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Trying to put together a month long cruise, Feb. to March timeframe. I would like to go Anegada to Anguilla and then south Antigua-Guadeloupe. Can I assume this will all be to weather and I will take a beating for a day or so? Anyone have any hints or better route to the southern leewards?
Thanks

Mike Beswick should chime in here as we have done a similar sail..

February to March will bring normal trade winds of 15-27 knots from the ENE. Seas will be 4-7 feet. Higher winds and seas will be found in all the passes between islands. Watch out for northerly swells generated by storms further north during these winter months too, making your choice of anchorages important.

You will have the usual beat to Antigua from anywhere north of St. Barths so that is where you choose to go to Antigua or use the St. Barths, St. Kitts, Nevis, Guadeloupe route instead.

You should have some great sails!

Depending on conditions you might consider going right from BVI to Guadeloupe and getting the hard part out of the way on the front end. Anegada (assuming you clear out on VG and then leave from there within 24 hours) to Anguilla is an 85nm bash the whole way. Anegada to Guadeloupe is ~210 nm on a heading of about 135 degrees, so a ENE wind could get you there on one tack. If you want a break you could put in at Nevis or St. Kitts. Once you get to Guadalopue you’d be at your easternmost point and have relatively easy island hopping N, NW and W back to BVI.

I happen to be on Anegada right now, and have heard from reliable sources that clearing in/out by boat may be coming soon to Anegada. Of course, I'll see it when I believe it.

As Tom says, consider heading straight to Guadeloupe. As Maria_and_Steve point out, the trades should be north of east at that time of year so you've got a good chance of being able to sail the course to the southern end of Guadeloupe which is where you really, really want to go, the Isles des Saintes.

I've done both trips, several times with Mal (Manpot) crewing on at least a couple of occasions. Heading straight for Anguilla from Anegada is usually pretty horrible, heading for Guadeloupe the worst bit will probably be the first couple of hours after you leave the shelter of the BVI when you'll be in shallow, exposed seas. Once you get to the deep water things smooth out considerably. There is a shallow area just south of Saba (I forget the name of the bank) but after that it'll be good. If you are lucky with the wind, you'll also be passing close enough to Saba, Statia, St Kitts and Nevis, so you'll be able to head for shore if the crew need a rest.

Once you get to Guadeloupe you really must go to Isle des Saintes. I've never met anyone who didn't really enjoy them. From there, if you have time, I would have said head south to Dominica but I understand it got hit really badly by Irma and I don't know what it is now like. So, instead of Dominica, head north up the west coast of Guadeloupe to Deshaies. One of my favourite places and the setting for the BBC series that you may have seen, Death In Paradise.

From Deshaies, I'd go to Montserrat. I wouldn't bother with Antigua unless you really do have plenty of time. It's nice but nothing special apart from Nelson's Dockyard, in my opinion. If you go to Monnserrat then Mal will have contacts for you to go and see the volcano.

Then Nevis and St Kitts. Nevis is quiet and upmarket, St Kitts less so but a trip up Brimstone Hill is interesting. Ottley's Plantation is a great place for lunch. Then head to St Bart's. I've only been in low season and have able to dock where the superyachts are normally pulled in, right below the Dior, Hermes, Louis Vuitton and other assorted places to empty your wallet. February/March you'll probably be anchored a mile out!

Then across to St Martin and Anguilla. Very different places but I liked them both.

I'm very envious of you, my chance to spend a month wandering the Caribbean is now over but I look back fondly on those trips. Have fun.

Thanks all. I would like to avoid at all costs bashing to weather for 24 hours. My original rationale to go to Anguilla is that we will be a crew of 2, I have pretty significant off shore experience but the admiral none so watches are going to be interesting. I'm thinking going directly to Guadeloupe is probably a 48 hour sail??
I could stop at St. Kitt's saving a few hours, but was down that way last year and moorings/anchorages seemed a bit tenuous. Antigua has to be the terminating point as I will be dropping the boat off there. Lots of good advice here thank you, I may do some re routing and have the wife onboard out of Antigua to St. Croix and then the last week take the boat back to Antigua. The guy crew I will have onboard then always enjoy a upwind day or two!

