Skip to primary navigation Skip to content Skip to footer

Island Hopper Package: Oahu + Maui

Experience the very best of Hawaii’s two most iconic islands with this 12-night, dual-destination vacation package. Designed for travelers who want a seamless transition from the vibrant culture of Honolulu to the lush, world-class beaches of Maui, this itinerary offers a perfect balance of guided adventure and “island time” flexibility.

Your journey begins on Oahu with 6 nights at the legendary Outrigger Waikiki Beach Resort. Staying in an Ocean View room, you’ll be steps away from the surf of Waikiki and the island’s best dining. We’ve included all the essentials to make your Oahu stay unforgettable: a Majestic Circle Island Tour to see the North Shore and Nuʻuanu Pali Lookout, a historic visit to Pearl Harbor, and a 7-day LeaLea Trolley Pass for unlimited exploration. Your time on Oahu culminates with a sunset 3-Star Dinner Cruise, offering 360-degree views of the coastline.

Next, fly to Maui for 6 nights at the Outrigger Kaanapali Beach Resort, nestled on the golden sands of one of the world’s top-rated beaches. From your Premium Ocean View room, you’ll have easy access to the island’s most sought-after experiences. Witness a legendary Haleakala Sunrise from above the clouds and set sail on a Trilogy Snorkel and Sailing tour to explore West Maui’s pristine coral reefs.

With round-trip airport transfers included on both islands, we handle the logistics so you can focus on the memories. From the historic landmarks of Honolulu to the volcanic peaks of Maui, this is the ultimate stress-free Hawaii experience.

Key Highlights

  • Premium Ocean view rooms with private balcony
  • Explore Oahu’s top landmarks including Diamond Head, North Shore & more
  • Learn about Hawaii’s WWII history on the Pearl Harbor City Tour
  • Enjoy a 3-star dinner cruise while taking in a spectacular view of Oahu’s south shore
  • Unlimited rides around Waikiki with the LeaLea Trolley
  • Snorkel and sailing at Maui’s Kaanapali shore
  • A memorable Sunrise atop Haleakala
  • Worry-free arrival & departure with included airport transfers
  • Perfect mix of guided tours and free time to enjoy Waikiki your way

 

Included Activities

Majestic Circle Island Tour

Experience Oahu in one full day. Our Majestic Circle Island Tour loops the island with hotel pickup, small-group minibus comfort, and all admissions + lunch included. Stops include Nuʻuanu Pali Lookout, Byodo-In Temple, Tropical Farms, Waimea Valley, and Dole Plantation.

 

Booking period: May 8, 2026 to July 31, 2026

Special rates and availability are guaranteed for bookings made by this date.

PACKAGE PRICE

Season Price Additional Night
1/3/26 – 6/14 $ 4835.42 $ 690.00
6/15 – 8/15 $ 5045.42 $ 750.00
8/16 – 9/30 $ 4835.42 $ 690.00

WHAT'S INCLUDED

  • 6 nights at the Outrigger Waikiki Beach Resort – Ocean View room
  • 6 nights at the Outrigger Kaanapali Beach Resort – Premium Ocean View
  • Majestic Circle Island Tour (full-day sightseeing)
  • Pearl Harbor City Tour
  • 3-Star Dinner Cruise
  • LeaLea Trolley 7-Day Pass – unlimited rides
  • Maui Snorkeling aboard the Trilogy
  • A Sunrise tour atop Haleakala
  • Round-trip airport transfers
  • Taxes & fees

PERFECT FOR

  • First-time visitors wanting to experience the different “feel” of Hawaii by visiting 2 different islands
  • Couples looking for a full itinerary
  • Anyone who wants a stress-free, all-in-one Hawaii vacation

Frequently Asked Questions

What’s included in the Land Package?

This package includes:

Contact Form

  • This field is for validation purposes and should be left unchanged.