Spending 8 nights on JVD (1 nti Ali Babas and 7 nts The Hideout), checking out on May 2, flying home May 3 departing STT at 4:53pm, which gives us some flexibility on where to spend the night of the 2nd. Our room on JVD is not available to extend our stay another night so that's out. Looking at the following options, given most places don't allow single night bookings:

Emarald Beach Resort (STT) - originally planned to stay here but reviews have gotten really bad lately, including rats running across the bed and an employee shooting another employee at the restaurant a few months ago. I'm thinking hard pass on this. Let me know if I'm wrong.
Secret Harbour Beach Resort (STT) - looks nice, although close to $450 for one night
Westin St. John - also looks nice but $500 for one night and under construction.
Wyndham Tortola - Reasonable pricing, nice looking pool, long way from both ferries
Olga's Fancy (STT) - looks like a reasonable option but would love to still be on a beach if possible.
Maria's by the Sea (Tortola) - similar to Olga's, looks nice but doesn't scream vacation.
The Heritage Inn (Tortola) - reasonable price, great views, decent restaurant, pool, not sure about distance to ferry terminals
Ali Babas (JVD) - maybe we can convince them to let us do another single night booking? Just leaves us having to take two ferries to get back to our plane on departure day
Other options with availability - Sapphire Beach Resort near Red Hook or the following places on Tortola: Lighthouse Villas, Sugar Mill, Quitos, Longbay Beach, Sebastians

What would you do? Any other suggestions?

Is the Perfect Pineapple available on JVD? They may do one night. Olga’s over Maria’s.

Whatever hotel you choose I would get to St Thomas and spend the night there. It will make the trip home far more relaxing and less tiring.

George and I see things differently - I avoid St Thomas whenever possible. Lol. You have a late departing flight so should be fine heading back to USVI in the morning.

I feel like it makes no sense to try to stay in the BVI on the 2nd. It will just make your trip home on the 3rd that much more stressful/complicated.
Your timing is very lucky though! Interisland Boat services runs a ferry from Jost on Tuesdays back to USVI! It leaves at 3:30 and routes through St John, ending in Redhook.
Leaving the BVI on the 3rd just gives you more hoops to jump through.
You could consider staying in St John and not continuing on to STT that same day, although your options for one night are probably limited and pricey. Plus, you would have to be on the 11 or 11:15 outta there the next day so really, what is the point?
Since that ferry would take you right into RedHook I personally would probably lean to Sapphire Beach or Secret Harbor if they would accept only one night. Then all you deal with on departure day is a taxi to the airport. Since your flight is so late there should be no reason to try to get a place super close to the airport (like Emerald).

What GeorgeC1 said....get to St. Thomas. It will make everything easier and less stressful. We've been staying at Emerald Beach coming & going to St. John & the BVI at least 4x a year for decades and never had a problem. It has everything we need to relax right up until it's time to be at the airport....beach/bar, drinks, restaurant & pool. If we want to go shopping or eat somewhere else it's a quick taxi ride to town. You decide what time you need to be at the airport and you're less than 2 minutes away.

Not sure, but if we decide to stay on JVD for the last night I'd probably try to get Ali Baba's to let us book another 1 night stay so we'd be near the restaurants and bars and ferry terminal in Great Harbour vs another night on White Bay after a week there. My current thinking is to at least get one of the ferries behind us and go to Tortola or all the way to STT though.

I
I hear what you're saying about the convenience of Emerald but after reading a ton more reviews last night I'm even more inclined to pass. If nothing else, the Manager's responses to bad reviews is a real turn off. He accuses every one of them of lying or never even staying there, even if the person posts pictures backing up their stores. Good management will at least post a canned apology vs always blaming the customer or accusing them of being full of it.

I'm the same way, generally prefer to avoid St.Thomas and the husband really doesn't want to stay there unless necessary, although he leaves it up to me.

