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Hawaii Vacations

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Oahu and Maui by air

6 nights from $929*

158 Customer Reviews

Our #1 Bestseller in Hawaii! Called 'The Gathering Place', Oahu is the third largest Hawaiian island where you'll find a beach for all tastes and interests. Learn to ride the waves in Waikiki - where surfing was born - or enjoy the giant waves in the more remote surf beaches of North Shore. Then fly to Maui, voted the 'Best Island' by the readers of Conde Nast Traveler for 19 years. A beautiful and magical place with miles of perfect beaches, lush green valleys, and volcanic landscapes. Book your dream vacation now, and experience independent travel to Hawaii at its finest.

This is a flexible vacation package to Hawaii with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Round-trip air from the Continental USA to Hawaii
  • Hotel for 3 nights in Oahu (flexible)
  • Flight Oahu to Maui
  • Hotel for 3 nights in Maui (flexible)
  • Daily breakfast (if stated in hotel info)
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation like Pearl Harbour Excursion, Dinner Cruise, Luau Shows, and hiking Diamond Head Crater in Oahu; Snorkeling Adventure and Heleaka tour in Maui.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

6 nights from $929*

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6 nights from $926*
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6 nights from $926*
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6 nights from $949*
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Fantastic Hawaiian Duo!...Start your trip in Oahu or better known as'The Gathering Place', where many activities await for you; like windsurfing or kayaking in the remote islands of Kailua, snorkel in clear turquoise sea, hike through its mountains, and of course don't miss out of some surfing. Then fly to Kauai, named 'The Garden Isle' and pamper all your senses in this alluring island.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Round-trip air from the Continental USA to Hawaii
  • Hotel for 3 nights in Oahu (flexible)
  • Flight Oahu to Kauai
  • Hotel for 3 nights in Kauai (flexible)
  • Daily breakfast (if stated in hotel info)
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

6 nights from $926*
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Reverie Islands of Hawaii!!!...Start your vacation on Big Island, a place of contrast indeed!. Here you will find from volcanos to waterfalls, as well as lush vegetation in Puna Fern Forest or the lack of it at Kau desert. Then fly to Maui, home of crystal clear beaches, famous volcanoes, and the most exciting outdoor activities.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Round-trip air from the Continental USA to Hawaii
  • Hotel for 3 nights in Big Island (flexible)
  • Flight Big Island to Maui
  • Hotel for 3 nights in Maui (flexible)
  • Daily breakfast (if stated in hotel info)
  • This package priced with round trip air from LAX
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

6 nights from $926*
Customize it

 
 
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Hawaiian Paradise!!! Visit the energetic and exotic island of Maui, home of crystal clear beaches, famous volcanoes, and the most exciting outdoor activities. Then fly to Kauai, named'The Garden Isle' and pamper all of your senses in this alluring island. Either exploring the Waimea Canyon Park or catching a glimpse of their extraordinary spouting horn this is a place not to be missed!!!

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Round-trip air from the Continental USA to Hawaii
  • Hotel for 3 nights in Maui (flexible)
  • Flight Maui to Kauai
  • Hotel for 3 nights in Kauai (flexible)
  • Daily breakfast (if stated in hotel info)
  • This package priced with round trip air from LAX
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

6 nights from $949*
Customize it

 
 
suggested itineraries

Most visited Islands of Hawaii! Big island, larger than all of the other islands combined, and vast enough to hold 11 of the world's 13 climactic zones. From sandy beaches to snowcapped mountains and beautiful and exuberant volcanoes. See waterfalls, rainforests and botanical gardens in Hilo, enjoy the calm and crystal clear water of Kona; visit Hawaii Volcanoes National Park, and explore Kilauea, one of the world's most active volcanoes. Fly to Oahu, known as the 'heart and gathering place of Hawaii' where you will find a memorable Hawaiian experience with its culture, beautiful scenery, and pristine beaches.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Round-trip air from the Continental USA to Hawaii
  • Hotel for 3 nights in Big Island (flexible)
  • Flight Big Island to Oahu
  • Hotel for 3 nights in Oahu (flexible)
  • Daily breakfast (if stated in hotel info)
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

Customize It
 
 

Day-dream Hawaiian vacation!!!...Fly to Big Island and get venturesome, this place is the home of the most active volcanoes accompanied with lava deserts, emerald lush vegetation and white sand beaches, perfect fun for families, or romance for couples. Then fly toKauai, named 'The Garden Isle' and pamper all of your senses in this alluring island. Either exploring the Waimea Canyon Park or catching a glimpse of their extraordinary spouting horn. This is a place not to be missed!!!

