I have rented a villa for a month mid January 2023. I will have various groups of friends coming and going. I wish (like everyone) I had a crystal ball to see what life will look like by then. I’m feeling responsible for their travel - or at least for offering them the best option. I wanted them to buy tickets now as prices are still ok But bos - SJU involved cape air or one of the other seemingly erratic airlines. I feel like if everyone at least got to St Thomas in the worst case they could water taxi to VG. Tho wow - $$. No direct flights to STT from BOS as of now. But I’m afraid if I wait and see- the prices will just continue to increase. Private charter (island birds who I LOVE) is just too pricey from SJU for 7 people. Anyone have any thoughts/ experiences to share? ? And they’d likely be coming / going on Saturday which scares me too from what I’m hearing about STT. apologies for the droning. My mind is racing and in case you hadn’t noticed I’m a crazy planner. 😎😎

Cape Air is a quality operation. Like every regional they are struggling getting pilots but their statistics overall have been good. I have been watching the SJU-EIS market and they are by far the best choice. They have had some cancelations but when they cancel a flight they usually accommodate the passengers quickly or put on a extra section later.

We've already bought our tickets for December, so I don't think you're too early. If the prices drop significantly, we can buy the cheaper ticket and get a credit to use on the return flights, which we have not yet booked.

Cape Air has been relatively reliable. One time the checked bags came later because the plane was overweight and once we were moved to a later flight. In my opinion, your best options are through SJU on Jet Blue/Cape Air, either one ticket or separate tickets to SJU and then to VG or Beef.

If you have five people, Cape Air coupons are likely to save you money to Beef. Nervous flyers may want to avoid VG. The ferry from Trellis to Spanishtown is pretty easy.

Ok. Good to know. I appreciate the responses. Boston direct to SJU is easy. Then cape air. I think most of the people who post about an airline are the ones who had a bad experience. I’m sure most are smoother. Thank you!!

I am seeing JetBlue flying nonstop from Boston-why wouldn't you just take that? Cuts out the connecting flights. That flight has you landed by 12:05 with plenty of time for the ferries.

Alternately you could consider overnighting in STT on Friday and take the first ferries on Sat. You eliminate the fear of delays and having someone making the trip alone. Flying Friday vs Saturday may also save you enough to pay for Friday nights hotel (and drinks!).

If you are willing to pay for it - this far and away the best option. BOS -> SJU direct and then SJU -> VG with Cape Air.

RatmansWife had it correct: "If you have five people, Cape Air coupons are likely to save you money to Beef. Nervous flyers may want to avoid VG." A Cape Air "Travel Pass" is good for 10 segments and costs $2,500 and as per the company's website: "Please note: TravelPass accounts may have up to 5 travelers on a group account," and thus all five of you can get over here and back to SJU for $250 for each flight. https://www.capeair.com/travelpass/index.html

Caveats on Cape Air coupons: you have separate tickets, so there are checked bag fees; your bags will not be checked through. There is an advantage to having the Cape Air flight part of your primary ticket.

The travel pass is currently 2400 for 10 one way tickets. That’s 480 round trip plus bag fees.