So, here is my current thinking... love the idea of that 3:30 ferry from JVD>St. John>Redhook, except that it leaves us out of our hotel on JVD from 11:00 am until we leave for the ferry at 3:00 (they are sold out that night so late checkout not going to happen). Then, by the time we get to our hotel on STT it'll be like 5:00 so too late to really enjoy the beach or pool if they have one. Upside is that we get to sleep in both mornings, at least until check out time, and we don't have to take a ferry on the day of our flight.

If we stay on Tortola, we can hop on the 12:00 ferry after checkout from JVD and get to our hotel on Tortola by 1:00ish, giving us time to enjoy the beach/pool and relax for the rest of the day. Next morning, we could take the (11:30?) ferry from Road Town to CA and avoid that cab ride from Red Hook to STT. That would get us to CA 4.5 hours before our flight which should be more than enough time on a Wednesday.

With all the above being said, I'm leaning toward either Secret Harbour or Sapphire on STT or Quitos or Heritage Inn on Tortola. I've also emailed Myett's to see if they have availability but no response yet. They will only book single night stays up to two weeks in advance, so I won't know if that's an option for a couple more weeks.

Will your accommodations on Jost just let you store your luggage after check out?
Everyone has preferences for what they would do in your situation. You have a great handle on the logistics of your situation. You just need to decide how you prefer to spend your last day, how much moving place to place you are willing to do, how much you are willing to spend and how much stress you are willing endure for some extra beach hours.
You will figure it out!

I'm sure we could store our luggage after checkout on JVD. Do you have any thoughts on the specific hotels I've mentioned?

Edit: I just held a room at Quitos in CGB for now. I have about a week or so to cancel if we come up with a better plan. I think this has what we need though, a super clean nice room on a nice beach with a restaurant/bar, lovely views, small pool if the swells are up, and lots of bars/restaurants nearby if we want to go for a quick bar hop. There will be 2 cruise ships in port but they'll be gone by late afternoon so we're not too worried about them. RTFF hasn't published their May schedule yet but I'm assuming they will have an 11:30 to CA that morning. If not, we can always take the West End to Red Hook if needed.

LA, you have gotten some great tips from some very seasoned travelers. But I will agree with skipdastraw's last post. It is completely up to you how much you want to endure on your last day of vacation. We have done our last day on STT as well as the scramble to get to the airport on time just to have a few more hours on the island. After many years of doing both, once on the plane we chuckle and agree it was all worth it. Whatever you decide, you will have a great time. Enjoy!

Thanks Bill. Do you really think it will be a scramble to catch a 4:53 pm flight from an 11:30am ferry though?

YES!!!!!

Really? If the ferry gets into CA at 12:30pm and our flight is at 4:53pm (on a Wednesday), where is the scramble? I'm willing to hear you out on this. What am I missing?

Last time..IF the ferry gets in at 12.30 (unlikely).IF you get thro C and I n in about 30 mins(unlikely).Then you get a cab to the airport with 15 mins(unlikely).They want you checking in three hours pre flight.you do the math and seems if you are comfortable with it..then go for it.I would not but that seems like its me..I would go early..breakfast at Emerald Beach and stroll to the airport. You do seem to be locked into your plan so go for it..

I don't see the scramble on the 11:30.
You'll be in CA by 12:30
Assume an hour for customs give or take. That's 1:30.
15 minutes to the airport. 1:45....
Round all that up to a 2pm airport arrival and that still leaves you 3 hours to your flight.
Even adding another 30 minutes for delays, on a Wed I think 2.5 hours is feasible.

Thank you Manpot and Skipdastraw. I think we'll be okay staying in Tortola, but have not totally finalized our plan yet. Just found a couple reasonable condos available for 1 night at Sapphire so still going back and forth between Quitos on CGB or Sapphire near Red Hook.

If it were a Saturday or Sunday I would agree with Malcomb. But on a Wednesday you should be fine with the 11:30 ferry. Personally I would take an earlier ferry. Not for fear of getting to the airport on time. More to have a relaxing breakfast/lunch before having to deal with that awful airport. We love the outdoor bar at Emerald Beach and the food is decent. Then a 10 minute walk or a quick cap ride to STT. No stress.

