Cruising 101 Tips, Itineraries & What to Know Before You Go

🌴 Thinking about your first cruise? Or maybe you’re wondering what all the fuss is about? In this episode of Explorations All Over, host Russell Gibson breaks down everything you need to know before you set sail on a Caribbean cruise.

From choosing the right cabin and cruise line to understanding shore excursions, dining options, motion sickness remedies, and those sneaky hidden fees—this is your no-nonsense, highly entertaining intro to cruise life. You’ll also hear stories from Russell’s own cruising adventures and learn why a travel advisor might be your best travel companion.

💡 Whether you're packing for your first cruise or planning your fifth, this episode is full of smart tips, a few laughs, and even a lightning round of cruise do’s and don’ts.

🎧 Subscribe so you don’t miss our next episode—a journey to Japan in our second Far Flung Adventures installment!

Transcript

Caribbean Cruising 101

Ever dreamed of taking a cruise, but felt totally overwhelmed by all the choices? You’re not alone. After my chat with Kurt Oswald about how to pick the right cruise, I heard from a lot of you saying, “Okay… but where do I even begin?”

So in this episode, I’m backing things up a bit — and devoting the full show to the cruise curious: those of you who’ve thought about cruising but never quite pulled the trigger.

I’m Russ, and this is Explorations All Over.

Today’s episode is your no-stress, beginner-friendly guide to cruising — with a focus on the Caribbean, because for most first-timers, that’s where the journey begins.

Let’s dive in.

Why the Caribbean? For starters, it’s the cruise capital of the world.  For most U.S. travelers, it’s also incredibly convenient. There are a number of departure ports — especially in Florida — including Miami, Ft. Lauderdale, and Port Canaveral, making it easy to get to the ship without long-haul flights or complicated connections. and you can hop on for a weekend or a week (or more). Whether you’re traveling solo, as a couple, with friends, or with your entire extended family in tow, there’s something in the Caribbean for you.

One of the biggest tips Kurt Oswald shared in Episode 5 — and I agree — is to plan early. Ideally, a year in advance. Why? Because the more time you give yourself, the better chance you have to get the ship, itinerary, cabin, and price point that works for you. It also gives you time to research excursions, dining, and even travel insurance — all without stress.

And cruising itself? I like to think of it as checking into your hotel once — and waking up somewhere new every day. No unpacking and repacking. No airports. Just your floating resort taking you where you want to go.

That said, nothing is locked in stone. Cruise lines (and travel advisors) understand that plans can change. Most cruises offer flexible cancellation policies, and if you’re working with an advisor, they can handle the heavy lifting — rebooking, changing dates, and helping you decide what’s worth locking in early.

The Caribbean is also super flexible in terms of trip length. You’ll find quick getaways — perfect if you’re just dipping your toe into cruising — or longer escapes. But by far, the most common cruise length is 7 nights, usually sailing Saturday to Saturday or Sunday to Sunday. The first day you board, the last day you disembark — and in between, island hopping.

And just a heads-up: In an upcoming episode, I’ll be chatting with Dee Kroger, who runs her own travel agency, Cruise Planners. We’ll be diving into how to match the right cruise line to the right traveler. So, if you’re wondering whether you're more Carnival or Celebrity, you’ll want to tune in for that.

Make sure to follow the podcast so you don’t miss it!Top of Form

Bottom of Form

Okay, you’ve decided on the Caribbean. Great choice — now let’s look at the different kinds of Caribbean cruises.

Most itineraries are divided into three regions, each with its own personality:

1. Eastern Caribbean

Think St. Thomas, St. Maarten, and Puerto Rico. These islands are known for gorgeous beaches, excellent shopping, and rich colonial history. Great for first-timers who want a balance of fun and culture.

2. Western Caribbean

Here you’ll find ports like Cozumel, Grand Cayman, and Jamaica. This route leans more toward adventure: snorkeling, Mayan ruins, waterfalls, and jungle excursions. If you're the type who likes to get off the ship and explore, this may be your jam.

