Cowes is a sailing mecca. A couple of places on the high st offer sailing/learning experiences. Pricey though, although you might get a group discount. If you don’t like sailing, bring a good book. 😀 Certainly enough pubs and cafes to keep you going for the week.
If you’re here when Cowes Week (2nd week in August this year) or the Round The Island race (next weekend) is on, Cowes has a bit of a festival atmosphere going on. Although I find it all a bit corporate, and you get an influx that conforms largely to the Hooray Henry and Henrietta sailing stereotype.
There’s a bike/car hire place in the middle of town, opposite the Pier View pub. The one that doesn’t have a view of the pier, there not being one. Well worth hiring a bike cos the island is a great place for on or off-road cycling. Probably the best thing about it.
The Little Glosters in Gurnard Marsh is probably worth the 2-mile schlep along the coast from Cowes. Great grub and situation, with views along the Solent.
Yarmouth is a nice day trip – walk inland along the River Yar to the Red Lion in Freshwater, have lunch and walk back.
The Buddle Inn and the lighthouse at St Catherine’s Point, on the southernmost tip of the island, is a nice pub/walk/POI combo.
Osborne House is over in East Cowes, if wandering round stately homes’n’gardens is your thing.
Carisbrooke Castle is in Newport, if wandering round slightly older and more fortified stately homes’n’gardens is your thing.
The Needles is good, as BigYinn says – the old Battery/Rocket site is pretty spectacular and has some fascinating history to it.
Isleofwightseakayaking.co.uk are worth checking out if you want to do some sea kayaking – they’re based at Freshwater Bay but do their thing at various points on the island, depending on the weather.
Appledurcombe House, a ruined stately home and estate in Wroxall, has a falconry centre which is good if you’ve got kids in your group.
This post was brought to you by the Cowes and District Tourist Board. Enjoy your stay!