You might consider spending the night at the Lovango Cay Resort. I imagine you'd have to clear customs on St. John first, but they have a ferry to shuttle you over. They would also shuttle you to Red Hook the next morning. I don't know the cost for a room, but I'm guessing it's pretty salty. Even so, we've stayed on a ball there a couple of times and had dinner at the restaurant. Very impressive digs.

Shifty - they have a two night minimum at Lovango. Tents and treehouses range between 1000 and 1500 a night last time I checked.

It looks like we could book one night on Lovango but it's $1800 with tax, ouch. Trying to keep this last night under $500, which seems crazy for an overnight, but that's the Virgin Islands, lol. Even Emerald is over $300 with taxes/fees. I don't mind spending another hundred or two to have a clean and functioning room, or better yet a nice room. We have considered the Westin on St. John too, at least that would get us on the proper side of customs/immigration the day before, but they are apparently doing a lot of construction right now. Not sure we want to shell out $560 to listen to hammering and sawing all afternoon.

Edit: Just looked at that room on Lovango for fun. Holy smokes, that looks nice. Booking site says it's 10333 ft². Is that right?! Wow. Still not going to spend that much though, lol.

I tend to agree with Manpot on the scheduling of the ferry and the airport, however, I will say that the last 2 times I have flown out of STT (January 10 which was a Tuesday and March 21 which was a Tuesday) it has not been bad. In fact this past Tuesday there wasn't even a line at the American counter...which is unheard of. So then I was thinking that it was just because it was a Tuesday but my daughter flew out on March 19, which was a Sunday and had the same experience. I'm crossing my fingers that maybe they have figured some things out??? Regardless, I would get over to STT and stay there for my last day so that I have a little wiggle room.

Thank you for the feedback Sue. Glad to hear about American since we're flying with them too! Where do you recommend staying on STT for a night, if we decide to go that route? Looks like Sapphire or Secret Harbour are our best bets, or maybe Olgas (although that one doesn't give me a big vacation vibe). I can't bring myself to stay at Emerald with so many BAD reviews and a manager who dismisses them all.

Dont know where those reviews for Emerald Beach are coming from...read my reviews on TripAdvisor..

Only other places I can think to suggest on STT is Bolongo Bay. Haven't been since before Irma but prior it was a nice beach, pool, beach bar, walkable restaurant and the bay was filled with turtles. Only a few minutes outside of Charlotte Amalie.
Marriott Frenchmans would be great since it's brand new and opening May but I'm not seeing availability. You could try calling.

Thank you, will look at those suggestions. A new place just popped up in the search engines named "The Pink Palm Hotel" in Charlotte Amalie. Looks pretty nice and has great reviews although only a few so far. Anyone familiar with this place? Is this a good or bad part of town?

https://pinkpalmhotel.com/

Just called Frenchman's Reef. They are taking reservations starting May 15 as of now; however, they may take earlier reservations as they firm up their official opening date. Sounds like it may be an option, but we won't know for a few more weeks on that one.

Just booked Emerald Beach for my return home for May 23..

Just booked Emerald Beach for my return home for May 23..

Since we own a place on St. Thomas, I don't really have first hand experience on places to stay. My family has stayed at Windward Passage before and it served its purpose of being a place to stay prior to taking the ferry the next morning. I have read about people saying not to go out at night from there and personally, I think that is a bit dramatic but I would definitely be cautious at night. Regardless, this doesn't sound like what you are looking for. My condo is in the Bolongo Bay area so I am very familiar with Bolongo Bay Resort, as we walk down there a lot for food and drinks. It is an older hotel but seems to be clean and taken care of...it is not the Ritz though. The beach is OK. It is a bit rocky in spots and not the perfect white sand beach you dream of but the views are great. It has a nice pool that overlooks the bay and we have always been happy with the food there at Iggie's. There is also another restaurant at the opposite end of the beach called Mim's that has amazing food. They are known for their curry lobster, among other things. Bolongo is on the southeast side of the island so you are looking at about a 20 minute cab ride, which is not as far as Red Hook or Sapphire but certainly further than Emerald Beach. If it were me, I would just stay at Emerald Beach. It is close to the ferry and airport, has a great beach and a restaurant on site. I know people who have stayed there and thought it was just fine.

