is always worth a look, with the nearby Osteria Le Logge vaults storing around 11,000 bottles. 


Ready for more? We have compiled a list of 20 hotel and restaurant destinations in Tuscany for you on pillowandpepper.com – each one of them tested in person, on location. 

We hope you have a wonderful time planning the perfect trip, and an even lovelier time in Tuscany!

Buon viaggio!