Cruising 101: A Beginners Guide to Cruising

Norwegian Cruise Line in Jamaica

If you’ve ever been curious about cruising — or maybe even skeptical — you’re not alone. I’ve spent years working for and with several cruise companies, and I’ve heard every question, every misconception, and every “I’m not really a cruise person” comment you can imagine.

But here’s the truth: Cruising isn’t one thing. It’s not one style, one ship, or one type of traveler. It’s a whole world of travel options — and most people only know a tiny piece of it.

So let’s start simple. Let’s break down what cruising actually is, why it’s so popular, and how to figure out whether it might be right for you.

This is the first post in a series where I’ll walk you through the basics, debunk myths, and help you choose the cruise style that fits your personality, pace, and travel goals.

🚢 What Even Is a Cruise? (Yes, I’m serious)

Let’s make this simple: a cruise is like a floating hotel that moves. That’s it. You unpack once, and you see the world.

But depending on the type of cruise you choose, that “floating hotel” might feel like:

• A resort

• A boutique inn

• A safari lodge

• A cultural immersion trip

• A luxury retreat

• A basecamp for adventure

• A destination

This is why cruising is so misunderstood — people assume all ships are the same we all know they’re thinking mega-liners. They’re not even close.

🌍 The Three Main Types of Cruises (And Why They’re So Different)

1. Ocean Cruises

Think big ships, small ships or luxury yachts, lots of dining options, entertainment, nightlife, family-friendly and adults only options, and a mix of travelers. Just like a hotel, right? Perfect for: first‑timers, families, couples, groups, people who want variety.

2. River Cruises

Smaller, intimate ships, slower pace, culture‑focused itineraries, and docking right in the heart of cities. Imagine always being surrounded by country-side and beautiful scenery at every point of the journey. Perfect for: foodies, history lovers, adults, travelers who want depth over crowds.

3. Expedition Cruises

Small ships built for adventure that take you to the most remote destinations of the world — think Antarctica, the Arctic, the Galápagos. Often include expert guides, wildlife encounters, and educational programs offering a once-in-a-lifetime experience.  Perfect for: nature lovers, photographers, bucket‑list travelers, explorers.

Each one offers a completely different experience. Choosing the right type is the key to loving your journey.

🧭 Why People Love Cruising (Even If They Didn’t Expect To)

Here’s what I’ve seen again and again from travelers, including myself:

• They love waking up somewhere new every day

• They love seeing multiple countries and destinations with one set of flights and only having to unpack once (seriously guys, that’s a huge flex!)

• They love not having to plan every detail

• They love the mix of relaxation and exploration

• They love the value (yes, value — more on that in a future post)

• They love the community and connection onboard

• They love the up close and personal view of the sunrise and sunset on the horizon (or maybe that’s just me)

Cruising takes the stress out of travel without taking away the adventure.

🏨 Cruise vs. Hotel: The Simplest Comparison

A hotel gives you one destination that you can really explore in depth. A cruise gives you the option to see multiple destinations on the same itinerary while waking up in a new city every day.

A hotel gives you a room. A cruise gives you a room, entertainment, food, transportation, and activities — all in one place. And, if you’re lucky, it’s all included!

It’s not that one is better than the other. They’re just different tools for different types of trips.

Here’s what I always suggest to travelers because both of these types of people exist. If you’re going somewhere new, go on the cruise first to explore many countries or cities at once and see which one gives you butterflies. On the next trip, go back to that destination that gave you butterflies at a hotel and spend more time in the location to explore further.

💬 Why I’m Writing This Series

After working for a cruise company, I know there is a huge buzz around cruising right now. If you’re still living on fears that you had 20 years ago, you’re missing out on something great. Because cruising has changed, it’s evolved, it’s got a solution for every type of traveler.

And then it dawned on me, it’s not that people dislike cruising—it’s just that people don’t understand it yet.

So, this series will break it all down in a way that’s simple, honest, and helpful. No jargon. No sales pitch. Just real insight from someone who has the insight.

🌟 What’s Coming Next in the Series

Here’s what I’ll cover in upcoming posts:

• Ocean vs. River vs. Expedition: How to Choose the Right One

• Cruising Myths, Debunked

• The Value of Cruising

• How to Pick the Perfect Itinerary

• Cruising vs. Land Travel: Which One Fits Your Style

And more — because trust me, I’ve got stories.