Thank you for all the information, Sue! Looks like Bolongo doesn't usually take single night reservations. There are couple random sites selling them, but I haven't heard of any of those sites so probably won't risk that. If we do stay on STT we'd be coming in via Red Hook on the Tuesday afternoon JVD>STJ>Red Hook ferry, so any location from Red Hook to the airport area would work for us. Emerald certainly sounds like the convenient choice. I'm really struggling with those reviews though, several mentioned rates/mice in the rooms and one of the newest reviews had two tarantulas in their room. Every other review says no hot water. I just, no.

You are struggling HARD with either just getting a place out of convenience and to lay your head or to feel as though you are extending your vacation. I am always of the extending vacation variety. I haven't been to Emerald in a few years but our last impression was that of convenience and adequacy, not of comfort and fun. The bar was crowded and there was no garbage management, making it smell like a frat house. We tried to relax on the beach but I became distracted by the disregard by guests for proper trash removal and started doing my own beach clean up. I picked up hundreds of drink straws before I gave up. The room was clean although we did have some issues with hot water. Breakfast the next day was fine. That was my experience. You get a convenient location, decent food, access to a bar and a beach prickled with straws and clueless vacationers. Is it "fine", yes. Will you feel like you are still on vacation, "no".
Bolongo would have been a good choice if they did one night.
Found this one- (sapphire isn't the most convenient location but overall only adds a few more travel minutes)
https://www.airbnb.com/rooms/484686...ession_id=p3_1679746699_BJgRn9XleajNjV0A

Emerald Beach has got progressively nicer in the last ten years.I have never seen a rodent in or around my rooms which are always neat and clean...and ocean front. I love the beach bar with Tyler serving and the restaurant for breakfast. I usually dine at The French Quarter Bistro and, for high end Oceana...both a short cab ride from Emerald. I sound like a broken record but that's why I stay there coming and going to Tortola.For me its a great way to start the last leg of my trip home.And the front desk staff and wait staff are all friendly and welcoming..(Unlike Windward Passage).

I understand wanting to stay in a nice place to continue the vacation vibe, I probably spend more time stressing about where I stay than anyone else I know.

How about spending the last night at the Sugar Mill on Tortola? It’s a lovely place with a wonderful restaurant and definitely has a vacation vibe. Then, in the morning, take a taxi to EIS. Hop on a Cape Air flight to STT. Looks like they are 288 per person. Super easy clearing in to customs there (last time it took us all of 10 minutes), and you’re right on the airport grounds.

I am The Sugar Mill's biggest fan..they have officially called me "family". I think they are best all around on Tortola..from food, atmosphere, guest relations.All that said I dont think they do one night bookings...

I did an online availability check. They gave me the option to book one night, so possibly they changed their policy, unless it’s a glitch in the system. I love the Sugar Mill.

Good to hear..owners Dennis and Mary and managers Rupert and Andrea are the best..

Good to hear..owners Dennis and Mary and managers Rupert and Andrea are the best..

You guys are all so helpful! I shared some of the feedback with my husband and he now agrees we should spend the night on St. Thomas. I've since gone down the VRBO and Air B&B rabbit hole, lol. Mostly looking at Sapphire Village, but what's the scoop on Point Pleasant? Haven't seen it discussed much but this condo looks pretty nice, especially for the price. Is there any reason to avoid this complex?
Point Pleasant condo

Oh, and Skipdastraw, thanks for that link. Definitely looking at some of that host's properties. That 12:00 check out is really appealing!

No reason to avoid Point Pleasant. Ironically enough we looked at purchasing this exact condo years ago. It's a nice spot with great views. There are on site amenities and Margaritaville is right next door. There used to be a path from Point Pleasant to Margaritaville but not sure if it is still there post-Irma. Margaritaville is on a beautiful beach (My honeymoon spot when it was the Renaissance Grand 20 years ago!) and I imagine would be a good bar/vacation vibe.
The only downside is that PP in general is on a hillside and there is alot of uphill walking although that particular condo is closer to the amenities so it would be more about dragging luggage than lots of back and forth.
It's close Redhook, which as I said, I think getting to STT is your best way of doing this stress-free and maximizing time. I think you would be happy there. I would stay there and I am picky.

