How to Plan Your First Cruise: Choosing Dates, Ships & Itineraries

Planning your first cruise can feel overwhelming, but travel advisors Ryan and Julie break down the entire process in this comprehensive beginner's guide. In this first episode of their three-part Cruising 101 series, they cover the essential planning steps you need to take before booking your cruise vacation.

Starting with choosing your travel dates, Ryan and Julie discuss key factors including celebrations and milestones, work and school schedules, and special themed cruises like Halloween on the High Seas or Marvel Days at Sea. They share important timing considerations, from Wave Season promotions to age-specific requirements that could impact your vacation experience.

The hosts then dive into selecting the right ship and itinerary for your needs. For first-time cruisers, they recommend specific cruise lines: Virgin Voyages, Princess, Celebrity, or smaller Royal Caribbean ships for adults, and Disney Cruise Line or Royal Caribbean for families. They explain why mid-size ships often work better than mega-ships for beginners, preventing that overwhelming feeling while still offering plenty of activities.

Itinerary selection varies by destination. For Caribbean cruises, they suggest 4-5 night sailings with stops at private islands like CocoCay or Castaway Cay. European and Mediterranean cruises require careful consideration of specific ports, pre- and post-cruise stays, and whether you prefer one-way or roundtrip sailings. Alaska cruises demand attention to port stops like Skagway, Ketchikan, and Juneau, each offering unique excursions from glacier viewing to whale watching.

River cruising receives special attention, with recommendations for European rivers like the Rhine and Danube as ideal starting points, before expanding to destinations in the United States, Africa, or South America. The episode concludes with a preview of parts two and three, which will cover preparing for your cruise and the embarkation/onboard experience.

Whether you're completely new to cruising or looking to plan your next voyage, this episode provides practical, expert advice to help you make informed decisions and avoid common mistakes.

Transcript

j_1_01-19-2026_142219 0:00

Hello and welcome to all things travel Planning. Your first cruise can be an overwhelming experience as your travel advisors. We are always here to make the process as easy as possible. And today we are sharing Cruising 1 0 1, a Beginner's Guide to Starting the Cruise Planning Process. All of this information that we're gonna share today and on the next two episodes is based on our experience and our expertise.

ryan_1_01-19-2026_142219 0:26

listen in with travel advisors, Ryan and Julie. I'm your travel professor teaching you everything you need to know to have a magical vacation, and she's a Disney loving Maryland mom of three and a specialist in family travel. And together we're the co-owners of Wonder and Beyond Travel. Whether we're discussing incredible destinations, top vacation tips, or sharing personal stories, it's always all things travel. Julie, it is the middle of January and we are in Arctic Chill here in Indiana. I'm looking at snow blowing outside of my office area here. It is really, really cold.

j_1_01-19-2026_142219 1:10

What is really cold? What does that

ryan_1_01-19-2026_142219 1:12

right now it is seven degrees and feels like negative 13.

j_1_01-19-2026_142219 1:17

Stop it. That is awful. It's 36 here, but feels like 20 something.

ryan_1_01-19-2026_142219 1:26

Okay.

j_1_01-19-2026_142219 1:26

also have some snow and I was on a phone call yesterday with a potential client. They live in Lake Tahoe. I know them'cause they used to live here

ryan_1_01-19-2026_142219 1:36

Mm-hmm.

j_1_01-19-2026_142219 1:37

here in Maryland. they were like, we just love it here so much. It's so beautiful. The weather is great year round. And I was like what's the weather today? She was like, we have two feet of snow, but it's 55 degrees. I was like, wow. Okay.

ryan_1_01-19-2026_142219 1:50

Usually in Indiana, that means it just turns into goopy mud.

j_1_01-19-2026_142219 1:54

I'm excited to share this cruising 1 0 1 followed by 1 0 2 and 1 0 3, because I just think this is gonna be a great quick guide for people. little nervous about cruising and I actually, I had a phone call this morning with a client where we were doing this exact thing, getting ready for their cruise.

ryan_1_01-19-2026_142219 2:15

Great. it corresponds well with what's called Wave season. if you're looking online or on. TV ads You're seeing a lot of cruising right now because this is the time of year when cruise lines are putting out specials and promos. So if you've thought about it and you're not quite sure, listen to this episode in the next couple, because we're going to get you all prepared for what cruising is gonna be like. But first, if you did not listen to last week's episode, go back and take a listen. Because we continued our best of series of all about Disney and we talked about the best of this and that when it comes to family vacations and adult vacations.

