Kauai, Maui, Big Island & Oahu 14 Days

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Self Guided Package

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Important: We DO NOT work on Sundays. All Sundays are free for self-arranged activities. Thank you for your respect for the Sabbath Day. Sincerely, SIT Management.

This Itinerary is a self guided 14 day tour of the islands of Maui, the Big Island of Hawaii, Kauai and Oahu.

Think of us as your own personal tour coordinator! We are here to iron out the details and fill your days with unique entertaining experiences. We recommend taking advantage of the numerous optional activities available through your SIT Vacations Escort. We are dedicated to helping you make the most of your time here in these beautiful isles! Please feel free to contact us for more details.

You will be notified of times and area for pick up and drop off to the airport and hotel, for tours and the luau dinner included in your package. Of course, the staff at SIT Vacations will always be available by phone or email to answer any questions you might have for the duration of your stay.

As this tour package is self guided you have the freedom to take charge of your vacation and take things at your own pace. The best way to experience the breathtaking Hawaiian Islands without compromising quality time with the ones who matter most.

Day 1: Welcome! E Komo Mai

Welcome to Hawaii, to the Garden Isle of Kaua'i! We welcome you with our warmest Aloha and a fresh flower lei upon your arrival to Lihue Airport.  Just a short 30min shuttle ride brings you to the Courtyard Marriott Hotel at Kapa'a. Check in, get settled and enjoy your first evening in Hawaii.

Day 2: Waimea Canyon

Its an early morning today as you head out to Kauai’s Waimea Canyon. This first tour will give you the chance to explore Waimea Canyon, also known as "The Grand Canyon of the South Pacific". Bring your camera as you will want to capture all you can of the lush green cliffs, waterfalls, and rich colorful valleys. Your tour leaves at 7:30am and will return at 1:30pm. The rest of the afternoon is yours to enjoy!

Day 3: Kapa’a Town

Today is your official introduction to Kauai’s quaint Kapa’a Town! Take it slow and explore the sights at your own pace, enjoy the numerous shops and intimate eateries along the waterfront. Sign up for an exciting outdoor excursion - However you chose to spend your day … Kapa’a is waiting.

Day 4: Maui

Welcome to Maui! We greet you with our warmest Aloha and a fresh flower Lei upon your arrival to Kahului International Airport. After baggage claim you will be transferred to the Kaanapali Beach Resort, a short 40 minute drive from the Airport. Check in, get settled and enjoy the rest of your first evening in beautiful Maui.

Day 5: The Road to Hana

Be ready for your official introduction to the island of Maui on your Road to Hana adventure. SIT Vacations will assist you in planning all the details! Choose between a self guided tour in your own rental vehicle or join an organized guided bus tour.

The Road to Hana is one of Hawaii’s most scenic coastal roadways, winding through gorgeous seaside cliffs, waterfalls and miles of pristine rainforest. Charge your camera and get plenty of rest because it will be a full day of exploring on Maui’s famous Road to Hana.

Day 6: Take it Easy

Today is all yours! Take advantage of the hotel amenities, kick back by the pool with a cool drink in hand or nap under a palm tree. Feel free to visit nearby Whaler’s Village, Kaanapali’s premier destination for shopping and dining. Speak with an SIT Vacations representative for more information on available optional activities while in Maui.

Day 7: Aloha Big Island

Today you fly to your third island of Hawaii, the home of the most active volcano in the world. Your 30 minute inter-island flight brings you to Kona International Airport. Your hotel is just 15 minutes from the airport in the little town of Kailua. Check in to your hotel and enjoy the rest of the day.

Day 8: So Much to Do

How about a little wind in your hair? Inquire about a rental car and cruise Big Island’s famed shoreline. Stop and see the sights, take in some sun from any number of beautiful beaches … all at your own pace.

You can also choose to take it easy and leave the driving to someone else! Join the guided Circle Island Bus tour; feel the heat at Volcano National Park and enjoy a tasty sample of local favorites from the Mauna Loa Chocolate Factory. Contact your SIT Vacations representative to book any number of available optional activities.

Day 9: A little R&R

Its your last day on the Big Island! Take a stroll down Kona’s Ali’i Drive in the historic Kailua Kona Village. Step back in time and take a tour of King Kamehameha’s royal residences where he spent his latter years. Get a taste of Kona at any of the numerous local eateries or get in some last minute shopping at the quaint waterfront shops. …. Or you can do nothing at all! Take a dip in the pool, get a massage – have a nap in the warm Kona sun. Its your day to enjoy! See your SIT Vacation representative to inquire about booking available optional activities.

Day 10: Oahu - “The Gathering Place"

Gathering Place”Oahu is known as Hawaii’s “gathering place” and it is here that you embark on the last leg of your Hawaiian excursion. After your arrival to the Honolulu International Airport a shuttle will transport you to nearby Waikiki. Time to Check in, get settled and kick back.  Looking for a night on the town? Waikiki has an abundance of evening entertainment to enjoy – Contact your SIT representative for suggestions on dinner, show and other available activity bookings.

Day 11: Pearl Harbor Memorial

Today you greet an early morning and head out to the revered Pearl Harbor Memorial. Learn more about the infamous events that impacted a nation and view the USS Arizona still resting in the harbor.

Because of heightened security the maximum size parcel allowed on the premises are compact camera cases. Lockers are available for a small fee for any other bags you may require. Your tour will begin with an early morning pick up from your hotel, returning again at around 1:30pm.

The rest of the day is yours to relax and explore.

Day 12: Waikiki

Today is your official introduction to exciting Waikiki! Take it slow and explore the sights of downtown at your own pace, enjoy the numerous shops and restaurants all along the Waikiki beachfront. Customize your experience and sign up for various optional activities unique to Waikiki. Information on available activities will be provided.  However you chose to spend your day … Waikiki is waiting.

Day 13: Luau

This is your last full day on the Island but the fun is just beginning!  Make it count today and get in a day of fun and sun on Waikiki Beach, do some last minute shopping or try something new – the day is yours to enjoy! Tonight is the night for Luau, a Hawaiian gathering of food and fun! Dress to impress and get ready to hula! Tonight you celebrate life and love island style. 

Pick up for your luau will be at 4:00pm and will return to your hotel at 9:00pm.

Day 14: Until We Meet Again

Your 14 day excursion comes to a close today. Check out will be between 11-12:00pm depending upon your hotel. A shuttle will pick you up according to your individual flight arrangements. 

Mahalo for visiting these beautiful isles of Hawaii and for choosing SIT Vacations as your host and guide. We hope you have enjoyed yourself as our guest and will choose us again to assist you with all your vacation needs. We wish you safe travels and hope to cross paths with you again. Aloha Friends!