List of vacation packages
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Oahu and Maui by Air
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Hawaii`s Bestseller. Visit: The Gathering Place; Oahu (the third largest island and most visited of the Hawaiian chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach. This vibrant island offers the best of both worlds-tropical verdure and a lively night scene). After spe ...
Oahu and Maui by Air
6 to 9+ nights from $929 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-10-25T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Oahu (Honolulu)and out of Maui
- Hotel for 3 nights in Oahu (Honolulu)
- Flight from Oahu (Honolulu) to Maui
- Hotel for 3 nights in Maui
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Maui and Kauai by Air
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Hawaiian Paradise!. Visit the energetic and exotic island of Maui (renowned worldwide for many things: its beauty, its atmosphere, its history, and its never-ending supply of pristine beaches, waterfalls, and gardens. The island beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales (during winter ...
Maui and Kauai by Air
6 to 9+ nights from $1,049 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-10-25T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Maui and out of Kauai
- Hotel for 3 nights in Maui
- Flight from Maui to Kauai
- Hotel for 3 nights in Kauai
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Oahu - Kauai - Maui by Air
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Escape to Hawaii, visiting these amazing islands. From The Gathering Place; Oahu (the third largest island and most visited of the Hawaiian chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach. This vibrant island offers the best of both worlds-tropical verdure and a liv ...
Oahu - Kauai - Maui by Air
6 to 9+ nights from $1,219 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-04-03T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Oahu (Honolulu) and out of Maui
- Hotel for 2 nights in Oahu (Honolulu)
- Flight from Oahu (Honolulu) to Kauai
- Hotel for 2 nights in Kauai
- Flight from Kauai to Maui
- Hotel for 2 nights in Maui
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Hawaii Big Island (Kona) and Maui by Air
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Reverie Islands of Hawaii!. Combine an amazing stay in Kona-Kailua (often referred to as Kona by locals, is a sunny seaside town located in the heart of the Kona district on the western coast of the Hawaii`s Big Island. The weather on this side of the island is almost always dry and sunny and there are many white sand beaches that are per ...
Hawaii Big Island (Kona) and Maui by Air
6 to 9+ nights from $1,269 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-09-02T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Hawaii Big Island (Kona) and out of Maui
- Hotel for 3 nights in Hawaii Big Island (Kona)
- Flight from Hawaii Big Island (Kona) to Maui
- Hotel for 3 nights in Maui
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Oahu - Kauai - Maui - Hawaii Big Island (Kona) by Air
8 to 12+ nights fromThis packages is recommended for 8 to 12+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Fantastic Hawaiian Adventure!. Get dazzled by these islands: Oahu (the third largest island and most visited of the Hawaiian chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach); then, Kauai (an island known for its natural beauty and its dramatic, beautiful sites; such ...
Oahu - Kauai - Maui - Hawaii Big Island (Kona) by Air
8 to 12+ nights from $1,869 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-04-03T00:00:00. Choose your own departure city and dates.
This 8 night sample itinerary includes:
- Flight into Oahu (Honolulu) and out of Kona
- Hotel for 2 nights in Oahu (Honolulu)
- Flight from Oahu (Honolulu) to Kauai
- Hotel for 2 nights in Kauai
- Flight from Kauai to Maui
- Hotel for 2 nights in Maui
- Flight from Maui to Hawaii Big Island (Kona)
- Hotel for 2 nights in Hawaii Big Island (Kona)
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Oahu - Hawaii Big Island (Kona) - Maui by Air
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Idyllic Islands Trip in Hawaii. Start your trip in Oahu (the third largest island and most visited of the Hawaiian chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach; then, Kona-Kailua (often referred to as Kona by locals, is a sunny seaside town located in the heart o ...
Oahu - Hawaii Big Island (Kona) - Maui by Air
6 to 9+ nights from $1,392 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-09-21T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Oahu (Honolulu) and out of Maui
- Hotel for 2 nights in Oahu (Honolulu)
- Flight from Oahu (Honolulu) to Hawaii Big Island (Kona)
- Hotel for 2 nights in Hawaii Big Island (Kona)
- Flight from Hawaii Big Island (Kona) to Maui
- Hotel for 2 nights in Maui
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Maui Getaway
5 to 7+ nights fromThis packages is recommended for 5 to 7+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Destination for true nature lovers in Maui!. Explore the Haleakala National Park, an active but non-erupting volcano that has become famous for its amazing sunsets that illuminate the sky with a multitude of colors. Stretch out on warm, golden sands or hit the surf for an unforgettable windsurfing or snorkeling session . enjoy the sceni ...
Maui Getaway
5 to 7+ nights from $928 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-09-25T00:00:00. Choose your own departure city and dates.
