How do I select a beginner destination? [closed]

I'm hopeful that I'm being specific enough to avoid being too broad/subjective. I would appreciate any pointers or edits where required to make this question work here.

I am a non-road-warrior/seasoned-traveller from the North East of England. I'm very inexperienced with regards to travel and I know very little about locations outside of the UK. My holidays have been almost exclusively in Scotland or the lake district. I've never been on a plane and the furthest I've ever travelled is Paris (didn't care for it - Disneyland was ok) and I'm pretty nervous about travelling in general.

My partner is somewhat different. She loves to travel and has been to china and on a few Mediterranean holidays etc. She's pretty adventurous and not a big worrier like me. She'd like me to pick a destination to travel to for my 30th.

We'll have a budget of <£1800 for travel and accommodation and I can't get more than 9 consecutive days away from work. I'd like to travel to a location that is reasonably safe (low crime rate) and friendly (accepting of foreigners), and English speaking would be a bonus. I'd rather it take less than one day to actually get there (and the same back - so probably Europe?). Neither I or my partner are particularly interested in a 'nightlife' or just lying on a beach for a week, and I'm not much use when it comes to activities like white water rafting etc. Easy going hiking, seeing a bit of nature and some nice, unusual landscapes, preferably with mild-cold weather would suit us both I think (/hope). We plan to travel in October. I don't think I'm allowed to say 'Scotland' (again).

I'd like an answer to cover what I need to know or should consider when choosing a location; What sort of costs (particularly hidden costs) I should be aware of; and I'd very much appreciate any suggestions of countries or regions that I should investigate based on my criteria.

Update: I should have mentioned that I had considered a cruise but my partner dismissed this based on the unpleasant thought of being cooped up on a ship with lots of people (we're not very social) and having only a tiny cabin to retreat to. A shame though because I like boats and I'm not keen on the thought of flying... (airports creep me out)

Best Answer

I'll make two suggestions:

A cruise. A 7 Day sailing takes you to multiple ports and you can be as active or inactive as you want. It's a great first step since you don't have to plan any of the logistics other than getting to the embarkation port
Walt Disney World. Other than the flight, long you for, not for the GF, it's an easy destination with lots to do. While we do speak 'Murican over here, it's close enough to English where you won't have any problems ;). October is a great time to visit Orlando to boot.