3. Southern Caribbean

This includes what are often called the ABC islands — Aruba, Bonaire, and Curaçao — along with Barbados and St. Lucia. These cruises tend to be a bit longer (often 10+ days) since they sail farther south, but the payoff is big: fewer crowds, unique culture, and spectacular scenery.

There are lots of other fantastic islands too — like St. Kitts, St. John, or Dominica — but these three categories cover most major itineraries.

Not sure which to pick? That’s where a travel advisor can really help. They’ll ask you questions like:

• “What kind of vacations have you loved in the past?”
• “Are you a beach lounger or an adventure-seeker?”
• “Is this a romantic escape or a friends’ getaway?”

A good advisor listens first — and then helps you narrow it all down.

A lot depends on what you’re looking for in this vacation. Do you want total relaxation? A non-stop party? Gourmet food? A chance to shop ‘til you drop? Work on your tan? Meet someone new?

These kinds of questions are exactly what a good travel advisor will ask. In fact, as Kurt mentioned in our earlier conversation, the first step is asking the right questions — not just about where you want to go, but what you want to feel while you're there.

It’s not a test — it’s a tool. These questions are meant to get you thinking, and to give your advisor something to work from. Because the truth is, there’s a cruise for everyone… but not every cruise is for you.

🚢 Let’s Talk About the Ship

Now, I’m saving the deep dive on specific cruise lines for that upcoming chat with Dee, but let’s talk about the ships themselves — starting with the cabins.

Almost every cruise ship offers the same basic cabin categories — they just use slightly different names. Here’s a quick breakdown:

Interior (Inside) Cabins

These have no windows — you’ll sleep in total darkness, which some people love. Newer ships may offer “virtual windows” — screens that show a live feed from outside, to help orient you. We once stayed in an interior cabin and I slept so hard, I woke up convinced it was the middle of the night — it was actually 10:30 a.m. and I’d missed breakfast. Great for deep sleepers. Not so great for brunch lovers.

Oceanview Cabins

These have a window or porthole looking out to the sea. The window doesn’t open, but you’ll get sunlight and a view.

Balcony (or Verandah) Staterooms

These include a private outdoor space where you can sit, read, sip coffee, or enjoy sailaway in peace. Once you try one, it’s hard to go back.

Suites

These vary widely. Some are just larger rooms with a sitting area. Others — like an Owner’s Suite — come with multiple bedrooms, bathrooms, a dining area, bar, and more. It’s basically a condo at sea.

You’ll also see terms like Deluxe, Superior, or Premium. Most of the time, those words don’t mean the layout is different — they refer to the location of the cabin. Midship is more stable than the front or back. Higher decks often mean better views. Two identical rooms can be priced very differently just based on where they sit on the ship.

As a general rule:

• Inside staterooms are the most affordable
• Suites are the most expensive
• And balconies tend to be the sweet spot for first-timers who want comfort without going all-in

Food is a major draw for many cruisers — and if you thought there was a wide variety of cabins, just wait until you see the dining options.

Traditionally, cruise ships centered their dining around the Main Dining Room, where all guests could be accommodated at set times. You’d select your preferred seating — usually around 6:30 or 8:00 p.m. — and your table size, though you weren’t always guaranteed your first choice.

Let me give you a personal example.

When Duncan and I first started cruising — after the amazing trip we took to Greece that I talked about in the first episode — we booked a cruise with Royal Caribbean. Why Royal Caribbean? Their tagline at the time was “Get Out There”, aimed at a younger, more active crowd. That felt like us.

When we booked that cruise, we were asked what time we wanted to dine and how large of a table we preferred. We chose the later seating — 8:00 p.m. — and requested a table for two.  What we got was a table for eight. But here’s the thing — by the second night, we were swapping life stories and wine recommendations like we’d all gone to college together. One guy even invited us to his daughter’s wedding. We didn’t go… but we were tempted.