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Round-trip air from the Continental USA to Hawaii
  • Hotel for 3 nights in Big Island (flexible)
  • Flight Big Island to Maui
  • Hotel for 3 nights in Kauai (flexible)
  • Daily breakfast (if stated in hotel info)
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

Customize It
 
 

Combine three Islands and get seduced by the special vibe that can only be found here. Some of the most famous beaches in the world, soaring mountain peaks, lave-spewing volcanos, rugged red-rock canyons and towering waterfalls. Truly paradise on earth!

Included:

  • Flight into Big Island and out of Maui
  • Hotel for 2 nights in Big Island
  • Flight Big Island to Kauai
  • Hotel for 2 nights in Kauai
  • Flight Kauai to Maui
  • Hotel for 2 nights in Maui
  • Daily breakfast (if stated in hotel info)
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

Customize It
 
 


Hawaian White Sand Beaches, land in Oahu also well know as 'The Gathering Place.Try surfing , windsurfing and body-boarding among other watersports .Then hop on into another paradaise, the tiny tropical island of Kauai , which has kept its charm, magic and mystery .Last but not least fly into the breathtaking Island of Maui and watch the migrating humpback whales and sunset on Haleakala.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Round-trip air from the Continental USA to Hawaii
  • Hotel for 2 nights in Oahu
  • Flight Oahu to Kauai
  • Hotel for 2 nights in Kauai
  • Flight Kauai to Maui
  • Hotel for 2 nights in Maui
  • Daily breakfast (if stated in hotel info)
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

Customize It
 
 

Exotic Island Experience!!!...Fly to Big Island and get venturesome. This place is the home of the most active volcanoes accompanied with lava deserts, emerald lush vegetation and white sand beaches, perfect fun for families, or romance for couples. Then fly to Kauai, named 'The Garden Isle' and pamper all of your senses in this alluring island. Either exploring the Waimea Canyon Park or catching a glimpse of their extraordinary spouting horn. Up next is Maui, home of crystal clear beaches, famous volcanoes, and the most exciting outdoor activities.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Round-trip air from the Continental USA to Hawaii
  • Hotel for 2 nights in Big Island (flexible)
  • Flight Big Island to Kauai
  • Hotel for 2 nights in Kauai (flexible)
  • Flight Kauai to Maui
  • Hotel for 2 nights in Maui (flexible)
  • Daily breakfast (if stated in hotel info)
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

Customize It
 
 

6 nights from $1,736*

The Best of Both Worlds!!!...Fly to Sydney, a city which is surrounded by one of the largest natural harbors, and immerse yourself into this vibrant and lively place. Here, visitors will find the perfect fusion of cultures, religions and modernity, which will provide them with a wide range of different activities that will make their trip be a once-in-a-lifetime experience. Then fly to Oahu or better known as 'The Gathering Place', where many activities await for you; like windsurfing or kayaking in the remote islands of Kailua, snorkel in clear turquoise sea, hike through its mountains, and of course don't miss out of some surfing!!!

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Flight into Sydney and out of Oahu (Hawaii)
  • Hotel for 3 nights in Sydney
  • Flight Sydney to Oahu
  • Hotel for 3 nights Oahu
  • Daily breakfast (if stated in hotel info)
  • Hotel taxes
  • Transfers and activities can be added at extra cost

Customize It
 
 

