What’s the Best Month to Cruise? Pros & Cons of Sailing Each Month of the Year

Let’s get one thing straight right at the start. There is no bad time to cruise. Whether you want to have a summer vacation or a winter getaway, the weather somewhere in the Caribbean is always warm and welcoming.

The weather can always be beautiful in the Caribbean, no matter when you sail. Still, there are definite advantages and disadvantages to sailing certain times of year.

That said, with our experiences having sailed seemingly every month on the calendar, we have found there are definite advantages and disadvantages to sailing each month of the year. For example, cruises in August offer the ability to sail when the kids are out of school (meaning entire families can travel together). On the other hand, August is also notorious for hurricanes disrupting travel to Caribbean ports.

As you’ll see below, there are trade-offs with each time of year to sail. No month is perfect. However, many of the potential downsides are manageable in our opinion — and shouldn’t deter you from taking a cruise when it fits your schedule and budget.

Taking a Cruise in January

Pros: We like sailing in January as one of the biggest advantages of cruising this time of year is price. During this time of year school is in session and many people are back at work after a holiday break. That means it’s difficult for many to cruise. Cruise lines typically have discounted rates to fill up the ship in January; the same cruise departing at the height of the busy summer can cost hundreds of dollars more than in January.

As well, when winter has gripped most of North America, the Caribbean still offers a warm getaway with lots of sunshine. It’s a welcome change from the snow and cold see in most areas.

Cons: If you are a family, it might be tough for you to take a January cruise. It will usually mean the kids have to skip a few days of school to take the trip. In addition, if you have to fly in for your cruise, there are chances of winter weather causing delays to your schedule. You’ll want to make sure you plan your flight to arrive the day before your cruise, just in case. 

As well, this time of year trips from the West Coast will still be cool and Alaskan cruises don’t start sailing until April/May.

Taking a Cruise in February

This cruise to Mexico in February featured sunny weather that had plenty of people out soaking up the sun.

Pros: February offers the same advantages to sailing as you see in January. Fares are normally discounted, with the ability to save hundreds on a cruise by sailing in February versus the height of the summer season. It’s also cold in most of the United States and Canada, making a warm getaway awfully enticing.

Cons: Like January, you might find it difficult to take time off after the holidays to enjoy a cruise. Doing so means spending vacation days early in the year and/or having the kids miss school. There are also still strong snowstorms in many parts of North America during February, meaning it’s possible that getting to the port can be an adventure if you have to fly in for your cruise from a northern city. 

As well, even if sailing to the Caribbean, the pools and water on a ship may still be too cool to enjoy fully. Don’t plan on spending much time in the water in our experience.

Taking a Cruise in March

Pros: With warmer weather and Spring Break, a cruise is on many people’s minds come March. In fact, if you are a Spring Breaker, this is a great time to sail as a cruise offers an affordable getaway to the beach without having to worry about flights or hotel. Just hop on the ship and start your vacation.

As well, if you’re headed to the Caribbean, March can be warm — but not too warm compared to the heat of the summer months.

Cons: If you aren’t a Spring Break fan, then this might not be the best month to sail. Cruises — especially shorter trips (3-5 days) — will have a younger crowd and more of a party atmosphere. You’ll also see a spike in prices starting in mid-March as cruise lines raise prices for trips that coincide with Spring Break.

Taking a Cruise in April

These trips in April featured lower prices and great weather in the Caribbean. Prices are lower than the summer and risk of bad weather is minimal.

Pros: April represents one of your last chances to get a deal on a cruise before the busy summer sailing season. Discounts and deals are still available up until about mid-May, giving you the chance to save a bundle on a trip compared to sailing just a month or two later. As well, the threat of snow is diminished in northern parts of the United States and hurricane season isn’t here yet for port cities. It’s hard to find better weather than what you get in April.

Cons: After Spring Break, it’s back to school and work for most people. That means many have a tough time taking a trip at this time a year. That’s unfortunate because April is the “Goldilocks” of cruise months for the Caribbean — it features affordable prices, good weather, and is before hurricane season gets cranked up, which always adds a wildcard to travel in the Caribbean.

Taking a Cruise in May

Pros: Heading into May, cruisers hitting the Caribbean can start to experience some warmer weather both at home and on their cruise. While the water and beach are typically warm enough for swimming and laying out even during the coldest winter months, it is a few degrees warmer in May, which can make it more inviting to hit the beach. For example, Cozumel’s average high in January is 83, compared to 91 degrees in May. If you’re the type who loves warm water, May is when things start to heat up.

Cons: If you wait until too late in the month, you’ll start to see higher prices for your cruise. The end of May marks the start of the summer cruising season, and fares start to jump up. One place where you can save? Cruises to Alaska typically start their season in May, and it’s the cheapest month to sail to that region. We’ve sailed Alaska this time of year and highly recommend it.

Taking a Cruise in June

Pros: If you want a summer getaway with warm weather and water, June is a great choice. Hurricane season starts June 1st, but it’s still rare that you’ll have a chance of a hurricane this early. Meanwhile, the Caribbean is starting to heat up so you can have a true beach summer vacation without worrying about it being too chilly either on the ship or in port. Also, with the kids out of school, you can take them on your trip without worrying about absences.

Cons: With schools out of session and the popular summer vacation season, fares spike for June and through the rest of summer. You’ll usually be paying more for the same cruise compared to taking it earlier in the year. As well, if you aren’t the type that likes to cruise with families on the ship, then keep in mind that summer months typically see an influx of kids.