In addition to the Main Dining Room, there were two other options: Chops, a steakhouse-style restaurant, and Portofino, an upscale Italian venue. Both came with a fee — I think it was around $15 per person at the time. Back then, the idea of paying to dine on a cruise felt strange to a lot of people. Wasn’t it all supposed to be included?

But those venues offered upgraded menus, smaller spaces, and personalized service. It felt intimate and special — a step above the main dining experience.

And that was the advent of what is now called Specialty Dining: for-a-fee venues that offer something different, something elevated.

These days — especially on the mega-ships — you’ll find dozens of dining options, from casual burger joints to fine dining venues rivaling anything you’d find ashore. And yes, they all come at a cost — sometimes minimal, sometimes splurge-worthy.

You can absolutely take a cruise and eat only in the Main Dining Room and buffet — and many do. But if food is a highlight for you, or if you’re celebrating something special, it might be worth setting aside some room in your budget for one or two specialty nights.

Also worth noting: smaller ships tend to have better overall food quality. And it makes sense — cooking for 300 people is very different than cooking for 7,000. So if you're a foodie, that might be something to keep in mind when choosing your cruise line or ship size.

🎭 Entertainment at Sea

Right up there with food is onboard entertainment — and cruise lines know how to put on a show.

Disney ships? Naturally, they feature Disney productions.
 Larger ships might offer full Broadway-style shows, with dazzling costumes, sets, and choreography.
Smaller ships? You’ll find entertainment that feels more tailored — often productions written and directed by the ship’s own staff.

There are also comedians, magicians, live musicians, and audience favorites like the Love and Marriage Show, where couples try to match each other’s answers to hilarious questions — with predictably unpredictable results.

Each evening, the cruise line delivers a daily program to your cabin — or pushes it to your cruise app — outlining the next day’s schedule. It includes everything from trivia contests to dance classes to spa specials.

Yes, you’re on vacation — but there’s still a schedule. If you’re taking a ship-sponsored excursion, you’ll need to plan around that too. And honestly? You can be busy from sunrise to long after sunset. Or you can do absolutely nothing. That’s the beauty of it.

🛳️ Sea Days vs. Port Days

Earlier I mentioned “sea days.” That’s when your ship isn’t in port — it’s just you, the open ocean, and everything the ship has to offer. That’s when the daily program (or cruise app) becomes your best friend. It helps you sort out how you want to spend your day… even if that’s doing absolutely nothing.

Now let’s talk about the opposite: port days — when you’re docked in a destination and adventure awaits.

🧭 Shore Excursions: Ship-Organized vs. DIY

If you’ve listened before, you know I’m a huge fan of research. HUGE.
Even before you book your cruise, you can usually find a detailed itinerary that shows where the ship will be each day. Once you know that, the question becomes: What do I want to do in each place?

Cruise lines make it easy by offering shore excursions — outings you can book directly through the ship. These range from:

• 🚌 Simple sightseeing tours (a bus with a guide sharing local highlights)
• 🍳 Small-group experiences like cooking classes with a local chef
• 🐠 Snorkeling, zip-lining, hiking, and other adventure options
• 🧘 Slower-paced cultural or scenic tours for guests who want a gentler day

Most cruise lines do a great job labeling each excursion by activity level, so you know whether something is appropriate for someone with limited mobility or whether it’s a strenuous trek up a volcano.

🆚 Can You Go the DIY Route?

Now, you may be wondering — Can I book these kinds of activities on my own?
Absolutely. In fact, Duncan and I do it all the time.

Why would you book independently? Simple: you’ll usually pay less. The same tour offered through the ship is often available directly through the vendor at a lower cost.

Why wouldn’t you? Well, the cruise lines like to push one key point:

“If your excursion is late, and you didn’t book through us, the ship won’t wait for you.”

To me, that’s a bit of a scare tactic. In 30+ years of traveling — often booking excursions independently — we have never missed a ship.

