From Puerto Rico To Five Islands: A First-Time Cruise Guide

A first cruise is a crash course in what you value when you travel. From a lively launch in San Juan to five Caribbean ports in seven days, we share the joy of bioluminescent kayaking, the calm of a French-side beach on Saint Martin, and the green, mountainous bliss of Grenada and Dominica. We also get candid about a tougher moment in Saint Lucia, where constant vendor pressure cut a solo city walk short—and how a simple plan with a vetted driver could have changed the day.

We dig into the money side most people underestimate. Solo supplements can double a fare, but there are smart workarounds: Virgin Voyages frequently offers better pricing and social programming for singles; Norwegian and select Royal Caribbean ships have limited studio cabins; Silversea reduces single supplements on some sailings. Beyond the sticker price, budget for gratuities, specialty dining, fitness classes, laundry, Wi‑Fi, and excursions—or pick a more inclusive line to avoid the nickel-and-dime feeling. If you’re wondering whether to book excursions at every stop, learn from our missteps: sometimes one well-chosen experience or a simple plan with a trusted local driver beats a packed bus and crowded viewpoints.

The real key is matching the cruise to who you are. If big crowds drain you, consider smaller ships or river cruises like AmaWaterways. If sand isn’t your happy place, look to Alaska or Scandinavia for fjords, hikes, and cooler air. Traveling with a friend? Set expectations upfront—sleep rhythms, alone time, and activity choices—so the cabin is shared but the day can be flexible. We close by looking ahead to Scandinavia as a better fit for our hiking-first style and invite you to think about your own 2026 plans.

If this helped you plan smarter, follow the show, share it with a friend who’s cruise-curious, and leave a quick review to tell us where you want to sail next.

Chapters

• 0:00 Tease And Welcome
• 0:15 First-Time Cruise Reveal
• 0:55 San Juan And Puerto Rico Adventures
• 2:01 Five Ports In Seven Days
• 2:11 Saint Martin Beach Day
• 2:46 Challenging Stop In Saint Lucia
• 4:39 Barbados, Grenada, Dominica Highlights
• 6:17 Traveling With A Friend
• 7:21 Solo Costs And Cruise Lines For Singles
• 8:20 Match Cruise To Your Personality
• 9:08 Hidden Fees And What’s Included
• 10:08 Excursions Vs Exploring On Your Own
• 11:26 Resources And Future Cruise Ideas
• 12:25 Upcoming Destinations For 2026

