Luxury Veneto Italy: a rare evening at the Marostica Living Chess Game
A 2026 invitation, biennial and barely-bookable
There are evenings that stay with you for life. Standing in a candlelit Veneto piazza on a soft September night, watching more than 650 performers in Renaissance costume bring a 600-year-old legend to life on a chessboard the size of a town square. The Marostica Living Chess Game takes place only once every two years, and the 2026 edition falls on Saturday, September 12.
Photo©: AssociazioneProMarostica
I've secured a block of 26 Tribune Silver seats for that evening through my Italian partner. It is, quite simply, one of the rarest event invitations Italy has to offer in 2026, and I'm quietly building a small, deeply curated Veneto journey around it.
If you've never made it past Venice and into the Veneto proper, this is the year.
The Veneto you haven't met yet
Most travelers arrive in Venice, give the city two or three days, and leave thinking they've seen the Veneto. They haven't. The region's interior is where some of Italy's most beautiful, and most overlooked, places quietly live.
Photo©: AssociazioneProMarostica
Marostica. A walled medieval town between two hilltop castles, famous for two things: its cherries, and the giant marble chessboard built into the floor of Piazza degli Scacchi. The square is paved with alternating squares of red and white Verona marble. For 364 days of the year, schoolchildren cross it on their way home. On the night of the Living Chess Game, it becomes the stage for a story that began in 1454, when, as the legend goes, two suitors agreed to settle their rivalry for the lord's daughter not by sword but by chess, played on the piazza floor with living pieces.
Bassano del Grappa. Andrea Palladio designed the covered wooden bridge that crosses the Brenta River here in the 16th century, and the same families, the Nardini and the Poli, have been making grappa from local pomace within sight of it for centuries. The morning ceramics market on the river is one of the prettiest in northern Italy.
Asolo. Carlo Scarpa called it the city of a hundred horizons. Eleonora Duse retired here. Robert Browning wrote a long poem named for the place. Freya Stark, perhaps the greatest 20th-century travel writer, made it her permanent home. It's a town for slow lunches on a terrace, and quiet afternoons with a glass of prosecco.
Photo©: AssociazioneProMarostica
The Prosecco Superiore DOCG hills. The UNESCO-listed vineyard terraces of Valdobbiadene and Conegliano, where the Glera grape produces the prosecco the world thinks it knows but mostly doesn't. (Most prosecco sold abroad is the lesser DOC bottling from the flat plains.) The DOCG estates are family-run, often by the third or fourth generation, and they're where I send clients who think they don't like prosecco.
Vicenza. Palladio's city. The Teatro Olimpico is the oldest surviving Renaissance theatre in the world, with its trompe-l'œil street scenes still intact since 1585. Villa La Rotonda sits just outside town. If you've ever visited Monticello in Virginia or any antebellum house in the American South, you've already been inside a building Palladio inspired.
Possagno. Antonio Canova's birthplace, with a gypsotheca holding the original plaster models from which his marble sculptures were carved. It's one of the quietest, most affecting small museums in Italy.
Treviso. Tiramisu was invented here in the 1960s. Radicchio rosso comes from the surrounding fields. The canals are quieter and more lived-in than Venice's.
This is the Veneto I plan trips around.
Experiences worth building a trip around
A few of the curated moments I'm weaving into the September 2026 itinerary:
A block of 26 Tribune Silver seats to the Marostica Living Chess Game on 12 September 2026, at 21:00. Tribune Silver is the numbered amphitheatre section, with clear sightlines over the chessboard and the floodlit Castello Inferiore behind it.
Photo©: Municipality of Marostica
A private tasting at a family-run grappa distillery in Bassano, hosted by a member of the family rather than a guide.
Photo©: pixabay/jackmac34
A private after-hours visit to the Teatro Olimpico in Vicenza, with a Palladio scholar walking you through the perspective tricks Scamozzi built into the painted set.
Photo©: Didier Descouens
A morning at a Palladian villa with the family still in residence. There are only a handful of these in private hands. My access is through long relationships, not online booking.
Photo©: Quinok
A bespoke prosecco harvest morning in late September at a single-vineyard DOCG estate, ending with a long lunch at the family's table.
