takeoff to

Hawaii

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

Offers by island

A Classic Conversation in Hawaii

In this special in-destination episode of the Know Zone Podcast, Reagan Vasquez, Strategic Account Manager at Classic Vacations®, takes listeners along on a familiarization journey through Hawaii’s Big Island and Oahu.
 

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

Up to 10% Off

Andaz Maui at Wailea Resort

Andaz Resort View
5 Nights from $2,199 Per Person

  • Takeoff to Hawaii 10% off Sunshine on Sale
  • A Reduced Rate
  • Daily Breakfast for all registered guests

Up to 20% Off

Fairmont Kea Lani

Fairmont Suite
5 nights from $2,599 Per Person

  • 5th Night Free with Daily Buffet Breakfast for Two
  • Every 5th Night Free
  • Daily buffet breakfast for two
  • Inspire Your Energy fitness classes, Cultural Activities, and Snorkel rentals are subject to space and availability. (Inclusions and price are subject to change at any time).
  • Overnight Self-Parking for one (1) vehicle per suite
  • Inspire Your Energy fitness classes
  • Pool and beach amenities including sunscreen and after sun care
  • Experience session with Pacific Dream Photography (reservation required, photos available for purchase)
  • Unlimited North America Long Distance calls (Canada and America)
  • Unlimited business internet access
  • Keiki Welcome Amenity
  • Hawaiian Canoe Experience
  • Weekly Cultural Activities
Read more

Up to $400 in Savings

Grand Wailea Maui, A Waldorf Astoria Resort

Terrace View Room
5 Nights from $2,679 Per Person

  • Takeoff to Hawaii up to $400 Instant Savings

Up to $400 in Savings

Ho'olei Villas at Grand Wailea

Three-Bedroom Garden View Villa
4 Nights from $5,069 Per Person

  • Takeoff to Hawaii up to $400 Instant Savings

Up to $300 in Savings

The Resort at Kapalua Bay, Maui

One Bedroom Residence
5 Nights from $4,129 Per Person

  • Takeoff to Hawaii Instant Savings
  • Up to $300 off 5 Night stays

Up to $977 in Savings

The Ritz-Carlton Maui, Kapalua

Deluxe Ocean View Room
4 nights from $1,999 Per Person

  • Breakfast for 2 in Ulana Restaurant
  • Signature daily experiences including guided labyrinth meditation walk, sunrise yoga and hula lessons.
  • Enhanced High Speed Internet Service
  • Kapalua Resort Shuttle Services (travel within Kapalua Resort area)
  • Complimentary photo session
  • Aloha welcome experience with a welcome drink and fresh flower or kukui nut lei.
  • Cultural History Tour
  • Resort activities (basketball, tennis, shuffleboard, croquet, pickleball)
Read more

Up to 10% Off

Hana-Maui Resort

Garden View Room
5 Nights from $1,879 Per Person

  • Takeoff to Hawaii 10% off Sunshine on Sale
  • A Reduced Rate
  • Daily Breakfast for all registered guests
  • Free WiFi
Read more

Up to 10% Off

Hyatt Regency Maui Resort & Spa

Resort View Room
5 Nights from $1,829 Per Person

  • Takeoff to Hawaii 10% off Sunshine on Sale
  • A reduced room rate
  • Daily Breakfast Buffet in Swan Court For All Registered Guests
  • Complimentary Wi-Fi internet in guest rooms and public areas
Read more

Up to $400 in Savings

The Westin Maui Resort & Spa, Ka'anapali

Hokupaa Ocean View
5 Nights from $3,249 Per Person

  • $400 off per 5 night stay in Hokupaa Tower
  • Daily Continental Breakfast.
  • Hors d’oeuvres in the Hokupaa Lounge.
  • Daily Enhance High-Speed Internet Access
  • Welcome Cocktail/Mocktail for Two
  • Daily Fitness Classes for (2) guests
  • Photo session and receive $50 off any photography package with Blink Photography, with digital images available for purchase – excludes single image purchases.
  • (2) Souvenir Water Bottles and Westin Maui Logo Bag upon arrival
  • Daily Hawaiian crafts and seasonal cultural activities for (2) guests
  • Daily Yoga for (2) guests
Read more