Transcript

SPEAKER_00: 0:00

Well, did you figure out where I went last week? Did I leave you on a cliffhanger? Did you figure it out? Well, I'm back to share where I went and what I did. Welcome to Solo Travel Adventures. I'm Cheryl Esh, your host. Well, I have a confession to make. I actually, part of where I went was I did my first cruise, believe it or not, folks. I have never cruised before, and so this was my first time. And so I'm going to share a little bit about where I went and some things I learned as a first-time cruiser. Now, if you've cruised a lot before, or more than once, I should say, uh, then you want to probably hang in there and listen to what I have to say about my first-time experience uh cruising for seven days. Well, let me share where I went first. I left out of Puerto Rico, San Juan, Puerto Rico, which was fabulous. I went a couple days early, got to see the old town, and did some other fun things. Even did the bioluminous little kayaking excursion, which was really cool. Uh, couldn't couldn't videotape it though, obviously, because it has to be really dark. And the moon was out when we went, so we really had to, um, they had to kind of make it really dark by covering us up on these tarps, which was kind of cool, and we did get to see it. And then I also did some uh waterfall slides in the national park there in Puerto Rico. So I had a lot of fun in Puerto Rico, then I boarded the ship, and we went to five ports. So that's a lot of ports to get to in seven days. We only had really one sea day because they would cruise overnight um when we were sleeping, which was awesome. So I went to Saint Martin, Saint Lucia, Barbados, Grenada, and Dominica. Now, St. Martin, uh, we I did some be a beach excursion, which is great because that's really, you know, you think about St. Martin, and it does have these beautiful beaches. I went on the French side as the island is separated. It's actually half of it's owned basically by the French and half is owned by the Dutch. And I had a good time just relaxing on a private beach, so to speak, and lounging on the lounge chairs with an umbrella. So it was a perfect first day excursion. Then I went to St. Lucia. I will have to say I did try to venture out after my short excursion in St. Lucia and wanted to really explore the city and check it out. However, was very um disenchanted by all the harassment I received as a single person trying to walk uh the streets by myself, and um actually only got like about a block and a half into the city and decided to turn around because the harassment was just constant, not just from taxi drivers, tour guides, um, people trying to sell their wares, um, people out in the street, just vendors and such, just kind of being very aggressive in trying to almost like kind of attack the tourist because I know they do rely on uh actually all those islands rely a lot on tourism for their uh GDP. And so I was a little disappointed with that because I do like to explore my own, but I actually didn't feel safe in St. Lucia. That may not be everybody's experience, um, but I did do an excursion which was safe. It's just when I was trying to uh go out on my own to explore that it got a little dicey. And so I think if I had considered maybe just hiring a driver uh to kind of take me around and explore on my own timing, that might have been a better option at St. Lucia. Um then we did uh Barbados, which was fun, and I went with my my friend, she came on that that particular one with me. Um oh St. Lucia was uh also I really wanted to explore the the pitones, which are these mountain peaks, and you can do some hiking, but we just did a boat tour, and I really I you know if I were ever to go back to St. Lucia, I would definitely do, you know, I'm a hiker, so I would definitely see about trying to get some hiking in, and that would have really made made my day or made my trip and St. Lucia, but otherwise I did get to see it on a boat, so that was all good. Um then we went to Grenada and um Dominica, those two were actually very similar, and I love them both. Um, they are lush and green and mountainous, and it was just gorgeous um driving around, going to again some rainforest type areas, seeing waterfalls and all that fun stuff, and getting a I had a short opportunity to do a tidy hike. Uh, would have loved to had more time there in Grenada to do a little bit more, but got a little taste of um Grenada and Dominica and really enjoyed those two islands. I think because of just that lush greenness and just being in, you know, seeing more of nature, and it was I'm honestly I'm not much of a beach person, so of course, you know, those first two days we did do beach excursions and those were fine, but I would rather be hiking, as you might know. So that's where I went, and I had a blast, and so I'm gonna share a little bit too of kind of some important things to consider if you are going on a cruise. Now, I did not go solo, I actually went with a friend, and we've been this friend and I have been living together for about 11 months, so we get along wonderfully. And what I would suggest that if you are planning to do a cruise and you are planning to go with somebody, because point number one is cruising solo is usually more expensive. Um, there are some, and I'll get to a few of the cruise lines that do offer some uh solo options that are not typically in most cases, a solo traveler would have to pay what's called the single supplement if you're not familiar with that. Essentially, you're paying for the double occupancy. Meaning, I would, if I didn't go with my friend Danielle, I would have had to probably pay for both both of our fees, basically as though there were a second person joining me. So it would have been double the price because um I'm not aware of Princess offering um discounts for solo travelers. So if you are cruising with somebody and you do decide to travel with someone, make sure you are a good match with that person. And I would sit down too with that person and talk about your expectations. Danielle and I got along great. We thought a lot alike, we liked a lot of the same things, but there were moments when I did I did two excursions without her, so we didn't do everything together. And then there were times when she wanted to sort of decompress in the evening, and I would just go out on the deck, do some reading. So we did have some separate time, which was good, but we did have a wonderful time laughing about certain things on our cruise. So make sure who you are traveling with, if you are going with somebody that you get along with them, you talk about all the things like are they a morning person? Are you a morning person? Do they want to stay up late? What kind of activities do they like to do? Because you have to mesh a lot