This 5 night sample itinerary includes:
- Flight into and out of Maui
- Hotel for 5 nights in Maui
- Hotel Hawaii taxes
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Hawaii Big Island (Kona) - Kauai - Maui by Air
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Special vibe that can only be found in Hawaii. Discover: Kona-Kailua (often referred to as Kona by locals, is a sunny seaside town located in the heart of the Kona district on the western coast of the Hawaii`s Big Island. The weather on this side of the island is almost always dry and sunny and there are many white sand beaches that are p ...
Hawaii Big Island (Kona) - Kauai - Maui by Air
6 to 9+ nights from $1,389 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-05-06T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Hawaii Big Island (Kona) and out of Maui
- Hotel for 2 nights in Hawaii Big Island (Kona)
- Flight from Hawaii Big Island (Kona) to Kauai
- Hotel for 2 nights in Kauai
- Flight from Kauai to Maui
- Hotel for 2 nights in Maui
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Maui Getaway (Self Drive)
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Say Aloha in Maui. Discover this fantastic and the second largest Hawaiian island; beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales, during winter months, farm-to-table cuisine and the magnificent sunrise and sunset from Haleakala; with a Rental Car. What Makes Tripmasters Vacation Packages D ...
Maui Getaway (Self Drive)
6 to 9+ nights from $2,547 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-08-24T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into and out of Maui
- Rental Car for 7 days
- Hotel for 6 nights in Maui
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Oahu - Maui - Hawaii Big Island Beach and Volcano
8 to 12+ nights fromThis packages is recommended for 8 to 12+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Unforgettable Hawaiian Trip!!!. Start in Oahu (the third largest island and most visited of the Hawaiian chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach); up next, catch a flight to Maui (the island beloved for its world-famous beaches, the sacred Iao Valley, views ...
Oahu - Maui - Hawaii Big Island Beach and Volcano
8 to 12+ nights from $2,019 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-04-03T00:00:00. Choose your own departure city and dates.
This 8 night sample itinerary includes:
- Flight into Oahu (Honolulu) and out of Hilo
- Hotel for 2 nights is Oahu (Honolulu)
- Flight from Oahu (Honolulu) to Maui
- Hotel for 2 nights in Maui
- Flight from Maui to Hawaii Big Island (Kona)
- Rental Car for 5 Days
- Hotel for 2 nights in Hawaii Big Island (Kona)
- Hotel for 2 nights in Hawaii Big Island (Hilo)
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Oahu - Maui - Hilo by Air
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Hawaiian Dream!. Combine pleasant stays in Oahu (the third largest island and most visited of the Hawaiian chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach); up next, Maui (the island beloved for its world-famous beaches, the sacred Iao Valley, views of migrating hum ...
Oahu - Maui - Hilo by Air
6 to 9+ nights from $1,224 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-10-04T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Oahu (Honolulu) and out of Hilo
- Hotel for 2 nights in Oahu (Honolulu)
- Flight from Oahu (Honolulu) to Maui
- Hotel for 2 nights in Maui
- Flight from Maui to Hawaii Big Island (Hilo)
- Hotel for 2 nights in Hawaii Big Island (Hilo)
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Oahu - Maui and Kauai (Self Drive)
9 to 13+ nights fromThis packages is recommended for 9 to 13+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
This once in a life time get away is at your grasp in Hawaii!. Begin in Oahu (the third largest island and most visited of the Hawaiian chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach). Next, steel away in Maui (the island beloved for its world-famous beaches, the ...
Oahu - Maui and Kauai (Self Drive)
9 to 13+ nights from $2,233 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-10-14T00:00:00. Choose your own departure city and dates.
This 9 night sample itinerary includes:
- Flight into Oahu (Honolulu) and out of Kauai
- Hotel for 3 nights in Oahu (Honolulu)
- Rental Car for 4 days
- Flight from Oahu (Honolulu) to Maui
- Hotel for 3 nights in Maui
- Rental Car for 4 days
- Flight from Maui to Kauai
- Hotel for 3 nights in Kauai
- Rental Car for 4 days
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Maui Escape
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Discover Maui!. This fantastic and the second largest Hawaiian island; beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales, during winter months, farm-to-table cuisine and the magnificent sunrise and sunset from Haleakala. Many visitors enjoy the Road to Hana (aka the Hana Highway) as is winds i ...
Maui Escape
6 to 9+ nights from $966 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-10-08T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into and out of Maui
- Hotel for 6 nights in Maui
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Maui - Big Island Beach and Volcano (Self Drive)
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Combine these Islands and get seduced by the special vibe that can only be found in Hawaii. Start in Maui (the island beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales (during winter months, farm-to-table cuisine and the magnificent sunrise and sunset from Haleakala); and up next, catch a flig ...
