β¨ Celebrating Our 20th Anniversary β¨
Two islands Β· Ten days Β· Five travelers
Tap any day to expand. Blue = travel days Β· Green = Oahu Β· Gold = Big Island
Located in the heart of Waikiki, the Hyatt Place Waikiki Beach puts you steps from the famous beach strip, restaurants, and shopping. With a 2 Queen + Sofa Bed Premium room, the whole family sleeps comfortably. Free breakfast every morning is a big bonus β saves money and starts each day without the hassle of finding a place to eat.
One of Oahu's most celebrated luaus, set in the lush greenery of Waimea Valley. The evening begins with a flower lei greeting and kava ceremony, followed by traditional cooking demonstrations, a full luau feast, and a spectacular Polynesian show featuring fire knife dancing. 2 Adults + 1 Youth + 2 Children.
The iconic crescent of Waikiki Beach β calm, swimmable water, lifeguards on duty, great for all ages. Bodyboarding, surfing lessons, and outrigger canoe rides available right on the beach.
Hike the rim of an extinct volcanic crater from the inside out β paved path, switchbacks, 99 steps, and a 225-foot tunnel through the crater wall. Panoramic views of Waikiki, the lighthouse, and the Pacific at the top. Historic WWII military bunkers the kids will love.
Hale'iwa town, Waimea Bay, Sunset Beach, and the famous shrimp trucks (Giovanni's!). The windward drive through the Ko'olau Mountains is stunning. Great for a full day out.
Hawaii's premier shopping destination with 350+ stores, a great food court, and an outdoor atmosphere. 10 minutes from Waikiki by trolley or Uber. Perfect for a slower-paced afternoon.
A rare two-bedroom, two-bathroom condo just a 10-minute walk from Kailua Pier, waterfront restaurants, and the Pacific Ocean. Unlike a hotel room, this gives the family real space: a full kitchen for grocery savings, two separate bathrooms, and room to spread out after a long day of adventure. Booked via VRBO.
The #1 snorkeling spot near Kona β sea turtles are almost guaranteed, plus tropical fish and healthy coral right at the shore. No boat needed. 5 minutes from the condo by car.
Giant manta rays (10β14 ft wingspan) glide up from the deep to feed on plankton attracted by underwater lights β and you float right above them. One of the most unique ocean experiences in the world. 3 Adults + 2 Children booked.
Walk through an actual lava tube, peer into the KΔ«lauea crater, and drive Chain of Craters Road to the Pacific coastline. This is unlike any national park on the mainland β an absolute must.
Drive your rental car up to the Visitor Information Station at 9,200 ft β above the clouds. Watch the sunset, then stay for free stargazing with volunteer telescopes. The Milky Way is clearly visible with the naked eye.
A wide, gently sloping white sand beach with calm, turquoise water β consistently rated one of the best beaches in the United States. Great for swimming, bodyboarding, and a long beach day.
Arguably the best snorkeling on the Big Island β exceptional coral, incredibly clear water, sea turtles, spinner dolphins. Right next to Pu'uhonua o HΕnaunau National Historical Park (worth a visit too).
The slopes above Kona are covered in coffee farms. Greenwell Farms and Kona Joe Coffee both offer free tours and tastings β a fun half-morning activity on the way to or from the volcano.
Ali'i Drive waterfront, Kailua Pier (spinner dolphins often swim here in the morning!), Kona Brewing Company, local fish tacos, shave ice, and sunset views. The town is small and very walkable.
The rental car is essential on Big Island β unlike Oahu, there's no real public transit and destinations are spread across a large island. Booked via Costco Travel with unlimited mileage.
| Pick-Up | Tuesday, August 4 β ~Noon (after flight arrives at 12:16 PM) |
| Drop-Off | Sunday, August 9 β by 8:00 PM (before 9:06 PM flight) |
| Duration | 5 days |
| Location | Kailua-Kona β near KOA airport |
| Mileage | Unlimited |
| Booked via | Costco Travel |
| Insurance | Use Chase Sapphire card (primary CDW coverage) β see private notes |
| π’ Kahalu'u Beach Park | ~5 min south Β· 3 miles |
| ποΈ Hapuna Beach | ~30 min north Β· 25 miles |
| π€Ώ Two Step / HΕnaunau | ~30 min south Β· 20 miles |
| β°οΈ Mauna Kea Visitor Center | ~45 min Β· 35 miles |
| π Volcanoes National Park | ~1.5β2 hrs south Β· 97 miles |
Check-out is by 11:00 AM on Sunday, August 9. Please complete the following before leaving:
Where to eat, what to try, and what to stock in the condo
Lunch: Makai Food Court at Ala Moana Center β excellent local Hawaiian food. Teriyaki chicken, fresh fish, Asian options. ~$12β15/person.
