A classic Caribean escape.
I am sure there are people who have their own views (which is strange of them, as I am always right), but I think Nonsuch bay offers the best winter family sailing you can find (and it is pretty amazing and popular in summer too).
I took my immediate family (wife, two small girls: Amelie 3 and Eloise 1) and my in laws (husband and wife, young in spirit, young in body) for a multi generational ten days in a three bed roomed apartment overlooking the harbour - one of about 40 beach front villas and cottages there. I chose October principally because I could fly using air miles,also beacause Nonsuch gave me a very good deal, and further I expected nothing from the weather other than some warmth. What we got was the same Caribbean weather I have encountered in March, December, November and January previously: warmth, sun, wind, fluffy clouds, the daily squall and the odd hour or two of cloud every other day. Apparently there isn't that much difference from month to month, unless a hurricane comes close, and you know about those well in advance.
A charismatic holiday destination
After a remarkably pleasant day flight from Gatwick (I say remarkable as we were travelling with two small children in the economy centre bank of three seats), we arrived on the tarmac with a hot blast of Caribbean air. After a half hour struggle through customs (top tip: get those forms filled in on the flight, and walk fast off the plane), bags were waiting, and so was Vernon the driver, 20 feet from the carousel. It doesn't take long to adjust to the complete change in atmosphere on Antigua (another tip - have shorts in your hand luggage), and as we bounced along the pot holed roads for the 40 minute drive, jelly water in hand (chilled coconut water straight from the nut - I now have two child addicts) we felt very much on holiday before we had arrived. You cannot answer the question 'what makes the Caribbean such a charismatic holiday destination' very well. There is something there: space, a cosseting warmth, fluffy clouds, the sea, great depth of colour, and there is something missing: noise, angst, pressure. You feel when there that the area has never suffered the industrial revolution, and therefore never been cajoled into accepting American work practices and hours. Test how long it takes each member of the family to adjust to the new tempo: My father in law hit the ground running (or strolling), and I came last, finally leaving the phone in my room on about the third day.
As with all holidays, one of the great relaxants is lessening the things you have to do, and increasing the things you want to do (as opposed to holidays of yore, where the idea was to do nothing at all). Nonsuch provides something that all families would gain a huge amount by taking up: sailing (third top tip - this is an activity that you can enjoy as a family for the rest of your lives). As a novice sailor and married into a tribe of salty sea dogs, it was a given that my children would be raised on boats, and that at the very least I would need to know my aft from my elbow. This is the best environment I have seen to learn how to sail, to try out various boats and catamarans (and kite surfing and windsurfing apparently) and to do so with a warm bath underneath you, rather than the gritty Solent or Bristol Channel. You also do so with the wonderfully happy and encouraging team there offering white glove service, meaning you don't need to rig or de-rig the boat (a hassle for beginners, but something that more experienced sailors seem to love). When I was there they were teaching me, another couple of Mums and Dads as well as seven year olds, and giving smaller children trips around the bay on motor boats to get a feel for the sport. Everyone had the space and the time to learn in their own way and to boost their confidence. For the experienced there were keel boats, a quiver of dinghies, catamarans, with races throughout the week and people on hand to crew, to helm, to teach and to act as safety. They were lovely people.
A wonderful holiday
There were also people enjoying a holiday and honeymoons there ignoring the sailing, and just using the three swimming pools (all infinity), the sandy beach, the small bar and restaurant or sitting on their terraces enjoying the breeze. Being brand new the palms haven't grown up yet, but it is a well ordered and cleverly laid out place where everyone has a view. The rooms themselves are immaculate: stylishly and comprehensively equipped with good quality furniture and excellent kitchens (a godsend for us in feeding children at a moments notice). Most of all they were spacious, and we were happy to spend afternoons at home too. They have a kids club based around the warmth of the team there, and offer day trips to desert islands as well as villas overlooking the resort. There is talk of a spa, a shop and tennis courts for the future. Would I go back? Of course - I would go every year and pretty much any time of the year too. Every member of the family adored it, and we adored being together there. Enough space to separate, but enough fun to do lots together. A wonderful holiday.