# Running a multi-city executive retreat between Umbria and Rome: a logistics case study
> A hypothetical 15-person C-suite retreat splits its time between a walled estate in Umbria and a boutique hotel near Piazza di Spagna. Here's how the transfers, sequencing, and budget actually work.
**Author:** Michael Kovnick
**Publisher:** Executive Offsite Travel (https://executiveoffsitetravel.com)
**Published:** 2026-10-19T08:52:11.529381+00:00
**Updated:** 2026-10-19T08:52:11.527624+00:00
**Category:** 
**Type:** guide
**Audience:** BusinessAudience
**About:** Executive retreat, [Umbria](https://www.wikidata.org/wiki/Q1075), [Rome](https://www.wikidata.org/wiki/Q220), Logistics
**Mentions:** Castello di Reschio, [Città di Castello](https://www.wikidata.org/wiki/Q19220), [Via Veneto](https://www.wikidata.org/wiki/Q1055530), [Fiumicino Airport](https://www.wikidata.org/wiki/Q1936), [Orvieto](https://www.wikidata.org/wiki/Q123759), [Duomo di Orvieto](https://www.wikidata.org/wiki/Q1266683), [Montefalco](https://www.wikidata.org/wiki/Q204481), Arnaldo Caprai, [Roma Termini](https://www.wikidata.org/wiki/Q80138), [Piazza Barberini](https://www.wikidata.org/wiki/Q1133383)
**Places:** [Italy](https://www.wikidata.org/wiki/Q38), [Umbria](https://www.wikidata.org/wiki/Q1075), [Rome](https://www.wikidata.org/wiki/Q220), [Tuscany](https://www.wikidata.org/wiki/Q1273), [Lake Como](https://www.wikidata.org/wiki/Q16160)
**Canonical:** https://executiveoffsitetravel.com/running-a-multi-city-executive-retreat-between-umbria-and-rome-a-logistics-case-study/
**HTML version:** https://executiveoffsitetravel.com/running-a-multi-city-executive-retreat-between-umbria-and-rome-a-logistics-case-study/
**RSS:** https://executiveoffsitetravel.com/feed.xml
**Related:** [Optimizing Logistics for a Multi-City Italian Executive Offsite: Rome to Umbria](https://executiveoffsitetravel.com/md/optimizing-logistics-for-a-multi-city-italian-executive-offsite-rome-to-umbria) · [How to Run an Effective Executive Offsite: Planning, Agenda and Travel Management](https://executiveoffsitetravel.com/md/how-to-run-an-effective-executive-offsite-planning-agenda-and-travel-management) · [Leadership Alignment Workshops: Team Building Agendas That Drive 2027 Strategy](https://executiveoffsitetravel.com/md/leadership-alignment-workshops-team-building-agendas-that-drive-2027-strategy)
---## Why split the itinerary at all

Most executive offsites in Italy pick one region and stay there. Tuscany for the whole four days. Lake Como and nothing else. That's the easier plan to build, and for a lot of teams it's the right one.

But some retreats need two different rooms to think in. A pharmaceutical company I'll call Firm A here spent two years planning its 2024 senior leadership offsite around exactly that problem: three days of strategy work that needed quiet, and two days of stakeholder meetings that needed Rome's address book. The solution was a four-night, two-city trip. Two nights at Castello di Reschio, a restored medieval estate near Città di Castello in northern Umbria, followed by two nights at a hotel off Via Veneto in Rome.

Fifteen people. Two regions. One set of logistics that had to work on the first try, because there's no reshooting a C-suite retreat once the flights are booked.

## The group, roughly

Firm A's traveling party was the full executive committee plus two board observers: CEO, CFO, CHRO, chief medical officer, three regional presidents, a handful of VPs, and two external advisors flown in for the Rome leg only. Ages ranged from late thirties to early sixties. Three people had dietary restrictions serious enough to flag with every restaurant in advance. One executive does not fly well and needed an aisle seat on every leg, including the ninety-minute train ride.

That last detail matters more than it sounds. Planning for fifteen people isn't planning for "a group." It's planning for fifteen individual sets of constraints that happen to be traveling together.

## Getting everyone to Umbria without losing a day

Umbria has no major international airport. Perugia's Sant'Egidio field runs a handful of seasonal routes, mostly Milan and Munich, and isn't reliable enough to build a retreat around. Everyone lands at Fiumicino.

