🛳️ New to Cruising? Start Here!

So you’re cruise-curious (or you panic-booked a sailing at 2 a.m. and now you’re wondering what you’ve done). Breathe. You’re in the right place. This page is your step-by-step roadmap from “no idea what I’m doing” to “confident cruiser with a drink in hand and zero panic in your eyes.”

We’re Adam & Mary from Hollett’s At Sea – cruise-obsessed travel advisors who believe your vacation should start with a cocktail, not confusion.

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How to Use This Roadmap

This page is built so you can follow it top to bottom like a checklist, or jump to the section you need most. Save it, screenshot it, send it to the friend who keeps asking “wait, what’s included?”

• Step 1 – Get the Big Picture (Watch First)
• Step 2 – Pick the Right Cruise (for you)
• Step 3 – Documents, Passports & “Do I Really Need All That?”
• Step 4 – Protect Your Trip with Smart Insurance
• Step 5 – Budget Like a Pro & Avoid Cruise Money Traps
• Step 6 – Pack Without Overthinking (Free List)
• Step 7 – Plan the Fun Stuff & Get Free Help from Us

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Step 1 – Start with the “New to Cruising” Playlist

Before you deep-dive into fine print and Facebook comments, start with an easy win: watch our curated playlist made specifically for first-time cruisers. It answers the questions new cruisers ask us constantly.

If you prefer to read, our post First Time Cruise? Here’s Exactly What to Expect walks you through documents, what’s included, drink packages, Wi-Fi, muster drill, excursions, and more in plain English.

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Step 2 – Pick the Right Cruise (for you, not the internet)

Not all cruises are created equal. Before you book anything, you want to answer a few key questions:

• Who’s going? Adults-only vibe, couples trip, multigenerational chaos, or “just the two of us escaping the kids”?
• What’s the priority? Budget, ship activities, ports, food, kids’ clubs, or quiet relaxation?
• How long? 3–4 nights to “test the waters” or a full 7-night+ vacation?
• When? School breaks, hurricane season, or shoulder seasons when prices often behave better?

To keep this from turning into a 74-tab research spiral, we made a hub where you can either DIY or let us help:

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Step 3 – Documents, Passports & ID (Don’t Get Turned Away at the Pier)

This is the part nobody wants to think about, but it’s the part that can ruin a cruise in about 10 seconds if you get it wrong.

✔️ The short version

• For many round-trip cruises from U.S. ports, you may be able to sail with a certified birth certificate + government-issued photo ID.
• We still strongly recommend a valid passport (usually 6+ months beyond your return date).
• Always confirm exact requirements with your cruise line & official government sources for your itinerary.

We break this down, nice and simple, in: Do You Need a Passport for Your Cruise?

Once your documentation plan is set, save everything in multiple places:

• Physical folder for embarkation day
• Photos/scans of passports, IDs, and confirmations on your phone
• Backups in secure cloud storage

Want to see what happens if things go sideways? Our guide What Happens If You Miss Your Cruise Ship? shows you the step-by-step playbook so you can be prepared without obsessing over worst-case scenarios.

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Step 4 – Protect Your Trip with Smart Insurance

Is cruise insurance fun to think about? No. Is it the thing that can save you thousands when flights melt down or someone gets sick three days before sailing? Yes.

We explain exactly what cruise insurance can cover (and what it doesn’t) in: Why Travel Insurance is a Must-Have for Your Next Cruise (Even If You’re a Smooth Sailor)

When you’re new to cruising, here’s a simple checklist:

• Medical coverage at sea (your regular health insurance may not fully cover shipboard or foreign ports).
• Trip cancellation / interruption (illness, emergencies, etc.).
• Missed connection / delay if flights or weather mess with your embarkation day.
• Emergency evacuation (this can get very expensive very quickly).

You can buy insurance through the cruise line or a third-party provider. If you’d like a second pair of eyes, we can help you compare options when you plan through us.

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Step 5 – Budget Like a Pro & Avoid Cruise Money Traps

Surprise: the cruise fare isn’t the whole story. Onboard spending is where cruise lines quietly make a lot of their money. That doesn’t mean you have to; it just means you should know the game.

Start with the big picture

• Base fare: cabin + included food + standard entertainment.
• Likely extras: gratuities, drinks, Wi-Fi, specialty dining, excursions, spa, photos, shopping.
• Pre/post travel: flights, hotels, transfers, parking.

To dig into this without your eyes glazing over, we created: Cruise Price Traps EXPOSED! How Cruise Lines Get You to Spend More (and How to Beat Them)

Thinking about a drink package? Use the math, not your emotions. Our Cruise Drink Package Calculator helps you figure out if a package actually saves you money based on your real habits, not wishful thinking.

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Step 6 – Pack Without Overpacking (Free Cruise Packing List)

First-time cruisers almost always bring too much… and forget three important things. We’re trying to cure both problems.

Start with our free, printable packing list that’s been used by tons of cruisers:

For extra “don’t be that person” protection, we also recommend reading:

• 20 Things NOT to Do on a Cruise (That No One Tells You)

Those “don’ts” are pulled from real-life stories and a few personal embarrassments. Learn from us so you can skip your first “I can’t believe I did that” moment.

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Step 7 – Plan Excursions, Safety & “What If” Stuff

Once you know where you’re sailing and roughly what you’ll spend onboard, it’s time to plan the fun parts: port days, sea days, and how prepared you want to be for curveballs.

Ports & excursions

• Decide what kind of day you want at each port: beach, adventure, sightseeing, shopping, or “stay on the ship and enjoy empty pools.”
• Compare cruise-line excursions with reputable third-party tours and DIY options.
• Always check how far an excursion is from the port and how late you’ll be getting back.

To calm your inner “what if,” we’ve also written:

• Lost Your Passport on a Cruise? Here’s Exactly What to Do
• What Happens If You Miss Your Cruise Ship? How to Recover Fast

You don’t have to obsess over these, but reading them once before you sail can give you a lot of peace of mind.

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Want Us to Just Help You Plan It?

If you’re thinking, “This is helpful, but I’d rather have someone who actually knows ships and itineraries walk me through it,” that’s literally what we do.

We’re cruise travel advisors as well as content creators. When you plan your cruise with us:

• You get a real human (actually two of us) watching for deals, price drops, and better options.
• We help with the boring stuff: documents, insurance questions, logistics, and those “is this a terrible idea?” decisions.
• You still get access to all our free videos, blogs, and packing resources.

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Keep Learning: Hand-Picked Next Steps

• First Time Cruise? Here’s Exactly What to Expect
• Cruise Price Traps EXPOSED! How Cruise Lines Get You to Spend More (and How to Beat Them)
• Cruise Drink Package Calculator: Find Your Break-Even Point Fast
• Browse All Cruise Tips on the Blog

However you found us – TikTok, YouTube, Facebook, or late-night panic search – welcome aboard. You’re officially not “new and clueless” anymore. You’re “new and prepared,” which is a big upgrade.