A team spread over three or four cities can usually find a retreat destination everyone reaches nonstop. A team spread over twelve usually cannot, and the standard that works there is 80–90% of headcount flying direct, with the remaining connections chosen in advance rather than discovered at booking time.
Either way the destination list comes from the same place: the set of cities with a nonstop flight from every home airport on the roster. The sections below cover how to build that set, what to weigh once it exists, which cities suit which team shapes, how to price the shortlist before the vote, and a timeline for a retreat three or four months out.
Skip the spreadsheet
The more cities people are scattered across, the fewer destinations overlap, and cross-referencing airline route maps by hand is where retreat planning usually stalls.
Midway does the intersection in one search. Enter the departure cities and it returns every destination reachable by direct flight from all of them. The data covers the next twelve months of schedules, counts the airports of a metro area together, and is refreshed daily, so a retreat two quarters out is inside the window.
How you weigh that shortlist is its own topic. The offsite destinations cluster covers the full flight-first method and the step-by-step roster-to-shortlist guide walks through it airport by airport. What follows is the retreat-specific version.
Aim for 90% nonstop, not 100%
For a team in three or four cities, insisting everyone flies direct is realistic. For a team in twelve it can shrink the destination list to zero. The workable standard is a city where 80–90% of headcount flies nonstop, with the remaining connections treated as explicit line items: the colleague in Boise, the engineer in Berlin.
Two things make this fair over time. Decide who connects before booking rather than after, and rotate the burden, so that if the same office ate the connection last retreat, their convenience wins the tiebreak this time.
What matters when picking a city
Direct flights are the starting constraint. After that, four things separate the finalists.
Travel fatigue costs day one. If half the team lands after 15 hours of travel with a connection, Monday is a write-off. Direct flights mean people arrive able to work.
Budget goes further in some cities. The same $2,500 per person covers four days in Porto with room to spare. In Zurich it barely covers the hotel. A cheaper city often means a better retreat, because the extra dinner or the extra day is affordable.
Weather is worth a filter. Barcelona in October is 22°C and sunny. Barcelona in January is a coin flip. A walkable city with outdoor dining creates a different mood from one where everyone is huddled indoors.
Walkability. The retreat cities that work are compact, with hotel, co-working space and restaurants within walking distance. Coordinating rides for 15 people three times a day is its own job.
Cities that work, by team distribution
Mostly US-based
- Mexico City. Direct from most major US cities, affordable, very good food, warm year-round
- Denver. Central for coast-to-coast teams, outdoor activities, reasonable hotels; see the Denver profile
- Nashville. Well connected, walkable downtown, good restaurants, budget-friendly
For a deeper bench than three cities, the ranked list of US offsite cities covers ten with the flight-coverage numbers behind each. For a team split between the coasts, the coast-split guide is the shortcut.
Team split across US and Europe
- Lisbon. Direct flights from East Coast hubs and most of Europe, affordable, good weather, walkable. US nonstop coverage is thin beyond New York and Boston, so a West Coast contingent will connect; the international offsite guide explains when that trade is worth it
- Barcelona. Good connectivity from both continents, reliable weather spring through autumn, strong food scene
- Dublin. Easy access from both continents, compact centre, English-speaking, which simplifies logistics
- London. Nonstop from every major US tech hub and every European base, which keeps total travel down for a transatlantic team. Costs more on the ground
Put a price on the shortlist before the vote
A destination vote works better when each option carries a number. Before sharing the shortlist, run the flight cost estimate for each finalist: cheapest direct round-trip per origin, times headcount, plus a 30% buffer. “Porto: $19k in flights. Barcelona: $16k. Denver: $11k” changes the conversation, and it puts the number in front of the budget holder months before the invoices arrive.
The same arithmetic exposes the connection cost early. A connection typically adds 30–80% to a ticket plus half a day of travel, so a destination that forces six of them costs more than its fares suggest, in money and in day-one energy.
A timeline that works
The timeline below assumes a retreat three or four months out, which is the usual lead time for a distributed team.
Week 1. Run the Midway search. Share the top three to five options with the team, each with its estimated flight total. Keep the list short, because too many choices slows everything down.
Week 2. Quick vote, then book flights. Prices climb sharply inside six weeks of departure. For teams of 10 or more, a group booking through a travel agent can sometimes save 10–15%. If anyone’s passport is expired, and assume someone’s is, this is the week to find out rather than week 10.
Week 3. Lock down accommodation and a meeting space. Hotels with conference rooms keep things simple. Rentals work for teams under 10 and get complicated beyond that.
Week 4 onward. Plan the agenda. Schedule work sessions and team dinners, and leave gaps. A good share of what people remember from a retreat happens in the unstructured time: walking to lunch, drinks after dinner, the conversation that starts because nobody has anywhere to be.
From shortlist to booking
The largest risk in retreat planning is not picking the wrong city. It is spending so long choosing that there is no time left to plan the retreat itself. A city with direct flights, workable weather and a budget that fits beats a longer search for the ideal one.
The search returns the destinations the team can reach nonstop and the cheapest direct fare from each origin. Between two cities that both clear the flight bar, the decision usually comes down to venue dates and hotel availability, and those answers come from the hotels. The company offsite pillar guide covers the fuller planning cycle, from budgets to booking windows to venue logistics.