Oahu
Maui
Kauai
Hawaii Island

Hawaii Itineraries

 

Flights booked? We've got everything else

 

Plan your Hawaii vacation with the experts. With 60 years of providing unforgettable holidays to Hawaii, our roots run deep. So no matter whether you’re looking for a hotel or vacation rental, transportation, authentic island experiences, cruises or travel protection plans, we have you covered. What’s more, our team of travel advisors know and love the islands, and will be able to suggest authentic and meaningful experiences to help you plan a vacation that’s truly one-of-a-kind.

Here's what you can expect when you book with us:

 
  • EXCLUSIVE hotel deals on 4 islands
  • Condo vacation rentals
  • NCL Pride of America cruises
  • Pre- & post-cruise hotel stays
  • Airport transfers
  • Car rentals
  • Hundreds of sightseeing tours, luaus & activities
  • Travel protection coverage and cruise protection coverage

Book online or call our travel experts at 800-742-9244

 
Oahu

Oahu

The most popular island for travelers, surf famous Waikiki Beach, explore the North Shore's world-class waves, snorkel Hanauma Bay and visit the USS Arizona Memorial in Pearl Harbor.

 
 
Maui

Maui

Known for its magical ambiance, stroll the beaches of Wailea, discover the waterfalls of the Iao Valley, explore the Road to Hana or watch the sunset (or sunrise) from Haleakala.

 
 
Kauai

Kauai

Aptly named the Island of Discovery, explore the Wailua River valley, experience the grandeur of Waimea Canyon, sail the Napali Coast or splash in Hanalei Bay.

 
 
Island of Hawaii

Island of Hawaii

Explore a range of climate zones from snow-capped Mauna Kea to Waipio Valley and the Kohala Coast. Hike Kilauea or visit the black sands of Punalu'u Beach.

 
 
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]