Photo©: pexels.com/Andrea Mosti
A private boat along the Brenta Canal between Padua and Venice, stopping at the Palladian villas built by Venetian nobles as their summer estates, with a curator at each one.
Photo©: pexels.com/unitea
A late-afternoon stroll through Asolo, ending with cocktails on a terrace that looks out over the hills toward the Dolomites.
Photo©: Sally Hillman
Planning a Veneto journey around the Marostica Living Chess game?
The block of 26 seats is limited and will not be available again until 2028. If your dates fall anywhere near 12 September 2026, let's talk soon.
Anna Fishman, Olegana Travel Boutique
One of my clients put it better than I ever could:
“Intimate. You get to experience things that you cannot experience by being part of a large group.”
- Peggy A., Venice
When to go
Photo©: pexels.com/Ensar *
September. The most beautiful month in the Veneto, in my opinion. The summer heat has lifted, the light is golden, the grape harvest is beginning, and the tourist crowds are thinning. The Marostica Living Chess Game takes place every other September in even years, and 2026 is one of those years.
Late September and October. Prosecco harvest is in full swing in the DOCG hills. White truffles begin to appear on restaurant menus in the foothills. Asiago cheese is at its best.
May. Garden season at the Palladian villas. White asparagus in Bassano. Cherry blossoms above Marostica.
Avoid mid-July and August. The interior of the Veneto gets hot, and many family-run wineries and villas close for the August holiday.
A sample 7-day itinerary around the chess game
This is a sketch, not a script. Every Olegana itinerary is built from scratch around the traveler. But to give you a sense of the shape of a trip built around the evening of September 12, 2026:
🍇 Days 1 and 2: The Treviso Hills
Arrive Venice, private transfer to a restored 18th-century estate in the prosecco hills. A first afternoon of rest, a long welcome dinner with the property's chef, and the following morning at a DOCG vineyard.
Photo©: pixabay.com/daniFAB
🎨 Day 3: Asolo and Possagno
A slow morning in Asolo. Lunch on a terrace. A private visit to the Canova gypsotheca in Possagno in the afternoon.
Photo©: pexels.com/Nicola Toscan
🏛️ Day 4: Vicenza and the Palladian Villas
A private guide through Vicenza's Palladian centre, the Teatro Olimpico, and Villa La Rotonda. A late lunch at a family-run trattoria in the hills.
Photo©: pexels.com/Ksenia Chernaya
🥃 Day 5: Bassano del Grappa
The Ponte Vecchio at sunrise. A private grappa tasting before lunch. A late afternoon transfer to a small property near Marostica.
Photo©: pexels.com/Lorenza Magnaghi
♟️ Day 6: Marostica and the Living Chess Game
A leisurely day exploring the upper castle and the cherry orchards above the town. An aperitivo in the piazza before the game. The performance begins at 21:00 and runs roughly 90 minutes. A private transfer back to your hotel afterwards.
Photo©: Marostica Scacchi
🎭 Day 7: Padua and Departure
A private morning at the Scrovegni Chapel to see Giotto's frescoes (entry is timed and limited, and I book it months in advance). A long lunch at Caffè Pedrocchi. Private transfer to Venice for the flight home.
Photo©: pexels.com/Rodny Abreu
A 10-day version of this trip extends into Lake Garda or the Dolomites. A 14-day version adds Bologna and the Emilia-Romagna food region, or finishes on the Amalfi Coast.
Who this trip is for
Couples who love theatre and history. The Marostica game is opera, pageantry, and storytelling at once. If you've ever stood at the Verona Arena for an opera under the stars, this will move you in the same way.
Multi-destination travelers ready to leave Venice behind. If you've already done Venice once or twice, the Veneto interior is your next chapter. Most of my clients on this itinerary don't set foot in Venice itself until the day they fly home.
Food and wine devotees. The DOCG prosecco hills, the radicchio fields of Treviso, the white asparagus of Bassano, the cheeses of Asiago, the grappa of Bassano. This region is one of Italy's quietest culinary capitals.
