October is a tricky month to travel. The autumn chill has well and truly set in in Northern Europe, and in the south the resorts are shuttered and rain is common. For a proper holiday this month you need to head long haul, though as usual there will be some mid-haul holidays worth considering.
Since the ski season has not yet kicked in, October and November in Europe is mostly about city breaks. For cosy 'gemutlich' evenings try the German cities - Munich of course for Oktoberfest, or Berlin, or the eastern ciries of Prague, Budapest and Krakow. France and Spain (except the very south) are often cold and wet in October, though it's always worth being prepared for unseasonal spells of weather, and jetting off for a last minute break to, say, Barcelona, if the weather is unusually warm.
As always, Tenerife and Lanzarote provide the opportunity for a quick escape in October, as the weather will ne warm without being hot. The Red Sea resorts of Taba, Sharm and Hurghada are cooling off after the summer heat, and can provide a welcome dose of sun at this time of year. Also Dubai and Oman, which typically are hovering in the high 20s.
For long haul options, avoid the Caribbean or the soutrhern US, which are right now in the grip of Hurricane season. South east asia is still in the grip of the monsoon in October - but it's one of the best times of year to visit southern China, with warm temperatures and little rain. South Africa, too, is hotting up towards it's Christmas season, as is Australia, where spring is setting in - though avoid the north which will be wet. In fact for a dose of spring like bloom, try a long haul holiday to Sydney.
In the Gambia, the summer rains are largely over, but high season (November-February) has not kicked in yet. Prices are normally very competitive ahead of the Christmas rush, though half term week, as always, will come at a premium.