Next summer (2016) I am planning on taking my family of four, along with my sister in law and her two kids, and my father in law, on their first bareboat adventure. Though I've chartered in the BVI at least 5 times, I've always been crew. As such, I have a number of questions.

First, any tips on making this more cost effective? It seems that it's cheapest for our flights from Pittsburgh to fly to SJU and then into EIS rather than what we've traditionally done, which is fly into STT and then take the ferry. Any tips though on how to make this less expensive would be great. We're looking at about $650 PP now.

Second, I'm not sure I'll qualify to captain the boat, even though I've crewed a number of times and have sailing experience, I'd almost rather not have the stress. So, if we hire a captain, what is appropriate for a tip?

In terms of chartering boats, who do you recommend? I have gone through the Moorings several times, but interested in less expensive options if they exist. Right now I'm primarily looking at a Moorings 4000, 4 cabin cat. With a captain, however, this looks to run about $9000.

Any other suggestions would be great!

Honestly I would say you should probably book a charter with just you as skipper and your wife as first mate on a smaller mono for a week before you attempt to take guests. If you do hire a captain for this trip, the next trip you will in the same boat ( pun intended ) as you are now.

Sunsail has a early booking sail going on right now. Get 7 nights and pay for 6, keep in mind the first night is a sleep aboard. Or get 8 and pay for 7. Here is a listing for a 444. Request a captain to go with you the first day. Fill out their on line resume and see if you qualify. Then it is up to how confident you are with your experience. http://www.sunsail.com/yacht-charter/des...lb-content-tabs

I would suggest creating a "My Moorings account and complete the online boating resume to see what, if any, boats you qualify to captain. Then you will know what your options are and can go from there. It doesn't cost anything so no reason not to be sure.

Some places will put a captain on for a day. If you don't need them after they assess your skill, you drop them off.

Why not call and discuss your skills with a couple of charter companies.

Check out Blue Moon. Jim is a sponsor here. This may be just what you need for a great vacation.

From the Midwest I think $650 is normal - esp into EIS. we pay that into STT. TMM offers at 10% discount to repeat charterers.
If you're at all uncomfortable, I'd say hire a training captain. You'll have less stress and be able to gain confidence as you go along (we did this 10 yrs ago with TMM)

Check out CYOA Yacht Charters on St Thomas. They are offering 15% off 10+ day charters during the summer. They also have very skilled and personable captains that you'll actually pick up some sailing skills from.

We routinely fly from Pittsburgh and find flights to be $400~$500 cheaper per person flying to STT instead of EIS, and you arrive mid-afternoon instead of mid-evening.

Flying into STT and chartering from a St Thomas base versus BVI base you avoid the BVI ferry cost ($70 roundtrip x 8 persons) and BVI departure tax ($20 x 8) for $720 savings. For a 1 week charter with 8 persons I can provision for about $240 less in St Thomas than in BVI so total savings of nearly $1000. Add another $1000 savings if you would otherwise use a water taxi.

Also, you're on the boat at least 3-5 hours earlier and you avoid the physical & mental stress of standing in numerous lines (ferry, C&I), less loading/unloading bags onto ferry/taxis, additional taxi rides, worrying about whether BVI ferries will run or not, racing back to Roadtown on the last day to make the 10 am ferry, etc.

Regarding what you qualify for according to the website: the enthusiasm of the marketing department notwithstanding, it will be YOUR signature on the charter contract attesting to your stated abilities to competently handle the vessel in all conditions, etc.

Check out BVI Yacht Charters. Great customer service! Their boats are sometimes a bit older but they do a great job maintaining them. They are also within walking distance of grocery shopping, saving cab fare. Another money saver is that you don't have to rent snorkel equipment, they provide it free of charge.

650$ from the Midwest? What am I doing wrong? I live in the Midwest and have been paying almost double that.

Wow, so much information!

Thanks for the tip on the Sunsail 444... that boat looks absolutely perfect for our crew. I think i'm going to call sunsail and discuss my sailing background. The only things I'm nervous about are docking and anchoring. I've done both a ton as crew, but not ever as pilot. I have sail racing experience (albeit on much smaller boats) so understand the sailing aspects well, but docking in particular is something i would be somewhat nervous about. I would think picking up moorings on a cat would be even easier than a mono, so no real concerns there. I love the idea of a check-out captain for a day... might be something I ask for.

