From Maui’s golden beaches and Oahu’s legendary coastline to Kauai’s lush landscapes and the natural wonders of the Island of Hawaii, discover even more reasons to escape to the islands. Enjoy up to 40% savings, complimentary breakfasts, and up to $500 in added value at select resorts, along with thoughtful inclusions that make every stay more rewarding. Plus, receive a complimentary Alamo car rental upgrade* for travel through December 14, 2026.
For a limited time, experience the beauty, culture, and spirit of Hawaii with exceptional value.
Booking Window: 8/3/26 – 10/31/26
Travel Window: 8/3/26 – 5/31/27
* Car rental upgrade from a Compact to Standard and Full Size to Jeep Wrangler
From uncovering hidden gems and must-try local dishes to exploring what sets each resort apart, this episode offers firsthand insights into two of Hawaii’s most sought-after islands.
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.
Up to 10% Off
Andaz Resort View
5 Nights from $2,199 Per Person
Up to 20% Off
Fairmont Suite
5 nights from $2,599 Per Person
Up to $400 in Savings
Terrace View Room
5 Nights from $2,679 Per Person
Up to $400 in Savings
Three-Bedroom Garden View Villa
4 Nights from $5,069 Per Person
Up to $300 in Savings
One Bedroom Residence
5 Nights from $4,129 Per Person
Up to $977 in Savings
Deluxe Ocean View Room
4 nights from $1,999 Per Person
Up to 10% Off
Garden View Room
5 Nights from $1,879 Per Person
Up to 10% Off
Resort View Room
5 Nights from $1,829 Per Person
Up to $400 in Savings
Hokupaa Ocean View
5 Nights from $3,249 Per Person
Up to $250 in Savings
Resort View Room
5 Nights from $1,829 Per Person
Up to 35% Off
1 Bedroom Gold Fairway View Villa
5 Nights from $1,139 Per Person
Up to 35% Off
1 Bedroom Suite Mountain View
5 Nights from $1,759 Per Person
Up to $400 in Savings
Tower Standard Room
4 Nights from $599 Per Person
Up to $200 in Savings
Resort View Room
5 Nights from $1,779 Per Person
Up to 15% Off
1 Bedroom 1 Bath Ocean View Room Premium
4 Nights from $1,259 Per Person
Up to 15% Off
1 Bedroom 1 Bath – Garden View
4 Nights from $669 Per Person
Up to 35% Off
Premium Garden View
5 Nights from $929 Per Person
Up to 15% Off
Ocean Front Studio
4 Nights from $669 Per Person
Up to 15% Off
Studio with Kitchen Ocean Front
4 Nights from $979 Per Person
Up to 15% Off
Hotel Room Deluxe
4 Nights from $639 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.
$100 Savings
Club Resort View Room
4 nights from $2,679 Per Person
Up to $250 Off
Ocean View Room
3 Nights from $1,549 Per Person
Up to $200 Off
Golf Mountain View Room
4 Nights from $1,759 Per Person
Up to $250 Off
Resort View Room
5 Nights from $2,239 Per Person
Up to $250 Off
Historic Garden Room
3 Nights from $1,269 Per Person
Up to 15% Off
2 Bedroom Ocean Front
3 Nights from $1,469 Per Person
Up to $200 Off
Deluxe Partial Ocean View Room
4 nights from $1,719 Per Person
Up to 20% Off
Classic Room
3 Nights from $589 Per Person
Up to 10% Off
Rainbow Tower Ocean View
3 Nights from $949 Per Person
Up to 15% Off
Ocean Room
3 Nights from $529 Per Person
$100 Resort Credit
Ocean Front Harbor Room
3 Nights from $809 Per Person
Up to $250 in Savings
Partial Ocean View Room
3 Nights from $1,119 Per Person
$300 Savings
City View Junior Suite
3 nights from $1,179 Per Person
Up to 10% Off
1 Bedroom Standard Suite
3 Nights from $639 Per Person
Up to 10% Off
1 King Bed
3 Nights from $439 Per Person
Up to 40% Off
Waikiki View
3 Nights from $409 Per Person
Up to $150 in Savings
Tower Partial Ocean View
4 Nights from $619 Per Person
Up to 10% Off
City View Room
3 Nights from $379 Per Person
Up to $300 in Savings
Historic Banyan Room
3 Nights from $819 Per Person
Up to 40% Off
Resort View Room
3 Nights from $549 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.
Up to $400 in Savings
Mountain View Room
4 Nights from $2,539 Per Person
Up to 15% Off
Garden View Room
5 Nights from $2,929 Per Person
Up to 30% Off
Garden View Room
5 Nights from $1,309 Per Person
$150 in Savings
Ocean View
5 nights from $1,129 Per Person
Up to $100 in Savings
Deluxe Garden View Room
3 Nights from $ 1,019 Per Person
Up to 35% Off
1 Bedroom Garden View Room
5 Nights from $1,569 Per Person
Up to 15% Off
1 Bedroom 1 Bath Garden View
4 Nights from $989 Per Person
Up to 15% Off
Hotel Room Garden View
4 Nights from $509 Per Person
Up to 35% Off
1 Bedroom Garden View Room
5 Nights from $1,299 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.
Up to 20% Off
Fairmont Garden View Room
5 Nights from $1,779 Per Person
Up to $150 in Savings
Golf Vista
5 Nights from $3,949 Per Person
$100 Savings
Premier Ocean View Room
5 Nights from $2,839 Per Person
$400 Savings
Na Hale One Bedroom Oceanfront Suite
5 Nights from $3,289 Per Person
Up to 15% Off
1 Bedroom 2 Bath Partial Ocean View
4 Nights from $1,039 Per Person
Up to $500 in Savings
Mountain View Room
5 Nights from $3,099 Per Person
Palace Grand Resort View Room
5 Nights from $1,069 Per Person
45% Discounted Rate
Resort View Room
5 Nights from $829 Per Person
BOOK ONLINE NOW OR CALL +1 (800) 221-3949
Car upgrade is subject to availability at the time of booking. Classic Vacations offers customers access to vacation packages, which are provided by separate and independent vendors of travel services. Classic Vacations does not operate, control, or otherwise provide the services of the independent travel vendors. Offers are valid on new bookings only and cannot be applied to existing reservations. Prices shown are per person, land-only, based on double occupancy, and do not include optional excursions or other optional items unless expressly stated otherwise. Obvious errors and misprints are not binding. Offers are subject to availability at the time of booking and may be modified, replaced, or discontinued without prior notice. Prices are subject to change until full payment is received. Blackout dates, minimum night stays, air booking requirements, seasonal surcharges, resort fees (if applicable), and other restrictions may apply. Customers are responsible for purchasing travel insurance. Some offers may require the purchase of Classic Vacations’ Travel Smart Plan or a travel waiver for eligibility. Customers are responsible for paying any cancellation fees. Offers are not valid for Group Travel unless explicitly stated. Booking and travel dates may vary by offer. Additional promotions and alternative departure dates may be available, potentially resulting in different pricing or hotel inclusions. Customers are responsible for all applicable taxes and fees associated with a booking, including those associated with complimentary nights at hotels, where applicable. For properties where Classic Vacations offers dynamic pricing rates, prices are subject to change based on market conditions and external factors beyond Classic Vacations’ control. Additional terms and conditions may apply to specific offers. Please refer to the individual offer details for full terms. California Seller of Travel # 2079429. Registration as a seller of travel does not constitute approval by the State of California.