Up to $250 in Savings

Wailea Beach Resort Marriott

Resort View Room
5 Nights from $1,829 Per Person

  • Takeoff to Hawaii $250 Resort Credit

Up to 35% Off

Kapalua Villas Maui

1 Bedroom Gold Fairway View Villa
5 Nights from $1,139 Per Person

  • Savings up to 35%

Up to 35% Off

Outrigger Honua Kai Resort & Spa

1 Bedroom Suite Mountain View
5 Nights from $1,759 Per Person

  • Air Credit
  • Savings up to 35%

Up to $400 in Savings

Royal Lahaina Resort

Tower Standard Room
4 Nights from $599 Per Person

  • Takeoff to Hawaii Reduced Rate and Resort Credit
  • Special Reduced Rate when staying 4 nights or longer
  • $100 Resort Credit Per Room, Per Stay

Up to $200 in Savings

Sheraton Maui Resort & Spa

Resort View Room
5 Nights from $1,779 Per Person

  • Takeoff to Hawaii Instant Savings
  • $100 off a 5 night stay

Up to 15% Off

Aston at the Whaler on Kaanapali Beach

1 Bedroom 1 Bath Ocean View Room Premium
4 Nights from $1,259 Per Person

  • Heat Up Your Aloha Getaway and Save 15% off

Up to 15% Off

Aston Ka'anapali Shores

1 Bedroom 1 Bath – Garden View
4 Nights from $669 Per Person

  • Heat Up Your Aloha Getaway and Save 15% off

Up to 35% Off

Outrigger Ka‘anapali Beach Resort

Premium Garden View
5 Nights from $929 Per Person

  • Air Credit
  • Savings up to 35%

Up to 15% Off

Aston at Papakea Resort

Ocean Front Studio
4 Nights from $669 Per Person

  • Heat Up Your Aloha Getaway and Save 15% off

Up to 15% Off

Aston Mahana at Ka'anapali

Studio with Kitchen Ocean Front
4 Nights from $979 Per Person

  • Heat Up Your Aloha Getaway and Save 15% off

Up to 15% Off

Aston Maui Ka'anapali Villas

Hotel Room Deluxe
4 Nights from $639 Per Person

  • Heat Up Your Aloha Getaway and Save 15% off

O‘ahu​

$100 Savings

Four Seasons Resort Oahu at Ko'Olina

Club Resort View Room
4 nights from $2,679 Per Person

  • Stay Longer 4th Night Free and $100 Spending Credit per night
  • Club Accommodations include:
    • Exclusive access to the Club Lounge
    • Breakfast
    • Grab N Go Snacks
    • Premium Cocktail Service
    • Light afternoon hors d’oeuvres
    • Dedicated Club Concierge
    • 10 percent off Spa treatments
    • Complimentary valet parking
Read more

Up to $250 Off

Halekulani

Ocean View Room
3 Nights from $1,549 Per Person

  • Takeoff to Hawaii Instant Savings 3-Nights
  • A $150 instant booking savings when staying in an Ocean View Room
  • A $175 instant booking savings when staying in an Oceanfront View Room
  • A $250 instant booking savings when staying in Diamond Head Oceanfront Rooms
Read more

Up to $200 Off

The Kahala Hotel & Resort

Golf Mountain View Room
4 Nights from $1,759 Per Person

  • 2026 Takeoff to Hawaii 4-Nights
  • Early Check-In Or Late Check-Out, Based On Availability from $100-$250 off your 4 night stay
  • Discounted Daily Parking For (1) Vehicle For $40.00 ($60.00 Value Per Day)
Read more

Up to $250 Off

The Ritz-Carlton Oahu, Turtle Bay

Resort View Room
5 Nights from $2,239 Per Person

  • 2026 $150 Fall Takeoff Credit 5-Nights
  • $150 off a 5 nights stay and up to $250 off in Suites

Up to $250 Off

The Royal Hawaiian, A Luxury Collection Resort, Waikiki

Historic Garden Room
3 Nights from $1,269 Per Person

  • Takeoff to Hawaii Instant Savings 3-Nights
  • A reduced room rate
  • Daily Breakfast for Two

Up to 15% Off

Aston Waikiki Beach Tower

2 Bedroom Ocean Front
3 Nights from $1,469 Per Person

  • Heat Up Your Aloha Getaway and Save 15% off

Up to $200 Off

Ka Lai Waikiki Beach, LXR

Deluxe Partial Ocean View Room
4 nights from $1,719 Per Person

  • Takeoff to Hawaii Instant Savings 4-nights
  • A $200 instant booking savings for a 4-night stay combinable with all offers and Deluxe Partial Ocean View or higher
  • Waived Resort Fee
Read more