j_1_01-19-2026_142219 2:53

Okay, so let's start with one of the biggest pieces of your trip. Today's gonna be more about the planning and things that you're doing before your trip, and then we're gonna move into the next processes over the next episodes. the first thing we like to figure out with our clients is your dates for your travel. this is obviously the most important and will

ryan_1_01-19-2026_142219 3:11

Sure.

j_1_01-19-2026_142219 3:12

Almost everything else, depending on your itinerary. one of the first things I like to consider when you're choosing your dates is why are you cruising? And this reminded me of that idea Ryan

ryan_1_01-19-2026_142219 3:26

Yeah. Yeah.

j_1_01-19-2026_142219 3:27

Are there any celebrations? Are there any milestones? What is going on that is kind of motivating you? consider a cruise for your next vacation, and I think that can really help determine your dates as well.

ryan_1_01-19-2026_142219 3:42

I want to give one. Little bit of caution here that's very specific, but it may affect you. I had clients going on a Disney cruise several years ago, and it was three different families celebrating both the grandmother's birthday and the youngest daughter's birthday. The issue was the youngest daughter's birth date, because I don't remember what year they were celebrating, your date of birth is the first day of the cruise.

j_1_01-19-2026_142219 4:14

Mm-hmm.

ryan_1_01-19-2026_142219 4:14

problem was she was turning the next year during the cruise, and so she wasn't able to do a bunch of shore excursions because she wasn't old enough, even though she was with her birthdate. So that's the one where I would say be very careful if you're wanting to go celebrate and there's some age specific things, make sure you keep that in mind.

j_1_01-19-2026_142219 4:36

a lot of times that also comes into play when you're like two, turning three because it's

ryan_1_01-19-2026_142219 4:42

Yeah.

j_1_01-19-2026_142219 4:42

they're so much less expensive to take a 2-year-old than to take a 3-year-old. But then you can't go to the kids' club. you can, but you have to pay for it and, and you can't do Bty, BTY

ryan_1_01-19-2026_142219 4:52

Yep.

j_1_01-19-2026_142219 4:52

So, yeah, definitely a good point. The other thing you're gonna be thinking about with your dates is obviously your work schedules and your school schedules. Are you limited by only going over spring break, only going over summer? Are you limited to go over Christmas break because that's the only time you get off work? You know, how does that work for your family? And a lot of times this is what. The driver is just when you can you go. you are part of the other crowd, this can be really helpful if those things don't determine when you can go on vacation and you can think more about the crowd levels on the cruise, kind of that off season, peak season

ryan_1_01-19-2026_142219 5:33

So another thing to think about, is there a special type of cruise you want to go on? This may not be something that a first time cruiser, is privy to, but maybe it's the whole reason you're trying cruising for the first time. you could do a wine or beer cruise. I'm thinking specifically with River Cruises. You could do a music cruise. a company like American Cruise Lines will do a jazz cruise down the Mississippi. You could have a, a holiday themed cruise, Halloween or Christmas cruise with Disney Cruise Lines. The same with Marvel or Pixar Days at Sea. a lot of the cruise lines are doing specific themed cruises now to help people, have reasons to cruise, if you will. Also planning who's gonna go with you? sometimes this is a moving target for us because, well, my sister and her husband are go, well no, now they can't. Well, you know, we booked this cruise. Now we have other friends that want to go. and that's all great. We can deal with all of that. if you're going on a vacation and you may want to have some friends there. Always ask. A cruise is a perfect place to have friends or other family members go with you because you can spend time together, but you also can do your own things and have your own space. Then lastly, of course, do you have a specific destination in mind when we're talking about cruising? Ocean cruising? We really hit Mediterranean, Alaska, and the Caribbean when it comes to where do you want to cruise, but there's other places like Hawaii or other spots in Europe, the South Pacific, or if you're talking about river cruises, we think of the Danube and the Rhine, but there's also Christmas market cruises. There's tulip cruises in the Netherlands. But you can also now river cruise in the US you can river cruise in the Mekong River in Asia. You can river cruise in Columbia, in Africa. So what destination are you looking for and what cruise makes the most sense?

j_1_01-19-2026_142219 7:28

Yes, because specifically if you wanna do Alaska, there is a timeframe for those cruises. If you wanna do the Mediterranean, there's a timeframe for those. If you wanna see the Christmas markets, there's obviously a timeframe for those too. So sometimes knowing what you're looking for on your cruise can help you choose those dates. So those are all the things that we think you need to consider when you're choosing your dates for your careers. And that is the first step.