An unforgettable journey to the Best Pacific Destinations of New Zealand, Australia and Hawaii!...Auckland with its diverse landscapes provide countless opportunities to get immersed in nature. Sydney's irresistible combination of surf beaches, a sparkling natural harbour and the Sydney Opera House. Oahu's breathtaking scenery, spectacular sand beaches, lush tropical rainforests, and its rich cultural heritage.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Flight into Auckland and out of Oahu
  • Hotel for 3 nights in Auckland
  • Flight Auckland to Sydney
  • Hotel for 3 nights Sydney
  • Flight Sydney to Oahu
  • Hotel for 3 nights in Oahu
  • Daily breakfast (if stated in hotel info)
  • Hotel taxes
  • Transfers and activities can be added at extra cost

Customize It
 
 
6 nights from $1,282* 1 Customer Reviews

From Laid-Back to Ultramodern!!!...Start your trip in Oahu, or better known as 'The Gathering Place', where many activities await for you; like windsurfing or kayaking in the remote islands of Kailua, snorkel in clear turquoise sea, hike through its mountains, and of course don't miss out of some surfing! Then marvel at Tokyo, Japan?s most lively capital, which mixes the ultramodern with the traditional, featuring neon-lit skyscrapers and anime shops to cherry trees and temples. This city is famed for its vibrant food scene, and its trendy and fashion districts of Shibuya and Harajuku.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Flight into Hawaii (Oahu) and out of Tokyo
  • Hotel for 3 nights in Oahu
  • Flight Oahu to Tokyo
  • Hotel for 3 nights in Tokyo
  • Daily breakfast (if stated in hotel info)
  • Hotel taxes

Customize It
 
 
6 nights itineraries  

Two vibrant countries in just one trip!... In your way to Auckland enjoy a Hawaii stopover and visit Oahu, known as a place of breathtaking natural beauty. From glorious sunrises to dramatic sunsets and beyond, there is so much to do and enjoy in Hawaii. Fly to Auckland, one of theworld's top cities; land of idyllic islands and rolling green hills, the home of hospitality, world class wines and superb cuisine.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Flight into Hawaii (Oahu) and out of Auckland
  • Hotel for 3 nights in Oahu
  • Flight Oahu to Auckland
  • Hotel for 3 nights in Auckland
  • Daily breakfast (if stated in hotel info)
  • Hotel taxes

Customize It
 
 
9 nights from $2,373*

Island Hopping at its Best!!! Fly to Oahu, which offers white sandy beaches, palm trees, relaxation and much more. Whether you are feeling venturesome looking for new experiences or romantic waiting for the perfect sunset, this Island has it all. Then land in Auckland, with its diverse landscapes provide countless opportunities to get immersed in nature. Last but not least is Sydney, a city which is surrounded by one of the largest natural harbors, and immerse yourself into this vibrant and lively place. Here, visitors will find the perfect fusion of cultures, religions and modernity, which will provide them with a wide range of different activities that will make their trip be a once-in-a-lifetime experience.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Flight into Hawaii (Oahu) and out of Sydney
  • Hotel for 3 nights in Oahu
  • Flight Oahu to Auckland
  • Hotel for 3 nights in Auckland
  • Flight Auckland - Sydney
  • Hotel for 3 nights in Sydney
  • Daily breakfast (if stated in hotel info)
  • Hotel taxes

Customize It
 
 

Spend your vacation in the most magnificent cities of the beautiful island of Hawaii. Start your trip in the marvelous Kona district and be amazed by its out-of-this-world beaches and sunsets that will make you drop you jaw. Then drive to Hilo district, a place that is blessed with dramatic waterfalls, fertile rainforests and blooming gardens. Natural beauty at its finest!!!

Included:

  • Flight into Kona and out of Big Island (Hilo Airport)
  • Rental Car for 6 nights
  • Hotel for 3 nights in Big Island - Kona Beach
  • Hotel for 3 nights in Big Island - Hilo
  • Daily breakfast (if stated in hotel info)
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling

Customize It
 
 

Exotic, Energetic and Alluring!!! Start your trip in the fascinating island of Maui, home of crystal clear beaches, famous volcanoes, and the most exciting outdoor activities. Then visit the marvelous Kona district and be amazed by its out-of-this-world beaches and sunsets that will make you drop you jaw. Then drive to Hilo district, a place that is blessed with dramatic waterfalls, fertile rainforests and blooming gardens. Natural beauty at its finest.

