Big Island, Hawaii Adventure: A Day-by-Day Travel Guide
We celebrated our 10th anniversary in true adventurous style—with an unforgettable week on the island of Hawaii, also known as the Big Island! As the largest of the Hawaiian Islands, it offers everything from resort areas to raw natural beauty, making it the perfect place for an anniversary trip.
From hiking lush valleys and exploring multiple climate zones, to snorkeling crystal-clear coves and walking along black sanded beaches created by ancient lava flows, this trip had it all. We marveled at the power of volcanic activity, drove past active volcanoes like Mauna Loa, and even made it to the summit of Mauna Kea—the highest point in Hawaii and one of the best places in the world for stargazing. Whether we were on the sunny side of the island or venturing into more rugged terrain, we were constantly blown away by the variety of landscapes, from tropical forests to stark black sands.
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, stepped off the plane into that warm island air, and made our way straight to pick up our rental car—well, Jeep actually—from Budget Rental. If you're planning to explore the island of Hawaii (which you absolutely should), having a 4WD vehicle can really come in handy.
Some of the best sights, like lava fields and scenic overlooks, are down rougher roads, and let’s be real, driving around in a Jeep just feels right on the Big Island.
Our first stop wasn’t a waterfall or a beach—it was Target. Yep, very practical, but very important.
Groceries on the Big Island can get super pricey, especially in the more remote resort areas. So stocking up on essentials like snacks, breakfast items, drinks, sunscreen, and maybe even a bottle of wine or two will save you a lot of money.
If you're a Costco member, there's one right in Kona too, which is perfect if you're traveling as a family or staying in a vacation rental and plan to cook a bit. Trust us, when we saw the food prices at the resort, we gave our past selves a big pat on the back for thinking ahead. 😅
Plus, if your flight gets in early (like ours did) and your hotel check-in isn’t until 3:00 PM, it’s kind of a no-brainer to use that time to grab your groceries, maybe a quick lunch, and settle into the island vibe before making the drive out to your resort. Even if Kona isn’t where you’re staying, it’s worth the quick detour to get your shopping done while you’re near the big stores—after that, options get more limited and more expensive.
After grabbing groceries in Kona and soaking in those first few hours on the island of Hawaii, we made our way to our home base for the first part of the trip: the iconic Hilton Waikoloa Village on the sunny Kohala Coast.
This stretch of coastline is known for its beautiful weather, luxurious resort areas, and proximity to some of the Big Island’s best beaches and lava-sculpted landscapes. It’s the drier side of the island, which makes it perfect if you're chasing sunshine and beach days.
We spent our first three nights soaking in everything this massive oceanfront resort has to offer—and we do mean massive. The property is like a mini city with multiple pools, hot tubs, waterfalls, a saltwater lagoon where sea turtles swim freely, and even a tram and boat system that takes you around the resort (yes, it really has its own train!).
It was such a fun and unique way to kick off our trip. We scored a great deal by booking a condo through VRBO, which gave us more space, a kitchen to prep some meals, and made our stay way more budget-friendly. It’s a great option if you want the luxury of a resort without paying resort food prices for every single meal.
Speaking of food—just a heads up: while the property is stunning, the on-site dining was definitely pricey and honestly, not our favorite. Meals added up fast and didn’t always feel worth the splurge. This is where our earlier Target run came in clutch!
Having snacks and easy breakfast options in the condo saved us big time. We also recommend branching out and exploring off-property restaurants in nearby towns like Waikoloa Village or even heading down to Kona for a dinner adventure.
And the wildlife? Incredible. Within the first 10 minutes of arriving, we spotted an Eagle Ray gracefully gliding through the lagoon—seriously one of the coolest moments of the trip. The resort’s connection to nature and proximity to lava flows, black sanded beaches, and even views of Mauna Kea in the distance makes it a great jumping-off point for your Big Island adventures.
Whether you're kicking back in the pool, sipping coffee on your lanai, or planning your next day of exploring volcanic activity and climate zones across the island, Hilton Waikoloa Village is a solid base for your first few nights on the largest of the Hawaiian Islands.
🌴 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!
To be honest, we stopped here solely becuaes the Guide Along app told us to but we are really glad we did. Learning about the culture of the Big Island was one of our favorite parts of the trip and the small visitors center had an awesome national park ranger who was informative and freindly!
🚩 Stop 2: Hike Pololū Valley
This hike truly stole our hearts and left us with some of the most unforgettable memories of our entire trip. It’s one of those places that makes you stop in your tracks and say, “Wow… this is Hawaii.”
The trail itself is short but steep, descending quickly into a lush, vibrant green valley that feels almost untouched by time. As you make your way down, you’re surrounded by towering cliffs draped in vines and misty jungle foliage, with birds calling from deep within the trees. It feels like you’re stepping into a scene from a movie—raw, wild, and incredibly peaceful.
At the bottom of the trail, you're rewarded with a dramatic and stunning black sand beach, formed by centuries of volcanic activity and constant reshaping from the ocean’s powerful waves.
The contrast between the deep black sands, the bright blue water, and the vivid greenery of the valley is absolutely breathtaking. Waves crash along the shoreline while the sheer cliffs rise up behind you, making you feel small in the best possible way.
Be sure to bring plenty of water, especially if you're hiking in the heat, and wear shoes with good grip—the trail can be slippery in spots, and the climb back up is definitely a workout. There are no amenities down at the beach, which adds to the feeling of seclusion, but it also means you need to come prepared.
This isn’t just a hike—it’s an experience that engages all your senses and gives you a deeper appreciation for the natural beauty and power of the island of Hawaii. From the rustling leaves to the volcanic sands beneath your feet, this valley trail offers one of the most memorable adventures on the largest of the Hawaiian Islands. Totally worth every step.
🍤 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! 🌺