ryan_1_01-19-2026_142219 7:56

Well, before we talk about choosing your ship in your itinerary, Julie, I wanna talk about where in the world is Wonder and beyond Travel. I was contacted by one of my family members this week, and I am really honored to be helping her with their honeymoon. So my cousin's daughter, so so is a finishing up college in Arizona, and her and her fiance are gonna get married next fall in Arizona. they then want to embark on Walt Disney World. And a cruise. it was funny, the email that she sent me we're not super close, but she knows me well enough and she's like, we want to spend a day at Epcot. And then we found this cruise called Perfect Day at Coco K. Do you know anything about that? And I'm like, I know all about that. I can help you out. So I've been working with them too. To put that together. And it's fun because it's a young couple, right? It's a special event. It's a honeymoon. It's people who haven't done this type of travel before and I'm just really super excited.

j_1_01-19-2026_142219 8:56

Yeah. That's awesome. I love that idea.

ryan_1_01-19-2026_142219 8:59

We love celebrating with our clients and where they're headed It inspires curiosity and we can't wait to talk about their trip. And if you work with Julie and I, who knows, maybe your trip will be featured next.

j_1_01-19-2026_142219 9:11

All right, so the next big step in planning your cruise is to choose your ship slash itinerary. And I kind of am talking about these things together because sometimes they go hand in hand and it also depends who's cruising. Let's talk about picking your cruise ship first. If this is your first cruise and you're an adult, the best options that we would recommend would be Virgin Voyages, princess Cruise Line, celebrity, or maybe a smaller Royal Caribbean ship. If you're a family, Royal Caribbean and Disney cruise line are great for first time cruisers. If it's your first time river cruising, which you know, maybe you're a seasoned ocean cruiser and you're breaking into that river cruise market, cruise line and Alma waterways are really the best way to go for that introductory river cruise. I would also recommend a lot of these same. Cruise lines for seasoned cruisers, but you're gonna be experiencing different ships and, I don't know that I would recommend something like of the Seas or Star of This Sea, or the biggest ships out there for your first cruise because you're gonna be very overwhelmed. I think something smaller is just better.

ryan_1_01-19-2026_142219 10:24

I agree with that because there's too much on the ship, so therefore you're gonna feel stressed to try to. Visit the destinations and vice versa. I think going on a more mid-size ship that allows you a balance makes a lot of sense. And then once you've cruised a couple times and you want to experience the biggest and all the bells and whistles on the cruise ship, go for it.

j_1_01-19-2026_142219 10:47

yes. I think you also need to consider the size of your family and what your family needs. There are some cruise lines out there that more to larger families or cater more to groups of two or three. that is something to consider and will help you determine which exact ship you're going on, even. just talking about Royal Caribbean, they have such a vast fleet of ships. some ships have a lot of connecting rooms and some ships have a very small amount if you do have a larger family or you're wanting two rooms, that can definitely determine which ship you're gonna end up choosing. And of course, talk to your travel advisor about what your family's interested in, and that will ultimately help us narrow down the specific ship.

ryan_1_01-19-2026_142219 11:33

Yeah, we really help you. If nothing else break through all the noise. you know, just'cause you see it on TV doesn't mean that's the only option.

j_1_01-19-2026_142219 11:40

Mm-hmm.

ryan_1_01-19-2026_142219 11:41

help you find a couple options that fit exactly what you're looking for.

j_1_01-19-2026_142219 11:45

this really, really stands out to me, just with my client base is clients have a child who has not yet potty trained and they book a cruise because the pricing looks great. But that is usually an older ship. I see this happen a lot with Royal Caribbean. They book an older, smaller ship and then there's nothing for your non potty trained toddler to do on the pool deck. that's something I'm always talking to clients about who have younger, younger kids. and again, a lot of people don't even know that's a problem.

ryan_1_01-19-2026_142219 12:14

a lot of people for first timers think that, well, I just wanna try it. So one of these three night cruises might be best. And you know what? That was my first experience and it was a mistake. let me tell you why, because you get on the ship midday. So really by the time you get kind of acclimated, it's already dinner then it's time for a show or some activities or some bar hopping. then you go to bed, that's day one. you have two full days. And then you get off the ship the next morning after breakfast.

j_1_01-19-2026_142219 12:48

Yeah.

