Hmmm, now that’s not so easy. On some trips (think African safaris, Peru’s Machu Picchu Ride) yes – in fact you do – it’s obligatory. On many other trips, it’s at your discretion. The choice is really yours. But as professionals in the industry – just like wearing a helmet – we STRONGLY encourage you to buy travel insurance every time. We’ve used it to cancel our trip due to illness or a sick parent (in fact one of our clients slipped on a coffee spill at her home town departure airport and found herself riding an ambulance to the hospital for a broken elbow vs. riding a horse in Ireland) We’ve used it to claim for travel or baggage delays and also for broken pottery that we hand carried back on a plane (well, to be clear, we aren’t sure where it broke – but it was broken when got home, and not when we bought it). And if you should, on the off chance, happen to become sick or injured on a trip – the insurance will often pay for someone to travel over to be with you and assist you in getting home. The policies have all manner of options. And as mentioned previously, not only do we ride on vacation, we ride at home – and horses are horses. Even a broken toe can impact a vacation… think about it. The investment is small compared with the coverage.