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An Introduction to Cruising – Where and When to Cruise

The Grand Princess docked at Pier 27 in the heart of San Francisco

An Introduction to Cruising – Where and When to Cruise

Taking a cruise is my favorite kind of vacation. You unpack and pack just once, and every day you can wake up in a different city or even a different country. Cruises can be a tremendous bargain, as your fare includes your cabin, transportation between ports; unlimited food in a variety of venues; entertainment; pools and hot tubs and more. Optional packages offer unlimited bar drinks, wi-fi, and crew gratuities. Also available are shore excursions, spa visits, specialty dining, casinos – and art auctions!

You can tailor your cruise to your specific preferences by choosing the destination to which you’ll be cruising, the length of the cruise, where you’ll be sailing to and from, the size and style of the ship, the demographics of your fellow passengers and the type of cabin in which you’ll be staying.

Aboard the Royal Princess, sailing through the Alaska Glacier National Park.
Aboard the Royal Princess, sailing through the Alaska Glacier National Park.

Popular destinations include Alaska, the Caribbean, Europe, Asia, and Australia and New Zealand, as well as cruises across the Atlantic and Pacific Ocean. Ships depart from dozens of US cities as well as countless overseas locations. Ships range in size from hundreds of passengers to those holding more than 7,000. Ship styles range from tasteful floating hotels to full-blown amusement parks. You can choose to cruise with families, older folks, party animals, young couples and more. Cabins include inside cabins, balcony cabins and multi-room suites.

The first article in this series explores the cost of cruising and where and when to cruise. Future articles will help you choose a cruise line, a ship, and a cabin, and help you explore the many onboard experiences.


Given all that’s included, cruises can be a tremendous bargain. It’s easy to find cruise fares starting at less than $100 per day person, while you can also spend $6,000 per person per day for a multi-room luxury suite.

Here are some factors that influence how much your cruise will cost:

  • Which cruise line you choose: Disney, for example, tends to be more expensive than Carnival or Princess, while Regent Seven Seas is much more expensive than Disney. (I’ll discuss the various cruise lines in a later article.)
  • When you cruise: Summer and holidays are generally more expensive than winter, with spring and fall somewhere in the middle.
  • The length of the cruise: A 21-day cruise will cost more than a seven-day cruise…
  • The cabin you choose: Inside cabins are the least expensive, while balcony cabins can be twice the price of inside cabins; and mini-suites, suites and luxury suites are much more expensive.
  • When you book your cruise:
  • Cruises booked January through March, a period of time known as the wave season, often offer the lowest prices of the year regardless of when you’re actually sailing.

    • Black Friday and Cyber Monday often offer excellent deals as well.
    • You can sometimes find very low prices 30 to 90 days before a cruise if the ship has unsold cabins. Last-minute deals are great if you live close enough to drive to the ship. Otherwise, you may find that the cost of last-minute airfares wipes out your cruise fare savings.
  • If you pay full price or wait for cruises to go on sale. An easy way to find out about deals is to sign up for offers at each cruise line’s website. There’s no cost or obligation, and they’ll send you regular email offers and news.

Be aware that advertised prices generally do not include taxes, port charges or fees, each of which will increase your total cost. The prices also don’t include crew gratuities which start at about $16 per person per day and increase based on your cabin type. As always, these extra fees vary widely among cruise lines. Be aware that some cruise lines offer lower base fares and then add higher fees, so you really need to know the final price before you commit to a cruise.

In addition to the cost of the actual cruise, other potential costs are parking, or airfare to and from the ship and transfers to and from the ship. Other costs may include onboard expenses such as alcohol, wi-fi, spa, casino, specialty dining, shore excursions, and more. Be aware that you can easily spend as much on these extra cost items as you do on your cruise fare. (I’ll discuss these expenses in a future article.)

The Grand Princess docked at Pier 27 in the heart of San Francisco
The Grand Princess docked at Pier 27 in the heart of San Francisco

Deposits and refunds

Depending on how far in advance you book your cruise, you’ll either pay a deposit or you’ll be asked to pay the full fare along with any port charges, taxes, and fees.

  • Deposits: These can be as low as $1 during promotional events but are more likely to be $100 to $400 per person, with the higher deposits required on longer cruises. Deposits may or may not be refundable, so it’s important to ask, and if they are, how close to the departure date they’re fully refundable. Most cruise lines will offer a deadline – perhaps 90 days before your cruise – for a full refund. After that, the refundable portion of your deposit declines as the departure date approaches.
  • Payment in full: You’re more likely to have to pay the full fare – along with any port charges, taxes, and fees – if you book a cruise near its departure date. The cutoff date varies from cruise to cruise, and from cruise line to cruise line, with 90 days being a common cutoff.
BOLT roller coaster aboard Carnival's Oasis Class Mardi Gras cruise ship.
BOLT roller coaster aboard Carnival’s Oasis Class Mardi Gras cruise ship.

All-inclusive packages

Cruises on luxury lines such as Regent Seven Seas, Seabourn, Silversea and others include are truly all-inclusive and generally include alcoholic beverages, Wi-Fi, airport transfers, gratuities, laundry services, shore excursions, specialty restaurants and more.

Most cruise lines, however, will offer you an “all” inclusive option when or after you book your cruise. I put “all” in quotes because what’s included varies, and the price for the package varies dramatically from cruise line to cruise line. (I’ll talk about these packages in a later article.)