ryan_1_01-19-2026_142219 12:48

it's too quick. By the time you get comfortable being there and know where everything is, you're already done. we really recommend, for first time cruisers, a four to five night Caribbean itinerary. From a port that's easy for you to travel to makes a lot of sense. You get the experience, you get the time you need to get comfortable. You get both port time and usually with a four or five night, you also have a sea day I think that's the perfect way to go. Check for itineraries that stop at a cruise line's private island. We work with multiple cruise lines that have private islands and all of them really try to put their best foot forward when it comes to, your experience there. So you know you're gonna get a really good experience like someplace like Coco k Castaway, key lookout point, We're talking about Europe or the Mediterranean, what are specific stops that are important to you? do you want to see Spain? Do you want to see Rome? Do you want to see Greece? how much time are in those places? and where are you specifically stopping? We've talked about this before. If you're stopping in Veia, that's not Rome. That's a really decent bus ride to Rome. Doesn't mean you can't see it. But you're not, it's not like you're gonna be, you know, sailing up to the Vatican. Also with Europe and the Mediterranean, where would you want to do a pre cruise and a post cruise? do you want to spend a couple days in Rome and then go to the ship? Do you wanna spend a couple days in Barcelona after you disembark there? How do you want to handle that? Is this an introduction to Europe and does that make sense as a cruise? Maybe it does, maybe it doesn't. What length is best for your family? European cruises in the Mediterranean are not short cruises, so you're doing at least a week. And does that work with you? and what you wanna do?

j_1_01-19-2026_142219 14:41

Yeah, those are really great considerations for European itineraries, When those itineraries release, that's really like a. A big consideration is where are we stopping? Where are we to, you know, disembarking from, or, or you know, embarking and disembarking that requires a lot of thought when choosing those itineraries.

ryan_1_01-19-2026_142219 15:00

Yeah.

j_1_01-19-2026_142219 15:00

that this really comes into play is Alaska because there are so many Alaska itineraries that look really similar, but are slightly different and can really change what you're thinking of doing for your Alaska crews. you really need to consider your port stops and what those port stops are known for. So places like Skagway, ket, ACAN, Juno, and the glaciers. Not every cruise is gonna stop on all of those places. So do you really want to do that? You know that train in Skagway? Well, you better make sure Skagway is a port stop for you. Do you really wanna do whale watching in Juneau? We need to make sure that's on your itinerary as well. will mention there are some restrictions on cruisers from the United States when boarding a cruise that stops in Canada. Do your research on like the entry requirements and that may also help you consider your itinerary of if you wanna do a cruise that goes up to Canada or not.

ryan_1_01-19-2026_142219 15:58

So let's finish up by talking about river cruising. When you have considerations with river cruising, what do you want to see and where do you want to cruise? So for instance, if you are cruising the Rhine, you're most likely going to start or end in Amsterdam and start or end in Basel, Switzerland. what makes the most sense when it comes to travel? If you want to experience October Fest, you're not gonna be cruising on the send, you're gonna be cruising on the Danube in a very specific time of year. if you want to see fairytale castles, you need to be on the Rhine or, one of the offshoot rivers of the Rhine. So really, Just like with ocean cruising, river cruising is not one size fits all. It really depends on what it is you want to see. and I would say too, as you get more comfortable with river cruising or if you fall in love with it, like I have. What's next?

j_1_01-19-2026_142219 16:51

You.

ryan_1_01-19-2026_142219 16:52

Danube and the Rhine are the entry level for a lot of people. And then they start to think, where else can I river cruise? I could river cruise in the United States. I could be in Africa on the Nile. I could do, Columbia and South America. So there's a lot of expansions there. But really if you're starting out with true river cruising, I would always opt for a European cruise. That's just me. But I think my clients have had a good experience with that.

j_1_01-19-2026_142219 17:18

Agree. for river cruises, that is definitely the one that we say you are gonna need to do more than one.

ryan_1_01-19-2026_142219 17:24

Well, Julie, as we wrap up, what can we expect to see in parts two and three of this series?

j_1_01-19-2026_142219 17:32

All right, so today was all about, picking the cruise that you're gonna be going on. Part two and part three are gonna cover planning for that cruise, like prepping for it, what you're gonna do to

ryan_1_01-19-2026_142219 17:42

Yep.

j_1_01-19-2026_142219 17:43

and then the process of actually getting on the ship as well as things to do. While you're on the ship and then how to get off the ship. So we're really trying to walk you through that whole process of cruising because we know that it can be overwhelming.

ryan_1_01-19-2026_142219 18:00

The world is full of wonder and your next adventure is waiting. At Wonder and Beyond Travel, we work with you to create a one of a kind journey, taking the stress off your plate so you can focus on the joy of exploring and the memories that will stay with you forever. If you're ready to start planning or you just wanna dream a little bigger, head on over to Wonder and Beyond travel.com. We'd love to help you get started. We look forward to talking to you next week on All Things Travel, when we continue this series with Cruising 1 0 2, embarkation Day and Time on your cruise.