Working remote without regular team meet-ups means working remote on hard mode. Instead, meet up for the day each month, or for three days each quarter. When you do this, avoid the temptation to fill the time with pointless meetings, or a useless workshop.
To help team members bond, so they can collaborate effectively online, visit a city where a team member lives, and explore the city. When you do this right, you have fun, and stimulate interesting conversations between different team members. When you do this wrong, you waste a lot of time waiting around and failing to make decisions.
Check the weather forecast, and remind people to bring waterproofs if it might rain. You can stay comfortable in (light) rain with a decent jacket, but without one you’ll end up sitting inside all day. Ask everyone to bring a water bottle and a small bag to carry it. People don’t often walk for hours in one day and they’ll get thirsty, especially in warm weather or if the evening before ended late.
⭐️ Bonus points: show off your organisation prowess by handing out water bottles printed with your team name, and pack a small first-aid kit.
Choose somewhere indoors to meet at the start of the day where you can relax and chat while people arrive, instead of standing on a street corner getting annoyed because someone has a twenty-minute delay. Good options include meeting at a cafe for breakfast, or meeting in an office or hotel lobby after breakfast, e.g. at 10:00.
⭐️ Bonus points: if people travel from out of town, get everyone to arrive the day or evening before, and stay in a hotel at or near your starting point, to keep things simple in the morning.
Explore the city
Walk around the city, to create a shared co-located experience. You don’t need a specific destination, such as a museum visit. Instead, keep your options open.
Walking around a city enables fluid group conversations. As you walk, group members randomly change conversation partner, and discussion moves between pairs and larger groups, or the whole group. You lose this as soon as everyone stands still or sits down somewhere. Instead, seek out parks or wide riverside paths away from traffic.
⭐️ Bonus points: emphasise the expedition feeling with multi-modal transport, ideally including a boat. Get a group public transport day ticket and embrace the wholesomeness of feeling like schoolchildren on an excursion. Alternatively, use ride-sharing bikes or electric scooters to reach a location further away.
Take breaks, eat and drink together
Stop regularly for refreshments during the day, to take a break from walking, and to change pace. This also lets the locals show off their favourite coffee places. Plan lunch before lunchtime, to avoid asking hungry people to make decisions, or walk a long way.
Reserve a table for dinner at a restaurant, so you have a fixed plan for the start of the evening. Don’t make the reservation too early, so everyone has time for downtime at the end of the afternoon, to go to the office or crash in their hotel room.
⭐️ Bonus points: some kind of local food, if you have team members visiting from other countries.