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I've never been there as there's never been a particular reason to go. What are your plans? How long do you intend to stay and where do you want to go from there?
Depending on where you're flying into in order to get there could determine your plans.
Since you are not getting many responses, I will give you my input. We traded into IOM 30 years ago and really enjoyed it. The scenery was lovely and the people very nice. There was not a lot to do then but we just enjoyed the drive around the island.
Be aware you must take a car ferry over to the Isle from either Liverpool or another (further upcoast) and off the beaten path. I had arranged a t/s week when we came to England for family visit here.. but had to give up on getting to the place (in Port Erin) round the end of the island from the main ferry landing. It seems a very convenient locale though, and has grocers just across the St. and pubs tool...also a restaurant. Use of a rental car would allow you to explore... maybe even find the BeeGees house. That resort was called Cherry Orchard and sorry we missed it. Ferry system did NOT coinside with the other ground transp. we would've been using.
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