Maui - Big Island Beach and Volcano (Self Drive)
6 to 9+ nights from $1,964 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-11-15T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Maui and out of Big Island (Hilo)
- Hotel for 2 nights is Maui
- Flight from Maui to Hawaii Big Island (Kona)
- Rental Car for 5 days
- Hotel for 2 nights in Hawaii Big Island (Kona)
- Hotel for 2 nights in Hawaii Big Island (Hilo)
Driving Time
Kona - Hilo: 1 hr. 45 mins. approx.
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Hawaii Big Island (Kona) - Oahu and Maui (Self Drive)
9 to 13+ nights fromThis packages is recommended for 9 to 13+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
See beautiful Hawaii through popular destinations!. Visit Kona-Kailua (often referred to as Kona by locals, is a sunny seaside town located in the heart of the Kona district on the western coast of the Hawaii`s Big Island. The weather on this side of the island is almost always dry and sunny and there are many white sand beaches that are ...
Hawaii Big Island (Kona) - Oahu and Maui (Self Drive)
9 to 13+ nights from $2,250 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-10-21T00:00:00. Choose your own departure city and dates.
This 9 night sample itinerary includes:
- Flight into Hawaii Big Island (Kona) and out of Maui
- Hotel for 3 nights in Hawaii Big Island (Kona)
- Rental Car for 4 days
- Flight from Hawaii Big Island (Kona) to Oahu (Honolulu)
- Hotel for 3 nights in Oahu (Honolulu)
- Rental Car for 4 days
- Flight from Oahu (Honolulu) to Maui
- Hotel for 3 nights in Maui
- Rental Car for 4 days
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Maui and San Francisco by Air
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Enjoy the best of Maui and California!. Discover Start your trip in the fascinating island of Maui (the island beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales (during winter months, farm-to-table cuisine and the magnificent sunrise and sunset from Haleakala . After that, fly to San Francisco ...
Maui and San Francisco by Air
6 to 9+ nights from $1,158 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2026-02-17T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Maui and out of San Francisco
- Hotel for 3 nights in Maui
- Flight from Maui to San Francisco
- Hotel for 3 nights in San Francisco
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Maui and Molokai by Air
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
A Hawaiian Holiday is at your disposal with this customizable package. Spend amazing days, soaking in the sun; first, visiting; Maui (mix of beaches from white, black and red sand beaches, lush green valleys, volcanic landscapes, adventurous water sports, historic villages and rich culture), and then; Molokai (Hawaii’s fifth largest islan ...
Maui and Molokai by Air
6 to 9+ nights from $1,330 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-11-27T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Maui and out of Molokai
- Hotel for 3 nights in Maui
- Flight from Maui to Molokai
- Hotel for 3 nights in Molokai
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Hawaii Big Island (Kona) and Maui (Self Drive)
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Enjoy this Rental Car Package to venture through these amazing Hawaii Islands. Start your adventure in Kona-Kailua (often referred to as Kona by locals, is a sunny seaside town located in the heart of the Kona district on the western coast of the Hawaii`s Big Island. The weather on this side of the island is almost always dry and sunny an ...
Hawaii Big Island (Kona) and Maui (Self Drive)
6 to 9+ nights from $1,721 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-10-15T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Hawaii Big Island (Kona) and out of Maui
- Hotel for 3 nights in Hawaii Big Island (Kona)
- Rental Car for 4 days
- Flight from Hawaii Big Island (Kona) to Maui
- Hotel for 3 nights in Maui
- Rental Car for 4 days
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Oahu and Maui (Self Drive)
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Hawaii`s Success destinations by car!. Visit: The Gathering Place; Oahu (the third largest island and most visited of the Hawaiian Chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach. This vibrant island offers the best of both worlds-tropical verdure and a lively night ...
Oahu and Maui (Self Drive)
6 to 9+ nights from $1,835 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-10-13T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Oahu (Honolulu) and out of Maui
- Rental Car for 4 days
- Hotel for 3 nights in Oahu (Honolulu)
- Flight from Oahu (Honolulu) to Maui
- Rental Car for 4 days
- Hotel for 3 nights in Maui
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Hawaii Big Island (Kona) - Maui - Molokai by Air
6 to 9+ nights fromThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
A wonderful escape to Hawaii awaits you in this holiday package!. Visit Kona-Kailua (often referred to as Kona by locals, is a sunny seaside town located in the heart of the Kona district on the western coast of the Hawaii`s Big Island. The weather on this side of the island is almost always dry and sunny and there are many white sand bea ...
Hawaii Big Island (Kona) - Maui - Molokai by Air
6 to 9+ nights from $1,555 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-10-12T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Hawaii Big Island (Kona) and out of Molokai
- Hotel for 2 nights in Hawaii Big Island (Kona)
- Flight from Hawaii Big Island (Kona) to Maui
- Hotel for 2 nights in Maui
- Flight from Maui to Molakai
- Hotel for 2 nights in Molakai