Rileyroo

My partner and I spent a week on Grand Cayman in February going all around the island and never once felt even the least bit uncomfortable anywhere we went. We really enjoyed it. (...though our bank accounts did not :). Not a cheap place!)

I've never been to the other two places on your itinerary. I suspect you'll get a lot of opinions on Jamaica on this particular board, so I'll leave it to those more in the know.

Were you planning on doing ship excursions or other independently booked tours? Being part of a shepherded group would probably calm your nervousness a bit, although I know that's not everyone's cup of tea. We didn't spend a lot of time in the port area of Grand Cayman, but from what I recall, it struck me as fairly routine. There will no doubt be lots of people walking around, so chances are you'll just blend in as part of the crowd.

We had a couple of tours with them and they were great. Everyone was very nice. I think depending on the number of people, it'll be a van or small bus.

They seemed to have a huge presence when we were there. Every tourist destination we went we saw lots of Glory Tours workers milling about. I think a lot of third party tour booking services (Viator, etc.) must use them. We did a tour + airport dropoff excursion through the ship when we left Barbados, and it was Glory Tours who ran it.

There are fast track arrival services available at the airport that you may want to look into. For a fee (around $60 per person I think), someone meets you as soon as you enter the arrivals hall of the airport and directs you to a dedicated customs/immigration line so that you don't have to wait in line with all the other arriving passengers. Worked brilliantly for us. Yes, it's definitely a question whether it's worth 60 bucks a pop to do something that you could do for free by standing in line, but if time is of the essence, the value of that service goes up.

I have found that the type of motion felt on the bigger ships vs. the Windstar ones makes more of a difference to me. The constant, subtle, rolling movement of the bigger ships actually makes me more uneasy than the more in-your-face up and down motion of the smaller Windstar ones. I was nervous before my first Windstar cruise because of how the bigger ships made me feel, but I ended up not having a problem at all. Three Windstar cruises in (Spirit, Legend, Star), and I haven't even needed pills or anything else. And that's including one trip on the already mentioned experience to and from Barbados. Something about the small size of the ships and knowing where you are and what's happening at all times just doesn't mess with my head (and stomach) as much. Your experience may be different, of course, but hopefully this offers at least a bit of reassurance.

I had the same issue recently in St. Lucia where we had a private tour booked for a specific time. I went to the reception desk to ask about it and was told simply to show up in the morning and hope for a tender at the time we needed. It turns out that the only ship-sponsored excursion leaving at the time we needed to get off the ship had just a handful of people on it so we got on the tender no problem. At another port, however, there was quite a line of non-excursion people wanting to get off, so after the excursioners got to get on the tender first, only a few of the people waiting made it on. So I guess you never know. For what it's worth, I didn't see anyone offering to take people independently via zodiac on our trip.

We did Costa Rica a few years ago (the all Costa Rica itinerary, not the Panama Canal one), and from what I recall, a few of the ports were accessed as a wet landing via zodiac instead of by tender.

We also did this itinerary (more or less) on the Wind Spirit a few years ago and did the Windstar excursions all week. From what I recall, they were just fine, but if you choose to go Windstar all the way, I would at least suggest varying the types of activities you do. By the end of the week, walking through a park trying to spot monkeys--while still nice!--started to get a bit been-there-done-that. We did one zipline excursion, but since we had been in Costa Rica for a few days before the cruise and had done a great zipline already, the one on the excursion lost a bit of its luster and novelty.

I see that your time in San Juan del Sur is very short, which is a shame. We were able to make it up to Granada and did a short boat tour on the lake. I see that Granada isn't even on offer, which is not surprising given the short time. You should do something that gets you out, though, if for no other reason than to see the contrast between Nicaragua and Costa Rica. It's quite fascinating to see.

I would echo the impression that strenuous is really more about mobility than physical exertion. If you're reasonably fit and able to navigate stairs, gravel, dirt paths, etc. it shouldn't be a problem. The only exception would be a zipline excursion, where you might have to be able to help hoist yourself onto the wire or be able to slow yourself down with your arms/hands.

Enjoy! Costa Rica is as lovely as you're expecting it to be.

Just did this cruise as well and wanted to add: I can't remember if it's indicated clearly somewhere in the itinerary, but when you see an "overnight" at St. Lucia, it doesn't mean you can come and go at all hours. The last tender was at 5:45 pm or so as I recall. Not that there's a ton of stuff to do at Pigeon Island, but if you were planning to do an independent excursion, for example, and expected to get back on the ship at 8 pm, you would be in for a surprise.

Thanks for the reassurance and suggestions.

Hi everyone. We'll be on the Jewels itinerary next month stopping at Pigeon Island in St. Lucia. We are scheduled to arrive at 8 am. I'm wanting to arrange an independent tour to pick us up there.