That said, it comes down to your personal comfort level. Some travelers want the peace of mind that comes from booking through the ship — and that’s completely valid. For others, the flexibility, savings, and ability to support local guides directly is worth the DIY approach.

Just maybe don’t go with the guy on the pier holding a cardboard sign that says “#1 Tour! Trust Me.” Unless, of course, you’re in the mood for an adventure adventure.

🎧 “Hey, quick break before we get into packing tips and a few final cruise nuggets...

If you’re enjoying this episode and want even more travel storytelling, exclusive episodes, and behind-the-scenes content — consider subscribing to Explorations All Over.

These are in-depth, immersive episodes from some of the most remote and remarkable places Duncan and I have explored — like an African safari, Antarctica, and more.

Subscribing not only gives you access to all of that, it helps support this podcast so I can keep creating content for you. Just tap the link in the show notes or visit [your site or platform link here].

Now, let’s get back to the ship... and what to pack so you’re not the one stuck buying overpriced sunscreen onboard.”

So you’ve picked your itinerary, chosen a ship, and now you’re counting down the days. Let’s talk about what to do before you go — so you can focus on the fun once you’re on board.

First, book your flights. You can go the DIY route or enlist a travel advisor like Dee or Kurt who can help make sure your arrival and departure run smoothly. Either way, don’t leave this to the last minute. You don’t want your cruise starting with a mad dash through the airport.

🧳Let’s Talk Packing

Overpacking is the Achilles’ heel of cruising. It's so tempting to bring a different outfit for every day and night... and shoes to match. But trust me — after hauling a 52-pound suitcase through the Miami heat, you’ll rethink that.

Confession time: overpacking is my own personal cruising vice. I once brought eight polo shirts and only wore three. The others? Took a lovely vacation in the suitcase.

Here’s the real secret: on a 7-day Caribbean cruise, you’ll mostly wear T-shirts, shorts, a bathing suit — rinse and repeat. And yes, you can re-wear things! A small packet of detergent and a little bathroom sink laundry can go a long way. If you’ve got a verandah, you’ve got a great outdoor drying rack. Otherwise, the bathroom will do.

Eveningwear? That’s where it gets a bit trickier. Most cruise lines now go with “smart casual,” which usually means slacks and a collared shirt. No, your Margaritaville tee doesn’t count — even if it’s got buttons.

Some cruise lines allow jeans, some don’t. Some still have formal nights where a tux or suit wouldn’t be out of place. That’s more common on the smaller, more traditional lines. The takeaway? Check with your cruise line ahead of time.

🧢Essentials You Might Forget

In addition to clothes:

• Sunblock
• Hat
• Sunglasses
• Insect repellent
• Motion sickness pills (more on that in a sec)
• Power strip and charging cords
• A daypack for excursions

And of course, your passport and boarding docs. Keep them handy — not at the bottom of your suitcase under three layers of wrinkle-resistant khaki.

🧠Bonus Packing Hacks

• Magnetic hooks: cabins have metal walls. Boom — instant storage.
• Packing cubes: your suitcase turns into a mini dresser.
• Hanging shoe organizer: not just for shoes — great for organizing chargers, toiletries, and random stuff you somehow accumulated by day 3.

🌊Motion of the Ocean

Cruise ships today are equipped with stabilizers, which help minimize that side-to-side roll. Still, if the seas are rough, there’s only so much the captain can do.

If you’re prone to motion sickness, pack something. Bonine, Dramamine, Sea Bands — whatever works for you. But here’s the trick: take it before the rocking starts. Once your stomach’s doing the cha-cha, it’s too late.

That’s why I always listen for the captain’s noon update. If I hear the word “moderate,” I don’t wait — I medicate.

🏥What if You Get Sick on Board?

Yes, there’s a doctor. Yes, they can handle most things — even minor surgeries. But no, it’s not cheap. That onboard medical visit can cost more than a dinner at the Captain’s Table. Travel insurance is your best friend here. Make sure it covers medical care at sea.