Travel Window: now - 12/22/26

Up to 20% Off

Alohilani Resort Waikiki Beach

Classic Room
3 Nights from $589 Per Person

  • Takeoff to Hawaii Reduced Rate and Resort Credit 3-Nights
  • Special Reduced Rate
  • $100 Resort Credit Per Room, Per Stay

Up to 10% Off

Hilton Hawaiian Village Waikiki Beach Resort

Rainbow Tower Ocean View
3 Nights from $949 Per Person

  • A Reduced Room Rate
  • Wi-Fi access in your room and in most public areas around the resort
  • PlayStation 3 access with unlimited movies and games
  • Local, toll-free, and credit card calls (No access fee)
  • Hawaiian Village Cultural Activities
  • 10 percent off or one (1) category upgrade on a 2-day or more rental from National Rental Car located in Rainbow Bazaar in Hilton Hawaiian Village
  • 20 percent off the Adventure Sail on the Spirit of Aloha Catamaran
  • Outdoor Morning Exercise Classes
  • 10 percent off at Waikiki Beach Activities for beach chairs and umbrellas, kayaks, pedal boats, stand-up paddle boards and aqua cycles
  • 20 percent off the Elite Beach Package offered at Waikiki Beach Activities for our Lagoon beach. VIP Package includes 1 umbrella, 2 cushioned chaise lounge chairs, and other amenities
Read more

Up to 15% Off

Hyatt Regency Waikiki Beach Resort & Spa

Ocean Room
3 Nights from $529 Per Person

  • Takeoff to Hawaii 15% off Standard Rate
  • Reduced Room Rate
  • Premium Wi-Fi in guestrooms and public areas
  • Two (2) reusable souvenir Hyatt water bottles with water stations on each floor
  • One reusable Hyatt Regency Waikiki Tote Bag
  • Biki’ bicycle ride sharing service – one time credit of 4 USD per person (2 persons maximum)
  • Frozen treats provided poolside
  • Discounted surfing lessons and rental of beach equipment from Billabong
  • Daily Resort Interactive Cultural Activities including lei making, hula lessons and ukulele lessons
  • GoPro usage
  • Use of beach amenities and chairs
  • Use of beach toys for children
  • Long distance and international calls – up to 60 minutes per day
  • Morning Yoga Classes
  • Self-guided local tour of Waikiki via the Shaka Oahu app
  • 1 in-room movie rental per stay
  • Sunscreen available at the Pool Deck
  • House slippers and personal amenity items pre-set in guest room
  • Stayfit Gym access
  • In-room coffee and tea
  • Unlimited local and 1-800 telephone calls
  • Hyatt Corporation provides complimentary Wi-Fi in guest rooms and public areas in all hotel & resorts
Read more

$100 Resort Credit

Prince Waikiki

Ocean Front Harbor Room
3 Nights from $809 Per Person

  • Takeoff to Hawaii 3-Nights
  • Receive a $100 Resort Credit per room per stay when booking a 3 night stay

Up to $250 in Savings

Sheraton Waikiki Beach Resort

Partial Ocean View Room
3 Nights from $1,119 Per Person

  • Takeoff to Hawaii Instant Savings 3-Nights
  • A reduced room rate
  • Daily Breakfast for Two

$300 Savings

Waikiki Beach Marriott Resort and Spa

City View Junior Suite
3 nights from $1,179 Per Person

  • Takeoff to Hawaii $300 Instant Savings 5-Nights
  • Fitness Classes Daily
  • Cultural Classes Daily
  • $10 Off Premium Golf Club Rentals & Discounted Tee Times at Hawaii Tee Times
  • 30% Off Your Electric Bike Ride at Hele on Waikiki
  • Nanea Game Room Access (21+)
  • 2 Beach Chairs, 2 Boogie Boards, OR 1 Beach Chair and 1 Boogie Board from Waikiki Sand Bar
Read more

Up to 10% Off

Embassy Suites by Hilton Waikiki Beach Walk

1 Bedroom Standard Suite
3 Nights from $639 Per Person

  • 10% off with Breakfast
  • Daily Breakfast Buffet
  • Evening Reception
  • Cocktails
Read more

Up to 10% Off

Hyatt Centric Waikiki Beach

1 King Bed
3 Nights from $439 Per Person

  • Takeoff to Hawaii 10% off Sunshine on Sale
  • A Reduced Rate
  • Daily Breakfast for all registered guests

Up to 40% Off

Outrigger Waikiki Beachcomber Hotel

Waikiki View
3 Nights from $409 Per Person

  • Savings up to 40% and Kids Stay FREE!