What Beach is Right For You

Grace Bay, Turks & Caicos

(Because Not All Beaches — or Travelers — Are Created Equal)

Having worked in travel for most of my career—primarily in tropical destinations—I often get asked what the best beach is.

Some people think “a beach is a beach,” but those people have clearly never tried to relax on a windy coastline while being pelted with sand like a human exfoliation treatment. Beaches have personalities. Attitudes. Vibes. And choosing the wrong one can turn your dream vacation into a “why did I do this to myself” moment.

So let’s figure out which beach is actually right for you — based on your travel style, your energy, and your tolerance for chaos.

🏖️ If you want powdery-white sand with turquoise waters:

Turks & Caicos — Grace Bay

Arguably my favorite beach spanning the world, Grace Bay frequently tops “world’s best beach” lists from travel magazines and publications. Spanning 7 – 12 miles, there’s no shortage of space to find your quiet beach spot, even during peak season. The sand is famously fine and soft—often compared to powder while the bay is naturally sheltered by a barrier reef offshore, which keeps waves gentle and the water remarkably clear.

Grace Bay may just be the closest thing to a “perfect beach” with:

• Stunning views

• Relaxing atmosphere

• Warm, gentle water

• Clean, uncrowded stretches of sand

• Picture‑perfect sunsets

Tip: If you’re fortunate to stay in a resort located on Grace Bay, pay for an upgrade to ocean view. I promise you will regret not waking up to the calm turquoise waves every morning when you sip your coffee on your balcony as much as you would regret going all the way to Tahiti and not staying in an over-the-water bungalow. Pay for the ocean view. Every time.

🍹 If you want beach + nightlife + “I might make questionable decisions”:

Spain — Ibiza

If you want energy and entertainment, Ibiza is unmatched.

Globally known as the top party destination in Europe, Ibiza perfectly blends world‑class DJs and nightlife lovers with legendary beach clubs and pool parties, creating a lively daytime‑to‑nighttime atmosphere.

Ibiza has a beach for everyone. Enjoy hidden coves and rugged coastlines with beautiful turquoise waters or long stretches of calm beach.

Perfect for you if:

• you love a good beach club

• you want sun and chaos

• you enjoy meeting strangers who become your best friends for 48 hours

Tip: The island is small, so you can visit multiple beaches in a single day—each with a different vibe.

🌺 If you want romance, beauty, and “I’m the main character” energy:

French Polynesia — Bora Bora

This is the beach you go to when you want to feel like you’re starring in your own honeymoon, even if you’re single. The water is so blue it looks filtered. The bungalows are so pretty you’ll question your entire life choices.

Perfect for you if:

• you want luxury

• you want serenity

• you want to dramatically stare into the ocean and reflect on your life

• you want dramatic sunsets

Also perfect for couples, but honestly, go alone — it’s still magical if you seek adventure mixed with serenity and luxury.

🐠 If you want adventure and snorkeling:

Australia — Great Barrier Reef

This is for the traveler who wants to do all the things, not just tan. You’ll snorkel. You’ll dive. You’ll see fish that look like they were designed by a toddler with a crayon box.

Perfect for you if:

• you get bored lying still

• you want wildlife

• you want to brag about your trip for the next decade

Tip: If you want to get more attention from the wildlife, wear a bright-colored swimsuit. Fish are more genuinely curious about you if you look like part of the reef. But don’t touch anything… Australia’s creatures are beautiful but dramatic.

🐬 If you want turquoise water, boat days, and “I’m living my best life” energy:

Bahamas — Exuma

Exuma is the definition of “postcard perfect.” The water is neon turquoise, some of the clearest water in the world. The sand is white. The vibe is “I’m on a boat and I’m never going home.”

Perfect for you if:

• you want to swim with pigs

• you want boat days to go island hopping

• you want to feel like you have your own private beach, especially in the smaller cays

• you want to find shallow sandbars, reefs, blue holes and explore underwater caves

• you want beaches that look fake because they’re too perfect

Tip: Plan to spend at least one day on a boat — it’s the single best way to experience what makes the islands extraordinary. Exuma is all about shallow sandbars, hidden coves, and tiny cays you can only reach by boat, so a day trip opens up the real magic of the region. Like your budget, Exuma isn’t meant to be spent all in one place.

