Your guide to a better cruise.

Cruise Planning 101

Do you want to plan a better cruise? 

The things we do best

Cruise Matcher

We help you figure out where to cruise and what cruise line will match your lifestyle and travel preferences?

Cruise Better

We know how to cruise better and want to share our knowledge with you. We want you to love your cruise vacation choice, it's your vacation.

Are you ready to plan your cruise?

Cruise Planning made simple

Let me start off by saying that you could contact a travel agent and he or she would walk you through all the steps that I have compiled for you. But what’s the fun in that? Actually, most people will research their options before contacting a travel agent anyway, which is why I wanted to help you get to the good stuff before getting overwhelmed. 

Why listed to me? You can read up about my experience selling cruises here, but take it from me, I was a cruise sales person and I sat across the table from many customers who did not have a clue about the many options available for planning a perfect cruise vacation. It seems easy enough, sure, what’s so hard about looking on a cruise line’s website, picking a cruise and paying for it? But (cringing here), there is a better way. 

I am not proposing that you give up your travel freedom and call an 800 number to book a cruise. What I am suggestion (with enthusisam) is that you do dome preliminary research to make an informed decision. Well, you may be thinking, “that is what I am doing. After all, how hard can it be?” 

Here is why you need to read through my Cruise Planning 101 Guide to a Better Cruise.  I have enough experience matching cruise products to people that you will see the benefit in terms of time and money. 

It’s worth a look. 

Cruise Seasons

Before going through the cruise planning process, take some time to think about the cruise seasons. Sailing during peak season often brings crowds to the larger ships, and prices tend to be higher. Sailing during shoulder season is often less crowded (especially in busy port towns), and there are usually some enticing promotions. With that said, seasonal cruises where weather dictates inventory will sell out in advance and also will fetch top dollar.

June through August 
Peak: Late May thru late August
Shoulder: May thru early June; late Aug thru Sep.

Peak: during holidays, and typically late March thru July
Shoulder: December thru early April

Europe, Mediterranean and Greece
Peak: Late May—early Oct.
Shoulder: Late April, early November.

River Cruising in Europe
April through October

Peak: April thru early June; late Aug. thru Oct. 

Spring cruise destinations: Caribbean, River Cruises,, Mediterranean and Greece, Repositioning cruises

Summer cruise destinations: Bermuda, Baltic, Mediterranean and Greece, Alaska, 

Fall cruise destinations: Repositioning cruises, Canada and New England, Mediterranean and Greece

Winter cruise destinations:  Caribbean, Asia, South America, Antarctica, Panama Canal, Australia, Hawaii, Mexican Riviera

7 Steps to Cruise Planning


After you know when you can schedule your vacation, then it’s time to plan your cruise. Budget should alway be top-of-mind because how much money you can spend on your cruise will help with the final purchase decision. I have put together a Cruise Budget Planning spreadsheet that might help you figure out how to finance your cruise vacation, it’s worth a look.

  1. Choose a destination.
  2. Choose a cruise line.
  3. Make a purchase.
  4. Prepare for cruise.
  5. Pick shore excursions or plan for what you will do in port.
  6. Pre-arrange any shipboard activities that you can in advance. Such as make spa reservations, make reservations for alternative dining restaurants, make special requests well in advance of sailing.
  7. Make the most of the ship. Once you are onboard, there are some things you may want to buy like a drinks package, WiFi, maybe try to score an upgrade, if you like the cruise line consider putting a deposit down for a future cruise and score an onboard credit, if  it’s available.

Step 1 Choose Destination

Probably the hardest part of any cruise vacation (besides going home) is pre-cruise planning. A lot of thought and effort go into the research phase to discover where to cruise.  Each region is different and offers unique experiences. Typically a cruise passenger will choose to cruise close to home to see if they are suited for the sea, then they will venture off to a warm-weather destination. After that, the world of cruising opens up and you might be more inclined to try exotic or boutique cruise experiences. ink to places to cruise

First-time cruisers or seasoned cruisers will find plenty of ports to explore in these popular cruise destinations.




Australia/New Zealand



Canada/New England




River Cruises

South America

South Pacific

US Ports

Step 2 Pick a Cruise Line

The best cruise line for you is the one that you will feel most comfortable on. 

Learn about the cruise lines

The right cruise line for me, may not be a good match for you, but I can help guide you in the right direction. 

My #1 tip is to not pick a cruise line based only on price. You could possibly ruin your entire vacation.

Mainstream Cruise Lines

  • Carnival Cruise Line
  • Costa Cruises
  • Holland America Line
  • MSC Cruises
  • Norwegian Cruise Line
  • Princess Cruises
  • Royal Caribbean International



Premium Cruise Lines

  • Azamara Club Cruises
  • Celebrity Cruises
  • Cunard
  • Disney Cruise Line
  • Oceania Cruises
  • Paul Gauguin Cruises
  • Seabourn Cruise Line
  • Viking Ocean Cruises
  • Windstar Cruises

Luxury Cruise Lines

  • Crystal Cruises
  • Hapag-Lloyd Cruises
  • Regent Seven Seas Cruises
  • Silversea Cruises

River Cruise Lines

  • AmaWaterways
  • American Cruise Lines
  • American Queen Steamboat Company
  • Avalon Waterways
  • CroisiEurope
  • Crystal River Cruises
  • Tauck River Cruises
  • Uniworld Boutique River Cruise Collection
  • Viking River Cruises


Expedition Cruise Lines

  • Alaskan Dream Cruises
  • G Adventures
  • Hurtigruten
  • Lindblad Expeditions-National Geographic
  • Ponant
  • Quark Expeditions
  • Silversea Expeditions
  • UnCruise Adventures

As you can see, there are a lot of companies competing for your cruise vacation dollars.

Carnival Cruise Line is the largest, with 25 cruise ships, and counting (they will add at least four to the fleet in the next 5 years).  

Following right behind is Royal Caribbean, which currently has 24 cruise ships. 

Step 3 Purchase

Once you have put down your deposit, make sure to consider purchasing trip insurance. There are advantages to purchasing a policy at the onset of the deposit.

Step 4 Prep for Cruise

The fun begins. What will you need to bring on the cruise? Who will take care of your pets? How will you get to the port? What other details do you need to arrange in advance?

This is also a good time to visit the cruise line’s website and start your online registration. Use your booking number to pre-register.  The next two steps guide you through the steps of booking shore excursions and customizing your onboard experience.  We put together a rather large cruise packing list that you can check out to make sure you don’t forget something. 

Step 5 Pre-Book Shore Ex

Although you could always book shore excursions on the ship, popular activities sell out fast. You might also decide that you could explore on your own, or reserve an organized tour offered by an outside vendor. 

Step 6 Book Onboard Activities

Visit the cruise line’s website portal for booked guests and pre-purchase any onboard amentieis that strike your fancy. This is the time to book any alternative dining venues, if you can. So many times on the big ships you will be shut out of speciality dining reservations because the prime time spots go to guests in suites and passengers with loyalty program status. 

Step 7 Explore the Ship

After all that planning, it’s time to get onboard and explore the ship. Once you settle into your cabin, take time to explore the ship and make changes. For example, if you don’t like your dining option, visit the Maître d’ who will be available during limited hours on embarkation day to facilitate dining requests. Also, you may want to purchase a drinks package, which are only sold on the first couple of days on the ship. My favorite thing to do on embarkation day is to visit the library (if your ship has one) to borrow paperback books that guests left behind. 

Close Menu