Italy

The best of Italy: from Como to coast

An exclusive journey for The Journal Collection
italy

The Best of Italy: from Como to Coast

“Black Tomato devises distinct, upscale adventures” – WSJ

At Black Tomato, we’ve earned an award-winning reputation for curating immersive, tailor-made travel experiences. Our mission isn’t just about where you travel –but how you want to feel when you get there. That’s why we avoid box-ticking itineraries, tourist traps, and FOMO-fueled agendas; instead crafting journeys that go far deeper. With Black Tomato x The Journal Collection, we’re bringing this philosophy to life through exclusive, bespoke adventures created especially for subscribers.

This journey, designed for The Journal Collection, has been carefully crafted to capture Italy’s timeless allure. From sipping a cool limoncello spritz in a cliffside lemon grove and cruising in an Alfa Romeo across the shores of Lake Como to strolling between the temples of Rome’s Villa Borghese gardens – there’s a lot of life (and magic) to be found here. We can’t wait to show you, one passo at a time.

And as part of your exclusive offer, you’ll enjoy a complimentary wine tasting experience in the Tuscan countryside (you'll find the details below).

When

April to October

Price

From £15,500pp excl. flights
(based on 2 ppl sharing)

How long

12 nights
Ideal length
Days 1-3

Lake Como

Sitting at the base of the Alps, Lake Como’s deep blue water and scenic vistas have drawn people to its shores for centuries. In Como – known as the “Silk City” – you’ll find negozi (Italian shops) selling luxury silk accessories tucked between Romanesque churches and tavola caldas (eateries serving up hot, fresh bites on the go). Then there’s the lake itself, bordered by cobblestone promenades, public gardens, gelaterias, and elegant 16th-century villas.

Grand-Hotel-Tremezzo-at-night-in-Como-in-Italy
Grand-Hotel-Tremezzo-in-Como-view-in-Italy
Rooftop-Front-Suite-at-Grand-Hotel-Tremezzo-in-Como-in-Italy
Grand Hotel Tremezzo
Grand Hotel Tremezzo
Grand Hotel Tremezzo
Day 1
Glamorous Villas and Lakeside Bliss

Touching down in Milan, your private driver will ferry you to the perennially stylish shores of Lake Como – where you’ll stay for three nights in palatial luxury at Grand Hotel Tremezzo. Your first day and night will be spent settling in; relaxing at the hotel’s world-class spa within the 18th-century Villa Emilia, dining on traditional Marchesi dishes at the lakefront La Terrazza, and soaking up the sun at T Beach, the hotel’s private lido.

Alfa Romeo vintage car in Italy
Lake Como, Italy roads
Day 2
Go for a drive

After mapping out your route alongside your helpful concierge, you’ll pick up the keys to an Alfa Romeo Duetto Spider – your elegant transport for the day. Beside glittering Lake Como, you’ll cruise through the natural beauty of the surrounding area, passing green mountains, rolling valleys, and terracotta-tiled villages. And when you find your perfect spot, the brunch hamper provided will be on hand for one of the most scenic picnics of your life.

Take to the waters on Lake Como
Villa del Balbianello, Lake Como
Villa del Balbianello, Lake Como
Day 3
On the water

Swapping your Alfa Romeo for a traditional ‘battello’ (a small Italian boat synonymous with the lakes), it’s time to take to the water. You’ll experience the lake in all its splendour, visiting some of Como’s most iconic addresses: the Casino Royale film set of Villa del Balbianello, the wisteria-crawled Villa d’Este, “the Pearl”. We’ll also arrange for you to stop for a champagne picnic on a secluded island.

Days 4-6

Tuscany

Best known for its gently rolling hills and Renaissance treasures like Florence’s Uffizi gallery and its gravity-defying Duomo, Tuscany is seriously idyllic. The movie, Gladiator, framed its sweeping green countryside quite perfectly: a rural paradise, to which people are desperate to return. Cypress trees, wheat fields, and Renaissance settlements. Shall we?

Florence, Tuscany, Italy
Borgo Pignano
Borgo Pignano
Borgo Pignano
Borgo Pignano
Florence, Tuscany, Italy
Florence, Tuscany, Italy
Day 4
Tuscan Renaissance treasures

Leaving Como behind, you’ll arrive in Tuscany to rolling hills and the birthplace of the Renaissance: Florence. With one of our expert local guides, you’ll explore the city’s iconic sites – from the Ponte Vecchio to the grand hub of Piazza della Signoria and the magnificent Duomo. Now, for your hotel. Nestled deep in the Tuscan hills, you’ll head beyond the city to Borgo Pignano, where you’ll stay for the next three nights.

Chianti, Tuscany
Chianti, Tuscany
Chianti, Tuscany
Chianti, Tuscany
Day 5
A different kind of Vintage

Along the enchanting roads of the Chianti countryside, you’ll marvel as vineyards and olive groves unfurl over gentle hills. For your exclusive complimentary experience, we’ll take you to sample some locally-produced vintages at the Badia di Coltibuono winery, with its fortified former abbey, for a delicious wine tasting lunch. Then, to the Castello di Fonterutoli winery, where you’ll learn more Italian viniculture secrets.