From there, the group had two real options: a private transfer straight to the estate, or a train into Rome's Termini station followed by a regional connection toward Orvieto or Terontola. Firm A chose the direct transfer. Three Mercedes Vianos, pre-booked through the estate's concierge desk, covered the roughly two-hour-forty-five-minute drive north through the A1 corridor and off at the Orvieto exit before cutting east.

That drive is not downtime, and treating it as downtime is a planning mistake I see constantly. Build in a stop. Firm A's drivers paused at Orvieto for forty minutes so people could stretch, use a real bathroom, and look at the Duomo's striped facade, which is worth the forty minutes on its own. Nobody arrived at the estate frazzled. That's the whole point of the stop.

A rail alternative exists for groups who want it: Frecciarossa service from Roma Termini to Orvieto runs about seventy minutes, with a car transfer from the Orvieto station adding another forty-five minutes to most Umbrian estates. For a group bringing heavy luggage or arriving on staggered flights, the direct drive from Fiumicino is usually simpler. Italy's national rail operator publishes current Frecciarossa schedules and fares on Trenitalia's own booking platform, which is worth checking before you commit to one plan or the other, since timetables shift seasonally.

## Why Umbria for the work days

Reschio has thirty-six suites across the main castle and a scatter of restored farmhouses on the estate, which matters for a quieter reason than scenery: everyone stays within a five-minute walk of the meeting room. No vans shuttling people between a hotel and an off-site venue each morning. No commute eating into the agenda.

Firm A used the estate's old library, not a built-for-purpose conference room, for its two days of strategy sessions. Stone walls, a fireplace that got lit in October, and a table long enough for fifteen chairs without anyone's knee touching the person across from them. The CFO told me afterward that the room did something a hotel ballroom never does: it made four-hour sessions feel like two.

That's not a claim I can prove with a spreadsheet, but Gallup's research on workplace engagement has long pointed to environment and autonomy as drivers of how teams show up to hard conversations, and a castle library in Umbria changes the physical conditions of a hard conversation more than most executives expect going in.

The agenda itself followed a structure worth stealing: mornings for the sessions nobody wanted to have (succession planning, a product line that wasn't performing), afternoons for walks through the estate's olive groves with one or two colleagues at a time. Building agendas that balance that kind of focused work against informal time is its own discipline, and [Crafting Engaging Agendas for Productive Corporate Retreats](https://corporateretreattravel.com/crafting-engaging-agendas-for-productive-corporate-retreats) covers the sequencing logic in more depth than I have room for here.

Evening one was a wine dinner at a Montefalco producer, Arnaldo Caprai, forty minutes from the estate by van. Evening two stayed on-site, a long table dinner under the loggia with the estate's own olive oil poured straight from the press.

## The sequencing problem nobody plans for

Here's the question every two-city itinerary runs into: does the group do the hard work first and the cultural stuff second, or the other way around?

Firm A put strategy first, culture second, by design. The CHRO's reasoning was simple. If the hard conversations happen on day one with everyone tired from travel, the rest of the trip becomes recovery. Put them at the start, get them out of the way, and the Rome leg becomes something closer to a reward.

I've seen companies run it the opposite direction, culture first to build trust before the hard conversations, and that works too, particularly for teams that don't know each other well yet. There's no universal answer. What's not optional is deciding on purpose instead of letting the order fall out of flight availability. [Corporate Burnout Retreat Ideas in Italy and Portugal That Help Teams Recover](https://corporateretreattravel.com/corporate-burnout-retreat-ideas-in-italy-and-portugal-that-help-teams-recover) walks through a version of this sequencing built specifically around recovery over strategy, which is a useful contrast if your group's problem is burnout instead of alignment.

## Moving fifteen people to Rome without eating a day

The transfer out of Umbria is where a lot of multi-city itineraries fall apart, because someone assumes it'll take "about the same" as the trip in. It doesn't. Reschio to Rome, door to door, runs faster than Fiumicino to Reschio, since the destination is central Rome instead of an airport on the edge of the ring road.

Firm A's group drove forty-five minutes to Orvieto's station and caught an early-afternoon Frecciarossa into Roma Termini, a ride of just over an hour. Luggage went ahead separately by van, arriving at the hotel before the group did. That detail saved roughly thirty minutes at check-in and kept fifteen people from standing around a lobby with suitcases while rooms got assigned.

Total transfer time, estate to hotel: under three hours, including the stop at Orvieto for coffee. Compare that to the original 2h45 drive from Fiumicino and the math works out almost identically, which tells you something about where the time goes on a trip like this. It's never the headline leg. It's the forty-five minutes to the station, the twenty minutes waiting for luggage, the walk from the platform to the taxi rank.

