I need to buy charts for this trip. The Maptech chartbook Pr & Virgins would get me most of what I need, but the Imray Iolare are recommended as more detailed. Please comment on the differences so I can make a choice.

If you are going through the Bahamas get the Explorer Charts. They are available on the web or at most marine stores included West Marine. The NOAA, DMA and other charts are so old that the island's shapes aren't even the same anymore and the information is unreliable. Only the Explorer Charts are kept current and up to date.
As far as anywhere beyond the Bahamas, the same applies to the governmental charts but cruising guides can fill in the details about harbors, etc. Be sure to get Van Sant's Passages South book which is the "bible" for techniques to go to windward without pounding yourself to death.
Good Luck

Bluewater books, while not cheap, had everything and was very knowledgeable. The salesman had been to the DR many times. They recommended British Admirality chart that included the northern harbors for DR. Then I ordered a Maptech #10 and a Waterproof 53 for PR. Also was recommended a Wavey Line routing chart for Turks & caicos, as a supplement to my existing Maptech "All Bahamas" book. Looks like I am all set.

I just went through this same thing. For Bahamas, Explorer charts universally seem the best, though we have both Maptech and Explorer. For PR, we have the Maptech chartbook of PR and VI and it seemed the most cost effective, even though the VI part duplicated other charts.
For DR, its a problem. We have the Bellingham (DMA) charts, the Wavey Line and electronic C-MAP. For the DR north coast, Bluewater confirms that coverage is very spotty. Whether British Admiralty, US DMA or any other, there is not much. Bluewater thought that DMA and BA were roughly comparable, though I have not personally seen the BA charts of DR. I personally was underwhelmed by Wavey Line charts of the DR, even though they are better than nothing and recommended by Bluewater--for instance, they don't have a harbor chart of Luperon. For Luperon, the only decent harbor chart appears to be Steve Pavlidis's sketch and soundings chart in his T&C guide--that is awesome, as is his guide. The C-Map electronic charts are not a lot better or more detailed. For PR through Venezula, we like the Imray-Iolaire for digital raster charts and for planning charts (small-scale, like "1" and "1A-D". Also I-I for the Trinidad area, which is poorly covered in most of the chart books. We like the CYC charts for the VI through Grenada (they stop short of T & T).
Bellingham provides really nice BW copies of US govt charts, like DMA, which are cost effective, especially if you have electronic charting of the area (which one backs up which will remain a debate for another time).
FWIW. Others may have other ideas and opinions. I'd love to hear from someone who has better charts of the DR, or who have used the Softchart raster charts of DR or Maptech raster of DR--my guess is that they are copies of govt charts and not any more detailed.

M and the Group:

I don't think there has been much of a commercial demand to warrant additional charting of DR waters...and that's certainly true for Haiti. OTOH all the main ports we've been in - and a number of anchorages - are more than adequately charted for a sailboat by NIMA. One typically doesn't harbor hop along the DR coast; there's just not that much of it that's protected and therefore inviting.

Keep in mind that, even if you had a much more detailed chart with 10X the depth readings and lots more contour lines, you should still be eyeballing the water and taking your time when slipping in somewhere. Don't get fall too much in love with those electrons. <g>

FWIW we enjoyed using the Caribbean Cruising Guide (I may not have that title right...) written by Wallace Stone Sr. way back in the 60's/70's when sailing thru waters like Hispanolia. In the absence of other, more modern & detailed sketch charts, we found some great, safe places to pull in that they had documented well. The rocks really don't change all that often... <g>

Jack

Cool, Jack. Thanks for the info. Wonder if the Stone book is still available? Love the Pavlidis chart of Luperon, too--it is probably all that is necessary for that port.

M:

Stone & Blanchard did the original Chesapeake cruising guide, and the Caribbean one, and both were sold in such volume that I'll bet Amazon could produce a cheap copy immediately.

Jack

This was quite a trial of Jobe finding useful paper charts for this area. Below is a report on what I found. Bluewater books has everything in stock, most of the sales people had sailed or motored to the DR. One salesman sold me some stuff that was of no use at all.
Report:
Wavey Line Charts: Supposedly these have been corrected using WAAS GPS.
HIS 017 Good routing chart of Hispanola, with a few harbor charts, Harbors: Puerto Plata, Monte Christi/Manzanillo Bay, interior only of Bahia Samana, with no chart of entrance. Other harbor charts on south & east coasts. Very useful
HIS 020 Harbor charts of south shore DR, and west shore of Haiti, many harbor charts. Nothing of any use on north shore.
TC001 Great routing chart of Turks & Caicos.
TC002 Providenciales, very detailed, color.
TC003 Turks Islands, very detailed with dive sites (Not color).
British Admirality #463, 6 harbor charts of north shore, including entrance to Samana and Puerto Plata that are missing from HIS 017, but does not include any chart showing coastline. Seems to deviate from Wavey Line charts as to most GPS positions by about 1/4 mile.
Ocean Grafix "Charts on demand" 25673 of Mayaguez PR. Bluewater salesman stated that Maptech chartbook #10 (That I just bought from them)was woefully out of date for this area and I needed this. There was NO difference, they are the same chart.
ISS Waterproof chart #16, good routing chart from FL to PR, not much detail, except reverse side is detailed Mona Passage.
None of above have Luperon )-; . There is a good Luperon Harbor sketch in Van Sant's Gentleman's Guide to Passages South, Pg # 194.(Best, very complete book for DR info.) There is also reported to be one in Pavlidis' T&C guide.
Lee Haefele
Nauticat 33 Alesto

IMO VanSant's and Pavlidis' guides, coupled with several NIMA medium scale charts of the North Coast are quite sufficient: they comprise the most current/most relevant info for small yachts entering the various anchorages and estuaries while the NIMA charts allow for accurate coastal pilotage. As I mentioned, Stone's elderly Caribbean Cruising Guide is especially useful on the South Coast, for which there are no cruising guides. SSCA's CD of past Bulletins offers a number of reports on this coast, which are fairly current.

Jack