Let’s be honest: Not everyone loves snow. Sure, it looks magical in movies, but in real life? It’s cold, messy and requires way too much shoveling. By the time Christmas is over, the charm of winter fades fast. The lights come down, the carols stop, and all you’re left with are gray skies and icy sidewalks. If you’re like me, after the holidays, you’re ready to trade snow boots for flip-flops and find some sunshine.
That’s why I’m counting down the days until May, because that’s when paradise calls. Hawaii in May is my happy place, and here’s the best part: it’s the most affordable month to travel using my Hilton Grand Vacations Points. I reserved a two-bedroom Suite with an ocean view for fewer than 10,000 points. That’s practically a steal!
May is considered a shoulder season in Hawaii, which means fewer crowds, great weather and better deals. It’s warm but not hot, and the ocean temperature is perfect for swimming. Just thinking about those turquoise waters and soft sands makes me forget the snow piling up outside.
If you’ve been dreaming of Hawaii, May is your golden ticket. It’s the sweet spot between spring break chaos and the summer vacation surge. Plus, with HGV points, you can stretch your budget and still enjoy luxury accommodations. For me, it’s not just a vacation; it’s a sanity-saver after months of winter blues. It’s also a great time to catch up on some relaxing reading!

Why Alaska Shines During The Summer Months
But Hawaii isn’t the only destination on my radar. I’ve also been curious about Alaska. It’s a bucket-list spot for many, but let’s be real — I don’t want to freeze while I’m there. So, when is the best time to visit Alaska without feeling like you’re in an icebox? The answer: mid-June through early September. During these months, temperatures are mild — think 60s and 70s during the day — and the scenery is breathtaking. You’ll get long daylight hours, lush landscapes and the chance to see wildlife without bundling up in ten layers. It’s also prime time for cruises and outdoor adventures like hiking and fishing.
So, here’s the plan: survive winter, embrace the warmth in Hawaii this May, and then maybe tackle Alaska when the sun is shining and the glaciers are still awe-inspiring but not bone-chilling. Until then, I’ll keep sipping hot cocoa, dreaming of tropical breezes, and reminding myself that snow is temporary, but sunshine is just a plane ride away.
Key Takeaways
Visit Hawaii in May: May offers a sweet spot with fewer crowds, pleasant weather and better travel value compared to peak seasons.
Maximize HGV Points: Traveling in May can stretch Hilton Grand Vacations points further, making luxury stays more affordable.
Perfect Weather Balance: Expect warm temperatures and comfortable ocean conditions ideal for swimming and relaxation.
Post-Holiday Reset: A spring getaway to Hawaii provides a refreshing escape from winter fatigue and lingering cold weather.
Best Time for Alaska: Plan Alaska travel between mid-June and early September for mild temperatures, long daylight hours and prime outdoor experiences.
FAQs
Q: Why is May considered shoulder season in Hawaii?
A: May falls between spring break and summer travel peaks, resulting in lighter crowds, better availability and strong value.
Q: How do Hilton Grand Vacations points go further in May?
A: Lower travel demand often means fewer points are required to reserve larger or upgraded accommodations.
Q: What is the best time of year to visit Alaska?
A: Alaska is most comfortable from mid-June through early September when temperatures are milder and daylight hours are longer.
Q: Which destination is better for avoiding cold weather?
A: Hawaii offers warm weather year-round, while Alaska is best visited in summer for more comfortable conditions.









