Experience La Dolce Vita in Italy with WSJ+


April To October


From £5,214pp excl. flights
(based on 2 ppl sharing)

How long

8 nights ideal length

We’re working with WSJ+ to create entirely customizable and private trips for you, their members. Our Travel Experts are here to make your trip entirely your own. Private, customizable, and totally flexible. This is what we do. This month, we’re introducing a new highlight itinerary to Italy that you can embark on today. Take it ‘as is’ or customize it to your heart’s content.

Rolling hills, lustrous waters and food fit for the gods; Tuscany, Sorrento and Amalfi make an irresistible trio. On this eight-night escape, you’ll wind your way from verdant landscapes punctuated by cypress trees down to cliffsides in crumbling hues of pastel. Along the way, sample award-winning wines, cruise across the Mediterranean on a private yacht to Capri and learn to cook the Neapolitan way. An undeniably Italian escape, you really will be living la dolce vita.

To add extra magic to your time away, WSJ+ members will enjoy complimentary rental of a vintage Alfa Romeo Spider. The perfect way to explore the Tuscan hillsides, we’ll send you out with a map and a picnic basket and leave the rest up to you.

Exclusive to WSJ+ members

This trip has been designed exclusively for WSJ+ members, drawing on our travel experts’ in-depth knowledge of Italy. The experience, however, is yours and yours alone, with all of our trips private and customisable. What you’ll find below, therefore, is simply a suggestion. Our Travel Experts will work with you to devise an itinerary based on your inquiry, budget, group size, and desires. Typically, this will include everything from the experiences you do (and the guides that will take you there) to the hotels you’ll bed down in and the trains, planes and automobiles that will take you in between. We can also help with international flights, if you like.

WSJ+ members will receive:

  • Immersive experiences tailored to your interests. This could include anything from closed-door cellar access to private yacht trips.
  • Exclusive benefits to elevate your experience, including complimentary rental of a vintage Alfa Romeo Spider.
  • Stays in Italy’s most luxurious hotels.
  • Access to expert guides throughout.
  • Up-to-date COVID travel advice – including arrangements for any required PCR or antigen testing whilst travelling.
  • Unrivalled expertise in planning your trip to Italy.

Make this itinerary yours

Each and every Black Tomato trip is tailored exactly to who you are and what you want to do So tell us about yourself and we’ll create something that’s entirely you.

Start Planning

What to do

After landing in Florence, you’ll be whisked away to your own Tuscan sanctuary where you’ll experience authentic Italian style as you get lost in the beauty of the Tuscan hillside on a morning hot air balloon trip or an afternoon horseback ride. We’ll also whisk you off to Siena to sample traditional dishes, such as beef from the special Chianina breed of cattle, pasta e fagioli, and of course, truffles. Make sure you take some time to sample the wines from the many vineyards around Montalcino too. Tuscany is famous for its Chianti, and we can arrange for you to send a collection of your favourites home to remind you of your Tuscan retreat.

Waking up fully refreshed on day four, you’ll head south to the coastal town of Sorrento. Over the next couple of days, we recommend exploring the surrounding area by foot and by car. Sorrento town boasts beautiful churches, squares and a quaint marina. The 14th century San Francesco monastery is definitely worth a peek, with charming baroque cloisters and rich stucco decorations. Spend the afternoons cooling off in the waters of one of the many little beaches. We’d suggest the Marameo beach with deck chairs, floating water beds, gazebos and umbrellas all coloured to match the lush, blue water, or try the more unusual Cassano beach, renowned for its black volcanic sands.

Finally, top off your trip with three-nights on the Amalfi Coast. Settle in and spend some time exploring the fantastically preserved Roman towns of Pompeii and Herculaneum; go back in time and walk down the streets, enter the temples and sit in the amphitheatre. Or we’ll arrange for you to tour some of our favourite coastal villages such as Ravello, Amalfi and Positano, perhaps even taking a speedboat across to Capri for lunch. Feeling inspired by the cuisine? We’ll also arrange a Neapolitan cooking lesson with chef Raffaella D’Esposito and her family. For one final glimpse, you’ll then drive along the cliff tops of the Costiera Amalfitana as you wind your way back to the airport.

Where to stay

In Tuscany, the elegant Borgo Pignano awaits with its sprawling 750-acre estate and beautiful frescoed suites. Spend your first few nights here unwinding by the infinity pool and indulging in local produce matched by one of the best wine cellars we have ever seen. Then, in Sorrento, you’ll slip into luxury at the historic Bellevue Syrene. Built on the foundations of a Roman Villa by the Earls Mastrobuono in 1750, this stylish hotel has been frequented by celebrated writers, poets and artists. Be sure to take advantage of its standout wine cellar, made from a Roman grotto, and enjoy the fruits of Bacchus in an indulgent wine tasting.

Finally, you’ll check in to the dazzling Casa Angelina, perched on the cliff face of Praiano. The pure white colour scheme enhances the turquoise shades of the sea and you’ll see the silhouettes of the mountains from the comfort of your king-sized bed. From dining on the terrace to relaxing by the pool, you’ll seemingly do it all suspended somewhere between sky and sea.

Anything else?

This experience is yours and yours alone, so feel free to customise it however you wish. Over our years exploring Italy, we’ve built up a handy network of contacts and exclusive experiences and can help take your experience to the next level. In Tuscany, that might mean a trip into Florence and access to the usually off-limits Vasari Corridor in the revered Uffizi Gallery. Alternatively, it may be a touch of added indulgence on the Amalfi you’re after. Whatever it is, we have the answer.

Return to full WSJ+ collection

Where to rest your head

Borgo Pignano, Tuscany

Nestled deep in the remote Tuscan countryside, Borgo Pignano is a hidden gem that exudes authentic rural charm with a dose of magic. Set on…
View hotel

Bellevue Syrene, Sorrento

Built up on the remains of an ancient Roman Villa, the Bellevue Syrene is a luxury retreat perched on top of a Sorrento cliff side.…
View hotel

Casa Angelina, Amalfi Coast

Casa Angelina remains one of the best-kept secrets of the Amalfi Coast; a design hotel that blends subtly into the sheer cliffs and offers unparalleled…
View hotel

“Many companies brag about offering once-in-a-lifetime experiences. But with Black Tomato it’s not hyperbole”

“Black Tomato are one of the coolest things in the world. Don’t even try and live without them”

“Black Tomato is a super innovative company where the sky is the limit for their clients”

“Black Tomato prides itself on meeting customers every minor need or desires”

“Black Tomato is the choice provider of mind-expanding holidays”

“Black Tomato has made it a mission to keep the world of travel fresh, responsible, and exciting”

“Tailor-made travel experiences that truly get under the skin of a country and its people”

“Black Tomato is a leading luxury travel company that provides innovative and inspiring experiences”