Best Time to cruise: month by month guide for deals & tips

If you have ever asked yourself, or maybe performed countless online searches to figure out, “When is the best time to take a cruise?” — you’re in the right place. I feel that cruising is one of the most flexible ways to travel, but knowing the best time to cruise and looking at things month by month, can help you find those great deals, can save you a lot of money, and help you avoid the crowds. After all, if I was looking for large crowds, I’d head to Amsterdam during Kings Day where you’re surrounded by a million people all wearing orange … but that’s another post.

You can call it a cheat-sheet or quick reference guide, but wanting to know the when, where, and how of finding cruise deals, is why I created this Cruise Travel Planning Calendar — a month-by-month breakdown of the best-value destinations, seasonal price trends, and even repositioning cruise opportunities that most people overlook.

Whether you’re looking to sail to Alaska, the Caribbean, Europe, or Australia, here’s your guide to MAK’n the most of your cruise planning.

Cruise by the Calendar: Where to Go & When

Cruise pricing and experiences shift dramatically throughout the year. Here’s how to plan your cruise month-by-month:

January – March: Escape Season

Escape Season references the period of time immediately after the holidays, when savvy travelers take advantage of:

• Post-Holiday Price Drops: cruise lines often drop prices after the holiday rush, when demand temporarily cools.
• Lower Crowds, Better Availability: Families with school-aged kids typically don’t travel during this time, giving you easier cabin selection, less crowded ships and ports, and shorter lines in a more relaxed atmosphere.

Think of Escape season as “I need a vacation now”, and enjoy destinations including: Caribbean, Bahamas, Mexico, Panama Canal and short cruises.

Wave Season

Wave season is also from January – March, and is a great time to book a cruise for the coming year – as it’s actually the biggest cruise sales season. 

This is when you will find cruise lines offering their biggest booking deals, including:

• Free upgrades
• Prepaid gratuities
• Onboard credit
• “Kids sale free” offers
• Reduced deposits

Think of Wave season as “I’m planning my vacation for later”, and is ideal for booking future cruises for late spring, summer, and fall of the current year.

MAK’n It Work: Ideal season for warm weather destinations and getting great post-holiday deals, but watch out for price increases starting in late March with spring break increases. This is going to be the cheapest time to cruise the Caribbean.

April – May: Shoulder Season

Shoulder Season references the period of time between a destination’s peak season and off-season — a sweet spot when crowds are smaller, prices are lower, weather is still generally good, and deals are easier to find.

Keep in mind though that Shoulder season does vary by destination.  Here are a few specific examples:

Region/Cruise Type                                     Shoulder Season

Europe Cruises                                                April-May, Sept -Oct

Alaska Cruises                                                 May & Sept

Caribbean Cruises                                         May-early June, Sept -early Nov

Mediterranean Cruises                               April-May, Sept – Oct

MAK’n It Work: Shoulder season gives you a chance to score deals on some of the best destinations, such as the Mediterranean, Transatlantic repositioning cruises, Alaska (May) and Norther Europe.  This is the best time to cruise Europe before peak prices hit. More about Repositioning cruises below.

June – August: High Demand, High Seas

As the header suggests, while traveling in June – August on most itineraries you will never feel alone, there are still some tricks to getting good deals during these peak travel times.

• Best Cruise Destinations: Alaska, Northern Europe, Greek Isles
• Why This Works: Summer vacations = peak availability. There are great deals to be found during the peak summer months, though you will find crowded ships.
• MAK’n It Work: Try to book at least 9–12 months in advance for July & August dates and you will find some good deals. Read our post: Cruising on a Budget…Not on a Budget Cruise Line.
• Note: Cruising to Alaska in July is typically going to give you the best weather, though traveling in May (early season) and September and October (late season) will give you the best savings.

September – October: The Smart Sailor’s Season

Smart Sailor Season isn’t printed on a calendar, but experienced cruisers know when it hits. It’s that sweet spot when cruise prices drop, cabins are more available, and the onboard experience feels a little more relaxed. No long lines, no sky-high fares — just smooth sailing for those in the know.

• Best Cruise Destinations: Mediterranean (shoulder season), Canada/New England, Hawaii, Panama Canal
• Why This Works: Great weather + lower prices + thinner crowds
• MAK’n It Work: This is also the best time to grab a deal on a repositioning cruise from Europe to the U.S.  This is also the cheapest time to cruise to the Mediterranean.

November – December: Deals & Decorations

OK, so this isn’t an official season, but the name speaks for itself. It’s the most wonderful time to book (or take) a cruise — when ships sparkle with holiday cheer and cruise lines sprinkle in big savings. From Black Friday and Cyber Monday specials to year-end flash sales, this season offers savvy cruisers the chance to sail in style or plan ahead for next year at a great price.

• Best Cruise Destinations: Southern Caribbean, Panama Canal, Holiday cruises
• Why This Works: Great value early in November and early December. 
• MAK’n It Work: Prices usually surge for holiday cruises, so make sure to book those a year in advance to secure the best pricing

Repositioning Cruises: The Industry’s Hidden Gem

What is a repositioning cruise?
Repositioning cruises are a one-way itinerary offered twice each year, when cruise lines move their ships between seasonal home ports – often across the Atlantic or Pacific.  These cruises offer a tremendous value, though include many at-sea days, and typically have limited ports. 

Why Repositioning Cruises are a Must:

• Typically 10–15 nights
• They often offer unique ports of call
• Are about half the price per night of regular cruises.  As an example, you can book a 13-night Barcelona to Miami cruise for under $1,000 for an outside cabin. That’s only $76 per night!  You will find similar discounted pricing for balconies and suites as well.

When to Reposition:

• April is when the cruise lines move their ships from the Caribbean to various home ports in Europe
• October/November is when the cruise lines move their ships from Europe back to the Caribbean or U.S. ports.

With the right timing, smart planning, and a calendar in hand, you can cruise like an insider — without spending like one. Whether you’re escaping the winter, chasing European sunsets, or catching a repositioning steal, the sea is always in season if you know where (and when) to look.

So don’t just make travel plans. MAK waves.

Learn how to save money while extending your vacation by booking Back to Back Cruises.