We celebrated our 10th anniversary in true adventurous style—with an unforgettable week on the Big Island of Hawaii! The Big Island is the perfect place for an anniversary trip.

From hiking lush valleys and snorkeling crystal-clear coves to relaxing at resorts and soaking in local eats, this trip had it all. Here's our full itinerary so you can steal it for your own trip, with tips, must-see stops, and a few things we’d do differently next time.

But before we even dive in, let me tell you about the app that completely leveled up our trip:
🎧 GuideAlong — This GPS-based app is like having your own personal tour guide in the car. It tracks where you are and offers historical tidbits, fun stories, and recommendations as you drive. It made our road trips way more exciting and helped us discover places we never would have found on our own.

First Things First- Where To Stay On The Big Island

When we started planning our 10th anniversary trip, we knew we wanted a little bit of everything—adventure, relaxation, natural beauty, and culture. That’s why the Big Island of Hawaii was the perfect choice. It’s one of the few places where you can hike through a rainforest in the morning, relax by a resort pool in the afternoon, and snorkel with manta rays at night. To balance our love of comfort and exploration, we split our trip in two: the first half at a resort for some much-needed R&R, and the second half in a cozy Airbnb tucked in the jungle so we could dive into the wild side of the island. It turned out to be the perfect mix of laid-back and adventurous.

Before we dive into our day-by-day guide, here’s a quick breakdown of the major areas of the Big Island to help you get your bearings.

Kona (West side): Sunny, dry, and full of beaches. This is where most visitors stay. Great for snorkeling, coffee farms, and sunsets. Downside? It can feel more touristy and dry.
Waikoloa: North of Kona and home to large resorts like the Hilton. Perfect for families or anyone wanting easy beach access and amenities. Just be ready for resort pricing.
Hilo (East side): Lush, tropical, and way less touristy. You’ll find waterfalls, botanical gardens, and a more local vibe. The downside? It rains. A lot.
Volcano: Close to Hawaiʻi Volcanoes National Park. Great for hiking and exploring the park, but colder and more remote.
Waimea: Think rolling green hills and cowboy country. A beautiful contrast to the beach scenes but not near the ocean.
Captain Cook / South Kona: More rural and authentic, with amazing snorkeling and coffee farms. A peaceful escape from the crowds, but farther from many attractions.

We loved getting to experience several of these areas, and our trip felt fuller and more dynamic because of it. We ultimately opted for 3 days in Waikoloa at the Hilton resport and then 4 days in Captain Cook at an amazing Airbnb (details below, you should 100% absolutely consider staying there).

✈️ Arrival Day: Land, Load Up, and Settle In

We landed in Kona and picked up our rental car (jeep actually) from Budget rental!

Our first very practical—but very important—stop: Target. Groceries on the Big Island can get pricey, so stocking up on essentials here (or Costco, if you’re a member) will save you a lot. Trust us, we were so glad we did once we saw the food prices at the resort. 😅

Plus, if your flight gets in early and you can’t check in until 3:00 anyways, it makes it a no brainer to go ahead and stock up in Kona even if it’s a bit out of the way for you.

🏨 Check-in: Hilton Waikoloa Village

We spent our first three nights at the Hilton Waikoloa Village. This place is huge. Think: multiple pools and hot tubs, waterfalls, a lagoon with sea turtles, and even a train that runs through the property (yes, really!).
We scored a great deal on our stay from booking a Condo through VRBO , which made it totally worth it.

Just a heads up: the on-site food was very expensive and honestly, not our favorite. So we highly recommend having groceries on hand or exploring off-property dining.

Within the first 10 minutes of being at the resort, we saw this Eagle Ray in the lagoon!! So cool!

🌴 Day 1: Island Vintage Coffee, Scenic Drives, and Valley Hikes

We kicked off the first full day with a coconut latte and an açaí bowl from Island Vintage Coffee—10/10 recommend. This spot is a great vibe to start your day and just about a mile from the Hilton in the Royal Hawaiian Shopping Center.

Then we hit the road following our GuideAlong app, heading north along the coast!

🚩 Stop 1: Puʻukoholā Heiau National Historic Site

This sacred site, built by King Kamehameha I, is one of the last major sacred temples built in Hawaii. The structure is made from lava rock and holds incredible cultural and historical significance. It's an easy walk with lots of information and views of the ocean—and even some sharks swimming below the cliffs if you're lucky!

🚩 Stop 2: Hike Pololū Valley

This hike truly stole our hearts and left lasting memories. A short but steep trail takes you down into a lush, vibrant green valley, ultimately leading to a stunning black sand beach that is beautifully surrounded by towering cliffs and dense jungle. Be sure to bring plenty of water and wear shoes that provide a good grip—the climb back up is no joke, but the experience is 100% worth it in every way.

🍤 Lunch Stop: Bamboo Restaurant in Hawi

We stopped in the cute town of Hawi for lunch. The coconut shrimp and lilikoi iced tea at Bamboo were out of this world. And while you're in town, grab a cup at Hawi Coffee Mill—adorable spot, and great coffee.

🌄 Scenic Drive & Waimea

This part of the island is shockingly different from the coast. Rolling green hills, misty forests, and even cows—yes, cows! Welcome to Waimea, aka cowboy country. The elevation shift is dramatic and beautiful.

