Well...the Maptech Chartbook covers PR/ The Spanish Virgins and the US and BVI's extremely well. Once you head south from the Virgins the CYC chart Kits (distributed by Maptech) are the best and least expensive options and they include the waypoints from the dolyle cruising guides to the Windwards and Leewards.
The only area with poor mapping coverage is the passage from the Turks and Caicos to the Dominican Republic and from the DR across the Mona to PR. For these I would suggest the Pavlidas guide to the Turks and Caicos which has sketch
charts and excellent planning advice for the landfall in Luperon,DR. The WAVY
LINE chart is the best DR chart but it is not great. You may want to supplement it with Bruce VanSants "A gentlemans guide to passages south" which provides numerous sketch
charts of the DR north and west coast with waypoints to use.
BTW... you might find some of the guides on Amazon but a good source for ALL of the above is at
www.bluewaterweb.com AND they have knowlegeable people working there that actually seem to enjoy helping customers! No connection ...just one of my favorite stores.