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The Perfect Paradise Pairing

Escape to not one, but two pieces of paradise with this island-hopping itinerary for Kauai and Maui, Hawaii—plus how to make it possible, even in a pandemic.

Ready to get away? We are, too. Step out of the snow and into the sand with our on-site Concierge team’s top—safe, private, and fun—recommendations for things to see, eat, and do during a trip to Hawaii. Making your trip possible—even during a pandemic—just takes a little bit of planning. With Hawaii’s State Safe Travel Program, you’ll be good to go. 

Whether it is a romantic getaway or family vacation, Hawaii is the hideaway you’re seeking. Here’s how to make the most of your island escape. 


Kauai is also known as “The Garden Isle”—rightfully so, with its lush emerald forests and vast species of plants and flowers. Timbers Kauai is a designated “resort bubble”, so you may roam freely about the property (even if you’re quarantining) and enjoy its award-winning amenities and activities. Puddle-jumping to the neighboring island of Maui simply requires a negative COVID test.  


  • Golf on the Ocean Course with a stunning backdrop of the Pacific. 
  • Enjoy live music on Friday and Saturday nights, right there at the resort. 
  • Relax and pamper your body and soul with a massage at the spa. 
  • Challenge your tastebuds during a chocolate tasting with Lydgate Farm or try mead with Nani Moon Meadery. 
  • Explore the warm Hawaiian waters while sharpening your skills during a sea kayaking workshop. 


Maui is a land of many ecosystems, from jungle valleys to black sand beaches, pristine waters to towering volcanic peaks. The Club’s residences at Ho’olei Villas at Grand Wailea and Montage Kapalua Bay are more than ready to welcome Members with the spirit of aloha. While these are not designated “resort bubbles” and quarantining here is not permitted, avoid it with a negative COVID test taken 72 hours before your arrival.  


  • Take a Haleakala Sunrise Bike Tour where you’ll be driven up to the summit and ride down the volcano as the sun comes up over the island. 
  • Snorkel the coral wall off the nearby U-shaped island of Molokini, a partially submerged volcanic crater home to a plethora of colorful Hawaiian fish, sea turtles, manta rays, and more. 
  • Dine on fresh, locally-sourced cuisine and toast the sunset—mai tai in hand—on Merriman’s oceanfront lanai. 
  • Drive the famed Road to Hana, a winding 64-mile road crossing bridges, stunning waterfalls, and dramatic vistas. Stop for hikes, swims, and fresh-baked banana bread along the way. 
  • Tee off at one of the Kapalua Club’s championship courses with views of the Pacific. 


Avoid a mandatory 10-day quarantine upon your arrival by receiving a negative COVID test taken within 72 hours from your flight’s departure. When traveling from island to island, pre-test 72 hours before your departure flight. Upload your negative test results pre-travel on the mandatory Travel and Health Form. A negative result means no quarantine is needed—and you’re now welcome to travel freely about the island.   

For more details and updated travel requirements, be sure to visit Maui and Kauai’s Know Before You Go pages on The Source.