The Best Time to Book a Sandals Vacation

By Jim CampbellJim CampbellJim CampbellJim is the owner of A lifelong traveler, Jim's wanderlust has led him to spend months living on the Mayan Rivera, instruct SCUBA diving in Croatia, sail from San Diego to Hawaii, and cruise the Caribbean on a catamaran. Jim launched his honeymoon business while planning his own honeymoon in 2019. Since then, he has helped thousands of honeymooners plan their trips through his honeymoon travel agency.Meet Our Team | Updated on June 24, 2024 | Posted In: Sandals Resorts

by Debbi K. Kickham

Once I have the idea in my head that I am going to take a Sandals vacation, it is hard not to book it immediately and leave the following week. That is rarely a smart idea because this spontaneous decision often does not consider important factors such as the weather, crowds, or how much it could cost. So, when is the best time to book a Sandals all-inclusive, luxury vacation, based on these things?

A Sandals Resort vacation can be one of the most magical events you will ever experience. These gorgeous, ritzy resorts are all-inclusive — all of your gourmet restaurant meals, wines, spirits, beers, soft drinks, snacks, ice cream, cafe pastries, some watersports, and more — are factored into the price of your accommodations. Sandals also features everything you could possibly need, within the nightly hotel rate, offering you immense bang for your buck. (I mean, wouldn’t you love to get a free, delicious, gourmet coffee confection at 3 PM every afternoon, instead of reaching into your wallet and paying for it right there? That’s just one small example of how GREAT Sandals’ all-inclusive Resorts are). Furthermore, Sandals Resorts are located in some of the most beautiful, picture-postcard-beautiful Caribbean destinations. However, it doesn’t take much to put a damper on that vacation. (For example, you might not get the exact room you want in high season, whereas if you book in “off” season or “shoulder” season, you may have many more attractive options.) Following here is everything you need to know about the perfect, ideal timing to book your Sandals Resort honeymoon, second-honeymoon (complete with vow-renewal ceremony) or romantic vacation.

One word of warning — make sure to check your passport! (Personally, as a long-standing professional travel writer, I have found that the BEST, least expensive, and most convenient way to obtain or renew a passport is at

best time to book a sandals vacation

When to Book Based on Weather

Sandals Resorts don’t have the typical four-season weather you see in most of the United States. They only have two seasons, the wet season and the dry season. The temperature stays about the same year-round.

It may seem obvious that you should book your Sandals vacation during the dry season. Still, there are some advantages to booking in the wet season. There are also a few factors that can make the weather feel hotter or milder.

Wet Season

The wet season is also hurricane season, so I do not recommend booking your Sandals vacation from early June to late November. However, you may catch some fantastic deals during these months. If you’re trying to save money, these may be the months you’re looking for to book your Sandals vacation.

I recommend purchasing travel insurance if you decide to book during these months. That way, if a hurricane does decide to impede your vacation, you won’t be compromised, However, you should also expect to have rain almost every day, in the afternoons. 

Dry Season

Or as I like to call it, the “less-wet season.” You are more than likely to encounter light afternoon rains at least one day of your vacation year-round. This is what makes the islands tropical, and they wouldn’t be as lush without these rains. However, the technical dry season is from early January to late May.

During these months, you are much less likely to have rain ruin your entire vacation. Some islands, such as St. Lucia or parts of Jamaica, will only get rain at their highest peaks. Most other Caribbean islands will be a bit overcast every day, with some light showers here and there. 

Average Temperatures

The Caribbean has year-round warm weather, with the average temperatures ranging from 75°F to 85°F. Who doesn’t love that? That’s what makes it such a desirable winter getaway! What makes the difference is the position of the sun and the trade winds. 

The sun is highest in the Caribbean during the Summer, so it will feel much hotter because of the sun beating down on you. During the Winter, the sun moves to the Southern hemisphere, so the heat from the sun is not as direct. The temperatures will feel nicer during the Winter.  