Siena, Italy
Siena, Italy
Piazza del Campo, Siena
Day 6
Of perfect palazzos and almond ricciarelli

Today, you’ll explore the medieval streets of Siena, stepping over the threshold of the Piccolomini library to admire its collection of artworks by Pinturicchio, discovering the Gothic-style Palazzo Pubblico, and making your way to the renowned Piazza del Campo (the setting of the thrilling annual Palio horse race). Sipping on cappuccino and savouring ricciarelli (Sienese almond cookies), you’ll soak in the atmosphere of this beautiful city.

Days 7-9

Rome

The former capital of the Roman Empire and Republic, and the spiritual and physical seat of the Catholic Church, Rome – the “Eternal City” – rises in defiant splendour along the banks of the Tiber River. Between the Vatican, the Colosseum, and the Spanish Steps, you’ll find eateries serving up “cucina povera” (rustic cooking), rowboat renting on Villa Borghese Lake beside turtles, the Temple of Asclepius, and enoteche (rustic wine bars frequented by locals).

Trevi fountain, Rome
Rome at sunrise, Italy
Hotel de Russie, Rome
Hotel de Russie, Rome
Hotel de Russie, Rome
Hotel de Russie, Rome
Day 7
Welcome to the ‘Eternal City’

Leaving the charm of Tuscany for the grandeur of Rome, you’ll head south to Italy’s historic capital. Here, in the heart of the city, you’ll find Hotel de Russie. Just a stone’s throw from the Spanish Steps – and with striking views of the Piazza del Popolo – you’ll have the whole of Rome at your fingertips. You’ll settle in, exploring the hotel’s very own secret garden, sipping on cocktails at the bar, or simply looking out at the spectacular views from your private terrace.

Pantheon Fountain, Rome
Luxury vacations in Rome
Piazza del Popolo, Rome
Colloseum
Day 8
The heart of an ancient empire

Alongside an expert local guide, you’ll embark on an enchanting walking tour of the city. We’ll arrange for you to see it all: the Pantheon, the Spanish Steps, the Fountain of Four Rivers. Along the way, you’ll stroll along Via Margutta, browsing the street’s myriad galleries and ateliers, before making your way to the magnificent Piazza del Popolo. Pausing for breath, we’ll take you for a spot of “caffe”, Italian style.

Gelato in Rome
Gelateria, Rome
Day 9
Scoops upon scoops

Stepping into a traditional Roman gelateria, you’ll learn the secrets of making the freshest Italian-style ice cream. Alongside a gelato expert, you’ll enjoy a step-by-step workshop to create your own signature flavour (we find a dash of limoncello is always a good idea), before savouring scoops of your efforts. Fabulous, fresh, and full of flavour.

Days 10-12

The Amalfi Coast

Declared by UNESCO as an area of great physical beauty, the Costiera Amalfitana (the “Amalfi Coast”) stretches 50-kilometers along the southern edge of Italy’s sublime Sorrentine Peninsula. With fruitful lemon groves (many of which eventually produce limoncello), rugged cliffs jutting down into glittering waters, volcanic black sand beaches studded with orange and white striped parasols, and pastel-painted fishing villages, it’s the perfect place to unwind – and to breathe in some fresh sea air.

Amalfi Coast, Italy
Sorrento, Amalfi Coast
Amalfi Coast, Italy
Day 10
Beside the seaside

Venturing further south, your final stop is the inimitable Amalfi Coast. Delicately scented by the lemons which cling to its hillsides, and characterised by a wash of crumbling pastel buildings, there’s an unshakeable romance to this place. No more so than when seen from the cliffside terrace of Casa Angelina, where you’ll rest your head for the next three nights.

Day 11
Of grottos and dolci

Today, you’ll climb aboard a private speedboat towards the idyllic island of Capri. With a private guide and water chauffeur by your side, you’ll discover the island’s nautical sites: the Green Grotto, the Sailor’s Cave, and the endearing Heart Grotto. Next, you’ll pass through the love arch of the three Faraglioni rocks and stop for a breathtaking visit to the legendary Blue Grotto. And back onboard, you’ll enjoy a selection of traditional pastries and delicious local wines.

Amalfi Coast, Italy
Path of the Gods, Amalfi
Path of the Gods, Amalfi
Day 12
Follow the “Path of the Gods”

For an alternative view of the Amalfi Coast, we’ll take you down the iconic Path of the Gods – an ancient, meandering mule path up the cliffs. You’ll follow the path through rosemary-clad hillsides to reach Nocelle and the sweeping views it affords, passing shepherd’s huts and stone houses carved into the limestone. Descending 1700 steps down to Positano, cool off with an aperitivo or a quick dip in the sea. Or both.

View of Positano, Amalfi Coast, Luxury Italy trips
Day 13
Ciao for now

Today marks the end of your Italian travels. But as you leave the colourful cliffside towns of the Amalfi behind, we can’t help but think that you’ll be back. Presto.

So, ready to start?

Start Planning