Your Caribbean Vacation Timing Guide—Made Simple

(425 Reviews)
99% Recommended

Pam MacIntyre

Maple Grove, MN

Australia & New Zealand Specialist

New Zealand

In all my years as a Travel Professional, I’ve asked countless people, “What’s on your must-see list?” And without fail, New Zealand is always at the top! Honestly, who wouldn’t want to experience this majestic ...

New Zealand

In all my years as a Travel Professional, I’ve asked countless people, “What’s on your must-see list?” And without fail, New Zealand is always at the top! Honestly, who wouldn’t want to experience this majestic part of the world?

I was fortunate enough to visit both the North and South Islands, and what I love about New Zealand is that it offers the perfect blend of laid-back charm and action-packed adventure, all while being nothing short of epic.

The country is home to endless national parks, a rich Maori culture, and unforgettable experiences like sailing through the sounds while dolphins playfully follow your yacht. And let’s not forget the awe-inspiring moment of witnessing a sperm whale off the coast of Kaikoura—talk about jaw-dropping beauty!

Oh, and did I mention wine? If you’re a fan of great wine (and who isn’t?), New Zealand is a must-visit for its world-class Sauvignon Blanc, Chardonnay, Pinot Noir, Merlot, and more. How do I know? Because I couldn’t resist visiting a winery or two during my travels!

Honestly, I could go on and on about the magic of New Zealand, but if you’re reading this, you already know you want to explore this incredible part of the world. Let’s work together to create your perfect New Zealand adventure!

Australia

Let me start by saying, I’ve wanted to visit Australia since I was a child. Why, you ask? Well, to pet a kangaroo, of course! And yes, I did! Not only did I pet a kangaroo, but I actually fed FOUR at the same time. Childhood dream come true, right? And I can’t wait to go back for round two.

While I was in Sydney, I had the chance to experience the spectacular Vivid Sydney Festival, celebrating its 10th year. It was honestly WOW! Never in my wildest dreams did I think Australia would be so perfect to visit during their winter season. But coming from Minnesota, their “winter” felt more like our fall—absolutely ideal! Seeing the Sydney Opera House light up during the festival was something I’ll never forget.

And then there’s the Blue Mountains region—so lovely to explore on foot. From there, we ventured to Hunter Valley (known to the locals as "The Hunter"), where wine flowed freely, and every glass was more delicious than the last.

Australia’s size is truly hard to grasp until you’ve experienced it firsthand. To put it in perspective: Sydney would be in Florida, Cairns (home of the Great Barrier Reef) would be in Maine, Uluru (Ayers Rock) would be in Kansas, Melbourne would be in New Orleans, and Perth would be in Los Angeles.

Whether you're dreaming of visiting the world’s largest Great Barrier Reef, immersing yourself in Aboriginal culture, swimming with whale sharks, or gazing upon the majestic Uluru, Australia has endless possibilities waiting for you.

Let’s make your dream trip to Australia a reality—one that you’ll remember for the rest of your life!     

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Pam MacIntyre

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Caribbean Islands

When Is the Best Time to Go to the Caribbean? And Which Island Should You Choose?

Planning a Caribbean getaway? One of the first questions I get is: When’s the best time to go? The honest answer? It depends on what’s most important to you—whether that’s the best weather, the best prices, or maybe a bit of both.

December through April is the classic “sweet spot” for weather. You’ll find cooler temperatures, lower humidity, and less rain—a perfect escape from colder climates. Just a heads-up, June through November is hurricane season, and while May isn’t officially in that window, it can be rainy on some islands.

Keep in mind that traveling just before or after the peak season can also mean fewer crowds, which is perfect if you want a more peaceful experience.

That said, you don’t have to avoid all of hurricane season to get a good deal or nice weather. For example, early December (before the holidays) is often a fantastic time to visit. The weather is still great, but prices are generally more affordable compared to peak holiday months like January or February.

If you’re looking to break up a long winter but want to skip the holiday crowds, consider late January or late April. These times usually offer better rates than the busy months of February, March, and early April. So, if you’re coming from a cold place and want to escape the chill without stretching your budget, late January might be your sweet spot.

Best Islands by Season

Matching your timing with the right island can really make your trip shine. Here’s a quick guide to help you pick the perfect spot based on when you want to travel:

• December to April (Peak Season): This is prime time for sunny skies and lively vibes. Islands like Jamaica, St. Lucia, Barbados, and the Bahamas are buzzing with festivals, great weather, and plenty to do.


• May: A bit rainier on some islands, but places like Aruba and Bonaire—which sit outside the hurricane belt—stay mostly dry and sunny. Great if you want fewer crowds but good weather.


• June to November (Low Season/Hurricane Season): For travelers comfortable with occasional tropical showers and looking for deals, islands like the Dominican Republic and Puerto Rico are solid choices. Both offer fantastic all-inclusive resorts and plenty of activities year-round, plus they bounce back quickly after storms. 


• Off-the-Beaten-Path: If you want a more laid-back vibe, islands like Grenada, St. Vincent, and the Grenadines offer less crowded, authentic experiences—especially outside peak travel months.

Putting It All Together

Remember, it’s all about what matters most to you. Are you chasing sunshine and festivities? Searching for a quiet spot to unwind? Or hoping to find the best deals without risking bad weather? Whatever your goal, there’s a Caribbean island and travel window that fits perfectly.

Don’t forget to consider any special events or festivals that could make your trip even more memorable! For a full rundown of festivals and cultural happenings, check out my other blog: Caribbean vs. Mexico: Which Destination Fits You?

Together, we can review your priorities and craft a plan that matches your ideal vacation vibe, timing, and budget. Whether you want to lounge on white-sand beaches, dance at lively festivals, or explore hidden gems, your perfect Caribbean escape is waiting.