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Our Family’s Lake Como and Tuscany Getaway

Writer: Daniel Gibney
Daniel Gibney
Aug 30
7 min read

Updated: Sep 12


There is a particular kind of traveler—or simply the man who has learned to slow down—who believes that a region reveals itself not through its monuments, but through its tables. It was in this spirit that we descended upon Umbria and Tuscany, moving from hilltop to hilltop the way one might move from chapter to chapter in a novel one is reluctant to finish.

There is a particular kind of traveler - the family who has learned to slow down—who believes that a region reveals itself not through its monuments, but through its tables. It was in this spirit that we descended upon Umbria and Tuscany, moving from hilltop to hilltop the way one might move from chapter to chapter in a novel one is reluctant to finish.


Orvieto: A Trattoria Fit for a Count

Our journey began in Orvieto, that improbable city balanced atop a plinth of volcanic tuff as though the gods themselves had set it there to be admired from below. We dined at Trattoria La Palomba (https://www.orvietoviva.com/en/trattoria-la-palomba-orvieto/), a family-run establishment on Via Cipriano Manente that has, remarkably, been serving the Cinti family's recipes since 1965. The room possesses the unadorned dignity of a place that has never once considered reinvention: wooden beams overhead, walls the color of aged parchment, and a staff who move with the unhurried confidence of people entirely at ease in their own house.

I recommend, without reservation, the umbrichelli al tartufo—a thick, hand-rolled pasta native to the region, dressed simply in the black truffle for which Umbria's hills are quietly famous. It is a dish that asks for nothing but your attention. Pair it with a glass of the local Orvieto Classico, crisp and mineral, and you will understand why the Cinti family has never felt the need to change a thing.


Montalcino: Where the Wine Wears a Crown

From Orvieto we climbed north into the land of Brunello, to Montalcino, a fortress town so devoted to its wine that even the walls seem to hum with it. We took rooms at Hotel Vecchia Oliviera (https://vecchiaoliviera.com/en/), a former olive mill turned three-star hotel tucked against the old town gate at Porta Cerbaia. It is precisely the kind of quaint, unpretentious lodging a gentleman of modest means but exacting taste would choose: a panoramic pool, a sun-warmed terrace, and views across the Val d'Orcia that require no embellishment from me.

For dinner, we made our way just outside the town walls to Boccon DiVino (https://www.boccondivinomontalcino.it/web/en/inside), a restored farmhouse whose glassed-in terrace has been described, quite accurately, as a balcony suspended over the Tuscan countryside. As the sun set behind the Crete Senesi, we watched the hills turn the color of the wine in our glasses—a Brunello, naturally, dense with cherry and leather, the kind that seems to have absorbed the very sunset it now accompanies.


Montepulciano: A City Best Explored by the Glass

Montepulciano is a town built for wandering, and we did precisely that, letting the wine map our route rather than the other way around. The main artery, Via di Gracciano nel Corso, is lined with enotecas where a glass of Vino Nobile can be had for the price of a postcard, and we ducked into several: a taste at La Bottega del Nobile (https://tuscanpalace.com/recomendations), a pause at the historic Enoteca Contucci, and a final glass at La Vineria near the Fortezza, each pour a small argument for staying just a little longer. We closed the evening with dinner at Antica Trattoria il Marzocco (https://tuscanpalace.com/recomendations), where thirty years of the chef's experience showed plainly in a plate of pici with wild boar ragù.


Greve in Chianti: The Pink Villa

If Montepulciano taught us to wander, Greve in Chianti taught us to stay still. We lodged at Villa Vignamaggio (https://vignamaggio.com/), the storied pink-washed estate outside town that has been producing wine since 1404 and famously provided the setting for the film adaptation of Much Ado About Nothing. The villa's rose-colored façade rises above 400 hectares of vineyard and forest, and the estate bottles its own Chianti Classico, including a Gran Selezione they call Monna Lisa. We took our evening glass on the loggia, the vines running out toward Panzano in every direction, and understood at once why a house this color has never needed to apologize for standing out.

Below the villa, in the folded valley beneath Greve, we spent a night in a small Tuscan farmhouse—the kind with terracotta floors gone smooth from generations of bare feet, and a kitchen garden that supplied more of our breakfast than any market could.