Just FYI, during that time of year I would not swim off the beach in Water Bay which is where Margaritaville and Point Pleasant are located. It often fails the DPNR water test due to runoff. It is also known to get pretty bad sargassum, especially that time of year. Have you looked at Secret Harbor? We really like the beach there and the restaurant is really good as well.

Agree Caribbeangirl - the beach there can be very iffy this time of year. Secret Harbor is lovely - our good friends (that we met on JVD!) are getting married there next year.

It was maybe 10 years ago, but we spent our last night at Lindberg Bay. It was convenient in terms of walking to the airport. The beach is OK, pool is fine, and the restaurant bar was good.

Thank you again for all the great feedback everyone! We do have a "hillside studio" held at Secret Harbour for now, although I may still book at Sapphire since we can save about $200 staying there and it is just for one night. The beachfront at Secret Harbour is like another $150. How bad is the hill for the "hillside" rooms? I understand Sapphire Village has a serious hill too.

Edit: Actually, looks like we can get beachfront at Secret Harbour for only $40 more if we prepay and book direct through their website or $60 more with a flexible rate.

Sapphire depends on what building you are in. Just ask the owner if you are concerned.

Secret Harbour is a great choice! Quiet and beautiful, really nice upscale restaurant (Sunset Grill) and great casual space, too (The Patio).

The beach at Secret Harbor is much better than the one at Sapphire IMHO.

Thank you both for the feedback on Secret Harbour. We probably won't have much time to enjoy the beach after arriving on the 3:30 ferry from JVD but even a few minutes for a quick swim would be great. How is the beach at Secret Harbour compared to Emarald Beach, on the off chance that we decide to suck it up and save some money and end up at Emarald?

The beach at Secret Harbor is smaller by far compared to Emarald Beach.
Swimming is much better than Emerald.

Thanks LocalSailor. I think we're going to stick with Secret Harbour. Just re-booked for a Beachfront studio. At this point, what's a little extra to not be up the hill, lol. Thanks again for everyone's help and feedback! Will we be able to get a taxi from there to the airport easily upon departure?

As info for those looking at Emarald Beach Resort:

While I was looking into our options, I noticed that Emerald has two room categories on their web site: Premium and Superior. Most booking engines just have one option, "deluxe". I emailed them to find out the difference and they responded as follows:

"The superior rooms have some renovations including a remodeled bathroom, new A/C and mattresses."

The only way to guarantee a renovated room is to book a "superior".

Edit: I don't know that I even trust the above. Some of their premium rates are higher than superior and then they have "superior beachfront premium", which is most expensive.

Time for you to check out Emerald Beach....in person and see for yourself whether you like it or not...You can only tell so much by e mails and reviews..from one who rents a place that gets five stars...and then one!

Emerald Beach is not a 5 star resort. I've stayed there 2 or 3 times and would give it 2.5 stars. But the convenience of being close to STT, decent food in the restaurant and a really good beach bar more than made up for any shortcomings. Would I stay there again? Yep. I'd much rather hang out there than STT. It is our go to after returning from Anegada even if only for a few hours.

Thanks again Manpot and Bill. I don't need 5 star (sure I enjoy 5 star but can live without for a night, lol), but all this talk of rats, roaches, and tarantulas, oh my. The husband is now willing to try it (says rats won't kill us, ugh). We're booked at Secret Harbour but does seem a little nuts to spend $560 on an overnight. Still thinking about it. Also still considering Sapphire Village. Can stay there for about the same price as Emerald. Might be the better choice. If you haven't noticed, my OCD make travel planning a little challenging at times, lol. At least the week at The Hideout on JVD was a one and done easy choice!

I could probably curl some people's hair with the extent to which many Trip Advisor reviews are faked. Rankings in any market on TA are simply based on how many are positive, how many are negative, and people do band together to inflate positives and enlarge negatives out to ludicrous extent. .All it does is ensure that TA is a worthless compilation of drivel for the vacationer, and an unwelcome parasite to business.