It is about 48 hours straight to Guadeloupe so you do need to be able to rely on your crew to do that non-stop. I have also taken over 20 hours just to get as far as St Martin/Anguilla and during that trip, the only time I saw the inexperienced members of the crew was when they came on deck to throw up.

Forgot to ask what type/size of boat you are on? On a mono you stand a better chance of staying close to Saba, Statia and St Kitts giving you more options. I've been in to Basseterre marina on St Kitts a few times and it is a good option. I've also anchored off Bassterre which wasn't a lot of fun and in White House Bay which had good holding and was reasonably sheltered. There is a new marina near White House which wasn't there on my last visit so I don't know anything about it. If you make it as far as Nevis there are literally hundreds of moorings lined up along the west coast.

If the admiral has little experience, perhaps don't take her on the upwind bit. I never had a problem finding crew when I asked on TTOL in the old days. I'm sure some of my old crew are still lurking and would likely jump at the chance of an offshore adventure.

We usually grab one of the moorings on Nevis at Pinneys Beach for a yellow flagged overnight stop before proceeding the next morning to Guadeloupe. That helps break the trip up.

Portsmouth, Dominica is a great stop, even since the hurricanes of 2017. The moorings are back in place and the town is in much better shape than even the BVI's or St. Maarten. But of course Dominica had very basic conditions to repair too, when compared with St. Maarten and the BVI's Cruiser's Appreciation Week in Portsmouth for 2017 had over 75 boats each day in the anchorage!

As Mike said, the Saints are not to be missed and are only a short hop from Portsmouth, Dominica, the true Caribbean

I have done the Anegada Passage numerous times in that time frame [local school break], and had every kind of passage, short of a disaster, but I have always left from VG, either Round Rock or Pajaro Point, I favor the latter. The passage has been 16 -36 hours depending on the boat more than any other factor, bigger was better and motorsailing was sometimes needed for comfort or timing.
I am usually headed to St Barths but often stop in Simpson Bay SXM , an easy anchorage in the dark.
It is usually a beat to weather, but if you can wait for a better window it can be not bad. Big waves have been more of a problem for me. Easy to follow the overhead airplane lights heading into SXM all night too
Leaving from Anegada, avoiding the reef is a bit of a navigation event. And clearing out may be easier in VG.
Isles Les saintes is great as mentioned, Marie Galante is well worth a stop, St Barths, Nevis and Dominica are some of my favorite places to visit. Antigua as an ending will be fine.
You might consider treating an experienced friend along for the Passage and a few days in the Caribbean, it will be a relief for the Admiral for sure.
Have Fun!!

Just curious... When going direct from Anegada to Guadeloupe, do you pass east or west of St Kitts and Montserrat?

We went down the west side of St. Kitt's and the east side of Montserrat because the volcano was active at the time.

Thanks, again good advice. I'm reconsidering the route and may pick up boat in BVI/USVI then sail to Antigua, pick up the admiral and work our way back to BVI/USVI. Still some lumpy seas in the AP but downwind better than to weather.

Good move. Your chances of getting the admiral on second and subsequent offshore passages will be greatly enhanced by making the first offshore passage a nice, gentle, downwind sail. If the first is a 24 hour bash to windward with spray flying over the boat and a lot of banging and crashing, it may well be the last!

My wife was very nervous before her first overnight passage. Fortunately it was a three day sail from Martinique to the BVI and she was hooked.

This thread has brought back great memories of my wife and I doing a couple of these trips with Mike and Jean (and Mal) on Jeannius round trip from BVI. After leaving past Cooper we were on port tack for the Saints. However, as the wind moved more easterly Mike told us we could stay on port tack but the first land we would see would be South America - we opted to tack and go to St Kitts! During the night we were hard on the wind and in the morning my wife, in a forward cabin, reported the fun of being "levitated" from the bunk coming off some of the waves. What she missed was solid blue water all the way back to the cockpit.

When Mike reports some of his crew more visible while "feeding the fish", well, I represent that remark!!