The trips that work hardest are the ones where two things have to happen at once, in two different countries, and one of them is a wedding in Tuscany. Last summer, we built a trip for a member that started with a Tuscany wedding and ended at the Wimbledon finals, with a luggage incident in the middle that he never had to think about.

It went like this.

Tuscany, around the wedding. 

Five days at Terre di Baccio, a small property in the Chianti hills, chosen because it’s twenty minutes from where the ceremony was being held and because the entire suite at the top of the house was right for the family. The schedule was light by design: arrival, check-in already completed before the family landed, and the evening free. Saturday and Sunday belonged to the wedding. The days in between were ours to fill.

We added a couple’s massage in the suite on the morning after the ceremony, because the only thing more useful than an in-room massage on a wedding-recovery day is two of them. Lunch the same afternoon at Castello di Albola, a 12th-century estate in Radda with one of the more considered cellars in Chianti, followed by a private tour and tasting on the property. For the night we’d left open, we recommended a meal at Poggio Rosso, the Michelin-starred restaurant inside Borgo San Felice, fifteen minutes away which turned out to be the meal he later said was the best of the trip.

The suitcase that didn’t arrive. 

On the Frankfurt-to-Florence leg, our member’s checked luggage didn’t make the connection. He found out at the carousel in Florence, which is the worst possible time to find that out, wedding in two days, a suit involved, a member of his family in the wedding party. He sent us a single message from the airport.

By the time he reached the hotel, we had already opened tickets with the airline, were tracking the bag through three handlers, and had a backup wardrobe identified in Florence in case the suitcase didn’t surface in time. It surfaced. It was delivered to Terre di Baccio the next morning, before he was awake. He didn’t make a single phone call, didn’t fill out a single form, and didn’t think about it again until he saw it sitting in the hallway. The wedding went as planned.

This is what we mean when we say we handle the things our members shouldn’t have to handle. The bag was lost; the trip wasn’t.

London, and Wimbledon. 

From Florence, a short flight to London and three nights at The Peninsula London on Grosvenor Place, the new property that opened in 2023, which sits across from Hyde Park Corner with the kind of service standard you’d expect from the Peninsula in Hong Kong. Premier King, city view, a calm room to come back to after long days at the All England Club.

Wimbledon was the reason for the London leg. We sourced Centre Court Debenture tickets, the seats held in five-year blocks by a small group of debenture holders, traded in a tightly controlled secondary market, and almost impossible to source well without relationships. We picked the best ones available for the days he was attending. We also arranged access to one of the private restaurants on the grounds reserved for debenture holders and members of the club, a different kind of Wimbledon experience than most visitors ever see.

For the dinner before tennis, we recommended Petersham Nurseries Café, about fifteen minutes from the courts, known for its refined seasonal cooking and one Michelin star, and long regarded as one of the most charming and consistent kitchens in southwest London. For the final lunch in London before the flight home, La Petite Maison in Mayfair, the kind of long, easy, no-rush lunch that’s the right way to end a trip.

What this Tuscany Trip required

A wedding in Tuscany, an international transfer with a luggage incident, four nights in two cities, and one of the more difficult access requests in sport, all in nine days. None of it especially complicated on its own. Together, the kind of trip that requires the bookings to be sorted months ahead, the relationships to be in place, and someone on the other end of the phone when the bag doesn’t show up.

This is the kind of trip we plan months in advance for our members. The Debentures, the Peninsula room category, the Tuscan property close to a specific venue, all of it is sorted long before anyone packs a bag.

If a wedding abroad, a sporting event, or both are on the calendar for next summer, your concierge can begin the planning now. The earlier we start, the better the trip gets.