🌊 If you want dramatic cliffs, cinematic views, and “I’m in a movie” vibes:

Santorini, Greece — Black Sand, Red Sand, and Caldera Magic

If you’re questioning why Santorini made the list, I understand Santorini isn’t your typical beach destination — it’s the beach’s glamorous, dramatic, slightly mysterious cousin. The cliffs here don’t just rise; they perform. Whitewashed buildings spill down the caldera like they’re posing for a postcard, and the sunsets are so theatrical they deserve their own IMDb page.

But here’s the twist: Santorini’s beaches are unique—volcanic, bold, and unlike anything you’ve seen.

Perissa & Perivolos : These are the famous black‑sand beaches, created by ancient volcanic eruptions. The sand gets hot (like, “I’m doing a fire‑walk challenge” hot), but the vibe is unmatched — beach clubs, deep blue water, and a backdrop that looks like a movie set.

Red Beach: This one is straight out of a sci‑fi film. Rust‑colored cliffs. Deep red sand. Water that glows against the rock. It’s dramatic in the best way — the kind of place where you take a photo and people assume it’s edited.

Kamari Beach: Another black‑sand beauty, but with a more relaxed, family‑friendly vibe. Think loungers, tavernas, and that “I could stay here all day” energy.

Perfect for you if:

• you want beaches that feel different

• you love a dramatic backdrop

• you want photos that look like they belong in a travel magazine

• you enjoy a mix of cliffside luxury and unique shoreline

Santorini is the place where you can spend the morning tanning on black sand, the afternoon exploring red cliffs, and the evening watching the sun melt into the caldera like it’s performing just for you.

It’s romantic. It’s iconic. It’s cinematic.

And yes — it absolutely counts as a unique beach destination.

🌺 If you want culture, flavor, and beach bliss all in one place:

Jamaica — Seven Mile Beach, Negril

If you want a beach that comes with soul, rhythm, and personality, Jamaica is the destination. Seven Mile Beach isn’t just a stretch of sand — it’s a whole mood. Powder‑soft sand, turquoise water, reggae floating through the air, and sunsets so fiery they look like the sky is showing off.

But what makes Jamaica special isn’t just the beach — it’s the culture that wraps around you the moment you arrive.

You’ll hear music everywhere. You’ll taste flavors that ruin all other jerk chicken for you. You’ll meet people who make you feel like you’ve been friends for years.

You’ll feel the island’s heartbeat in everything — the food, the music, the energy, the warmth.

Perfect for you if:

• you want a beach with personality, not just pretty views

• you love music, dancing, and a little island spice

• you want culture woven into every moment

• you want to float in turquoise water by day and listen to live reggae by night

Seven Mile Beach gives you the best of both worlds: calm, dreamy beach days and vibrant, soulful nights. You can snorkel, sip rum punch, eat fresh seafood with your toes in the sand, and then wander into a beach bar where someone is singing Bob Marley under the stars.

It’s warm. It’s lively. It’s unforgettable. And it’s the perfect pick for anyone who wants their beach vacation to feel alive.

🧘‍♀️ If you want spiritual, calm, “I’m finding myself” energy:

Maldives

The Maldives is the ultimate “no one can reach me, I’m going off the grid” destination. Picture overwater villas, endless turquoise water, and a level of quiet so pure you can hear your own heartbeat. It’s peaceful in a way that feels luxurious — like the universe is giving you a private retreat.

This is where you go when you want to disappear from the world and reemerge as your best self.

You’ll float in warm, clear water. You’ll journal on your deck with nothing but ocean around you. You’ll watch the sunset from a hammock and suddenly understand why people say the Maldives changes you.

Perfect for you if:

• you want total peace and privacy

• you want to disconnect from everything

• you want a beach that feels like a sanctuary

• you want to heal in style

The Maldives is serene, dreamy, and deeply restorative — the kind of place where you remember who you are.

🌺 If you want adventure, nature, and “I’m living inside a postcard” energy:

Kauai, Hawaii — Hanalei Bay

Kauai is the kind of place that makes you believe the Earth has favorite children — and Hanalei Bay is clearly one of them. This isn’t just a beach; it’s a full‑body experience. Lush mountains wrap around a crescent of golden sand, waterfalls spill down cliffs like nature’s jewelry, and the whole scene looks like it was designed by a director who said, “Make it more breathtaking.”