For those who have been there, what time can I reasonably expect to be off the ship and ready to meet someone? I'm assuming the ship's excursioners will be let off first? The tour company said they could meet us at 8:30. Would we be able to be off by then? I don't want to commit to something and then find out we can't make it.

We typically go for the ship's offered excursions, but we weren't that excited by the offerings for St. Lucia so we thought we'd try to go off the grid a bit. Thanks for any info you might have.

We're getting close now! Anyone boarded Windstar in San Juan recently? How's the port? Is getting onboard an easy process?

Should be super easy. We were at one of the docks in the main Old San Juan port area. (There's another port across a small channel from Old San Juan where some ships dock, but that wasn't us.) We ended up getting there some time after 1pm so we didn't see whether there were a lot of people waiting and going in at the same time. But we just walked right through the security areas with our documents, bags through the x-ray, and that's it, easy peasy. We even had time to get back off the boat and run to a nearby drugstore for a few things.

I've boarded a large ship (Royal Caribbean I think?) at San Juan standing in huge lines in the heat and Windstar is NOTHING like that. My experiences have been that you end up getting to your stateroom and wondering how you got there cause it all happened so fast!

Thinking about this itinerary for March 2017. Can any past cruisers say whether the volcano is visible from the ship after departure - glowing?

When we left Montserrat, we did a "sail by" of sorts around the southern part of the island where we could get at least some view of the ash and destruction. The volcano itself had cloud cover over it, but even so, I'm not sure it would have been glowing. At least not in the bright orange visible lava sense.

We rented with Turbe and got an automatic no problem. In fact, I can't even remember choosing it as an option. Turbe was great. Met us right at the tender port, quick instructions and paperwork, and off we went. We didn't end up actually driving that much, so I didn't even need to get gas, but I remember seeing a couple of places.

We did this itinerary in January and really enjoyed it. We did go to Culebra, snorkelled with turtles on Tamarindo Beach, and did just a quick stop at Flamenco Beach.

In St. Barths we rented a car and drove around. Unfortunately, we didn't do much planning on what to see or do, so we ended up just driving around in circles. It was fun for a while, but we ended up getting rather bored with it. So we dropped the car off way early and walked around Gustavia for a bit. Saw Diane von Furstenberg walking down the street. Ate and had drinks at this great place called 25 Quarter--highly recommend! St. Barths is quite unlike any other Caribbean island I've ever been to. It really is like a chunk of France was broken off and dropped in the Caribbean.

Montserrat was amazing to see. We did the ship's excursion to the ruins at Plymouth, which I thought was great. If there's a private excursion that's described as being way better, I'd certainly consider looking into it.

My main memory of Jost Van Dyke is several of us from the ship parking ourselves at Foxy's using the free wifi to monitor a huge snowstorm that was on track to hit the northeast right when we were supposed to be coming back.

I would recommend doing something that takes you to the Baths at Virgin Gorda. The day we were there was the only day on the trip that we had rain, so that was kind of a bummer, but I found the Baths fun to walk and climb through despite the touristy nature of it.

Based on CC reviews, I was a bit concerned at the time with how much we'd enjoy the Legend, but everything was great. We tendered at every port except St. Martin. We were supposed to tender at Marigot, but due to sea conditions, we ended up docking in Philipsburg instead. Although the tenders aren't that burdensome, I will admit that it was nice to be able to walk on and off for once. It was funny cause we were docked right next to Anthem of the Seas, so we looked like a Smart car parked next to a bus.

We had cabin 222 (same location as 318 but one deck up) for the San Juan and Virgin Islands cruise in January and really enjoyed it. Like you, I wasn't sure it would be worth it at first but decided just to go for it.

I can't remember how much we took advantage of the open air when we were sailing, but when we had long days anchored, it was really nice to sit in the cabin with the doors open. There's also just enough bump-out space to be able to stand and rest your arms on the railing so that you can at least see straight out both sides, although it's not like you'd want to spend hours in that position.

As was mentioned earlier, the weather will play a big role on whether it's worth it. We had great weather on our cruise so we took advantage when we could. Of course, since we paid for the balcony, we also felt like we wanted to get our money's worth, so that probably contributed to the time spent standing there looking out as well. :)

Maybe my experience is atypical, but I experience significantly more seasickness on the larger ships than I did on the Wind Spirit. Even though the Wind Spirit definitely moves more, the type of motion on the larger ships is more disorienting to me.

I felt like the small size of the Wind Spirit helped my system process what was going on. As in, since I could see from one end of the ship to the other and see it moving up and down, my mind and my body could communicate clearly to each other as to what was going on.

On the big ships I am constantly taking pills. I feared the worst for the Wind Spirit, but I ended up not taking a single pill the whole time. I guess you just never know.