Up to $150 in Savings

Sheraton Princess Kaiulani Waikiki Beach

Tower Partial Ocean View
4 Nights from $619 Per Person

  • Takeoff to Hawaii Instant Savings 4-Nights
  • $150 Instant Savings per booking for 4-night stays in Renovated Tower Partial Ocean View, Renovated Tower Ocean, Princess Ocean and Renovated Tower High Ocean
    Combined with Stay and Save
  • Daily Enhanced High-speed Internet Access
  • Mi-Fi rental (one per room per stay) – personal device providing high speed WiFi anywhere on island
  • Complimentary Surfboard Storage. Available at the pool services desk lobby level
  • Daily meditation class for 2 guests
  • Twice daily Yoga classes for 2
  • Cultural activities for 2 guests, including Sunrise ceremony, Hula, Ukulele, Haku, Kupe (Bracelet),
    Lauhala (weaving), Story time with Tutu and Historic Tours, plus daily orchid/flower lei making. Some activities require reservations.
  • Souvenir tote beach bag per room per stay
Read more

Up to 10% Off

The Twin Fin Hotel

City View Room
3 Nights from $379 Per Person

  • Takeoff to Hawaii Reduced Rate 3-Nights
  • A Reduced Room Rate

Up to $300 in Savings

Moana Surfrider, A Westin Resort & Spa, Waikiki Beach

Historic Banyan Room
3 Nights from $819 Per Person

  • Takeoff to Hawaii Instant Savings 3-Nights

Up to 40% Off

Outrigger Reef Waikiki Beach Resort

Resort View Room
3 Nights from $549 Per Person

  • Savings up to 40% and Kids Stay FREE!
  • Voyager 47 Club access includes morning breakfast and evening appetizers with complimentary beverages

Kauaʻi

Up to $400 in Savings

1 Hotel Hanalei Bay

Mountain View Room
4 Nights from $2,539 Per Person

  • 2026 Takeoff to Hawaii 4-Nights $250-$400 Instant Savings

Up to 15% Off

Grand Hyatt Kauai Resort & Spa

Garden View Room
5 Nights from $2,929 Per Person

  • Takeoff to Hawaii 15% off Sunshine on Sale with Breakfast
  • Daily Breakfast for all Registered Guests
  • 15% off room rates

Up to 30% Off

Outrigger Kaua'i Beach Resort & Spa

Garden View Room
5 Nights from $1,309 Per Person

  • Savings up to 30% 5-Night Stay

$150 in Savings

Sheraton Kauai Coconut Beach Resort

Ocean View
5 nights from $1,129 Per Person

  • Stay 4 and Save with $150 Take Off to Hawaii Instant Savings 5-Nights
  • Self-Parking
  • Highspeed Internet (guestroom and public areas)
  • Beach chairs and umbrella rentals
  • Live local entertainment daily
  • Press reader (virtual publications)
  • Complimentary microwave use (located on certain guest floors)
  • Cruiser bikes
  • Resort Activities (These vary and will be listed on daily events schedule provided at check-in)
  • Complimentary local calls
  • Complimentary 1-800 calls
  • Hawaiian Cultural Activities (Lei Making, Hula, Hawaiian Language, Ukulele)
  • Lawn Games (On rain days, indoor games will be set up)
  • Fitness Center (24 hour access with guestroom key)
  • Business Center
  • In Room Exercise Band Kits (available upon request)
Read more

Up to $100 in Savings

Sheraton Kauai Resort

Deluxe Garden View Room
3 Nights from $ 1,019 Per Person

  • Takeoff to Hawaii $100 Insant Savings 3-Nights
  • Best Available Rate

Up to 35% Off

Waipouli Beach Resorts & Spa Kauai by Outrigger

1 Bedroom Garden View Room
5 Nights from $1,569 Per Person

  • Savings up to 35%

Up to 15% Off

Aston at Poipu Kai

1 Bedroom 1 Bath Garden View
4 Nights from $989 Per Person

  • Heat Up Your Aloha Getaway and Save 15% off

Up to 15% Off

Aston Islander on the Beach

Hotel Room Garden View
4 Nights from $509 Per Person

  • Heat Up Your Aloha Getaway and Save 15% off

Up to 35% Off

Kiahuna Plantation Resort Kauai by Outrigger

1 Bedroom Garden View Room
5 Nights from $1,299 Per Person

  • Savings up to 35%
  • Free parking
  • Free high speed in room internet access
  • Free local & Long Distance Phone Calls USA and Canada
Read more