with that, um, or at least have an understanding that, hey, we're gonna share a room, but everything else we're kind of gonna do on our own. So making sure those expectations are set ahead of time. Um, so some cruise lines that do offer some solo cabins. Uh, Virgin is the best. Um, they are the rebel and they do offer quite a bit of uh reduced solo pricing for their cruises. They have lots of activities on some of their ships that are more geared for single people. Um, that would be a first place to start if you're looking to do uh a cruise solo. Uh Norwegian cruise lines, they do have some studio-sized cabins, uh roughly 100 square feet. So uh depending on which ship, they also offer some solo cabins, uh, but those are limited, of course, and they go pretty fast. Same with Royal. Royal, for example, Symphony of the Sea, Wonder of the Sea, they do have some solo cabins, but they only have limited numbers in those uh for that size. Uh Silver Sea cruises, uh, they do offer only a 10 to 25% single supplement fee. So it's not quite double. That's also an opportunity to look into that. Um, so number two, I would also, before you even decide to cruise, I would first determine your travel personality. What are your needs? What are your likes, dislikes, because this will also help direct you to where you go on your cruise and what type of cruise you take. Okay, for example, let's say you are more of an introvert, don't like crowds, then you're gonna want to pick a smaller boat, not ones with thousands of people on it. So there are um like AMA waterways has smaller ships. Those are gonna be your river cruises. Um there are smaller ships out there that you could cruise and not be overwhelmed by all the crowds or people. Or maybe uh you're not a beach person, so a Caribbean cruise or an island cruise may not be where you want to go. Maybe you like Alaska or the Scandinavian countries, or you want to do a European or Greece or Italy kind of cruise to see those areas, and so there's plenty out there, many choices determining you know what you like. Do you like an active cruise? There are wellness cruises as well out there that you could choose from. So determine your personality and what you like and dislike, and this will guide you onto the type of cruise you should take. Number three, I would look out for this kind of caught me off guard because again, I'm a little green behind the ears when it comes to cruising. But if you've cruised, you know about this next point. Look out for hidden or extra charges. It's kind of annoying. Uh, you get a little extra bar uh charge, or are they you got to pay for laundry, or fitness classes were extra on my cruise. I did a princess cruise. Excursions, of course, are extra. That's kind of a given. And gratuity is extra. Usually that's added on at the end. Um, so if you weren't planning on that, just know that that is coming. There are some cruises that incorporate all of that, like everything is included. So these are going to be your probably your higher end uh types of cruises that include everything in the price, which is kind of nice because then you just pay this one price, you go in, you don't feel like you're being nickel and dimed with everything that you do on the ship. And then number four, now I did an excursion every day. So that's five ports. I did an excursion. But I realize it's not necessary to even do any excursions if you don't want to. If that's your choice, then I would say do a little research to see, of course, to what's on the island that you are interested in seeing. Maybe hire a taxi driver to drive you or um just explore the city, whatever port it's in. You don't have to do anything uh, you know, activity-wise. And maybe you just want to find a local beach and just relax. So uh it's not necessary to do the excursions. I did find that out, and I think if I were to do another cruise, uh I would do less excursions, maybe one or two, and then allow myself the because I do, I love to uh do things on my own timing. I think that was one of the frustrating things for me in being in a tour, is that you know, you're waiting on other people, you're being transported in these, you know, bumpy buses usually, and it's just um and you're going to these crowded, you know, sites that everybody goes to. You know, you think about there's more than one ship at the port at a time, and so all these ships are offering basically the same excursion, and so it gets really crowded when you get to certain uh points, whether it's a lookout point, or I did the Emerald Pool waterfall in Grenada. So that was pretty busy with lots of people making that same popular stop. So if you're like me and you'd rather be in control of what you do or do it on your own timing, then booking an excursion with a tour group may not be the avenue you want to take. I want to recommend a woman that um I just started following, and she is she cruises all the time. There's plenty out there, but I came across this one that is just very uh gives you a lot of tips on cruising. So aside from what I offered you, if you need more information, more experienced uh feedback on just different tips for cruising, then in on Instagram you can look up Dr underscore Melissa underscore Newman. She does a lot of just cruises on many different types of ships. Uh, she's done carnival, Norwegian, I mean she's pretty much and she's done royal, so she can tell you about the different cruise lines that are out there and give you her her taste on it. But my taste was do I want to do it again? I think so. I would definitely pick a different location. Um, my friend that I went with, uh Danielle, we started talking actually since we cruised so well together, because it's it's kind of hard to maybe find somebody that you feel um that you mesh well to do that type of travel with. Um, because you are in close quarters, um, and you're not able to escape each other. So uh we started talking about, you know, if I were to do another cruise, we thought maybe hitting some of those Scandinavian countries like Norway and Finland and Sweden and up there, doing a cruise up there, I think would be fabulous. And so I am open to that idea, but I'm not gonna cruise for a while. I'm still trying to plan my things that I'm doing for 2026. How about you? Have you decided where you're going in 2026? Well, let's hang in there. As I said, there's a couple more episodes before the end of the year, and one of my favorites that's coming out soon is going to be uh what are the most popular places, actual specific destinations that solo travelers, women solo travelers, uh can go to in 2026. So I'm looking forward to giving you that information uh in two weeks, I'll put that out for you. And maybe one of those places is a place you're planning to go in twenty twenty six.