We've been fortunate to have been to all these places this winter - one of the benefits of sailing your own boat I guess.
Guadeloupe is no Anguilla - that said, I'd go to both again in a heartbeat. Anguilla spec-TAC-ular beaches, Rendezvous Bay if not perfect gets about a 9.9995 rating on 10. The Anguilla House resort has a nice restaurant for lunch and drinks, you can rent loungers without having to stay there. Very laid back vibe, we really enjoyed BBQ lunch on 'The Strip' in the valley.
Guadeloupe is much more developed, bring all the French language skills you can and be prepared to speak sign language if you don't have a lot of French. Not to scare you off, just awareness that's all. We liked Deshaies in the north, cute town, great fresh croissants and breads, Pointe Malendure also nice, very good restaurants.

Have a look at the blog on our site, gives first hand no-holds-barred reviews of many of our stops along the way.

S/V Shirley Jean