On our last evening before Florence, we climbed higher still, up the winding road above the villa to Lamole, a hamlet so small it seems to have been forgotten by time on purpose. There, beside the thirteenth-century church of San Donato, we found Ristoro di Lamole (http://www.ristorodilamole.it/en/), a restaurant that has been run since 1993 by two friends, Filippo and Paolo, who still keep a small general store attached to the bar to serve the handful of families who call the village home. We took a table on the terrace, as any sensible person does, and watched the valley fall away toward Panzano while the light went gold and then violet. There was little pretense to the cooking—a plate of pici, a plank of local pecorino, a bottle of the house Chianti Classico—but the setting did the work that no menu could. It struck me, as we finished the last of the wine with the church bell marking the hour, that this was precisely the kind of evening one packs for Florence hoping never quite to leave behind.


Florence: A Bottle on the Hill

No visit to Florence is complete without an evening at Piazzale Michelangelo (https://www.travelcolorfully.com/piazza-michelangelo/), and I would go further: no evening there is complete without a bottle carried up in hand. We bought a Chianti from a small shop near the Arno, asked politely for the cork to be loosened, and climbed the twenty minutes of stairs to the terrace above the city. There we sat as the Duomo's dome caught fire in the last light, the Arno turning to hammered bronze below, and poured wine into borrowed cups while the whole of Florence hummed beneath us.

Afterward, over a dinner of ribollita and bistecca alla fiorentina, we allowed ourselves one final indulgence: carrying what remained of the bottle through the narrow streets back to our lodging, pausing at the Ponte Vecchio to watch the lights come up along the river. It is, I confess, not strictly permitted everywhere, but done discreetly and with a cup rather than a bottle raised to one's lips, it remains one of the great, quiet pleasures of an Italian evening—the city's history settling over you like a shawl.


Bellagio: A Mother's Chocolate Cake

We concluded our journey where the water meets the mountains, in Bellagio on Lake Como. Tucked up a narrow stairway between two restaurants, we found Aperitivo et Al (https://www.aperitivobellagio.com/food/?lang=en), a small, family-owned wine bar whose reputation rests as much on its cellar as on the chocolate cake the owner's mother bakes each morning. We ordered a glass of Sforzato, a raisined Nebbiolo from the shores nearby, and shared a slice of that cake—dense, unfussy, and gone before either of us could properly describe it. It is the sort of dish that resists analysis and simply demands a second fork.

For a classic aperitivo directly on the water, settle onto the promenade at Restaurant Suisse (https://www.hotelsuissebellagio.com/) and order an Aperol Spritz as the ferries cross the lake. The view toward the mountains is the real accompaniment: bright, unhurried, and unmistakably Bellagio. For dinner, Ristorante La Punta (https://www.ristorantelapunta.it/) occupies the tip of Punta Spartivento, where the lake opens in three directions and the setting is as memorable as the food.

Other worthwhile tables include Ristorante Bilacus (https://www.ristorantebilacus.com/), a long-standing favorite with a garden terrace, and Ittiturismo Mella (https://www.ittiturismomella.it/) in nearby San Giovanni, where the menu centers on freshly caught lake fish. For a more refined evening, Ristorante Salice Blu (https://www.saliceblu.it/) offers ambitious local cooking a short distance from the waterfront.

Bellagio also rewards travelers who make time for a drink at the grander hotels. The bar at Grand Hotel Villa Serbelloni (https://www.villaserbelloni.com/) is the choice for old-world glamour, while Hotel Du Lac & SPA (https://www.bellagiohoteldulac.com/) offers a terrace made for sunset aperitivo. Hotel Belvedere (https://belvederebellagio.com/) provides a quieter elevated view, and Hotel Florence (https://www.hotelflorencebellagio.it/) is a congenial harbor-side option. For a classic lakeside stay, consider Hotel Excelsior Splendide (https://hsplendide.com/) or Hotel Metropole Bellagio (https://hotelmetropolebellagio.it/). Availability and opening hours vary by season, so it is wise to check each property's website before setting out.

We also took the boat from Bellagio across the lake to Varenna, where we found a porch table overlooking the water at Bar Il Molo (https://www.barilmolovarenna.it/). With the lake moving gently below us and the mountains rising beyond the opposite shore, it was the perfect place to linger over an Aperol Spritz and watch the ferries come and go. The short crossing from Bellagio made the meal feel like a small excursion within the journey—one of those afternoons when the view becomes part of the menu. For ferry schedules, check Navigazione Laghi (https://www.navigazionelaghi.it/) before setting out, especially if you plan to return after dinner.

As with all good journeys, ours ended not with a monument but with a table, a glass, and the particular satisfaction of a cake made by someone's mother, in a town small enough that everyone still knows whose mother it was.


Cliff Notes

A practical, at-a-glance guide to the places, pours, meals, and views from the journey.

Planning note — Reserve popular terrace tables ahead of time and check seasonal opening hours and ferry schedules before traveling.


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