Leeward Island Chartering
Good morning both of you.
Having been a charter broker for 29 years, 1,000''s of clients, and a full year of cruising my own boat with wife and kids throughout the Caribbean, I can comfortably say the Leeward Islands is very easy and a wonderful transition from the BVI''s. For instruction, protected waters, and first-time charterers, I always recommend the BVI. That is why it is and will always be the #1 charter area in the world. You have 35 islands within a 15 mile radius and distances of no more than 4-5 miles. Personally, I have over 300 days in the BVI''s and know all the ''unknown'', less-populated anchorages which is normal considered ''local knowledge'' and not published in the cruising guides. Every service and amenity is available for all persons on your boat and it is a difficult place to match----------except for the crowds in the high season of Dec 15-April 15.
And definitely if you feel comfortable you should sail to Anegada, which most people feel is off limits, but you should allow 9-10 days to see the prime spots in the BVI as well as allowing 1/2 day sail each way to Anegada.
St Martin, the famous St Barts (12 miles away), and Anguilla (6 miles from St Martin) is also a very popular destination for charterers. The distances are short, line of sight navigation (no fog), very few reefs or areas of concern and phenomenal food, especially on St Barts & the French side of St Martin. If you could allow 10 days, I would definitely sail to Nevis and St Kitts, but it is approximately 44 miles from St Barts, so it obviously takes the better part of a day to get there. Once you have experience here, you could charter in Guadaloupe, Martinique, or the Windward Islands; but there the charter companies really want to see two somewhat qualified skippers or a resume which includes prior charters elsewhere. Here again a broker can help you fill in a resume or assess your skill levels.
You should ask you about 30 questions of the charter company or charter broker you use to better understand your skills, competence, seaworthy persons on your boat, quality of accommodations you usually choose on land, interests in cuisine while dining ashore (after all you are on vacation), budget, # of persons aboard, # of competent sailors, and much more. A qualified & knowledgeable charter broker or charter company can usually save you money on your charter, provide you with a wealth of knowledge, often direct you to savings on air ( I log all my clients on various internet web sites and contact tour operators to save clients money), provide charts (with highlights marked on them) and cruising guides; and we represent every charter company. A broker also stays abreast of all the designs, quality of service, destinations, etc..
SIZE OF BOATS:
Perhaps less than 5% of the worldwide fleet of thousands of charter boats are under 37'' because the charter companies cannot afford to operate smaller boats and the greatest demand has been for 46-50'' monohulls and more recently catamarans (for comfort and your non-sailing, non-heeling friends you invite). If you can operate a 32'' sailboat you can easily transition to a 40'' or larger boat, as it is no different than renting a 35'' motorhome when you can operate an automobile. As with the larger vehicle, the differences are primarily operating in confined quarters (docking & anchoring) and you will find you rarely ever dock while cruising in the Caribbean. I have a variety of checklists I provide clients which encourage the very first day certain exercises which you do after leaving the dock that will build your confidence on handling that larger vessel.
If only one person in your family is a sailor, I would suggest two things. Find a good sailing school closeby and encourage your partner to take a beginning sailing course or contact a school/charter company and request an instructor and a boat for two hours to teach the non-sailor how to start and stop an engine, hoist and drop the sails, operate a VHF radio, encourage the skipper to wear a safety harness when they leave the cockpit (to dramatically reduce the anxiety of your non-sailing spouse), tack, anchor,etc. . I will admit the BVI with all the mooring buoys make it so simple for a shorthanded skipper (with non-sailing spouse) to comfortable charter. When you return to charter company docks, they generally will not allow you to dock a boat yourself, but to use an end tie. A number of these overseas companies will provide a skipper/instructor for free (2-4 hours) or you can pay for one on a per day basis until you feel comfortable after 1 or more days.
BUY A STATEROOM or TAKE LESSONS ON YOUR OWN PRIVATE CHARTER
I often have clients who would feel more comfortable hiring an instructor/skipper/tour guide and if interested you can acquire either ASA or US Sailing Certifications during your holiday. A congenial, well-trained instructor can really enhance your learning vacation as well as building confidence for future charters anywhere in the world.
The options go on and on and that is why I enjoy my business, because I love to see people enjoy chartering and introducing couples to sailing together. If I can be of assistance please email me or call me at the numbers below. I would be happy to provide lots of unbiased information if you are interested.
Good luck in your future sailing ventures,