USVI and BVI are not bargain basement destinations. In a close online forum such as this, we all know that anyone who can afford to charter a half-million dollar floating private resort, isn't going to put up with sharing rooms with rodents and spiders. Geckos--- well, that's another story in the tropics, and they help keep the bugs down !

You make good points Breeze. I am well versed in sniffing out fake or questionable Trip Advisor reviews though. First thing is to look at the history of the person writing the review. Did they just sign up? How many other reviews do they have? Are they balanced and consistent with who they purport to be? Did they include pictures? Look for ongoing themes amongst multiple reviews, like no hot water and power outages. I also look at other sites, like Expedia's "verified" reviews where you have to book through them in order to post a verified review. I love Geckos by the way!

The scammers can be very amateurish in their postings but there are professional web reputation services available that can be impossible to detect. We once stopped to eat at a place that had perfect 5 star reviews. As soon as we walked in I questioned the reviews. I was 100% sure they were fake when we asked for menus and the waitress said, “well we only have 3 things and we are out of one of them”!

"If you haven't noticed, my OCD make travel planning a little challenging at times, lol."

That is not a bad thing. You are about to spend a bunch of money for some time in paradise. Plan and question everything!

I am with Breeze. I'll trust the advice of this board over TA anytime. This board and its contributors have been invaluable to us having mostly smooth and pleasurable vacations.

GeorgeC1, hilarious story!

Some people come to the Virgin Islands with unrealistic expectations. There will be water/power outages....and bugs....everywhere. To expect otherwise is unrealistic. I've stayed at Emerald Beach dozens of time over the past 40+ years and never seen a rat. It's about the convenience to me.....knowing exactly what time I need to be at the airport and being able to get there without having to wonder if I'll make it on time.

I was once in a decent downtown NYC hotel watching a football game on the TV when I noticed a rat on my bag also watching the game. It would not have bothered me much but it quickly became apparent that he was a Patriots fan and this was not acceptable!

Go back and read managements response from Emerald Beach to the "reviewer" who said they had rats in their room. Supposedly a block of seven rooms rented for a business trip. Management stated unequivocally that their group NEVER stayed at the property! We've stayed their many times on a last night and will do so again.

GeorgeC1 a Pats Rat?! Lol! Those are the absolute worst kind! RickinAtlanta, there are close to ten reviews in the last two years that mention rats and mice. Some in the rooms, some running around near the restaurant. The most recent review is suspect given that person signed up just to post that one review. If the Manager seemed to take other bad reviews more seriously, I'd be inclined to believe him that those people never stayed there; however, the Manager's poor handling of bad reviews is one of the biggest things that is turning me off of that hotel. He almost always accuses the person of lying or never having stayed there rather than offering a professional response. It makes it hard to know which ones are actually BS when he calls them all BS. He'd be better off with a canned response that at least sounded like he cared. At least he does acknowledge the power outages, which, as others have said are to be expected in the islands.

I don't doubt that you have all had decent stays there, but I also believe that some of the reviewers have run into a fair share of nasty conditions. At this point I've got it in my head that's it's going to be disgusting no matter what so why bother shelling out $300 just to go into it expecting it to suck. The price on our room at Secret Harbour just dropped $60 so now it's under my self-imposed $500 threshold. We're going to stick with that, at least for now.

By the way, you have to watch out for fakes in the Trip Advisor forums too. Many years ago, I caught a hotel Manager with multiple usernames promoting his hotel in the Belize forum, pretending to be past guests. I was already suspicious that someone was using multiple usernames when the wording in some comments was very similar, including grammatical errors. Then, he private messaged me under his manager name to offer a discount at his hotel, which they aren't supposed to do. The wording was just like all those other posts, so I called him out. He fessed up and begged and pleaded for me not to report him. I did not report him outright but did flag his extra usernames and let people in the forum know that "someone" was using fake accounts and to take those comments with a grain of salt.

I do hope you will finally relax wherever you end up.One thing I have learned is to trust the opinion of people I know and trust..and I know and trust quite a few here on TTOL so their opinions on places to stay, eat , drink etc rate highly with me..

