Remote Team Retreat Planning Guide 2026

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.

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
• Nashville — well-connected, walkable downtown, good restaurants, budget-friendly

Team split across US and Europe

• Lisbon — direct flights from major cities on both sides of the Atlantic, affordable, great weather, walkable
• Barcelona — excellent connectivity, reliable weather spring through fall, strong food scene
• Dublin — easy access from both continents, compact center, English-speaking (simplifies logistics)

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. Keep the list short; too many choices slows everything down.

Week 2 — Quick vote, then book flights. Prices only go up. For teams of 10+, a group booking through a travel agent can sometimes save 10–15%.

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.