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Booking Window: 02/02/26 – 03/20/26
Travel Window: 02/02/26 – 12/18/26
From Maui’s sun-drenched shores and Oahu’s iconic coastline to the dramatic beauty of Kauai and the natural wonders of the Big Island, experience Hawaii with exceptional value. Enjoy up to 40% savings, Free Breakfasts, and up to $500 in added value on select luxury resort stays, along with thoughtful resort inclusions and a complimentary Alamo car rental upgrade to explore each island in comfort. These limited-time offers are designed for travelers who seek elevated experiences, effortless travel, and unforgettable island escapes.
Maui is the perfect balance of relaxation and exploration. Known for upscale resorts, lush scenery, and iconic experiences like the Road to Hana and Haleakalā sunrise, it’s ideal for honeymooners, first-time Hawaii visitors, and clients who want variety without island-hopping.
Road to Hana
Take a breathtaking drive along Maui’s lush coastline, stopping at waterfalls, black sand beaches, and scenic overlooks.
Haleakalā National Park
Watch the sunrise or sunset from the summit of this towering volcano, offering panoramic views above the clouds.
Snorkeling at Molokini Crater
Explore crystal-clear waters teeming with marine life at this iconic crescent-shaped volcanic crater.
Classic Vacations partners with Project Expeditions so you can enjoy everything the island has to offer. Add excursions and tours to your bookings now.
10% Discounted Rate
Andaz Garden Room
5 Nights from $1,929 Per Person
$125 Savings
Fairmont Suite
5 Nights from $2,428 Per Person
$400 Savings
Garden 3 Bedroom Luxury Villa
5 Nights from $5,549 Per Person
$150 Savings
One Bedroom Garden Residence
5 Nights from $4,799 Per Person
10% Discount
Garden View Room
5 Nights from $1,809 Per Person
10% Discount
Resort View Room
5 Nights from $1,369 Per Person
$250 Savings
Garden View Room
5 Nights from $1,339 Per Person
$250 Savings
Kukahi Aina View Room
5 Nights from $1,279 Per Person
$300 Savings
1 Bedroom Suite Mountain View Room
4 Nights from $1,099 Per Person
$375 Savings
Gold Fairway View Villa
5 Nights from $1,049 Per Person
$480 Savings
Tower Standard Room
4 Nights from $509 Per Person
$250 Savings
Resort View Room
5 Nights from $1,269 Per Person
$150 Savings
Guest Room with King Bed, Sofa Bed, and Balcony
5 Nights from $929 Per Person
5% Discounted Rate
Garden View Room
5 Nights from $1,069 Per Person
$500 Discount
Deluxe Ocean View Room
4 Nights from $1,679 Per Person
$250 in Savings
Ocean View Room
5 Nights from $2,599 Per Person
Oʻahu blends vibrant city life with classic Hawaiian beauty. Home to Waikīkī, Pearl Harbor, and a thriving food and arts scene, it’s ideal for first-time visitors, families, and clients who want shopping, dining, nightlife, and easy access to culture—all on one island.
Hike Diamond Head Crater
Trek to the summit of this iconic volcanic crater for breathtaking panoramic views of Waikiki and the Pacific Ocean.
Snorkel at Hanauma Bay
Explore vibrant coral reefs and swim alongside tropical fish in this stunning marine conservation area.
Visit Pearl Harbor
Explore the historic USS Arizona Memorial and other World War II sites to honor the past and learn about the events of December 7, 1941.
Classic Vacations partners with Project Expeditions so you can enjoy everything the island has to offer. Add excursions and tours to your bookings now.
$150 Savings
Standard View Room
3 Nights from $1,059 Per Person
$150 Savings
Garden Residence
5 Nights from $4,799 Per Person
$150 Savings
Resort View Room
5Nights from $1,949 Per Person
$150 Savings
Historic Ocean Room
3 Nights from $769 Per Person
$450 Savings
Classic Room
3 Nights from $479 Per Person
$150 Savings
Waikiki City View Room
3 Nights from $469 Per Person
$100 Savings
Ocean View Room
3 Nights from $859 Per Person
$150 Savings
Partial Ocean View Room
3 Nights from $929 Per Person
$100 Savings
Waikiki City View Room
3 Nights from $359 Per Person
5% Discount
Level 8 Standard Suite
3 Nights from $569 Per Person
$150 Savings
Princess Ocean View Room
4 Nights from $429 Per Person
40% Discount
Waikiki City View Room with King Bed
3 Nights from $339 Per Person
$150 Savings
Historic Banyan Ocean Room
3 Nights from $929 Per Person
3% Discount
Resort View Room
3 Nights from $759 Per Person
Known as the “Garden Isle,” Kauaʻi is defined by emerald cliffs, waterfalls, and raw natural beauty. With fewer resorts and a quieter pace, it’s perfect for nature lovers, couples, and repeat Hawaii travelers seeking a more intimate, unplugged experience.
Explore the Nā Pali Coast
Take a boat tour, kayak, or helicopter ride to witness the stunning cliffs, waterfalls, and emerald valleys of this breathtaking coastline.
Hike the Kalalau Trail
Trek along this iconic 11-mile trail (or just a portion) for jaw-dropping views of the Pacific and lush Kauaʻi landscapes.
Visit Waimea Canyon
Known as the “Grand Canyon of the Pacific,” this awe-inspiring natural wonder offers scenic lookouts and incredible hiking trails.
Classic Vacations partners with Project Expeditions so you can enjoy everything the island has to offer. Add excursions and tours to your bookings now.
20% Discount
Garden View Room
5 Nights from $2,469 Per Person
40% Discount
Garden View Room
5 Nights from $799 Per Person
$300 Savings
Partial Ocean View Room
4 Nights from $1519 Per Person
$300 Savings
Garden View Room
4 Nights from $769 Per Person
The Big Island offers the most geographic diversity in Hawaiʻi, from black-sand beaches and active volcanoes to snow-capped mountains. Best for adventurous travelers, it rewards exploration and longer stays, with distinct regions that feel like multiple destinations in one.
Explore Hawaii Volcanoes National Park
Witness the awe-inspiring Kīlauea and Mauna Loa volcanoes, hike through lava fields, and see active volcanic landscapes.
Snorkel at Kealakekua Bay
Swim with vibrant marine life in crystal-clear waters near the famous Captain Cook Monument.
Stargaze at Mauna Kea
Experience breathtaking night skies from the summit or visitor center of one of the world’s best astronomical observation sites.
Classic Vacations partners with Project Expeditions so you can enjoy everything the island has to offer. Add excursions and tours to your bookings now.
$100 Savings
Golf Vista Room
5 Nights from $3,319 Per Person
$100 Savings
Premier Ocean View Room
5 Nights from $1,769 Per Person
$50 Savings
5% Discounted Rate
Resort View Room
5 Nights from $679 Per Person
*Car upgrade is subject to availability at the time of booking. Offers valid on select room categories. Blackout dates apply. Offers are valid on new bookings only. Offers are subject to availability at the time of booking and may be changed or discontinued at any time without notice. Blackout dates, minimum night stays, and minimum stay requirements are subject to change. Seasonal surcharges, resort fees (if any), and other restrictions may also apply. Offers are not valid for Group Travel. Some booking and travel dates may vary. Other promotions and departure dates are available which may result in a different rate and/or hotel inclusion. The customer is responsible for hotel taxes and fees on the free night offers, where applicable. For those properties where Classic Vacations has access to dynamic pricing rates, those rates will likely fluctuate from time to time based on market conditions and other factors beyond Classic Vacations control.