We're (way early) planning a charter for July 2025. I have Delta miles and am trying to figure out the best way to use them even though I can't book flights for another couple of months. There are 5 of us and I am trying to decide between flying from Houston to SJU or to STT. As best I can tell now, when it is too early to book flights, Delta miles to STT are a lot more than miles to SJU.

We've flown to STT for most of our recent trips but used Cape Air a couple of times from SJU, back when their flights were reasonably priced. Getting pricing on Cape Air or one of the other airlines is easily done but I'm looking for a rough idea of the charter cost for 5 from SJU to EIS and a recommendation for a charter company.

My best advice for SJU is fly in the day prior and head to EIS the next morning. It increases reliability and breaks up the travel. If booking separate tickets it reduces the misconnects.

Ahoy Captains,

Flights –
I agree with Capt. George, may I suggest You consider flying through San Juan P.R. (SJU) to the BVI (EIS).
There are more flights through San Juan (SJU) to the USA, than St. Thomas (STT) to the USA, so there is more flexibility in SJU for delays and re-booking, and possibly a better price through SJU.
Cape Air and Silver/Seaborne have Code share with some of the major airlines.
https://flights.capeair.com/en/partner-airlines-delta-airlines
https://thepointsguy.com/news/delta-adds-caribbean-codeshare-destinations-with-silver-airways/
https://distribution.delta.com/cont...tner-information/codeshare-partners.html
With most code share it is the responsibility of the Airline to get You and your crew and all the bags to the BVI regardless of weather, aircraft issues, or aircraft crew issues.
You can connect to an evening flight from SJU to the BVI and enjoy a Sleepaboard.
Please book directly with the Airline.
If You are brave enough, you may consider ‘hacking’ a separate ticket RT between SJU/BVI for a better price.
InterCaribbean is the cheapest, least reliable, and has no code share with US Airlines.

There are now numerous AA Daily Direct Non-Stop flights from Miami (MIA) to the BVI (EIS).
It has a return Direct (with a refueling stop in SJU) from EIS to MIA.
https://www.bvibeacon.com/american-airlines-to-up-miami-flights/
“MIA to Tortola, British Virgin Islands (EIS): Increasing to five peak-day flights starting Dec. 7”
https://www.msn.com/en-us/travel/ne...d117380b345e9bbc2dc71ffc3fe1f&ei=110

The STT Ferry cost is about $100 each way with Taxi and Taxes and Baggage costs.
The ferries are now within about $100 of the price of a flight with all the Taxes and Taxis and Baggage fees.

Here is some FYI for searching and finding Flights -
Clear all your Cookies, History, and Temporary Files.
https://download.cnet.com/Glary-Utilities/3000-18512_4-10508531.html
https://download.cnet.com/CCleaner/3000-18512_4-10315544.html
Start with the Source -
https://matrix.itasoftware.com/search -
Instead of 'Search Exact Date' choose 'Calendar'
Hopefully a few useful links -
Synopsis of sites with Fare Forecasts & Alerts - https://techpp.com/2014/05/05/airfare-price-predictor/
Study of When to Buy - https://www.godsavethepoints.com/predict-flight-prices-google-flights/
Regardless of the Date You Fly, it is often more economical to Buy The Ticket on-line mid-week. Check after 6 PM EST on Tuesday or all of Wednesday.
If you are concerned about the On Time Performance of a specific flight -
https://flightaware.com/ - and Enter your 'Departure' and 'Arrival'
Choose your Flight from the 'Ident' Column
Scroll down to see the past few Past Flights and choose 'View More Flight History'
Option to 'Join' for free for a 3 month history.

For Taxi Service may I suggest -
BVI RoadTown & West End - Mr. George - 1.284.499.2656
BVI Airport - Mr. Dougie - 1.284.542.8000
STT Airport - Mr. Kevin Taxi - 1.340.643.0025

I Need More Quality Cats for Chartering !
Fair Winds, Brent
thecaptainscompass.com Yacht Charters and Management
heatseekerinternational.com 5% Comm and Sales-Tax-Free Yacht Brokerage

We should have enough Delta miles to get all 5 of us to SJU or, depending on how many miles it takes, 4 of us to STT so the main flight will be on Delta. What we have done several times flying from Houston is catch a late night flight from Houston to Atlanta, overnight in Atlanta and catch the first flight out to either SJU or STT. That gives us a lot more protection against flight delays,

As time gets closer I'll check out the charter flight companies price for 5 from SJU to EIS and decide if we want to splurge on a charter or just hop on Sliver. We'll probably do the latter.

If you fly into EIS you still have to pay cab fares on this end. I spend the night on STT now both ways, at The Emerald Beach ,enjoy a great etouffe at The French Quarter Bistro..breakfast next morning and a mid day flight getting me to SFO early evening..works for me,,,

5 is a perfect number for Island Birds 5 seater...we are taking them down on Saturday and had 8 (for their 9 seater) but now 2 are coming later so their 9 seater is a little pricier. I flew Silver a couple of months ago and not only were they on time but their new planes were really nice. Remember to build in extra fees for charter that are included in commercial ticket. I am sure George can opine on what they are.

Unfortunately we may be 5 but we pack heavy so if we chartered with Island Birds it would need to be the 9 seater. We like going to STT and would probably take a water taxi if we might be late. We always build an extra hotel day on the front end of the charter so we can decompress before the start. We are pretty eager to get to the BVI from the moment we get off the plane. The problem is that we're using Delta miles which limits the number of options to get from Houston to STT on the same day.

Good to hear about Silver which may well be our option if we go through SJU. The couple of times, many years ago, we did the SJU to EIS leg on Cape Air were amazing but they've priced themselves out of consideration.

Thanks for all the advice. We'll figure it out in a couple of months when flight schedules for next July are published. This will be our 15th charter. In all cases to me planning the trip increased the excitement and anticipation of getting back there.