The trade winds come from the East, so it will feel cooler if your Sandals resort is on the East side of the island. Therefore, you should stay when the sun is highest during the Summer if your chosen resort is on the East side of the island. If you’re planning a Sandals’ vacation in the Winter, choose a Sandals resort on the West side, so you don’t catch those winds as much.

When to Book for the Best Deal

Booking to get the best deal primarily depends on when there is the most demand for a Sandals vacation. However, a few other factors can make the prices vary, like the holidays and the dates that Sandals runs special offers. 

Low Season

The low season is when there is a very low demand for a Sandals vacation. You’ve probably already guessed when the low season is, but if you haven’t, it’s during the wet season. That’s when Sandals lowers their rates significantly to encourage people to book during these times. 

The low season is from July to early November. Rates can be as low as $225 per person nightly, depending on what Sandals resort you book. You can also find good deals on excursions and other extras at your preferred Sandals resort during this time. This just might be the time to book yourself in an overwater bungalow, which, in my humble opinion, is the thrill of a lifetime. When you’re in the warm, tropical waters, in which your bungalow sits, who cares about a few raindrops? Inside, you can enjoy “Fish TV” as the bungalows have glass floor panels, enabling you to see the gorgeous fish right below. In a word, it’s unforgettable.

High Season

High season is when anyone and everyone makes their way down to the Caribbean, to escape the cold. The high season is from December to mid-April. During this time, demand for a room at Sandals — especially an overwater bungalow — is exceptionally high, so they book up fast and often sell out. There is limited availability during these months, meaning that Sandals resorts can charge more, so be advised. 

Although high season generally costs more, it does not mean you can’t find a good deal! Sandals has special deals for last-minute bookings year-round. They’ll give you a discounted rate on rooms that people have canceled or just haven’t booked yet. By last minute, I mean within the week, so you better have your bags packed, your passports up-to-date, and be ready to go if you plan on booking any last-minute deals offering great savings. 

Shoulder Season

Shoulder seasons are the months bordering the low season and the high season. These are November to Early December and April to June. I typically book my vacations during the shoulder seasons because you can get a decent rate while avoiding huge crowds and bad weather. I call this “getting high end without the high spend.” Clearly, it is “luxury for less,” and a smart way to travel. Just as you can get great savings on a wedding during the shoulder season, the same rules apply to honeymoons in the shoulder season — the financial savings can be enormous.

Typically April to June will be slightly cheaper than November to December because there aren’t many significant holidays bordering those months. Holidays bring the prices back up, which I will review in the next section. You also have more selection with three months to choose from instead of one. 


No matter the season or weather, holidays will always evoke price increases, more than any other time. This is due to many people booking their Sandals vacation during holidays because they already have time off from work. In other words, they don’t have to use as many PTO days.

Holidays are basically extensions of high season — and the absolute most popular time to escape. Christmas, Father’s and Mother’s Day, New Year’s Day, Memorial Day, and Thanksgiving are all holidays when you should avoid booking a Sandals vacation. (In other words, just stay home with your sweetie.)

Sandals Special Discounts

Besides the last-minute travel discount I mentioned above, Sandals offers many other amazing discounts and deals on specific dates. When booking, you can check for special discounts on your room by clicking on the “View Qualifying Specials” tab. 

Some of the specials that they offer are 45% to 65% off rack rate, up to $635 instant credit, and the perfect gift sale. Some specials can be used in combination with others. There is also the very impressive Sandals 777 deal that changes every week. This could be a real game-changer for you — Each week, Sandals offers a special promotion on 7 select rooms, for 7 days where you can take advantage of an additional 7% off Sandals or Beaches rack rates. Whatever you do, don’t overlook this option.

Best Time to Book Based on Crowds

The crowds and the cost of booking a Sandals vacation are directly correlated. Fewer crowds mean a lower price and vice versa. So let’s look at the crowds from the perspective of what type of vacation you are seeking.

best time to book a sandals vacation

Low-Season Crowds

Low-season crowds mean there will be fewer people on vacation. Fewer people means you can make last-minute-bookings, won’t have to worry about not having a lounger at the pool, and have all the space you could need on the sands. It’s like having your own private beach! (And you absolutely must take advantage of the huge Sandals floatie rings in the water, where you two can curl up together in the middle of the ocean. It’s the very definition of relaxation — and romance.)

