Originally Posted by
khmen
Never been there before but the woman I'm seeing has asked me to go to Bestival with her in September which is held there. If I go I might stretch the trip out to include a couple of days exploring the island beforehand. Anything you'd particularly recommend to see or do in a couple of days?
The Island does get very busy in the summer especially when there's a festy going on so the centre and north of the island are best avoided.
Sandown on the SE coast has the best beach, should be cool enough by then for a brave soul to take a dip. From the pier you can walk east along to Yaverland then up over the cliffs to the top of Culver Down on the eastern tip on the Island for some great views. Or you can walk west along the coastal promenade to Shanklin which is a pleasant and sheltered walk, along the far end of Shanklin seafront there are some good pub/restaurants with terraces.
Ventnor on the southern tip is a quiet but quite pretty Victorian town with a small beach, the approaches to it and the hills above it offer some great views.
Further west the more picturesque open spaces begin. There's a good pub in Chale called the Wight Mouse Inn and from there you walk to Chale Chine which is a natural cut through the cliffs down to the beach under the cliffs which is usually pretty deserted and is where many of the islands fossils are found.
Then along the military road with some great scenery to Freshwater and the walk over Tennyson Down, even if you don't do the full hike to the Needles the walk up to the monument is pretty easy and the views are breathtaking, especially over to the mainland coast. You can avoid the main car park and find some residential side streets where you can park for free.
Totland bay on the other side of the headland is a nice little spot that's secluded and off the tourist trail.
There's a cafe or two and the calm water and fine sand are ideal for a swim.
So many more places and the island is covered with footpaths and bridleways, if there's a hill you like the look of you can find a way up it, and like many rural locations taking the back roads leads to some beautiful places.
A real gem is Carisbrooke Castle, most definitely worth taking a picnic of sorts and after walking the walls finding a nice spot to lay down in the grass and relax for an hour or two, weather permitting of course.