Bareboat Sailboat Fun

November 12, 2009 8:13 AM

Looking for advice on a Christmas week sailing trip

My fiancé and I are interested in a bareboat sailing trip during the week between Christmas and New Year’s. I have done some research online about destinations, and while many sound appealing, it seems like we might be able to do this most inexpensively if we focus on the Florida Keys area. We will be traveling from the Boston area and would be most comfortable on a 30-36 foot boat (fiancé owns and has much experience with his own 30-foot boat). My question to MeFites is this – have you charted a bareboat trip in Florida? Can you recommend a specific company/person to contact so I am not anonymously reaching out via google searches? If I am wrong in my assumption that Florida will be less expensive, tell me where we can go instead and find a great deal. I am trying to keep our total cost for airfare and the boat at less than $3500.

posted by DuckGirl to Travel & Transportation (6 answers total)

I have no charter experience, but my father has skippered several charters with his buddies through The Moorings in the BVIs and Belize, and had a very positive experience each time. They don't have a Florida Keys option, however. Based on what I've heard from my father, I think you're looking at more than $3,500 for a week, especially over Christmas. :(

Is there any chance you could get vacation time together slightly later in the year, maybe February? Prices have been more reasonable off-peak, or so he tells me.
posted by Alterscape at 8:19 AM on November 12, 2009

I've done some looking to charter out of Florida as well (want to hit the Dry Tortugas), and I was shocked- shocked- at how expensive it was. I recall the BVI actually being cheaper, though that doesn't include the airfare/travel time. You can also check out the Bahamas and the Grenadines, though those are more challenging sailing/nav than either Florida or the BVI. In Florida, all of the 35'-40' boats I was finding were all over $3500 just for the boat for the week, to say nothing of food and transportation. Your best bet to keep costs down is to go in summer, though- the "low season" rates are MUCH better.

(Slight derail: sailors and sailing companies have the worst internet presence of anyone anywhere EVER. Your best bet to find a charter company is to pick up a few issues of Cruising World and Sail and read the classifieds in the back.)
posted by zap rowsdower at 8:59 AM on November 12, 2009

Yeah, you're going to have trouble finding anything that week since it's the busiest all year. I would browse the St. Martin listings at LateSail to get a sense of what they do and then request a quote — they're usually very flexible. St. Martin is easy and cheap because you can JetBlue right to the harbor through JFK.
posted by nicwolff at 10:04 AM on November 12, 2009

I've bareboat chartered twice in the British Virgin Islands. Both times with Sunsail. Alterscape mentioned The Moorings above. Those two companies are kinda the defaults and both have locations all over the world. Both have decent websites for booking. Their prices are decent and give you a good midrange idea of cost because they are the baseline that other smaller charter companies have to compete with.

Christmas is definitely going to be the peak price. The seasonal change is dramatic. Peak season will cost you 1,500 to 2,000 more.
posted by Babblesort at 12:36 PM on November 12, 2009

Yes you can bareboat, yes it will be expensive. It helps to have some sort of certification or paper you can wave around at the operators saying that you have taken a course at some point in your life.
posted by captaincrouton at 1:54 PM on November 12, 2009

The Florida Keys are difficult to sail because of the many shallow areas. I don't know how many charter companies even do business there. I recommend the Virgin Islands. Does it have to be over Christmas and New Years? Expect a lot of company wherever you go. A couple of years ago we chartered with Moorings out of Tortola BVI the week of New Years and our only complaint was that it was more crowded than we had ever seen it. All the good moorings in all our favorite harbors were over loaded with boats. We wouldn't do it again over the holidays.
posted by birdwatcher at 2:59 PM on November 12, 2009