If you're there on a Wednesday, check out the Paniolo Dinner—a farm-to-table experience with local beef and music. It books out fast, so reserve early!

🌅 Sunset Dinner: Lava Lava Beach Club

Back in Waikoloa, we had dinner at Lava Lava Beach Club. Great food, toes-in-the-sand dining, and the sunset? Absolutely unreal.

🧘 Day 2: Pool Day at the Hilton

We spent this day soaking up the sun and taking full advantage of the Hilton’s amenities. Highlights include:

Floating in the saltwater lagoon
Watching sea turtles swim right by
Riding the boat shuttle between parts of the resort
Relaxing in the adults-only hot tub overlooking the ocean

It was the perfect way to recover after our active first day.

🚗 Day 3: Waipiʻo Valley, Honokaʻa & Hilo Road Trip

We started early for a full-day road trip to the east side of the island.

🚩 Stop: Waipiʻo Valley Lookout

A dramatic, lush valley carved into the northeastern coastline. You can’t drive into the valley unless you have a 4WD and permits, but the overlook is stunning. There's also a secret star of this stop:

🍍 Waipiʻo Fruit Shack

Right off the road, conveniently located near the lookout, is this charming little stand that serves up the most delicious tropical smoothies and offers an incredible selection of fresh fruit we experienced throughout the entire trip. Don’t miss out on this delightful stop!

🥟 Lunch in Honokaʻa: I Luv Dumplings

Yes. Yes. Yes. This place is unassuming, but the dumplings are phenomenal. Full of flavor, great prices, and the friendliest staff. 5 stars, no notes.

🌋 Drive to Hilo

The road winds through waterfalls, rainforests, and jaw-dropping views. We loved the drive almost as much as the destinations. Expect the whole trip from Waikoloa to Hilo and back to take about 3-5 hours, depending on stops.

🌅 Day 4: Check-in at Captain Cook Airbnb

We said goodbye to the Hilton and moved to this incredible Airbnb in Captain Cook: link.
This place was heaven. Secluded, lush, peaceful, and with unreal sunset views. It was the perfect jungle escape and felt way more “authentic Hawaii” than the resort.

🍽️ Dinner: Island Lava Java – Beautiful outdoor seating, great fish dishes, and yummy desserts.

🛶 Day 5: Kayaking to Captain Cook Monument

We rented kayaks from Kona Boys (highly recommend—super helpful and easy process) and paddled out to Kealakekua Bay and the Captain Cook Monument.

This is one of the best snorkeling spots on the island—crystal clear water, vibrant coral, and fish everywhere. The area is rich in history too, as it’s where Captain James Cook first arrived (and later met his end).

This was one of our favorite experiences of the entire trip.

🌟 Anniversary Dinner: Walua Social
Upscale, intimate, and so good. The pasta? Amazing. The cocktails? Top notch. Perfect place for a special dinner.

🌋 Day 6: Volcanoes National Park

We made the long but scenic drive to Hawai’i Volcanoes National Park. We just missed seeing the volcano erupt by one day—heartbreaking! But the park was still incredible.

We hiked the Kīlauea Iki Trail and Crater Rim Trail—an otherworldly loop that goes from lush rainforest into a hardened lava lake. The views of the crater and distant steam vents were unforgettable.

🗺️ Pro Tip: Pack layers! It gets chilly at this elevation.

🌞 Day 7: Beach + Coffee + Manta Rays

☕ Breakfast at HICO Coffee
This was hands down our favorite coffee shop on the island. Their avocado toast is chef’s kiss, and the lattes were perfection. I had the Tuna avocado toast and Jackson had the salmon and they were both absolutely incredible.

🏖️ Beach Day at Kekaha Kai State Park
A bit of a bumpy road in (you’ll want a high-clearance vehicle or patience), but totally worth it. This beach is stunning—soft white sand, turquoise water, and hardly any crowds. A hidden gem.

The bumpy road to the beach was

🌊 Night Dive with Manta Rays – Big Island Divers
We ended our unforgettable trip with an unreal nighttime diving adventure that far exceeded our expectations in every possible way. Manta rays danced and glided gracefully and elegantly all around us—these massive, enchanting creatures shone beautifully under the soft lights illuminating the water's surface. Big Island Divers offers a fantastic range of both diving and snorkeling options to cater to a variety of different levels of experience, ensuring that everyone can enjoy the stunning underwater world.

I know this feels like a stretch to many people- the ocean, at night, with massive 16 ft creatures! But truly, it is once in a lifetime and I can’t recomend it enough.

What We Would Change

Honestly, there isn’t a ton about this trip that we would change except for this one thing: we wish we had stayed in the Airbnb first and stayed in the resort on the back end. We naturally did more exploring and adventuring when we were staying at the Airbnb and it might have been nice to have a few relaxing days on the end of our trip before heading home.

Final Thoughts

Our anniversary trip to the Big Island had a little of everything: resort relaxation, off-the-beaten-path exploration, cultural immersion, and outdoor adventure. Whether you're celebrating something special or just looking to explore the Big Island beyond the usual stops, this itinerary has you covered.

Let me know if you want help customizing it for a shorter trip, traveling with kids, or doing it all on a budget! 🌺

Big Island Adventure: A Day-by-Day Travel Guide