Long term planning is not our strong suit. Buying tickets even six months out is a major accomplishment. Normally we'll go down over the holidays, come back for a couple weeks, then go down for a couple more months.

We have the Cape Air coupon book, so I looked for Southwest tickets in January from San Juan. I thought they opened their schedule six months ahead, but they're only taking reservations through January 4! That's 3 1/2 months from now.

Am I missing something? The BVI won't let you in without a return ticket. I guess the Cape Air book will do, but this sure doesn't facilitate planning.

Did a test from IAD to SJU on SW
Saw some fine print at the bottom...

"We are currently accepting air reservations through January 5, 2022.
On September 16, 2021 we will open our schedule for sale through April 24, 2022. This date is subject to change! Please check back frequently."

Thank you, CWoody. Missed the fine print and I was a day too soon. On the plus side for SW, we booked for Dec. 7. They changed the flight schedule, which apparently allows us to reschedule within two weeks on either side for the same price.

Is Cape Air still selling coupon books? Price?
Edit: Looked it up on their website. 10 pass coupon book for SJU EIS route is 2000.00 or 400.00 per round trip. Currently you can book a round trip for 260.00.

GeorgeC1, thanks for that information. Any idea why someone would pay so much more (~50%) for the 10 pass coupon book - other than to lock in its price as against future possible increases. Alternatively do the coupon books enable one to avoid change fees, and thus are perhaps worth the extra cost?

I'm curious as to the rationale for such a significant price disparity. Looking forward to your thoughts as well as those from others.

When we left in June, a single one-way ticket on the flight we needed was something like $460. That is not unusual. We, and many of our neighbors, get the coupon books as they generally work out cheaper. And they do offer flexibility.

George, double check your numbers. On both the Cape Air website and Google Flights, a round-trip in Dec./Jan. is about $700 - higher on certain dates/times.

I plugged multiple dates for Nov and Dec into Hotwire and Kayak. They all came up with 266 dollar options but not on CapeAir. In the past I was able to book directly in the American website for about that price. For those same dates I see 700 round trip. 379 to fly round trip US to SJU and then 700 for the last 120 miles on American. Booking directly with Cape Air was high 400 range. Not that long ago the standard round trip was about 180 on Cape Air.
As far as the passes you can purchase a 10 coupon book for 2000.00. They are valid for 1 year from the date of purchase and you can list 5 people eligible to use the passes. No booking restrictions and they can be canceled or rebooked up to 24 hours prior with no penalties that I saw.

Southwest just opened up more dates, but from January they're only flying once a week San Juan-Memphis (through Tampa). Looks like we'll be on American!

George, I don't ever recall a $180 r/t on Cape Air. In fact, all our neighbors say they pay more for that last leg than to get to San Juan!

There is a caveat on the coupon book: the software only allows them to transfer baggage with United. Although they partner with other carriers, you have to pick up your bags and recheck (and pay) for them.

Prices are crazy..it cost me $150 more a couple of weeks ago to fly to Chicago to hook up with Tom Garvey and Prof Ashmore...than it did to fly San Francisco to St Thomas on Oct 3..$544 round trip. That may be the cheapest I have paid in years!

GeorgeC1, and others, thanks so much. I'm trying to plan for travel from Boston to VG, and still struggling with whether going to San Juan and flying to Beef Island makes the most sense or going to St. Thomas and then either then taking a ferry or a flight.

My understanding is that although it's not an authorized point of entry now, Taddy Bay Airport on VG will be opening in December, so perhaps another option there.