Expert Advice

Here's How I Got 3 Hawaii Vacations in 1 Trip by Island Hopping

One Elite Premier Owner shares insider tips for maximizing your time at Hilton Grand Vacations' Hawaii resorts

Eric Z
Picture of group of surf boards standing alongside road, Maui, Hawaii.

If you're like me, one week on any of the Hawaiian Islands is never enough time, especially if you're not flying from the West Coast. So, if you're lucky enough to have the points and stay two to three weeks or more, take it. You'll really get a chance to see the diverse landscapes of the islands and experience a few different Hilton Grand Vacations Hawaii resorts

Hilton Grand Vacations Owners posing for family picture, Hawaii.   

Once, we took a month-long trip and decided to break it up between three islands: the Big Island, Oahu and Maui.

It was like having three different vacations in a row, from the very different landscape to the distinct vibe of each island. We started at Kings' Land, a Hilton Grand Vacations Club, on the Big Island, and nothing compares to the beautiful, rugged lava landscape.

We love this property because it's not on the ocean and offers a more relaxed and tranquil feel, yet it has access to shopping and restaurants just down the road.

I love that we began our vacation here and that this resort offers a pre-arrival food order service. So, after a long 13-hour flight, we immediately had food stocked for the next day.

Beautiful image of lava rock scenery at Kings' Land, a HIlton Grand Vacations Club, Big Island, Hawaii.    

Insider tip: Be sure to check out the often missed, cold plunge pool tucked in the corner of the adult pool.

Next up: Ocean Tower, a Hilton Grand Vacations Club, located inside Hilton Waikoloa Village®, complete with activities, shopping, restaurants on-site and stunning ocean view rooms. It's a little busier and has more of a resort feel than Kings' Land, but it's relaxing, nonetheless. 

The newly remodeled rings of the tower offer modern touches and oceanfront views of the sunset. Ocean Tower also provides storage for cold food and freezer storage for frozen items if your room isn't ready when you arrive. So, you can shop for food and start enjoying your stay right away. 

Hilton Grand Vacations Owners posing for family picture at Buddha Point, Ocean Tower, a Hilton Grand Vacations Club, Big Island, Hawaii.    

Insider tip: if you've already seen a few sunsets and want to experience something different, hop on the canal boats right at sunset and listen to the birds enjoying the sunset from inside the rings of Ocean tower. Trust me; you'll never hear anything like it again.

We finished our trip on Oahu — city life with palm trees. You can relax and enjoy the ocean or get the hustle and bustle feel of a big city. Flights run almost every half hour between the islands for less than $100, so it's super easy to island-hop for a day trip like we took to Maui

We island-hopped to get a sneak peek of Maui Bay Villas, a Hilton Grand Vacations Club, and then do some shopping in Lahaina. 

For our final stay, we chose to get another beautiful view of the ocean and lagoon from the newest tower at Hilton Hawaiian Village®, The Grand Islander, a Hilton Grand Vacations Club. The Grand Islander is located toward the back of the Village, so it's an easy walk to the high-end shopping and dining found off of Kalakaua Avenue. 

Insider tip: Save your receipts when you shop at any of the three ABC stores in the Village, and once you hit certain levels predetermined dollar amounts (think: $100 and above) you can pick from a list of complimentary items.

If you save up and reach the higher dollar amounts, the free items are nicer or you can get multiples of the lower dollar amount rewards. For example, you could recieve three souvenir bags versus one t-shirt. Its a great way to get souvenir gifts and useful vacation items like towels — just for shopping for necessities like food and sundries. 

Read "I Booked a 3-Bedroom Penthouse Suite at Grand Waikikian, a Hilton Grand Vacations Club — Here's What It Was Like" for another story about maximizing your time at Hilton Grand Vacations' Hawaii resorts. 


Hilton Grand Vacations Explorer, Eric Z.

Eric Z

Seasoned Owner and returning Explorer, Eric made his home resort The Grand Islander by Hilton Grand Vacations in 2006 and never looked back on life before vacation ownership — quickly climbing the ownership tiers, reaching Elite Premier status. As an Elite Premier Owner, he and his family including, his wife, teenage son and parents, regularly enjoy elevated access to some of the best amenities and services offered to Members, such as extended vacations. 

Over the years, his travel has afforded him unforgettable father and son trips, priceless multigenerational family vacations and even his once-in-a-lifetime destination wedding at Kings' Land by Hilton Grand Vacations in Hilton Waikoloa Village. He's your go-to guide for practical vacation ownership tips and says, "I love Hilton Grand Vacations and the opportunity to share what I've learned over the years."

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