Big Island

Up to 20% Off

Fairmont Orchid

Fairmont Garden View Room
5 Nights from $1,779 Per Person

  • 5th Night Free with Daily Buffet Breakfast for Two
  • Wellness classes. Weekly wellness activity calendar available at fairmontorchid.com
  • Shuttle service within the Mauna Lani Resort.
  • Golf Valet. Handling and storage of personal golf clubs during your stay.
  • Branded reusable water bottle for each registered guest per stay, to be filled at purified water stations located throughout the resort.
  • Coffee and tea service in the lobby between 5:00 a.m. and 6:30 a.m.
  • Hawaiian Cultural Classes & Resort Activities. Weekly activity schedule available at fairmontorchid.com.
  • RunGo guided tours.
  • Lei greeting upon arrival.
  • Snorkel equipment rental for one hour (available to each guest, per day—resort use only). Guests who purchase Fun & Sun passes may sign out snorkel equipment multiple times per day.
  • Pool amenities (sunscreen, water, and fruit service).
  • Washer and dryer usage, including product.
  • 45-minute photo session with Pacific Dream Photography.
Read more

Up to $150 in Savings

Mauna Kea Beach Hotel, Autograph Collection

Golf Vista
5 Nights from $3,949 Per Person

  • Takeoff to Hawaii $150 Instant Savings 5-Nights

$100 Savings

The Westin Hapuna Beach Resort

Premier Ocean View Room
5 Nights from $2,839 Per Person

  • Takeoff to Hawaii $100 Instant Savings 5-Nights

$400 Savings

Waikoloa Beach Marriott

Na Hale One Bedroom Oceanfront Suite
5 Nights from $3,289 Per Person

  • Takeoff to Hawaii $400 Instant Savings 5-nights
  • Best Available Rate
  • $400 Instant Savings
  • Enhanced High Speed Internet Access
  • (2) Waikoloa Specialty Welcome Drinks (1 time only)
  • 2 Daily Pool Fitness up to 2 people
  • Daily Cultural Activities – (5) per day – Lei Making,
    Hula Lessons, Hawaiian Language, Hawaiian Games, Walking Tour, Ukulele Lessons for up to 2 people
  • Daily Tennis Court Rental for 2, Rackets and Tennis Balls for 2
  • Shell Lei Upon Arrival
  • Complimentary self-service laundry and detergent
Read more

Up to 15% Off

Aston Kona by the Sea

1 Bedroom 2 Bath Partial Ocean View
4 Nights from $1,039 Per Person

  • Heat Up Your Aloha Getaway and Save 15% off

Up to $500 in Savings

Mauna Lani, Auberge Collection

Mountain View Room
5 Nights from $3,099 Per Person

  • 2026 Takeoff to Hawaii 5-Nights
  • $500 Resort Credit
    Resort Credit is redeemable at the following outlets: HaLani, Ha Bar, Pool and Beach, Kainalu and Surf Shack, Spa, The Market, Canoe House, In Room Dining, Milo Store, Mauna Lani Golf Course, and Mauna Lani Sports Fitness Center.
    *It cannot be redeemed at GOOP, or to cover taxes, room cost, or resort fees
Read more
Up to $150 Savings & Earn extra 5% bonus commission for a limited time

Hilton Waikoloa Village

Palace Grand Resort View Room
5 Nights from $1,069 Per Person

  • Takeoff to Hawaii Instant Savings 5-Nights
  • Receive an instant booking credit up to $150 per booking per stay when staying 5 nights or longer
  • A Mandatory $50 plus tax per night, per room resort fee (to be paid direct to the resort) includes:
    • Dolphin Splash Experience
    • StoriBox Photo Keepsake
    • Cultural Experiences
    • Daily Wellness Classes
    • 10% savings on Lagoon Activities
    • 10% savings on Hawaii Nautical bookings
    • Shuttle service to Kings’ Shops and Queens’ Marketplace
    • High-speed internet access throughout the resort
    • One (1) 30-minute Tennis or Pickleball court rental per stay
Read more

45% Discounted Rate

Outrigger Kona Resort & Spa

Resort View Room
5 Nights from $829 Per Person

  • Save up to 45% for 5-Nightsand Kids Stay Free!
  • No extra guest charges for children under the age of 18 who are staying in a guest room of paying adults and utilizing existing beds.
Read more

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.