Your Next Date Just Got a Whole Lot More Interesting
Forget the usual routine. Instead of sitting across from each other at a table, what if you could explore together, solve a mystery, and laugh your way through hidden streets and scenic views?
Bailiwick Trails offers couples a refreshing, self-guided experience that turns a day out into a story you’ll remember.
Build Connection, Not Just Plans
Our trails are designed to bring people closer — whether it’s a first date, an anniversary, or a “we just need something different” afternoon. Walk, talk, and think your way through puzzles and clues that engage both your brains and your bond.
- ✅ Designed for adults, not children’s entertainment
- ✅ No booking or schedule — go when you’re ready
- ✅ Do it together, at your own pace
- ✅ Works on any smartphone or can be printed
What Makes This Better Than the Pub?
You’ve done the restaurants. You’ve walked the beach. This is your chance to *experience something together.* Shared challenges create connection, and a Bailiwick Trail is a guaranteed conversation starter.
“We got totally absorbed in the clues — and ended up holding hands more than we had in months.” – Emma & Ryan, St. Martin
Zero Awkwardness. 100% Fun.
No groups. No pressure. No one watching. Just the two of you exploring, uncovering stories, and finding joy in being curious again.
“Honestly? Best date we’ve ever had. Like a little real-world escape room, but with history and scenery.” – Rachel, Guernsey
A Brilliant Day Out for Less Than a Round of Drinks
Every trail is just £9.99. That’s it. No subscriptions, no upsells. Just a genuinely good time that’ll leave you feeling connected, adventurous, and a little proud of yourselves.
Where Will You Go Together?
Whether you live on the island or you’re just visiting, our couples-friendly trails are the perfect excuse to ditch your usual routine and do something memorable instead.