An Unforgettable, Active Hawaii Family Vacation

Trade the winter frost for warm, welcoming beaches on The Big Island of Hawaii this winter holiday season. The 60 mile stretch of Kona District on the Big Island is known for calm, clear waters and luxury beach-side villas and estates. There are 20 beaches in the Kona district – almost all of which offer swimming and snorkeling opportunities.

October through March, also known as the wet season – one of two seasons experienced in Hawaii – is considered to be a great time to visit the Big Island of Hawaii. Specifically, this season is best for the big surf and whale-watching. The temperatures during the fall and winter months hover around the low 80’s, compared to high 80’s in the spring and summer.

Whenever you decide to visit, there are plenty of things to do, for either yourself or the whole family. Read on to find out about some excellent Hawaiian activities you can enjoy this fall and winter.

Windsurfing Kona Hawaii Winter | Hawaii Luxury Rentals

Surf The Wind

Looking to do something other than lounge around the pool and soak in the sun? Try windsurfing, a popular sport in Hawaii — Kona is a well known surfing spot. During the winter months the winds die down providing a gentler experience for beginners. If your balance is strong, and the winds are gentle, you can often pick up windsurfing in about an hour. If speed is not your métier, try SUP, also known as paddle boarding.

Yacht in the Ocean | Hawaii Luxury Rentals

Sail Away

Various sailing tours and private sailboat charters are available right in the Kona District. Hawaii Yachts, for example, offers full day or even multiple day luxury yacht rentals, sailing lessons, spa at sea and sunset cruises on the Big Island.

Hawaiian Hula Dancers | Hawaii Luxury Rentals

Hula Kahiko at Hawai’i Volcanoes National Park

Enjoy an outdoor presentation of traditional hula and chant, featuring local performers on December 19th, at the hula platform located near Volcano Art Center Gallery. Bring a sitting mat and sun/rain gear.

Hawaii Volcano | Hawaii Luxury Rentals

Visit a Volcano

Catch a lava display at Hawaii Volcanoes National Park and explore newly created steam vents, and giant craters. The park also offers opportunities to do a Crater Rim drive tour, drive the Chain of Craters Road, hiking and biking.

Ironman | Hawaii Luxury Rentals

Watch The Ironman World Championship Live

If you do decide to hit the beach before December, the Ironman World Championship takes place on October 10 – while you have to pre-qualify to enter, you can still enjoy watching the grueling event.

There is also an IronKids competition for children 2 to 14 years of age on October 6th, with open registration.

Dining | Hawaii Luxury Rentals

Eat like a King or Queen

Hawaii’s Chef Fest is a celebration of high-profile dinners, interactive cooking classes, and culinary and wine experiences. Some of today’s top chefs come together to cook, teach and entertain in an intimate and relaxed beach setting.

Hualalai Estate | Hawaii Luxury Rentals

The Hualalai Estate

The best part? Hawaii is about relaxation, so if you decide to stay with us, your personal destination host will plan every detail of your trip, so all you have to do is relax and enjoy your free time.

When you arrive, we’ll have freshly prepared mai tais plus island-inspired eats to enjoy as your host takes you on a tour of the home. Reward yourself with this unforgettable, lavish, private beach-side vacation. You’ll feel right at home in our incredible five-bedroom estate with full access to amenities at the renowned Four Seasons Resort.

One especially thrilling activity we offer during your stay allows you to explore the Hawai‘i Volcanoes National Park area by helicopter and on foot – including sinking your toes into a beautiful black sand beach and sipping award-winning coffee.