Engineers in Berlin. Product manager in Toronto. Designers in San Francisco. A few people in New York. Leadership approved the budget for an annual retreat, and now someone has to figure out where everyone goes.
This is usually where things stall. Someone throws out Lisbon. Someone else checks flights from San Francisco — no direct route. A spreadsheet appears. The thread goes quiet. Two weeks later, you’ve settled on a city nobody’s excited about because it was the only one left.
Skip the spreadsheet
The core problem is simple: you need a city with direct flights from all your team’s locations. The more cities people are scattered across, the fewer destinations overlap.
Midway handles this in seconds. Plug in your departure cities, and it returns every destination reachable by direct flight from all of them. No cross-referencing airline websites. You have a shortlist before your coffee gets cold.
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: pick a city where 80–90% of headcount flies nonstop, and treat the remaining connections as explicit, chosen line items — the colleague in Boise, the engineer in Berlin.
Two things make this fair over time. Decide who connects before booking, not after. And rotate the burden: if the same office ate the connection last retreat, their convenience wins a tiebreak this time.
What actually matters when picking a city
Direct flights are the starting constraint. After that:
Travel fatigue kills day one. If half the team lands after 15 hours of travel with a connection, Monday is a write-off. Direct flights mean people show up ready to work, not recovering.
Budget goes further in the right place. The same $2,500 per person covers 4 days in Porto with room to spare. In Zurich, it barely covers the hotel. A cheaper city doesn’t mean a worse experience — often it means a better one, because you can afford the extra dinner or an extra day.
Weather isn’t everything, but it’s not nothing. Barcelona in October is 22°C and sunny. Barcelona in January is a coin flip. A walkable city with outdoor dining creates a different energy than one where everyone’s huddled indoors.
Walkability matters. The best retreat cities are compact. Hotel, co-working space, restaurants — all within walking distance. No one wants to coordinate Ubers for 15 people three times a day.
Cities that work, by team distribution
Mostly US-based
- Mexico City — direct from most major US cities, affordable, incredible 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. Bicoastal team? 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, great weather, walkable. One caveat: 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 — excellent connectivity from both continents, reliable weather spring through fall, strong food scene
- Dublin — easy access from both continents, compact center, English-speaking (simplifies logistics)
- London — the total-travel-time winner for transatlantic teams: nonstop from every major US tech hub and every European base. 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 five-minute flight cost estimate for each finalist: cheapest direct round-trip per origin × headcount, plus a 30% buffer. “Porto: $19k in flights. Barcelona: $16k. Denver: $11k” changes the conversation — and protects whoever’s planning from a budget surprise six weeks later.
The same arithmetic exposes the connection tax early. A connection typically adds 30–80% to a ticket plus half a day of travel; a destination that forces six of them is more expensive than its fares suggest, in money and in day-one energy.
A timeline that actually works
For a retreat 3–4 months out:
Week 1 — Run the Midway search. Share the top 3–5 options with the team, each with its estimated flight total. Keep the list short; too many choices slows everything down.
Week 2 — Quick vote, then book flights. Prices only go up — sharply so inside six weeks of departure. For teams of 10+, a group booking through a travel agent can sometimes save 10–15%. If anyone’s passport is expired (assume someone’s is), this is the week to find out, not week 10.
Week 3 — Lock down accommodation and a meeting space. Hotels with conference rooms keep things simple. Airbnbs work for teams under 10 but get complicated beyond that.
Week 4 onward — Plan the agenda. Schedule work sessions and team dinners, but leave gaps. Some of the best retreat moments happen during unstructured time — walking to lunch, grabbing drinks after dinner, the conversation that starts because nobody has anywhere to be.
Don’t overthink it
The biggest risk isn’t picking the wrong city. It’s spending so long choosing that you run out of time to plan the actual retreat. A solid destination with direct flights, decent weather, and a workable budget beats the “perfect” city that took three months of debate.
Start with the flights. If everyone can get there easily, the rest falls into place. The company offsite pillar guide covers the fuller planning cycle — budgets, booking windows, venue logistics — when you need more than a retreat-sized plan.