This boat takes out more than six. I've never been on it. I found it when I was looking for daysails.

Calypso
http://calypsovi.com/index.html

Many of the 6pac boats will do a tandem trip with another boat as well.

Hey K- what did you end up choosing for a daysail? Sorry if I missed an updated post on this, I'm juggling too many balls lately to remember much. We're heading back in November, have a sailboat ourselves back up here in Buzzards Bay, but thought we might head out with someone on this trip for a day sail if they go somewhere we haven't been yet. We did a couple of evening or half day sails from Maho but there was no wind on either trip. What would you recommend- I looked at the Calypso site but IMHO, it was way too expensive for a half day anything.

Don't laugh but we ended up going out on 5 boat trips! 4 of them were sailboats. My preferred mode of transportation in the VI was by boat. The four sailboats we went out on only took 6 passengers. Our first trip was with Captain Pat of Ike Witt out of STT American Yacht Harbor, the second was with Captain Ron of the Alaunt also out of STT and we actually left from the dock by his bar/restaurant Latitude 18 (but I think he may have gotten an ear full from someone for letting us park there), our third trip was a snorkel/sunset sail with Captain Rick and Robin Gallup on Long Distance out of Coral Bay STJ. The last one was a daysail with Captain Phil on The Wayward Sailor out of Cruz Bay STJ. I enjoyed each one of them and can recommend all of them unless you are looking for a party boat.

The least expensive was Captain Rick and Robin Gallup. They sailed us out to Flanagan Island and Robin guided us on a snorkel around. If you do a full daysail with them I believe they also stop to snorkel at Newfound Bay on the far East End of STJ. I think they also take people to snorkel the mangroves. Captain Rick was very nice and changed his sailing schedule to accommodate our plans for the day. We hiked the Rams Head Trail that morning and met up with Captain Rick for a 2pm sail.
http://www.bookitvi.com/longdist.htm

You will read all over this board how wonderful Captain Phil is and he lives up to his reputation. He took us to two snorkel stops around Little St. James. His sail is quite an educational experience. He also will join you in the water and help you locate octopus and other sea creatures. He has a love for the ocean creatures and you walk away with a real appreciation for the beautiful underwater world.

http://www.waywardsailor.net/snorkeling_sailing/index.htm

We also took a motor boat trip with Stormy Petrel/Pirates Penny to Virgin Gorda for a tour of The Baths, then to Cooper Island for lunch and another snorkel stop at The Indians. This was our most expensive boat trip but we thought the tour was well worth it. $125 per person plus customs of $20 and gratuity in April.
http://www.charterboat.vi/stormypetrel.html

If you are interested in my trip report - warning it is long and detailed - here is a link:

https://www.vinow.com/wwwtalk/read.php?4,53488,53488#msg-53488

Happy Sailing!

Thanks KH! Very informative. We've done the Limnos powerboat charter to the Baths but these other sails might be fun, particularly since they may go to snorkling locations we haven't been to before. I won't laugh, don't worry. My husband has been twisting my arm for YEARS to just bareboat a sailboat and sail around but I have no interest in that. But a couple of trips per vacation sound good to me.
If you ever go to St. Martin, I highly recommend the catamaran sailing trips to Anguilla and/or the America's Cup "races" we did there- both were excellent and worth the money.

Karrieb: Don't turn up your nose at a sailboat charter. If you don't want to cook and clean, a crewed yacht is a wonderful way to see the area. You have your own tour guide, chef, bartender, private accomodations- it is really a special vacation. It got me hooked, many years ago!

Go Calypso, and go full day to Jost. You will not regret it...