Hi, I've done this a couple of times. They have an ipad and you can choose the style of watch, dial, casing, strap etc. You can also monogram the back. Yes, if you order 2 you get a wooden box, which honestly is not THAT super special. Just a brown wooden box. I don't think it's worth it to get a second watch just for the box honestly. One of our orders was held up because they said the box needed something engraved and it was stuck in Switzerland for weeks. Sounded really fancy, but when we got it, the engraving was just a small thing on a small metal plate, AND they forgot to glue it on!

I do love the watches I got and they were in combinations not typically available. Just be aware that some dials are only available for certain style of watches. For example, the dial I chose was only available on a Nantucket style watch. It took 4-5 months for one set to arrive, and like 10-11 months for the second set. Don't know why the big difference! It's a fun event, hope you enjoy!