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Hawaii Vacation Packages

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Best Hawaii Vacation Package

suggested itineraries

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 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:

  • Flight into Hawaii Big Island and out of Kauai
  • Hotel for 3 nights in Hawaii Big Island
  • Flight from Hawaii Big Island to Kauai
  • Hotel for 3 nights in Kauai
  • 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!

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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
  • 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:

  • Flight into Oahu and out of Maui
  • Hotel for 2 nights in Oahu
  • Flight from Oahu to Kauai
  • Hotel for 2 nights in Kauai
  • Flight from Kauai to Maui
  • Hotel for 2 nights in Maui
  • 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:

  • Flight into Hawaii Big Island and out of Maui
  • Hotel for 2 nights in Hawaii Big Island
  • Flight from Hawaii Big Island to Kauai
  • Hotel for 2 nights in Kauai
  • Flight from Kauai to Maui
  • Hotel for 2 nights in Maui
  • 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
 
 

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

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An unforgettable journey to the Best Pacific Destinations! Start your vacation in Auckland, with its diverse landscapes provide countless opportunities to get immersed in nature. Then escape to Sydney, irresistible combination of surf beaches, a sparkling natural harbour and the Sydney Opera House. Then fly to Oahu, spectacular sand beaches, lush tropical rainforests, and its rich cultural heritage. This is a truly unique experience you won't want to miss.

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

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6 nights from $1,956* 4 Customer Reviews

From Ultramodern city to laid-back Island Start your trip in 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. 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 Tokyo and out of Oahu
  • Hotel for 3 nights in Tokyo
  • Flight Tokyo - Oahu
  • Hotel for 3 nights in Oahu

Customize It
 
 

Enjoy the thrill of this fantastic combination! Begin your trip in San Francisco, known as the "The City by the Bay", home to world-famous attractions such as Alcatraz Island and the Golden Gate Bridge, San Francisco's iconic landmark and one of the most photographed bridge in the world. Do not miss the opportunity to enjoy amazing views from Pier 39, located in San Francisco's Fisherman's Wharf an area known for its shops, restaurants, and beautiful setting along the waterfront. up next is Oahu, a paradise for just about anyone, blessed with fantastic attractions that you will cherish for a lifetime. Explore Oahu's top sights including the historic Iolani Palace, Waikiki Beach and Pearl Harbor. A trip to Oahu is not complete without a visit to Diamond Head and Manoa Falls. Last but not least is Los Angeles, offering countless attractions such as sandy beaches, amusement parks and spectacular architecture. Los Angeles' highlights include Hollywood, Getty Villa and the beautiful Santa Monica and Venice beaches. You cannot leave Los Angeles without a visit to Disneyland, a top destination for visitors who want to enjoy a magical day.

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 San Francisco and out of Los Angeles
  • Hotel for 2 nights in San Francisco
  • Flight San Francisco to Oahu
  • Hotel for 2 nights in Oahu
  • Flight Oahu to Los Angeles
  • Hotel for 2 nights in Los Angeles

Customize It
 
 
9 nights from $2,626*

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

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 Hawaii Big Island (Hilo Airport)
  • Rental Car for 7 days
  • Hotel for 3 nights in Hawaii Big Island - Kona Beach
  • Hotel for 3 nights in Hawaii Big Island - Hilo
  • 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 $1,324* 2 Customer Reviews

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
  • 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 $1,502* 10 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 4 Days
  • Hotel for 2 nights in Big Island - Kona Beach
  • Hotel for 2 nights in Big Island - Hilo
  • 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
 
 

Breathtaking Beaches and Stunning Architecture! First arrive on Big Island to enjoy this fantastic getaway, there is no doubt that Big Island is truly a paradise for just about anyone. Here you will be able to see its dramatic volcanoes and beautiful beaches scattered around the island. Visit the Hawaii Volcanoes National Park, and then go to the Maunea Kea Observatory which is the best place for stargazing. Up next is Maui, filled with a wide range of things to see and do. Explore Haleakala National Park to enjoy incredible views over the entire island, then wander around Kaanapali Beach where you will find some of the island's best hotels and resorts, plus an array of dining, shopping and entertainment options. Last but not least is San Francisco, known as "The Golden City", home to world-famous attractions including The Golden Gate Bridge and Alcatraz Island. Take a walk around Fisherman's Wharf, an iconic neighborhood packed of dining and shopping options in a beautiful setting along the waterfront.

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 Big Island and out of San Francisco
  • Hotel for 2 nights in Big Island-Kona
  • Flight Big Island-Kona to Maui
  • Hotel for 2 nights in Maui
  • Flight Maui to San Francisco
  • Hotel for 2 nights in San Francisco

Customize It
 
 

Browse all 49 customizable packages  or  Build Your Own Itinerary

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Customer Reviews
4.7 out of 5 stars

1713 Reviews

All hotels were very nice and clean and very helpful.
All island trips were will planned.

Mark W ...
Everything was as expected.

Arun B ...
Everything was perfect! We had an amazing trip and can't wait to travel with Tripmasters again.

Laura N ...
We traveled to Hawaii via Alaska Airlines. Stayed on the Big Island and then flewto Oahu. The hotels were excellent, rental cars were ready and the ...
Read more - See this traveler's itinerary
Traveled on: September 29
We traveled to Hawaii via Alaska Airlines. Stayed on the Big Island and then flewto Oahu. The hotels were excellent, rental cars were ready and the fl ...
Read more - See this traveler's itinerary
Traveled on: September 29

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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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