Taking a Cruise in July

Cruise in July
July features warm (hot!) weather if going to the Caribbean or The Bahamas, along with higher prices. Alaskan cruises are also at their peak this time of year.

Pros: Like June, you’ll find warm and sunny days filling July. And with the kids out of classes, you’ll have the opportunity to sail without missing school, making it an ideal time to cruise if you are traveling with kids. While it is warm in the Caribbean, regular afternoon “pop-up” showers can help cool things off during the heat of the afternoon. This also represents the height of the Alaskan cruise season, offering the most options (albeit at higher prices) of the year.

Cons: The biggest negative with sailing in July is hot weather. On sunny days, it can get downright hot in many Caribbean ports. If you aren’t used to the heat and humidity, it can be draining. As well, you should start to look out for hurricanes and tropical storms during July — especially if traveling later in the month. While cruise ships will avoid any storms, they can be unpredictable and cause changes to your itinerary.

Also, just keep in mind that you should expect the highest cruise fares of the year during this time.

Taking a Cruise in August

Pros: Consider August the last hurrah if you want to be able to cruise with the kids out of school. While the weather is hot, being able to travel as a family without missing school days is the biggest draw of sailing in this month. If the kids don’t start back until September, then you can sometimes find deals late in the month that can save you considerably on your cruise fare.

Cons: Similar to July, you can run into weather issues in August. Specifically, the heat and humidity is at its worst in the Caribbean during August. While afternoon showers can cool things off, they are not a guarantee. You also have to start worrying seriously about hurricanes. Late August is reaching the peak of hurricane season. While the chances are low that your specific cruise will be hit by a storm (cruise lines steer clears of storms as much as possible), it could disrupt your trip if a hurricane hits a port of call.

Taking a Cruise in September

Pros: With the busy summer cruise season past, students back to school, and summer vacations in the rear view mirror, September offers a “shoulder” season of sorts. While the Caribbean is still warm — perfect for those that want to hit the beach and the water — cruise fares are heavily discounted versus the expensive summer months. In other words, you get the warm weather of the summer with the lower prices of the fall. As well, your cruise is likely to have fewer kids onboard. It’s also the last chance to sail Alaska for the season, when crowds are fewer and fares are generally cheaper.

Cons: September actually marks the peak of hurricane season. Historically, the first week of the month is the busiest for storms and then activity quickly drops off later in the month. Still, even if your ship isn’t directly impacted by a storm, it can cause issues at Caribbean ports.

Taking a Cruise in October

Cruise in October
Cruising in October features a great mix of good weather with affordable prices. It’s one of our favorite months to sail.

Pros: If you’re not wanting to deal with heat, then October is a great time to visit the Caribbean. While the humidity is always a factor, October sees the start of a cooling trend in the weather. As well, while hurricanes can occur in October, the season is largely over so you don’t have to worry about them disrupting your trip as much. Finally, cruise prices also fall during this time of year, meaning you can book a solid deal without spending a bundle.

Cons: It shouldn’t be a surprise that April and October are two months that we consider great times to sail. Like April, the biggest con is that it can be difficult for people with kids to travel without taking their children out of school for a few days. Apart from that, the month sees good weather and cheaper fares, and it’s before the harsh winter hits many places in the U.S. and Canada, disrupting air travel to the port or the weather in the port city.

Taking a Cruise in November

Pros: By the time November rolls around, people are starting to think of warmer weather, especially if you live in a cold area. Taking a trip during this month can lead you away from the cold and gray to the warm and blue. It’s also a great time to find cheap cruises, apart from trips that sail during the Thanksgiving holiday (which are more expensive).

Cons: Scheduling around the Thanksgiving holiday can be tough, and if you have to fly to your cruise during the busiest travel time in the United States, it can mean dealing with long lines and delays at airports. Apart from that, November is a great time to book a cruise with cheap deals and nice weather in the Caribbean and The Bahamas.

Taking a Cruise in December

Pros: The period between Thanksgiving and Christmas is one of the absolute cheapest times to sail. With many people not looking to travel between these two major holidays, cruise lines slash fares. It’s not unusual to see a trip costing 50% less than a comparable trip during the summer. Needless to say, cruising in December is also a big draw for people wanting to get away from the snow and cold of many places in the north.

Cons: Trying to fit a cruise between Thanksgiving and Christmas can be tough for many schedules. And while many people take a cruise during Christmas itself, those trips are more expensive. If you are traveling by air, be ready for the possibility of delays due to weather and holiday travel crowds.

What Are the Least Expensive Months to Sail?

If you want to sail for cheap, then we suggest looking at months like January, February, April, May, September and October. We find that rates during these months tend to be less expensive than for the same cruise if headed to the Caribbean. During these times fewer people are traveling, leading to generally lower cruise fare.

If headed to Alaska, then the months are more limited. The season runs largely from May through September. In this case the ‘shoulder’ months of May and September offer the lowest prices.

So Which Month Is Best to Cruise?

As mentioned above, there is no “bad” time to sail. However, if we had our pick, we would suggest either April or October if you need to fly into a cruise port. The generally good weather and low prices combine to make it a cheap and easy time to sail.

If you are within driving distance of a port, then you can expand these months to include early winter months and later fall months. During these times the weather on a cruise will be warmer than back home, prices are very affordable, and if driving, you can get to the port without worrying about airline delays.

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