One of the best ways to fit a race into your island cruising is to race in a charter-boat class at the BVI Spring Regatta, St. Maarten Heineken Regatta, Angostura Tobago Sailweek, or Rolex Antigua Sailing Week. Another great information source for Caribbean sailing is CaribbeanRacing.com.Some companies make it easy by providing entry, yacht prep and measurement, and other support for an additional fee (plus damage deposit). By the way, the BVI Spring Regatta has been stretched to cover most of a week so it now includes a sailing festival segment; this features point-to-point races and other fun events that may suit crews who prefer to race with a lower adrenaline output.At each of these events, you can extend your stay to take time cruising the nearby islands before or after the regatta. And if your cruising crew isn’t inclined to race with you, they may be quite happy hanging by the pool at a resort like the Bitter End YC on Virgin Gorda or Sunsail’s Club Colonna on Antigua.If I were going to repeat the trip I described in my Sailing World story (Jan/Feb. ’06), I’d take two weeks instead of 8 days so I could slow the pace while cruising in the British Virgin Islands, explore more of St. John-and then sail all three days of the International Rolex Regatta if I could find a crewing job. If I couldn’t take the extra time, I’d probably simplify the plan by chartering with a company in the USVIs.If you don’t know someone who needs crew in the islands, consider staying ashore, inviting a couple racing friends along, and chartering an IC24 from Racing In Paradise. This growing keelboat class races both the Rolex event (USVI) and the Spring Regatta (BVIs). The IC24s often don’t use chutes, so a wider range of ages and crew abilities can handle the boats. RIP also schedules others charter race events out of the Nanny Cay resort on Tortola.http://www.nannycay.comIf you work in the airline industry, don’t miss The Moorings Interline Regatta in the BVIs each fall. This popular four-day bareboat regatta has been running for years and includes several party and lay days.