Staff Spotlight: Hawaii with Outrigger

 There's nothing like hearing about a destination from someone who's just returned with fresh memories and insider insights. Travel advisor Anna Maria recently visited Hawaii, staying at Outrigger properties on both Maui and the Big Island's Kona coast. From watching whales breach off Maui's shores to exploring the volcanic wonders of Kona, she experienced firsthand what makes Hawaii such a captivating destination—and why Outrigger's authentic Hawaiian hospitality creates the perfect home base for island exploration.

Whether you're dreaming of your first Hawaiian getaway or planning a return visit to the islands, her insights will help you make the most of every moment in paradise. In this Q&A-style blog post, she shares everything from must-see attractions and hidden gems to practical packing tips and the cultural experiences that made her trip truly unforgettable. Get ready to start planning your own Hawaiian escape!

OUTRIGGER Kāʻanapali Beach Resort

Image courtesy of outrigger.com

OUTRIGGER Kona Resort & Spa

Image courtesy of outrigger.com

How would you compare the experiences at the two Outrigger properties in Maui and Kona?

The only major difference from switching over from one hotel to another was location. Both staff at the Outriggers are exceptional, willing to assist and both were very clean and great locations.

What amenities did the Outrigger hotels offer that enhanced your Hawaii experience?

You will receive reusable water bottles which you can use throughout the resort and on your excursions! They also gave drawstring bags to use as well for the beach and/or pool!

What activities or excursions would you recommend on Maui that shouldn't be missed?

Whale watching if you are there during the season which is December through April. If you are a big snorkeler, it is a great island for that too! Road to Hana is an amazing journey as well, just make sure you have a tough stomach.

How does the Big Island (Kona) experience differ from Maui for travelers?

The big Island is the largest most diverse and less developed island, with active volcanoes, and lush forests. Maui is smaller, more developed with more sandy beaches and a mix of resorts and hiking.

What was your experience with dining at the Outrigger properties versus exploring local restaurants?

  • On Maui the Outrigger has a Maui Brew restaurant on property which is a great place to watch the sunset!
  • Outrigger Kaanapali has multiple great restaurants to chose from.
  • Something special about the Outriggers is that they all offer live music entertainment every night, so no matter where you go, you will find some.

What's the ideal length of stay on each island to fully appreciate what they offer?

  • Maui can be a destination for 7 days and stay in a couple different places on the island.
  • Kona I would say 3 nights.

How easy was it to arrange island-hopping transportation, and do you have any tips?

Super easy to arrange! Honestly it is easier than traveling in the states. Smaller airports and they are all outdoors, which is awesome. You can show up 60-45 mins before your flight.

What beaches near the Outrigger properties would you recommend and why?

Maui- Kaanapali beach is right in front of the resort and was amazing!

What cultural experiences unique to each island did you enjoy?

  • The history of Hawaii is amazing, and Outrigger is one of the few hotels which has cultural centers in each of their hotels. They also provide different activities to interact guests in the cultural and history.
  • We had a goodbye ceremony on Maui which was very touching, and brought some people to tears.

What items should travelers pack for a dual-island Hawaii vacation that they might not consider?

Bring sunscreen and A LOT of it. Sunscreen can be expensive there, and you may not realize how much you will use, people often forget the UVs are higher there. Also do not forget the charges for phones.

Anything else you would like to add / that you think clients should know?

Take the trip!

Interested in visiting Hawaii? Contact Anna Maria or another one of our knowledgeable travel advisors below!

Trip Quote Request

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