Don Herman Everything you need to know about how to plan a cruise, in the order we’d do it.
I remember planning my first cruise. Or rather, I remember trying to plan my first cruise. I had no idea what I was doing. I looked at the promo material, thought everything looked great, signed up online and waited for it all to happen.
Then reality showed up. I’d missed the deadlines for securing excursions and booking specialty dinners. And the cabin I’d been assigned was right under the Lido deck pool area, so the joggers and chair movers woke me up at 7:30 every single morning. I made a lot of mistakes because I didn’t know any better.
And yet, Alaska was magical: glaciers, totem poles, coffee on a balcony surrounded by floating ice. It just could have gone a lot more smoothly.
That’s why we wrote this guide. If you’re wondering how to plan a cruise without repeating my mistakes, you’re in the right place. Over more than two dozen ocean and river cruises together, Dwaine and I have learned what really matters. This cruise planning guide breaks it all into 13 steps, in the order we’d tackle them. Follow along from start to finish, or jump to the step where you’re stuck.
The goal is simple: walk into that first conversation with a travel agent informed, not flustered.
How to Plan a Cruise: Your 13-Step Roadmap
Missed excursion deadlines? That’s Step 9. The noisy cabin? Step 5. Everything else I got wrong is in here somewhere, too.
1. What a Cruise Really Costs
Start with the dream, then put real numbers to it. See what a cruise costs beyond the fare, so nothing surprises you later.
2. Choose Your Cruise Type
Ocean or river? Mega-ship or small ship? Find the style that fits how you like to travel.
3. Cruise Itinerary Planning Tips
Where to go, when to go, and how ports, sea days and seasons shape the trip.
4. Decide How to Book
Travel agent, cruise line direct or online? Compare your options, and learn how fare tiers work so you know what you’re paying for.
5. How to Choose a Cruise Cabin
Inside, oceanview, balcony or suite, plus where on the ship you’ll want to be (and which decks to avoid).
6. How to Lock In and Protect Your Booking
Deposits, payment deadlines and travel insurance, so a change of plans doesn’t cost you the trip.
7. Pre- and Post-Cruise Stays
Getting to the ship, and whether to add a night or two on either end.
8. Are Cruise Drink and Wifi Packages Worth It?
Drinks, wifi and other extras. Which are worth paying for, and which aren’t?
9. How to Book Cruise Shore Excursions
Ship excursions or independent tours? How to book, and how to keep your days in port relaxed.
10. Pre-Cruise Requirements Checklist
Documents, check-in and the final to-do list before you leave home.
11. Cruise Embarkation Day Tips
What to expect from the pier to your first evening onboard.
12. Make the Most of Your Days Onboard
First-time cruiser advice for getting the most out of your days at sea.
13. Cruise Disembarkation Tips
Getting off the ship smoothly and wrapping up the trip.
Frequently Asked Questions
How far in advance should you plan a cruise?
Earlier than you think. Popular sailings, especially Alaska and river cruises, often sell the best cabins and dates months ahead, and early booking gives you more choice on ship, cabin and excursions. Also watch the deadlines after you book, like final payment and excursion or dining reservations. I missed a few on my first cruise. See Cruise Itinerary Planning Tips and Decide How to Book.
How much should you budget for a cruise?
The fare is only the starting point. Budget for taxes and port fees, gratuities, shore excursions, drink and wifi packages, airfare, travel insurance, and any hotel nights before or after the cruise. Add those up before you commit so nothing surprises you onboard. Our budgeting guide walks through each category in What a Cruise Really Costs.
Is it better to book through a travel agent or the cruise line?
Both work, and the right choice depends on how much guidance you want. A travel agent can answer questions, compare fare types and help sort out cabins, while booking direct gives you full control. Either way, know what you want before you call. We compare the options in Decide How to Book. Personally, we use an online travel agent — one assigned to us with a direct line we can call. It’s so helpful to have someone who can answer questions and maybe get you out of a jam!
What should first-time cruisers know before booking?
Know your priorities before you book: the cruise style, the itinerary, and the cabin. Check where the cabin sits on the ship (noise from above or below matters more than you’d expect), and understand what your fare includes before paying for upgrades. Start with Choose Your Cruise Type and How to Choose a Cruise Cabin.
The State Department’s tips for cruise passengers are a good checklist, too.
Do you need travel insurance for a cruise?
It’s worth serious consideration. A cruise is a big, mostly prepaid commitment, and plans can change for reasons you can’t control. Policies differ in what they cover, so read the details before you buy. We cover the basics in How to Lock In and Protect Your Booking.