As far as flights, I am consistently finding it cheaper to fly into EIS than STT. Best fares seem to be around $650 PP and get us in early afternoon to beef island.

Where is the sunsail base and where do you typically provision?

Thanks everyone! I'm so excited to go back as it's been 8 years since my last BVI charter. Things have certainly changed a bit though since my first in 1985!

I wrote up and sent a resume to Moorings. When it was time for boat orientation, I asked the girl doing the intro if she had read it.
Nope she had not!
I think they are more concerned with you having their insurance policy than anything else.

Talk to horizon and others. They may compete for your business.

You won't dock if returning to Moorings/Sunsail. They will board and bring you in.
Most overnights are on moorings. You crew will need some help, practice and encouragement helps. But they will get the hang of it.

Piece of cake from the helm of most cats in BVI. Twins 20' feet apart will turn on a dime. Lock the helm when going astern.

Go for it.

The only time you might need to dock is to pull sling side for water.

I'm at about the same experience level as you are. I've been at the helm quite a bit, but with other extremely qualified captains onboard. Without knowing the ages and abilities of your crew its hard to assess their ability to help. There are times on a sail boats where things happen and you need some brawn to help deal with the situation, you are probably well aware of that having been crew. If you are the brawn, that means you need someone who is a competent skipper to take the helm while you resolve the issue. I agree with Teammac on getting a smaller boat for you and your wife to handle before getting others involved. We've been out with larger groups, while extremely fun as a group, the skipper needs skill and confidence. My 2 cents is spend the money on a captain and enjoy your vacation!!! <img src="http://www.traveltalkonline.com/forums/images/graemlins/circle.gif" alt="" />

You should be able to arrange to do some practice anchoring and docking with the captain until you get the hang of it. If you're on a budget do some shopping around on boats.

Sunsail is in the same marina with Moorings and Footloose. Riteway is a short walk away but you can order online and have them deliver to the boat then do some last minute shopping when you arrive.

That's a very good arrival time and fare into EIS from the Midwest!

I booked IND to STT in late August for a December trip and paid just over $600. EIS was at least $200 more. If you can get $650 for EIS, sounds good to me. Set up a Kayak account and watch the price.

agree with dalegoldy... don't overstate your experience or take a chance with a boat that you/your crew aren't confident with. Relax, and take a captain for a few days, and use the time to grow your experience and knowledge. The downside of taking a chance is so much worse, and causes unnecessary stress! <img src="http://www.traveltalkonline.com/forums/images/graemlins/toast.gif" alt="" />

Check out Conch Charters, they have some older boats, but maintain them very well. Not sure when you are going, but they have 10 days for the price of 7 in April.

They take the boat out of the dock and back in on your return.

I checked SJU to EIS airfare the other day for early June 2016 and it was running $600 pp. I was shocked.

I was trying to get the most bang for the buck when I put my first trip together in 2014. I found Pro Valor to have very good rates. We were down around 5k for a 44' cat without AC. I took ASA 101, 103/104 before booking the trip. They booked me a checkout captain for the first day since my classes were on a mono. You might look into this as an option for you. THe biggest value I found on the checkout captain was that he was an excellent teacher. I never felt like I was being quizzed or tested. After he verified me, he then spent the rest of the time with the crew teaching them what to do while I was sailing. He worked with me on picking up the mooring ball, then he worked with them, then later he worked solely with them on raising and lowering the sails and then what to do while tacking, etc. I went over my itinerary with him in detail and he had some great ideas for me to ammend our plan. The whole thing was a great experience.

EDIT: We booked 10 days for 7 in early June and $4500 on the boat in 2014

The SJU->EIS gamed by them to catch those who are making a late afternoon connection from the US. If you overnight in SJU and take the morning SJU-EIS flight its much less. (generally 1/3)

If you originate from as far as the west coast I would think you have to overnight somewhere anyway.