I do hope you will finally relax wherever you end up.One thing I have learned is to trust the opinion of people I know and trust..and I know and trust quite a few here on TTOL so their opinions on places to stay, eat , drink etc rate highly with me..

I think at this point, even if Emerald Beach was a 5 star resort, you would be sleeping with one eye open. It's in your head. I would be the same. Really no reason to stress over it. Emerald checks the convenience box but it's not like you are missing out on some bucket list place. Just enjoy Secret Harbour with a clear mind, drink in hand and hopefully an amazing BVI experience to reflect on!

I'm way late to this thread but I'm with George at the top. Prior to our January 2023 trip I hadn't spent a night in St. Thomas since our honeymoon in 1987. This time we bookended a 12 JVD day visit with a night at St. Thomas both coming in and going out. We stayed in the Frenchtown area and loved it. We found that it made the travel days so much less stressful. We discovered the Frenchtown Bistro and had a great meal and a great time. Wake up and things are much more leisurely. After 12 nights in JVD, going over late afternoon before our travel day was no sacrifice. We'll do that from now on for most trips. In June we're getting in at 12:30 so we'll go all the way to Jost on arrival day. When we were in our 30's-50's going all the way was ok. But we're in our early 60's now and enjoy taking it a little easier. And we discovered something new.

lol! You made my day, George.

Then definitely don't stay at Emerald Beach as MANY have suggested who have stayed there and had good experiences.

Thank you for the feedback JCfromNC. Where did you stay in Frenchtown, and did you like the accommodations? 12 nights on JVD sounds amazing! Where did you stay there? What are your favorite restaurants?

RickinAtlanta, don't worry, we won't

After all this debating and research, our room on JVD just opened up for our last night so we're staying there. Just canceled Secret Harbour.

Now, we just need to decide which ferries to take to catch our flight leaving STT at 4:53 pm:

9am Great Harbour to West End, 11:30 am Road Town to Charlotte Amalie - leaning toward this option to have shorter taxi ride to airport on STT
9am Great Harbour to West End, 11:30 am West End to Red Hook (stops in Cruz Bay to clear customs) - is this better than the option above? Is it faster to clear customs in Cruz Bay vs Charlotte Amalie?
7am Great Harbour to West End, 10am Road Town to Charlotte Amalie - safest bet but not our preference, we're not morning people, at all
9am Great Harbour to West End, 10am Road Town to Charlotte Amalie - is this even possible? Would be our favorite option if doable.

I would choose option 1. Not because of the taxi rides-you have a taxi ride from West End to RT which is about the same. The benefit of this one is that you get right into Charlotte Amalie. I would drop my bags at the taxi stand for later and go enjoy a nice lunch and some shopping before heading to the airport around 3ish.
Option 4 is not doable.

Thank you Skpdastraw. That was my logic on option 1 as well, get the taxi ride over with during the downtime between ferries. We'll probably go straight to the airport though. We like to give ourselves an extra hour or so buffer time, just in case.

I would wait to see what time you clear customs to decide when to head to the airport. If you blew through customs you could potentially have 4 hours before your flight. If the airport happens to not be busy, you will be sitting around for a very long time with really crappy food choices. If you don't think you have time for a potentially long sit down lunch, I would suggest Bumpa's in town. They are a quick, order at the counter place that does really good food. Whatever you do, don't go to that airport 4 hours ahead on an empty stomach.

We don’t find the shopping compelling in STT (and many shops are only open when the cruise ships are in). I suggest grabbing a bite at the Petite Pump Room upstairs at the terminal (great breakfast).

Yup- If you don't have much time to kill, Petite Pump room would work. Last time we made it through customs in 15 minutes so it all depends on your schedule. We enjoy walking into town to get a little exercise before the inevitable hours of sitting in the airport and on the plane. Glady's is another really popular option.

I second Bumpa's!

Thank you all for the tips! Will make a list and keep it handy in case we get through customs quickly! Nothing worse than sitting around a boring airport for hours before boarding our long [censored] flights back to Los Angeles.