Who’s Behind This Guide
We’re Don and Dwaine, retired travelers who have been together almost 30 years, and we’ve been comparing cruise notes for most of them. Our cruises include the Caribbean, Alaska, the Panama Canal, the British Isles, a Norway northern lights sailing, the Nile, and the Rhine, Danube and Elbe rivers. Our experience is mostly on Princess and Viking, and we try to point out when there are differences in the cruise lines. We don’t rewrite press releases. Everything in this guide comes from trips we’ve actually taken, mistakes included.
Ready to Get Started?
Start with What a Cruise Really Costs
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Hello Don,
I’ve never been on a cruise, but an Alaska cruise is very high on my list of things I want to do, so I definitely have questions! For someone taking their very first cruise, how far in advance would you recommend booking? And with Alaska specifically, is there a particular time of year you think is best for a first trip?
Your section about choosing a cabin also got me thinking. If I’m going all the way to Alaska, I feel like I’d want a balcony so I could actually sit outside and enjoy the scenery. Do you think a balcony is worth the extra cost on that type of cruise, or would you put that money toward excursions instead?
I have a feeling once I finally start planning this trip I’m going to have a million more questions.
Angela M 🙂
For Alaska, I recommend a full year in advance. These are some of the most popular cruises out there, so they do fill up fast – and even if they aren’t full, if you’re picky about cabin location, THOSE fill up fastest. I think a shoulder season for Alaska is really nice – late August after the kids are in school things really slow down onboard.
For Alaska, IMO, a balcony is a MUST. It really is pleasant to sit out and watch the scenery go by, especially if you choose the full one-way itinerary (Anchorage to Vancouver). The circuit through Tracey Arm is OK, but once you’ve done the full Glacier Bay, nothing else compares. https://cowboyconcierge.biz/cr…
An article after my own heart, especially since we are planning an Alaskan cruise for next year. You are right, there are a lot of mistakes one can make when planning a cruise.
The two that we made last time was buying a soft drink package, and discovering the free options were enough when we got on board and the other was booking an expensive excursion on the ship and on getting there discovering that the same excursion could be booked at the port at half the cost.
Oh, yeah, I have a whole post on the drinks packages alone! They are intentionally confusing, but I think I found the best way to figure out if they are worth it. Check out the article at https://cowboyconcierge.biz/ar…
Something I would probably worry about on a first cruise is seasickness, especially if I had never spent much time on a ship before. Does the type of cabin or its location make much difference for someone who is sensitive to motion? I have heard that lower decks and cabins closer to the middle of the ship can feel more stable, but I’m not sure how much that matters in practice. Would you consider this when choosing a cabin?
I have a good section that deals with that very issue. I feel for people who are prone, as neither Dwaine nor I have ever had a problem – but we’ve known others who have. Yes, the location of the cabin makes a difference, but preparation makes a bigger difference. The prescription Scopolamine is the best, but Damamine works too, IF you take it before you feel sick! It does nothing to cure you after you’re already nauseous. For more: https://cowboyconcierge.biz/fi…
Thanks, Don, for sharing the less glamorous side of that first Alaska cruise, because chair-moving noise definitely isn’t part of the balcony-coffee dream! When choosing a cabin, what do you and Dwaine check beyond the deck plan to get a better sense of how quiet it will be?
For someone planning their first cruise, how do you keep track of excursion and dining reservation windows when those dates fall well before departure? Do you have a go-to calendar system, or does your travel agent help flag those deadlines?
That’s one area the cruise lines aren’t terrific about. They do send out an email announcing when the windows are open for excursion booking, but it’s easy to miss. I put a note in my personal calendar at 3-month intervals before the cruise date and it prompts me to check to see if they’re open. The dining is usually open right away, BUT some cruise lines won’t let you book specialty dining until you’ve paid in full, so if your reservation doesn’t “take”, that may be why.
Oh this is my dream.
With my family, hopefully, when I am fully retired, I can fulfill this.
Which country is the best to start a cruise with the whole family? I live in Canada BTW, and I’m originally from the Philippines.
My hubby used to be a seaman and he always says he have gone to this country and that, and it’s so hard to convince him to travel as as family. How can I convince him? Any tips?
Marita
For you, an Alaska cruise would work really well. Many ships leave out of Vancouver and travel up to Anchorage, via Glacier Bay. An Alaska cruise is perfect for a family – we’ve done it ourselves with a group of six and everyone had a great time. The nice thing is, there’s very little work you have to do in planning – everything is taken care of, from lodging and meals to entertainment. All you need to do is settle on any excursions you may want (whale watching, a trip to a glacier, bear-watching, even fishing.) If you’re on the eastern coast, there are leaf-peeper cruises up the St. Lawrence around to Maine that are also beautiful. Best of luck!