Big Island Anniversary Trip
For our first anniversary, we decided to go back to the Big Island, Hawaii. We considered somewhere new, somewhere international, but the more we talked about it, the more it made sense to return to the place where everything started for us.
In November 2023, we found ourselves on the Big Island of Hawaii, where we got engaged, creating one of our most meaningful memories.
Since we didn’t have the chance to fully explore the island during our proposal trip, we wanted our anniversary visit to be more intentional. This time, we wanted to slow down, explore the local towns, visit Hawai’i Volcanoes National Park and chase waterfalls.
The Breakdown
Destination: Big Island, Hawaii
Trip Length: 7 nights
Trip Timeframe: Early November
Total Spend: $2421.62
Booking Platforms:
Flight: American Airlines
Stay: Hilton
First-Time Traveler Score: ★★★★★
Our Stay
Our first stay was at the Mauna Kea, which felt smaller, quieter and directly on a swimmable beach. This time, we stayed at the Hilton Waikoloa Village, and it felt completely different, very family friendly. The property is HUGE. You take trams or boats to get between towers. There are multiple pools, lagoons, restaurants and walking paths. It feels more like a destination on its own than a traditional hotel.
There's no true beach directly on or by the property, which is something to factor in, but there's plenty of activities on-site. If you want a trip where you can fill your days without ever getting in a car, this kind of resort makes that easy.
We booked the hotel with a combination of Hilton Points and Free Night Rewards totaling 320,000 Hilton Points + 2 Free Night Rewards.
Activities
This trip was intentionally slower than most of our itineraries. We balanced exploring with a lot of time simply relaxing and enjoying where we were staying.
Professional sunrise photo session
Explore Kailua-Kona & Hilo
Hawai'i Volcanoes National Park
Kohala Coast
Kailua Pier
Bay View Farm
Punalu'u Black Sand Beach
Nahuku - Thurston Lava Tube
Rainbow Falls
Akaka Falls State Park
Waipi'o Valley
Parker Ranch
Seeing an active eruption at Hawai'i Volcanoes National Park was something we didn't expect to experience. It was easily the most memorable moment of the trip.
Dining
We had some great meals in both Kona and Hilo, but honestly the best food moments were the simplest.
Grabbing fresh poke from the Queens' Marketplace and picking up spam musubi to eat casually back the resort ended up being our favorites. It felt local, easy and exactly what we wanted after long days of exploring. Not every memorable meal needs a reservation and $$$!
Two Ladies Kitchen - Popular mochi spot, highly recommend calling ahead and ordering pick-up because the line can get insanely long!
Things We Learned (So You Don't Have To)
Purchase Hilton Points Strategically - If you're eyeing higher end Hilton properties, it can sometimes make more sense to purchase Hilton Honors Points during one of their bonus promotions and book in Points rather than paying the full cash rate. Hilton frequently runs limited-time offers where you can receive 80-100% bonus points on purchased points. When redeemed for high nightly rate resorts, especially in Hawaii, the math can work in your favor! Always compare the total cost of buying points vs. the cash rate, including taxes and resort fees, before booking!
Consider a Premium Hilton Credit Card - If you like to travel regularly, consider the Hilton Honors American Express Aspire card, which can significantly offset high resort costs. It includes automatic Diamond status, an annual Free Night Reward that can be used at many properties and statement credits that can help cover resort charges. For destinations like Hawaii, where nightly rates are high, those benefits alone can justify the annual fee if you use them intentionally. As always, compare the annual fee to the realistic value you'll actually use.