Be realistic when deciding what horse riding ability you have. If you're a beginner, it would not only be dangerous to sign up for an experienced riders trek (as they'll have less supervision and take more challenging routes), but you won't be fit or able enough to keep up with the others!
Decide whereabouts in Hampshire you'd like to visit whilst trekking. To make the most of everything the county has to offer, it's best to choose a trek that encompasses all the best bits, including trips into the New Forest and sunset beach rides. Again, bear in mind that if you're very unfit, spending 3 or 4 hours straight on horse back will be hard work! Choose a holiday with a relaxed route if this is the case.
Get in touch with the Hampshire tourist board and the British Horse Society (see Resources below) who will be able to recommend accredited riding schools and companies that offer horse riding and pony trekking holidays. You could also try doing your own searches for them on the internet, but do make sure the instructors are properly BHS qualified and there will be adequate supervision on the trek before you book anything.
Request brochures from the holiday companies or riding schools, or ask them to send you details via email. Some of the bigger places have their own websites where you can read full itineraries of their treks. Shop around before you book anything--the holidays on offer can vary drastically on the quality of accommodation and food you'll get and the number of other people who'll be trekking in your group.
Remember to pack appropriate clothes for your riding holiday. The riding school or organiser will usually provide hard hats but you should make sure you have some flat soled, sturdy shoes with a tiny heel to ride in. High heels and platforms are of course completely out of the question! Remember as well that riding all day in jeans can get pretty uncomfortable; take a pair of tracksuit trousers or jodhpurs instead.
