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Hawaii is our most requested destination at out Virtuoso Luxury Travel concierge, not least because there are some fantastic beach hotels. We have picked the best in our review of the best Four Seasons resorts in Hawaii. If you are looking for decent hotel rooms and flights at reasonable prices, our travel tip is to travel to Hawaii when it is less popular.

The good news is that Southwest Airlines will soon to enter the game for this routing, so flights from the US mainland have never been cheaper to get to these magical islands.

The Most Expensive Time To Visit Hawaii

Don’t expect the best deals between mid-December through to mid-April. Everyone wants to get away for the winter so Hawaii is super popular at this time of the year. You may be able to buy a cheap flight during these dates, but don’t expect the Four Seasons Maui to shower you with deals. If you must travel in the high season, January or February tend to be cheaper than December and March.

The Cheapest Time to Visit Hawaii

The Fall months tend to be the cheapest, from September to mid-December. Expect 3 for 2 and 4 for 3 hotel deals and airfare savings of more than 10%. Our Luxury Travel Concierge can get you free upgrades and breakfast if you want to stay at a luxury hotel.

The Best Weather in Hawaii

Rainfall is lowest from April through to September, although it can be quite rainy right through to November. I have been to Hawaii in August and stayed in Waikiki and it was hot but moist, with rain and cloud most days. Often, when the rain passed, at least some of the day was sunny too. If you are looking to avoid the rain I would suggest avoiding Honolulu and heading straight over to Wailea on Maui or the gorgeous Four Seasons on Lanai.

It is important to remember that the Hawaiian islands have a wet and a dry side, which will affect whether you experience rain much more than the incoming weather systems. When it is raining in Honolulu it may well be sunny in Wailea on Maui, so choose your resort location well.

The Best Times to Go Whale-watching

You will find humpback whales off the islands’ coasts from December through to May. February is thought to be the peak.

So What’s The Best Time To Go To Hawaii

The best time of year to visit Hawaii to avoid the crowds and to get those cheap flights and hotel rooms is probably May or September. Make sure you choose a sunny resort on the right side of each island and you will be in for a treat.

That said, I love Hawaii before Christmas. Screw the prices, there is nothing like hearing Elvis warbling Christmas tunes as you dig your toes into warm sand. For me, thats Hawaii.

Best Airlines To Fly To Hawaii

We have detailed the best airlines to fly to Hawaii in First Class. The airline you will chose will depend largely on your departure airport. Hawaiian Airlines in First is a great choice if you don’t want to travel in Coach.

Cheaper Hawaii Flights & Hotels

Remember to always check any luxury hotel prices and Premium Economy, Business or First Class flights prices with our Luxury Travel Concierge before booking. We offer free upgrades and breakfasts at luxury hotels like Four Seasons and discounts on premium flights.

Top Tip: If you are US based, you can fly to Asia, Hawaii or Europe for free on American by taking out just one (free) credit card. Read more in our easy guide.

Disclosure: Our property, service and product reviews are sponsored by the proprietor or brand being appraised. All opinions remain our own and are in no way influenced by the sponsor.