💸Hidden Costs of Cruising

You paid your fare — but is that it? Not quite. Here are a few extras that can add up:

• Internet package: Some lines include it, most charge. And “basic” often means “painfully slow.”
• Beverage package: Whether it’s soda or spritzers, paying as you go can get pricey.
• Specialty dining: That steakhouse or sushi bar? Not included. Research ahead on sites like Cruise Critic to see if it’s worth the splurge.
• Shore excursions: Ship-run tours are vetted and reliable — but often more expensive. DIY options can save money, but come with more uncertainty.
• Spa services: Massages at sea? Heavenly. The bill? Not so much.
• Gratuities: You’ll often get a list of suggested amounts. My take? Tip generously when service is excellent — it makes someone’s day.

🔚Last-Minute Reminders

• Book early for better pricing and cabin selection
• Feeling overwhelmed? Use a travel advisor
• Download your cruise line’s app and sign up for their loyalty program
• Familiarize yourself with the ship layout
• Visit Cruise Critic chat boards — tons of insider tips
• Set your phone to airplane mode after embarkation to avoid roaming fees
• And most importantly — enjoy yourself!

Don’t overschedule. Don’t overthink. And don’t forget — it’s okay to do absolutely nothing.

⚡️LIGHTNING ROUND: Cruise Edition

Let’s wrap things up with a lightning round — quick answers to the most common cruise questions I get:

Q: Do I need a passport?
A: Yes — even if you’re sailing roundtrip from the U.S., it’s the smartest move. Some islands require one if you have to fly home unexpectedly.  The U.S. also requires Real ID, so have that handy as well.

Q: Will I get bored on a sea day?
A: Only if you try to. Trivia, pool time, spa, books, bingo, naps, live music — it’s all there.

Q: Can I bring alcohol onboard?
A: Depends on the line. Some allow one bottle of wine per person. Others, none. Check your cruise line’s alcohol policy before you sneak that rum into your suitcase.

Q: Do I need to dress up?
A: Not unless you want to. “Smart casual” is usually the minimum for dinner. Tuxes and gowns? Totally optional. Unless you’re into that. In which case — sparkle on.

Q: What if I’m cruising solo?
A: DO IT. Cruises are great for solo travelers. There are activities, meet-ups, even cabins designed just for one.

Q: Will I gain weight?
A: Look, you’re surrounded by buffets, soft serve, and midnight pizza. You do the math.

Q: Drink of choice on deck?
A: Anything rum. Because when in the Caribbean...

Q: Favorite onboard activity?
A: Trivia contests. I get weirdly competitive.

Q: Cruising pet peeve?
A: People who “reserve” deck chairs at 6am and then disappear until noon.  They’re called chair hogs, and there’s a reason.

Q: Best tip for a first-timer?
A: Don’t overplan. Leave room for spontaneity — that’s where the real magic happens.

Q: Will I want to cruise again?
A: Honestly? Probably before you even disembark.

🎧 OUTRO

So there you have it — your crash course in Caribbean Cruising 101. Whether this is your very first sailing or your fiftieth, I hope it’s given you the tips, ideas, and confidence to plan your perfect voyage.

And now, it’s time to set our sights on something a little farther afield… because in our next episode, we’re heading to Japan for the first subscriber only episode in my Far Flung Adventures series.

This was a trip unlike anything Duncan and I have ever done — starting with a week exploring on land before boarding a 17-day Silversea cruise around the islands of Japan. We stayed in a ryokan, soaked in onsen baths, met one of the most gracious hosts we’ve ever encountered, and saw Japan from a perspective few travelers get to experience.

You don’t want to miss it — so follow the podcast on Spotify, Apple Podcasts, or wherever you listen, so you’ll be the first to hear it when it drops.

Until next time, I’m Russ — and I’ll see you soon.

[Music swells and fades out]

Until next time — safe travels.  I’m Russ and thanks for joining me on Explorations All Over.