Changing product URLs - bad idea?

Trying to get some advice on a stalemate between my web developer and my SEO advisor.

I'm currently project managing a website migration for a travel company who sell cycling holidays. We wanted to move our old website from Joomla to Wordpress, as it is, but our developer said it would be better to build it in Wordpress from scratch, with most of the same structures and URLs and an updated, cleaner design.

We're now moving over much of the content to the new Wordpress site and I noticed that the web developer has changed the URLs slightly for many of the products (holidays) in the test website. He has built a new search filter for the products, and is building the product pages and URLs around this.

Initially, I thought the fact the URLs have changed was a red flag, and I have gone back to him to ask him if he can maintain all current URLs but he has said that he genuinely thinks the new structure will be much better as it makes much more sense in relation to the structure of the website (I do agree but not sure from an SEO pov). He said he will add redirects for all of the old URLs.

For example:

Current URL (old website): /cycling-holidays/italy-6-day-mountain-tour

His proposed change (new website): /cycling-holidays/italy/mountain-tours/6-day-mountain-tour

The proposed change makes way more sense in terms of a new breadcrumb structure he has built but an SEO advisor I know said that it's better to maintain all of the URLs as they were when migrating. The majority of our sales and revenue comes via Organic Search so it's really important for us not to lose rankings when migrating.

TLDR: Is it better to maintain all URLs when migrating a site with high rankings even if changing them makes more sense for UX and site structure?

submitted by /u/keane10
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