Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024

Post originally Published March 31, 2024 || Last Updated March 31, 2024

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Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Strategies for Visiting the Aloha State in 2024":


Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024

One strategy is to take advantage of fare wars. Monitor flight deals closely, as airlines like Hawaiian, Alaska and Southwest compete for travelers with rock-bottom fares. Sign up for deal alerts and be ready to book when you see Hawaii flights under $300 roundtrip.

Another approach is to use points and miles. Flights to Hawaii can be a steal with airline miles, especially off-peak. Stockpile miles with a new credit card bonus and watch for low award rates. Consider less popular islands like Kauai and the Big Island over crowded Oahu.

Hotel points are also valuable in Hawaii. Major chains like Marriott have a strong presence. Take advantage of free night certificates and discounted point redemptions to cover your lodging. Condos and vacation rentals can also be a good value if you have a large group.

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  1. Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Strategies for Visiting the Aloha State in 2024":
  2. Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Maximizing Airline Miles for Inter-Island Flights
  3. Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Redeeming Hotel Rewards for Luxurious Hawaiian Stays
  4. Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Uncovering the Best Transfer Partner Deals for Hawaii
  5. Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Mixing and Matching Points to Cover the Entire Trip
  6. Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Timing Your Travel to Snag the Sweetest Award Availability
  7. Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Hidden Gem Activities to Enhance Your Hawaiian Getaway

Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Maximizing Airline Miles for Inter-Island Flights


Once you've secured your flight to Hawaii, you'll likely want to explore the different islands during your stay. Fortunately, there are ways to use your airline miles to get between the islands without breaking the bank.
Hawaiian Airlines is the dominant carrier for inter-island flights, and they offer a variety of mileage redemption options. For example, you can book a one-way flight between any two Hawaiian islands for just 7,500 Hawaiian Miles. This makes it incredibly easy to island hop using your points.
Even if you don't have Hawaiian Miles, you can leverage other airline programs to book these short flights. American Airlines AAdvantage members can book inter-island flights on Hawaiian Airlines for just 5,000 miles one-way. United MileagePlus members can book the same flights for 7,500 miles.
The key is to be flexible with your travel dates and keep an eye out for award space. Inter-island flights can sometimes open up award availability closer to the travel date, so don't be afraid to book last-minute if you spot a good deal.
Another strategy is to position yourself on the "right" island before your main trip. For example, if you're planning to spend most of your time on Maui, it may be worth flying into Honolulu on miles and then hopping over to Maui using a cheap cash fare or more miles. This can help you save your points for the longer, more expensive flights.

Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Redeeming Hotel Rewards for Luxurious Hawaiian Stays


Once you've secured your flights to Hawaii using airline miles or fare deals, it's time to turn your attention to lodging. Fortunately, Hawaii offers a wealth of opportunities to utilize hotel loyalty points for free nights and big savings.
Major hotel chains have a strong presence across the islands, making it easy to find rewarding redemption options. Marriott, Hilton, and Hyatt all have multiple properties in Hawaii, ranging from beachfront resorts to urban hotels. By strategically redeeming your points, you can enjoy luxurious accommodations without the hefty price tag.
Marriott, in particular, has an impressive lineup of high-end resorts in Hawaii. The Ritz-Carlton Residences, Waikiki Beach and the Sheraton Kona Resort & Spa at Keauhou Bay are two stunning options that can be booked for as little as 50,000 Marriott Bonvoy points per night. With the right credit card sign-up bonuses, you can easily acquire enough points for a week-long stay.
For Hilton loyalists, the Hilton Hawaiian Village Waikiki Beach Resort and the Grand Wailea, A Waldorf Astoria Resort offer exceptional value when booked with Hilton Honors points. These properties regularly sell for $500+ per night, but you can often secure rooms for 80,000-100,000 points, a fraction of the cash rate.
Hyatt's portfolio in Hawaii is smaller but equally impressive. The Andaz Maui at Wailea Resort is a standout, with its sleek design, infinity pools, and prime beachfront location. Redemptions here start at just 25,000 World of Hyatt points per night, making it an excellent use of your hard-earned points.
Beyond the major chains, you can also find rewarding redemption opportunities with smaller, more boutique properties. The Moana Surfrider, A Westin Resort & Spa, Waikiki Beach is a historic Beaux-Arts-style hotel that can be booked for 50,000 Marriott points per night, offering a unique and luxurious Hawaiian experience.

Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Uncovering the Best Transfer Partner Deals for Hawaii


Beyond redeeming your airline miles and hotel points directly, strategic use of credit card transfer partners can unlock even greater value for your Hawaiian getaway. By transferring points from flexible reward programs like Chase Ultimate Rewards, Amex Membership Rewards, or Citi ThankYou Points, you can access a vast network of airline and hotel partners to maximize your redemptions.
For flights, consider transferring your points to programs like United MileagePlus, Singapore KrisFlyer, or Avianca LifeMiles. These can provide excellent value for flights to Hawaii, often costing as little as 35,000 miles roundtrip in economy class. United, in particular, offers a wide range of flight options, including nonstop service from numerous mainland U.S. cities.
Alternatively, you can transfer points to Hyatt, Marriott, or Hilton to book luxurious hotel stays. Hyatt's partnership with American Airlines allows you to book flights and hotels together for maximum efficiency. Redeem your Hyatt points at properties like the stunning Andaz Maui at Wailea Resort for as little as 20,000 points per night.
Marriott Bonvoy is another powerhouse program with a vast portfolio of hotels across Hawaii. By transferring points from cards like the Amex Platinum or Chase Sapphire Preferred, you can book award nights at properties like the Ritz-Carlton Residences, Waikiki Beach for just 50,000 points per night.
Don't forget about Hilton Honors as well. Through cards like the Amex Hilton Surpass or Hilton Aspire, you can quickly amass enough Hilton points for luxurious stays at resorts like the Hilton Hawaiian Village Waikiki Beach Resort. These redemptions can regularly save you hundreds of dollars per night compared to the cash rate.

Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Mixing and Matching Points to Cover the Entire Trip


Maximizing the value of your various travel rewards programs is key to covering an entire Hawaiian vacation on points. With a savvy mix-and-match approach, you can tap into the strengths of each program at every step of your trip.

Start by identifying the best options for flights. Programs like United MileagePlus and American AAdvantage can get you to Hawaii for 35,000-50,000 miles roundtrip if you're flexible on dates. Supplement with Southwest points if they offer one of their famous fare sales.

For inter-island flights, leverage Hawaiian and other alliance partner award charts to hop between islands for 5,000-7,500 miles each way. Stock up on Hawaiian miles with targeted credit card bonuses.
When it comes to lodging, focus your Marriott and Hilton points on high-end resort redemptions. But don’t rule out Hyatt’s more boutique gems like the Andaz Maui. Aim to cover at least a portion of your hotel nights on points.
Fill in gaps with Southwest points, Chase UR transfers, or Amex MR transfers where needed. For example, cover car rentals with Southwest points or UR transfers to National Car Rental. Use flexible points for any activities too.
The key is pooling points across programs to take advantage of each one's sweet spots. Don't wed yourself to just one loyalty program. And consider supplementing points with occasional cash bookings where it makes sense.

Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Timing Your Travel to Snag the Sweetest Award Availability


When it comes to booking award flights to Hawaii, timing is everything. Airlines often release award seats in waves, with the best availability typically occurring several months in advance. By monitoring award space and being poised to book as soon as seats become available, you can secure the most coveted flights using your hard-earned miles.
One of the key factors to keep in mind is the high demand for travel to Hawaii, especially during peak seasons like summer and the holidays. Airline award programs often release their award inventory in batches, with the most desirable flights going quickly. To get ahead of the competition, set up alerts with your loyalty programs and check award availability regularly, even if your travel dates are flexible.
For the best chances of finding saver-level award seats, aim to book your flights to Hawaii at least 6-9 months in advance. This will give you the widest range of options, including nonstop flights on preferred carriers. Be prepared to act fast when you see award space open up, as it can disappear in a matter of minutes.
Another strategy is to consider flying during off-peak seasons or shoulder seasons. Demand tends to be lower during the late spring and early fall, which can translate to better award availability and lower redemption rates. For example, you may be able to book a roundtrip flight to Hawaii for just 35,000 miles during these less popular travel periods.
If you're flexible on your travel dates, use tools like Google Flights to identify the lowest-priced award flights. The calendar view can be particularly helpful in spotting the cheapest days to fly. By adjusting your departure and return dates by a day or two, you may be able to shave thousands of miles off your redemption.
Finally, don't be afraid to get creative with your routing. Sometimes, flying into a secondary airport like Kahului (OGG) on Maui or Kona (KOA) on the Big Island can open up more award availability than booking straight to Honolulu (HNL). This extra step can be worth it if it means securing your preferred flights and dates.

Scoring a Hawaiian Vacation on Points: Strategies for Visiting the Aloha State in 2024 - Hidden Gem Activities to Enhance Your Hawaiian Getaway


Beyond the well-trodden tourist trails, Hawaii offers a wealth of hidden gems that can truly elevate your island experience. While the iconic beaches, lush rainforests, and dramatic volcanic landscapes are undoubtedly alluring, it's the lesser-known adventures that often leave the most indelible memories.
One such gem is the Kalalau Trail on the island of Kauai. This strenuous 11-mile hike along the Na Pali Coast rewards adventurous travelers with breathtaking vistas of towering sea cliffs, cascading waterfalls, and pristine beaches. Though not for the faint of heart, the sense of accomplishment and the sheer beauty of the landscape make this trek a must for outdoor enthusiasts.
For a more serene experience, consider a visit to the Polihale State Park on the western side of Kauai. This remote stretch of beach boasts stunning sunsets, towering sand dunes, and a peaceful ambiance that feels worlds away from the busier parts of the island. Pack a picnic, find a secluded spot, and simply soak in the tranquility of this hidden gem.
On the island of Hawaii, the "Big Island," explore the lesser-known Waipio Valley. Accessible only by guided tour or a grueling hike down a steep, unpaved road, this lush, secluded oasis is home to towering waterfalls, taro farms, and a black sand beach that feels like something out of a dream. The journey here is just as rewarding as the destination itself.
For a truly unique cultural experience, consider attending a traditional Hawaiian luau on the island of Molokai. Far from the tourist-centric productions found on other islands, these intimate gatherings offer an authentic glimpse into the music, dance, and cuisine that define Hawaiian heritage. Engage with the local community, savor the flavors of authentic Hawaiian dishes, and immerse yourself in the rich traditions of this often-overlooked island.

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