Dinner: π₯ Anniversary Dinner β Earl's Kitchen + Bar β BOOKED, 8:00 PM Β· Modern, lively Β· ~$40β60/person.
Breakfast: Hotel breakfast before or after the hike (back by 9 AM β ).
Lunch: Marukame Udon π β fast, cheap, kid-friendly Japanese noodles. ~5 min walk, expect a line but it moves fast.
Treat: Leonard's Bakery malasadas β Portuguese fried doughnuts, an Honolulu icon. ~5 min from hotel. ~$1.50 each.
Dinner: Duke's Waikiki π½οΈ β beachfront, lively, kids menu. Great sunset views at Outrigger Waikiki on the Beach.
Lunch: Giovanni's Shrimp Truck π¦ β the most famous shrimp truck on the North Shore. Garlic shrimp plate ~$14. Cash preferred.
Shave Ice: Matsumoto's Shave Ice in Hale'iwa β legendary. Best right after Giovanni's.
Dinner: Included at Toa Luau β full feast β
| Day 5 Β· Aug 4 | Ali'i Drive restaurants β explore Kona on arrival night |
| Day 6 Β· Aug 5 | Farewell dinner β Huggo's on the Rocks β 7:00 PM reservation confirmed Β· Ali'i Drive, oceanfront |
| Day 7 Β· Aug 6 | Cook at condo β you'll be exhausted after Volcanoes Β· pasta or rotisserie chicken from KTA |
| Day 8 Β· Aug 7 | Early dinner 5 PM before manta ray tour β Umekes Fish Market or Ali'i Drive |
| Day 9 Β· Aug 8 | Lunch in Waimea β northern loop day (Hapuna β Waimea β Mauna Kea) Β· farm-to-table dining town Β· no Kona dinner tonight |
| Day 10 Β· Aug 9 | Lunch in Kona town before heading to airport |
Fresh poke made daily β tuna, salmon, and octopus options. ~$12β15/lb. Pack in the cooler bag for beach lunches. Stock up here on Day 5 arrival evening.
The #1 rated poke spot in Kailua-Kona. Fresh tuna, salmon, and octopus poke bowls. Casual counter service, incredible quality. Perfect for an early dinner before the manta ray tour.
Open-air brewpub in Kona. Great pizza, fish tacos, and burgers. Lively family-friendly atmosphere. Their Longboard Island Lager is the local beer of choice. Good for a casual lunch or afternoon stop.
The main strip in Kona with restaurants along the waterfront. Beautiful sunset views. Great for first night exploration and the special farewell dinner on your last full Big Island evening.
Very limited food options inside Hawaii Volcanoes National Park. Pack lunch and snacks from the condo or grab items at KTA before you leave. Don't skip this β it's a 1.5β2 hr drive each way.
Local coffee shops pour authentic Kona coffee grown on the slopes above town. On Day 10, visit a coffee farm (Greenwell Farms or Kona Joe) for a free tour and buy beans to take home β far cheaper than the airport.
| Airport snacks (Jul 31) | $30β50 |
| Oahu lunches + dinners (4 days) | $400β500 |
| KTA grocery run (Aug 4) | $200β250 |
| Big Island restaurant dinners | $400β500 |
| Plate lunch / lunch spots | $200β300 |
| Snacks + drinks ongoing | $100β150 |
| Total estimate | ~$1,330β1,750 |
Hawaii's most iconic food. Fresh fish marinated in soy sauce, sesame oil, and spices over rice. Available everywhere. Best: KTA poke bar or Umekes Fish Market in Kona.
A Hawaiian diner staple β rice topped with a beef burger, fried egg, and brown gravy. Hearty breakfast or lunch. Order with beef gravy to keep it pork-free.
Shrimp from nearby aquaculture farms cooked in butter, garlic, and spices with rice. Giovanni's is the most famous truck on the North Shore. ~$14/plate. Cash preferred.
Finely shaved ice with Hawaiian fruit syrups β completely different from a mainland snow cone. Matsumoto's in Hale'iwa is the most famous spot on the island. A must for the kids.
Portuguese fried doughnuts brought to Hawaii by sugar plantation workers β now an island staple. Leonard's Bakery is the iconic stop. Warm, sugary, amazing. Great treat on Day 2 or 3.
Two scoops of rice + mac salad + protein. Order teriyaki chicken, fish, or beef. ~$12β15/person. Found everywhere in Kona town and Waikiki. Filling and affordable.
August is peak mango season β local mangoes are incredibly sweet, inexpensive, and unlike anything from the mainland. Buy at KTA or any farmers market. The kids will be obsessed.
Rich, smooth, world-famous. Visit a farm on Day 10 for a free tour and tasting. Buy beans as souvenirs β far cheaper at the farm than at the airport or tourist shops.