We decided to go South before crossing the Atlantic, I left Puerto Mogan in Gran Canaria on 18 Oct to go to the Cape Verde Islands. The islands are somewhat poor but water and diesel are available, you might want to stock up on food in the Canaries though. We visited the islands of Sal (cheap diesel available from adjacent to the anchorage) Boa Vista (not that much to inspire one) and then Santiago (Praia the capital of the Cape Verde Islands is much better provisioned). We departed for Barbados somewhat early in the season and had a delightful passage to Barbados (16 days and 6 hours) the wind never got above 20kts and we ran for 10 days under twin poled Genoas and never had to toucht the sails !!
Obtain a copy of "The Atlantic Crossing Guide" by RCC Pilotage Foundation and printed by Adlard Coles Ltd; this book will answer most of your questions!
The Atlantic Crossing Guide should be top of your list for advice. It is by Anne Hammick and widely available in chandlers at around £30.
If you are new to long-distance cruising, three good general books are Bill & Laurel Cooper "Sell Up and Sail" (new edition due shortly); Geoff Pack "Ocean Cruising Countdown" (out of print, but still available); Beth Leonard "The Voyager's Handbook" (1998).
There is a definite time of year for going. From the UK, leave in August-September with a view to crossing from the Canaries in November-December. Returning, leave the Carribbean/US in May. So start plannning now!