However, you must realize that the low season is during the wet season. That means you are more likely to encounter rain, more humid conditions, and possibly even cancellations due to hurricanes. Although this may be a minor factor if you have flexible dates and travel insurance.

I prefer the low season because I like to book things spontaneously. During low season, I know there will most likely be more openings on tours, activities, and spa treatments that I want to schedule on the same day — or a day in advance. I’m also not one to shy away from a bit of rain — in my opinion, tropical-rain-soaked days are always a GREAT day to sleep a little later (and cuddle more with my sweetheart Bill), get in a solid workout at Sandals’ excellent onsite gym (I am always WOWED by Sandals’ fitness centers), to be followed by one or two perfect pamperings in the upscale Red Lane Spa that Sandals is famous for. (Try the Moondrop Dreams massage or get a great hair blowout in the salon. You will look all-the-more-fabulous in your honeymoon photos!)

High-Season Crowds 

High season (Winter here in the USA) is when everyone goes to the Caribbean because the weather is excellent, and because these are the colder months in the States. If you are booking during high season, you will need to book everything extremely far in advance. You will also be sharing space with a lot of other people.

Some travelers like the high season because you’ll get the chance to meet other folks from all over, and every day is like one big party. (You’ll meet all kinds of great people, whether you’re just walking hand-in-hand from your room to the pool, sitting next to an interesting couple at dinner, or both wow-ing over the Nutella crepes at the Cafe de Paris. That certainly has been my experience, when staying at Sandals with my husband Bill. ) However, you’ll probably have a hard time finding a spot at the pool and may have to book some activities before you even leave for your trip to ensure that you secure an opening.

Shoulder-Season Crowds

Shoulder-season crowds are a nice “in between” of the low season and high season. There will be people there, but not so much that you’ll have difficulty booking activities or finding a nice spot to yourself on the beach. You’ll also have plenty of chances to socialize without it being overbearing.

The weather is hit-or-miss during this time because it’s right on the border of the wet season and dry season. You may get some showers here and there, but most likely not your entire trip. You never really know during the shoulder season, and most of the time, the forecast isn’t even super accurate. But rest assured, you can still enjoy all of your time at Sandals, even if it’s raining. During the day, you can have a great lunch, enjoy the various bars, canoodle under a palapa, get a massage or facial, and maybe even go snorkeling!

How Far in Advance to Book a Sandals Vacation

The further in advance you book your Sandals vacation, the better. You can book a Sandals vacation up to two years in advance. Still, I’m not particularly eager to book until a year beforehand with a two or three-month leeway. This gives me enough time to plan life events accordingly and ensures I have a wide choice of rooms.

If you wait too long to book your Sandals vacation, rooms will start dwindling, and the rates can even increase. This is because the demand for an individual room goes up when there is less available.

The only exception to this rule is if you are highly flexible and want to leave for your vacation immediately. With Sandals’ last-minute travel deals, you can get $50-$100 off the nightly rate. This kind of spontaneity makes it just as inexpensive as if you booked it a year in advance and sometimes even cheaper. 

The Overall Best Time to Book a Sandals Vacation

Overall, I prefer to book my Sandals vacations during the Spring shoulder season, from April to June. You will likely have decent weather during this time, and it will be less crowded than during the high season. It is also not around the major vacation holidays, or Thanksgiving and Christmas. And I always try to book a Sandals’ overwater bungalow — one of the world’s most exquisite escapes.

There are always plenty of rooms to choose and you can book all your activities for the week once you arrive. You don’t have to worry about waking up early to get that perfect spot on the beach or missing out on any of the restaurants because they’re already reserved for the week. You can simply enjoy your time there without the stress of too many other travelers or bad weather.

But no matter when you book — trust me – you’re going to have the time of your life at Sandals, where, as its founder Butch Stewart always used to say (and is the title of his biographical book), “All That’s Good!”

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