Included:

  • Flight into Maui and out of Big Island (Hilo Airport)
  • Hotel for 2 nights in Maui
  • Flight Maui - Kona
  • Rental Car for 4 nights
  • Hotel for 2 nights in Big Island - Kona Beach
  • Hotel for 2 nights in Big Island - Hilo
  • Daily breakfast (if stated in hotel info)
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling

Customize It
 
 
6 nights from $1,097* 6 Customer Reviews

Hawaii at its Best!...Start your trip in Oahu or better known as 'The Gathering Place', where many activities await for you; like windsurfing or kayaking in the remote islands of Kailua, snorkel in clear turquoise sea, hike through its mountains, and of course don't miss out of some surfing. Up next is the energetic and exotic island of Maui, home of crystal clear beaches, famous volcanoes, and the most exciting outdoor activities. Finish your vacation in Hilo, a place that is blessed with dramatic waterfalls, fertile rainforests and blooming gardens.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Flight into Oahu and out of Big Island (Hilo Airport)
  • Hotel for 2 nights in Oahu
  • Flight Oahu - Maui
  • Hotel for 2 nights in Maui
  • Flight Maui - Hilo
  • Hotel for 2 nights in Big Island - Hilo
  • Daily breakfast (if stated in hotel info)
  • Hotel Hawaii taxes
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

Customize It
 
 

Unforgettable Hawaiian Journey!!! Start your trip in Oahu, or better known as 'The Gathering Place', where many activities await for you; like windsurfing or kayaking in the remote islands of Kailua, snorkel in clear turquoise sea, hike through its mountains, and of course don't miss out of some surfing. Then drive to Maui, home of crystal clear beaches, famous volcanoes, and the most exciting outdoor activities. Up next visit the marvelous Kona district and be amazed by its out-of-this-world beaches and sunsets that will make you drop you jaw. Then drive to Hilo district, a place that is blessed with dramatic waterfalls, fertile rainforests and blooming gardens. Natural beauty at its finest.

This is a flexible package with daily departures from anywhere in the USA or Canada. Choose your length of stay. Pick your own flights, hotels and activities. Add, remove or reorder cities.

Included:

  • Flight into Oahu and out of Big Island (Hilo Airport)
  • Hotel for 2 nights is Oahu
  • Flight Oahu - Maui
  • Hotel for 2 nights in Maui
  • Flight Maui - Big Island (Kona International Airport)
  • Rental Car for 5 Days
  • Hotel for 2 nights in Big Island - Kona Beach
  • Hotel for 2 nights in Big Island - Hilo
  • Daily breakfast (if stated in hotel info)
  • Plus a wide range of optional activities to add and book with instant confirmation.

  • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling!

Customize It
 
 

Browse all 38 suggested itineraries  or  Build Your Own Itinerary

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Customer Reviews
We selected the rental cars from the list online. However at each island we would find out the vehicle is not big enough for our family so we have no ...
Really good. One of my friend, who travelled with you suggested your site and I'll do the same for my other friends

Vija R ...
You guys were actually amazing. It was really easy to check in and out of the hotels and the flights were as promised. Only bad thing was the actual a ...
Everything that Tripmasters did was very organized and went well. The Maui lodging (Napili Shore by Outrigger) was nice, only complaint was no air con ...
Need to improve upon the car rental. Wad bookes an economy and needed a SUV or Van ...
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* Sample prices displayed include international and domestic airline tickets as per itinerary and ALL airline-related taxes and fuel surcharges and are per person, based on double occupancy, and are dynamic in nature. Prices do not include insurance or delivery charges which are optional and customizable by the traveler. The airfare portion of the itinerary price is based on economy class, midweek departure. Prices do not include fees for carry on or checked baggage which can add additional fees per ticket on a roundtrip flight based on carrier charges. It also does not include any entrance fees or visa fees that may be charged at international airports. Some cities may charge local taxes that can only be collected by hotel at destination.
Prices were accurate at the time we posted them. Sample prices were for a specific travel date and specific departure airport, as indicated. Your prices will vary according to departure cities and travel dates. We do not control prices (airlines and hotel reservation systems do). Prices may change dynamically and at times significantly numerous times during any given day.
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