Photo©: istock/valentinrussanov
Cultural travelers. Palladio, Giotto, Canova, Tiepolo. The Veneto interior is denser with great art than almost anywhere outside Florence.
Small private groups. Because I'm holding a block of 26 seats, this is also one of the few moments in 2026 when I can host an entire small private group, an extended family, a circle of friends, or two or three couples traveling together, around a single shared evening.
Women drawn to the Veneto who can't make the September date. If September 12, 2026 doesn't suit your calendar but this region has been on your mind, my Spring 2027 women's group tour to Venice, Asolo, and the Prosecco Hills covers many of the same Veneto landmarks (Asolo, Bassano del Grappa, the UNESCO Prosecco DOCG hills, a Valpolicella estate lunch, five unhurried nights in Venice) over nine days in early April, with a small group of women travelers. Many of my Veneto clients begin there.
Connecting destinations
The Veneto sits at the centre of northern Italy, which makes it one of the easiest regions to pair.
Lake Garda is 90 minutes west, with the lemon groves of Limone and the lakefront grand hotels of Sirmione.
Photo©: Olegana Travel Boutique
The Dolomites are 90 minutes north, with Cortina d'Ampezzo and the alpine huts above it.
Photo©: Olegana Travel Boutique
Venice is one hour east, for travelers who want to bookend the trip on the lagoon.
Photo©: Olegana Travel Boutique
Verona is one hour west, for opera lovers timing the Marostica game alongside a final performance at the Arena.
Photo©: Olegana Travel Boutique
Bologna is 90 minutes south, for an Emilia-Romagna food extension into Modena and Parma.
Photo©: pixabay.com/RitaMichelon
Lake Bled in Slovenia is three hours east, for travelers extending the journey eastward.
Photo©: pexels.com/Matthew Cefai
Why work with a luxury travel advisor
The Marostica Living Chess Game sells out months in advance. The block of seats I'm holding came to me through a long-standing relationship with my Italian destination management partner, not through any public ticketing portal. This is the difference an advisor makes.
The same applies, quietly, to every other detail of this trip. The family-owned grappa distillery that doesn't take walk-in tours. The Palladian villa whose owner opens her home as a personal favour. The curator at the Scrovegni Chapel who unlocks the second viewing slot of the day so my clients aren't herded through with strangers. None of this is bookable online. All of it is built on relationships I've spent years building in person.
When clients ask me what they're really paying for when they work with Olegana, this is my honest answer. They're paying for access, judgment, and the time it took me to build the relationships that turn a generic Italy trip into a singular one.
Anna Fishman, the visionary and soulful force behind Olegana Travel Boutique, orchestrates transformative journeys where meticulously curated adventures meet authentic connection and exquisite, bespoke exploration.
Let's plan this!
If your 2026 calendar has any flexibility around 12 September, this is one of the most singular experiences Italy has to offer that year. I'm personally curating the Veneto journey built around it, and the seat block is genuinely limited.
Grab a time on my calendar for a free consultation here!
Frequently Asked Questions
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Every two years, on the second weekend of September in even-numbered years. The next edition after 2026 will be 2028.
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Tribune Silver is the numbered amphitheatre section. It's one of the better seating categories, with clear sightlines over the chessboard and the floodlit Lower Castle behind it. The full venue holds 3,600 seats.
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I'm holding a block of 26 Tribune Silver seats. Availability is first come, first served, and any unclaimed seats will return to my Italian partner once the block deadline passes.
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About 90 minutes by private transfer. Most of my clients arrive into Venice (VCE), spend a few days in the Veneto interior, and never set foot in Venice itself until departure. Others book the trip as a Venice-and-Veneto pairing.
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The performance is open-air in mid-September. Bring layers, including a light wrap. Smart-casual is the right register. Heels are not advisable on cobblestones.
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Yes. The performance is family-friendly, runs roughly 90 minutes, and is visually spectacular. That said, the 21:00 start time means younger children may not make it through the full programme. I'd suggest 10 and up as a comfortable minimum.
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Absolutely. The Veneto is one of the easiest Italian regions to extend in any direction, and many of my clients add three to five days in either Lake Garda or the Dolomites.