Skip to main content

The Perfect Paradise Pairing

Escape to not one but two pieces of paradise with this island-hopping itinerary for Kauai and Maui, Hawaii

Ready to get away? We are, too. Step out of the snow and into the sand with our on-site Concierge team’s top recommendations for things to see, eat, and do during a trip to Hawaii. Making your trip possible just takes a little bit of planning.

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. Enjoy Timbers Kauai's award-winning amenities and activities.


  • 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.


  • 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.