Hanalei Bay is where you go when you want your beach day with a side of adventure. You can paddleboard in calm morning water, surf gentle waves by afternoon, and wander into town for shaved ice and fresh poke when you need a break. And if you’re feeling bold, the nearby trails and lookouts will absolutely deliver those iconic moments.

Perfect for you if:

• you want beaches surrounded by lush, cinematic scenery

• you love a mix of relaxation and adventure

• you want to snorkel, paddleboard, or hike between beach naps

• you want nature to be the main character

Kauai gives you that rare combination of beauty + adventure + serenity. It’s peaceful without being boring, wild without being overwhelming, and stunning in a way that makes you consider canceling your return flight.

It’s the kind of place where you don’t just take photos — you take deep breaths.

🌞 Final Thoughts: Your Perfect Beach Is Out There

At the end of the day, the right beach isn’t just about sand or water — it’s about the version of you that shows up there. Maybe you’re craving adventure. Maybe you want culture and connection. Maybe you need a reset, a romance, a dramatic view, or a moment that reminds you how big and beautiful the world can be.

There’s a beach for every mood, every chapter, every version of yourself you’re still becoming.

Whether you end up floating in Maldives-blue water, wandering Kauai’s lush coastline, dancing on Jamaica’s Seven Mile Beach, or watching the sun melt into the caldera in Santorini, the right place has a way of finding you when you need it most.

Let the ocean pull you exactly where you’re meant to go. Your perfect beach — and your next story — is waiting.

Red Eyes Over Red Flags

There comes a point in life when you realize exhaustion is temporary, but emotional chaos has a way over overstaying its welcome.

Red-eye flights get a bad rap. They can leave you sleepless, exhausted and questioning life choices at 5:00 a.m., and occasionally with back pain. But, then again, so do men with red flags. The difference is… a red eye takes me somewhere new and exciting and leaves me with an abundance of adrenaline and excitement to get me through the day. Whereas a man with red flags makes me question if it’s even worth getting out of bed that day. The most exciting place he takes me is a trip to go see a therapist to uncover the mental gymnastics he’s played on my mind.

At least a red-eye flight is honest. You know exactly what you’re getting into. You know up front you’re going to be uncomfortable and lose some sleep. Red flags? They’re disguised in lies and make you believe they’re charming, but you’re just left with confusion and bullshit.

I once dated someone who only showed up or texted when it was convenient. Plans were always tentative. Texts came in waves. When I would bring it up, I would be gaslit. That same month, I booked a quick weekend getaway to visit a friend. With no vacation time, I took the red eye, and arrived exhausted, makeup smudged, and running on fumes—yet I had felt lighter than I had in weeks. It occurred to me I was willing to be tired for the experiences and people who showed up, but bending myself into knots for someone who didn’t.

We’re so quick to take the chance on something that appears amazing, even if we know it’s covered in red flags. But the honest option that may pose minor inconveniences but you know exactly what you get often gets disregarded.

Why I’ll Always Take The Red Eye:

·       If you live on the west coast and you travel east, you gain an entire day with a red eye without having to take an extra day off work!

·       If you get to the resort after 5pm, you are paying the hotel for a day you didn’t get. You’re also paying the airline for a seat to sit in all day that same day! You’re paying for a day that you didn’t get.

·       2:30 a.m. wake up calls? No, thank you! Living in Los Angeles, I could have to leave the house 4-5 hours before my flight time thanks to 24-7 traffic hell. With a 6:00 a.m. flight, that would mean getting up when my friends are just getting home from the clubs.

·       I’ll never get tired of watching a sunrise from 35,000 ft. in the air

Essentially, I look at red-eye flights as an initial setback that pays off! It appears bad at first but the outcome is so much better than what you expected. Essentially—the opposite of a red flag.

Why I Stopped Accepting the Red Flags

While a red eye has a destination, the red flags just keep you circling. It’s an ongoing flight that you can’t get off.

I’d rather:

·       Be tired than confused

·       Be jet-lagged than emotionally drained

·       Arrive groggy with excitement instead of rested and unsettled

Sleep can be recovered quickly. Trust takes forever to recover.

Preferring a red eye doesn’t mean I enjoy discomfort. It means I prefer to sacrifice a little discomfort on the front end to have more time to enjoy and play on the back end.

Final Boarding Call

These days, if I have to choose between temporary discomfort and long-term misalignment, I’m grabbing the carry-on and heading to the gate.

I prefer a red eye over red flags. At least one of them gets me where I’m going and where I belong.