Istanbul's Blue Mosque from aboard the Carnival Freedom.
Istanbul’s Blue Mosque from aboard the Carnival Freedom.


Cruise lines visit more than 1,200 ports of call, so you can sail almost anywhere in the world. Popular destinations near the United States include Alaska, the Caribbean and Mexico, while popular international destinations include the Mediterranean, Norway, Asia, Europe, and Australia/New Zealand. These destinations are often served by multiple cruise lines, each of which may deploy several ships to the region. In the 2022 Alaska season, for example, cruise lines deployed a total of 60 cruise ships to the region.

Some destinations, such as Alaska, Europe, and South America, are seasonal. Ships might spend the Northern Hemisphere’s summer in Alaska, for example, and then move to South America during their summer months. (Cruises between these regions are called “repositioning” cruises and are often available at bargain prices. More on these later.)


Some cruise itineraries visit a different port almost every day, while others include scenic cruising or sea days. And most Caribbean cruises include visits to a cruise line’s private island.

Once you’ve decided on a region, such as Alaska or the Caribbean, you can then choose the ports you’d like to visit. It’s worth noting that with a few exceptions, cruise ships tend to spend a single day in each port, arriving in the morning and departing in the late afternoon or evening.

Ports come in three varieties:

  1. Ports like San Francisco or San Diego, where the ship docks near a major downtown area and you’ll find many attractions within walking distance or a short Uber or taxi ride away. You’ll also be able to choose a wide variety of shore excursions for attractions both close to the ship as well as those further away.
  2. Ports like many of those in Alaska and the Caribbean, where the ship docks in the heart of a small town which offers a limited number of local attractions, and where you’ll also have lots of shore excursions to choose from.
  3. Ports that are far from the cities they serve. Ships visiting Rome, for example, dock in Civitavecchia, which is about an hour away. Paris is served by Le Havre which is about two hours away, and London is served by Southamption which is also about two hours away. In some of these ports, you can use public transportation or shuttles to reach the city, while in others you may need to sign up for a shore excursion to get into the city.
Harvest Caye Norwegian Cruise Lines has a private island located off the southern coast of Belize.
Harvest Caye Norwegian Cruise Lines has a private island located off the southern coast of Belize.

Private Islands

Most major cruise lines operating in the Caribbean have created their own private islands. If you like sun, beaches and pools, these islands are for you! If you don’t (like me) they may not add much to your cruise.

Most private islands include beaches and pools, lounge chairs, a buffet lunch, and water and iced tea. They also offer extra cost bars, souvenir shops and beach equipment rentals. Some islands include extra cost water parks, cabanas, restaurants, wi-fi and various shore excursions. Cruise ships are able to dock at some islands, while tenders are required at others.

Scenic Cruising

Cruises to regions such as Alaska, New Zealand, Norway, and South America often include one or more days devoted to “scenic cruising” which might include sailing through or up to glaciers and fjords.

Sea Days

Depending on your itinerary, the length of the cruise and where you start and end your cruise, your itinerary may include “sea days” while your ship sails between ports. A one-week Alaska cruise might include a single sea day, while a 15-day repositioning cruise from Europe to the US might include 10 sea days. Depending on the cruise line, sea days may be filled with back-to-back activities including enrichment / educational lectures, shows, Q&A with the crew, and much more. Some people love days in port, others (including me) love sea days, while others like a mix of the two.

When choosing an itinerary, make sure you’re happy with the mix of port days, scenic cruising, sea days, and if applicable, private islands.

Repositioning Cruises

One of my favorites!  As I mentioned, cruise ships often spend part of the year in one region, such as the Mediterranean, and then move to a different region, such as the Caribbean, for the rest of the year. The cruises between these regions are called “repositioning” cruises and typically take place in the spring and the fall. Common cruises include Europe to Florida, Alaska to California, North America to South America, Asia to the US, and then back again six months or so later.

The length of these cruises vary from several days, in the case of Alaska to California, to two or three weeks, for- North America to South America. Some of the cruises include several port days, while others may offer only a few or even no port days at all.

Since these cruises often start and end at ports very far apart, and since they include many sea days versus port days, the cruise lines offer these cruises at VERY low prices.


In the Northern Hemisphere, May, September, and October generally offer the best weather and smallest crowds, while November, March and April are the best months in the Southern Hemisphere. Having said that, here are some other considerations:

Alaska – The official cruise season is from May to September, and you can find countless articles outlining the pros and cons of each of these months. Based on nearly a dozen visits to Alaska, however, it’s pretty clear the weather is absolutely not predictable and can be warm and sunny one week and cold and rainy the next. Days are longer during the summer months, and the ships and the ports will be crowded. Some research before you select a cruise will help you pick dates that best accommodate your preferences.

Caribbean – December through April offers the best weather, while August to September is peak hurricane season.

Stay tuned for the next article, where I’ll help you choose a cruise line, a ship, and a cabin!

Dave Archer is a retired business executive who has traveled internationally for business and pleasure for over 40 years and has visited nearly 100 countries in Asia-Pacific, Europe, South America, Australia, and Middle East/Africa. Dave is also an avid cruiser with nearly 50 cruises under his lifejacket, uh, belt.

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