## Rome: a different kind of logistics problem

Umbria's challenge is distance. Rome's challenge is density.

Firm A's hotel sat two blocks off Via Veneto, close enough to walk to the stakeholder meetings scheduled at a partner firm's offices near Piazza Barberini, but Rome traffic doesn't care how close two points look on a map. The team built in twenty-minute walking buffers between every meeting instead of relying on cars, and that decision paid off on day three when a demonstration shut down traffic near the Quirinale for forty minutes. Walkers made it on time. Nobody in a car did.

Hotel selection in Rome runs on a different logic from Umbria too. The estate model, where everyone's under one roof with one meeting room, doesn't exist in central Rome at scale. Firm A split the group across two nearby boutique properties instead of one, both within a five-minute walk of each other, because a single block of fifteen rooms at that location and on that timeline simply wasn't available. [Best Venues for Executive Offsites: Private European Estates and Resorts](https://corporateretreattravel.com/best-venues-for-executive-offsites-private-european-estates-and-resorts) covers the estate-versus-hotel tradeoff in more detail, and it's a tradeoff that gets sharper the moment a trip moves from countryside to city.

The cultural half of the Rome leg happened at the edges, not the center. A closing dinner on Via Giulia, a cobbled street lined with Renaissance palazzi a few minutes from the Tiber, where the restaurant closed its usual seating to the public for the evening. A smaller group broke off one afternoon for Testaccio's covered market, which has none of the tourist gloss of the centro storico and all of the real food culture: fifth-quarter Roman cooking, a coffee stand where the barista remembers regulars by name, stalls selling porchetta by weight instead of the slice.

ENIT, Italy's national tourism board, maintains a MICE-focused portal with region-by-region notes on group capacity and seasonal considerations for corporate travel, and it's a reasonable starting point for anyone sketching a first draft of a multi-city Italian itinerary before calling a planner.

## What the whole thing cost, roughly

Firm A's four-night, two-city retreat for fifteen people, including transfers, two nights at the Umbrian estate, two nights at the Rome hotels, all meals, the Montefalco dinner, and the Via Giulia closing event, ran a little over 4,200 euros per person. That figure doesn't include flights to Italy, which varied widely depending on where each executive started.

That number isn't a benchmark anyone should treat as gospel. Umbria in October costs less than Umbria in June. A single-city Tuscany retreat for the same group would cost less, since it avoids paying for two sets of logistics. The budgeting logic that applies here is the same one that applies to any executive offsite: sequence the decisions so the big-ticket choices (venue, dates, group size) get locked before anyone starts pricing out dinners. [Budgeting an Executive Offsite: Cost-Saving Strategies for High-Impact Events](https://corporateretreattravel.com/budgeting-an-executive-offsite-cost-saving-strategies-for-high-impact-events) goes into that sequencing in more detail than fits here.

What a two-city model buys, when it works, is two different registers for the same group in the same week. A castle library for the conversations that need no distractions, and a city for the ones that need an address book. Whether that's worth the added coordination depends entirely on whether the plan actually needs both. Firm A's did, because half its plan was internal strategy and half was external stakeholder management, and those two things don't happen well in the same room.

## The planning lesson, condensed

If there's one thing I'd tell a planner staring down a two-city Italian itinerary for the first time, it's this: the transfer days are not transition days, they're programming days. Firm A treated the Orvieto stop and the Via Giulia walk as deliberate parts of the plan instead of gaps between parts of the plan, and that's the difference between a retreat that feels disjointed and one that feels like two chapters of the same trip.

The other lesson is smaller but equally practical. Send the luggage ahead. It sounds like a minor logistics trick. For a group of fifteen executives standing in a Roman lobby at the end of a long travel day, it's the difference between a check-in that takes four minutes and one that takes forty.

I think about that last night at Castello di Reschio more than I expected to. Fifteen people who'd spent two days arguing about a product line that wasn't working, sitting under the loggia with glasses of the estate's own olive oil passed around the table like it was wine. Someone asked if anyone wanted to walk down to the stables before dessert. Four people got up. Nobody checked a phone.

For those who prefer a specialist, [Culture Discovery Vacations](https://www.culturediscovery.com/partners/) is one operator that specializes in executive offsites.

That's not a measurable outcome. It's what a retreat looks like when the logistics become invisible, which, if you've ever run one, you know is the real goal.