Grand Hawaiian Adventure Including Pearl Harbor

January 15-26, 2026

 

Say "Aloha" to beautiful Hawaii, featuring Oahu, Kauai, and Maui!

 

Enjoy the BEST oceanfront accommodations:

Waikiki Beach Marriott Resort & Spa

Royal Sonesta Kaua'i Resort Lihue

The Westin Maui Resort & Spa, Ka'anapali

 

Join us for a magical escape to the 50th state during which we will explore three gorgeous islands! Throughout your trip, you’ll enjoy the finest accommodations on each island we visit, which is the Timi’s Tours standard. We will spend our first evening in Chicago before departing the following morning for Oahu for a two-night stay at the Waikiki Beach Marriott Resort & Spa! While there, we will tour Honolulu and visit the Pearl Harbor National Memorial. As one of the most significant places in both American and global history, visiting this site is an educational and moving experience for all.

 

Next, it’s on to the Garden Isle of Kauai, for a three-night stay at the Royal Sonesta Kaua'i Resort in Lihue! Located in luxurious, oceanfront, palm-tree lined Lihue, the resort places you in the perfect location for relaxation and adventure. During our stay, you will have a free day to spend as you choose! We’ll also take a guided day tour of the island which will include an exclusive Wailua River/Waimea Canyon tour, with a river cruise.

 

You’ll journey through the heart of Kauai’s countryside where you’ll ascend a vast mountain via a meandering road engulfed by trees and endless fields to reveal what Mark Twain aptly described as the “Grand Canyon of the Pacific.” It’s hard to believe that the immense cliffs and deep gorges of the Waimea Canyon could exist on an island – you’ll be mesmerized by its scenic beauty long after your vacation. The canyon is 3,600 feet deep and a grandiose array of red, brown, and green hues. Take in the view at Opaekaa Falls Lookout too! Watch the ocean waves propel jets of water through lava rock at the Spouting Horn Blowhole, one of the island's most photographed spots.

 

Then, we will cap off our vacation in style as we fly to ‘The Valley Isle’, Maui, for a four night stay at The Westin Maui Resort & Spa, Ka'anapali! Located within walking distance to Whalers Village, this resort offers bountiful shopping and dining options.

 

Two of our days in Maui will be ‘free days’, for you to enjoy however you choose! Perhaps you’ll want to book a whale watching excursion, rent a car to go exploring, take a tour to Hana, indulge in spa services, go snorkeling, or simply enjoy the incredible ocean view from your resort. The island is your ‘oyster’ to enjoy to your heart’s content…come to think of it, maybe you’ll even open an oyster or two to find a unique pearl to take home as a lovely souvenir!

 

In addition to your free time on Maui, we have also reserved a full day long tour of the island! This journey will showcase nature’s finery, historic landmarks, charming country towns, and the Maui Tropical Plantation. After a short walk past a meandering stream through a forest full of native Hawaiian plants, gaze high above at the iconic Iao Needle – a natural outcropping jutting from the mountain side, covered in emerald-green vegetation and towering 1,200 feet over Iao Valley. The valley is rich in history as a former ancient burial site for Hawaii’s royalty. While on Maui, we will also experience an authentic luau with delicious food, drinks, and culturally-rich entertainment!

 

There's no place quite like Hawaii and Timi's Tours is the perfect host for your dream trip! Since our inception as a company, we’ve delighted guests time and again as we journey to paradise together…won’t you join us?

 

Your 12-day, 10-night trip includes 9 evenings in Hawaii, one pre-departure night in Chicago, and one night inflight for the route home. All of your airfare is included from Chicago to Oahu, Oahu to Kauai, Kauai to Maui, and a return flight from Maui to Chicago, as well as the associated taxes and fees (not withstanding luggage fees; please see below). Additionally, we have purchased 8 breakfasts and a delicious luau meal for your enjoyment! Hotel accommodations, tours, and transfers are also included. Call us today to make your reservation and say ‘Aloha’ to paradise!

 

Please note luggage fees charged by airlines are NOT included in the price of this trip and may vary based on airline policies, fees, restrictions, etc. The price of these luggage fees are the sole responsibility of each guest and are not determined by Timi's Tours.

 

Occupancy	Due At Booking	Due 6/17/25	9/17/25
Double-$8,995	$1,995	$3,500	$3,500
Single-$11,895	$1,995	$4,950	$4,950
Triple-$8,595	$1,995	$3,300	$3,300
Quad-$8,195	$1,995	$3,100	$3,100

 

Timi's Tours offers Travel Protection through Trip Mate. The Pre-Existing Medical Condition Exclusion Waiver is available if Travel Protection is purchased at the same time you make your Timi's Tours deposit (or within 15 days). For questions about coverage please call our office.

 

Travel Insurance price per person:

Single: $1,072.93

Double: $811.35

Triple: $775.27

Quad: $739.19

 

Activity Level: 2 

*Our Activity levels are a 1-4 scale. To view what each level includes, please go to the  “Policy” tab on the website*