🌺 Hawaii β€” Here We Come!

✨ Celebrating Our 20th Anniversary ✨

Two islands Β· Ten days Β· Five travelers

β€”
Days
β€”
Hours
β€”
Mins

πŸ“…
Jul 31 – Aug 9
Travel Dates
πŸŒ™
9 Nights
4 Oahu Β· 5 Big Island
πŸ‘¨β€πŸ‘©β€πŸ‘§β€πŸ‘§
5 Travelers
Family of Five
🏝️
2 Islands
Oahu + Big Island
✈️ Chicago (ORD) β†’ πŸ–οΈ Honolulu, Oahu
Jul 31 – Aug 4 Β· 4 nights
β†’ πŸŒ‹ Kailua-Kona, Big Island
Aug 4 – Aug 9 Β· 5 nights
β†’ ✈️ Chicago (ORD)
Alaska Airlines
Chicago β†’ Honolulu
Friday, July 31, 2026
3:43 PM
11:35 PM
πŸ“ Seattle (SEA) β€” 2h 8m layover Β· ORD β†’ SEA β†’ HNL
Alaska as Hawaiian Airlines Β· AS 1068
Honolulu β†’ Kailua-Kona
Tuesday, August 4, 2026
10:59 AM
11:46 AM
🏝️ HNL β†’ KOA Β· ~47 min flight
Delta Airlines
Kailua-Kona β†’ Chicago
Sunday, August 9, 2026
9:06 PM
4:43 PM
πŸ“ Seattle (SEA) β€” 4h 35m layover Β· KOA β†’ SEA β†’ ORD
⚠️ Arrives Monday, August 10
Day 1
✈️ Departure β€” Chicago to Honolulu
Friday, July 31, 2026
✈️ ORD β†’ SEA β†’ HNL Β· 3:43 PM
β–Ό
3:43 PMDepart Chicago O'Hare (ORD) β€” Alaska Airlines
ORD β†’ SEA β†’ HNL
LayoverSeattle (SEA) β€” 2h 8m connection
11:35 PMArrive Honolulu (HNL) 🌺
Check in to Hyatt Place Waikiki Beach β€” late arrival
πŸ›’ AirportBefore leaving HNL: ABC Store near baggage claim
Hotel restaurant is closed at midnight β€” grab water Γ— 5, snacks, and light food for the kids
Day 2
πŸ–οΈ First Full Day in Waikiki
Saturday, August 1, 2026
βœ… Earl’s Kitchen + Bar β€” 8:00 PM BOOKED
β–Ό
MorningHotel breakfast (included!) β€” fuel up for the day
Late AMWaikiki Beach β€” first Hawaii swim 🌊
Beach is right in front of the hotel area
AfternoonAla Moana Shopping Center πŸ›οΈ
~10 min by Uber or trolley Β· 350+ stores Β· great food court Β· don't miss the Makai Food Court for local eats
8:00 PM πŸ₯‚ Anniversary Dinner β€” Earl's Kitchen + Bar βœ… BOOKED
Modern, lively atmosphere Β· Waikiki Β· ~$40–60/person
Day 3
πŸ—» Diamond Head + πŸ–οΈ Waikiki
Sunday, August 2, 2026
πŸ—» Diamond Head hike Β· πŸ–οΈ Waikiki afternoon
β–Ό
7:00 AMDiamond Head State Monument πŸ—» β€” 7:00–8:00 AM entry slot
1.8-mile round-trip Β· crater rim Β· paved path β†’ stairs β†’ 225-ft tunnel β†’ summit Β· ~90 min total Β· go early to beat the heat and crowds
🎟️ Buy tickets July 3 at 6:00 AM Chicago time at gostateparks.hawaii.gov/diamondhead β€” $5/person Β· opens exactly 1 month before
⚠️ Confirm Hyatt Place breakfast hours β€” hotel breakfast is at 9:00 AM return βœ… if open that late
~9:30 AMBack to hotel Β· rest and cool down Β· breakfast if still serving
AfternoonWaikiki Beach β€” swim, relax, people-watch 🌊
Beach is steps from the hotel
Treat🍩 Leonard's Bakery malasadas β€” iconic Portuguese fried doughnuts
933 Kapahulu Ave, ~5 min from hotel Β· ~$1.50 each Β· grab for the kids!
Lunch🍜 Marukame Udon β€” fast, cheap, kid-friendly Japanese noodles
2310 Kuhio Ave Β· ~5 min walk Β· expect a line but it moves fast
EveningSunset walk along the beach Β· 🍽️ Dinner: Duke's Waikiki β€” beachfront, lively, kids menu
Outrigger Waikiki on the Beach Β· great for sunset views with the family
Day 4
🌿 North Shore + 🌺 Toa Luau at Waimea Valley
Monday, August 3, 2026
βœ… Toa Luau β€” 5:00 PM BOOKED
β–Ό
8:00 AMQuick hotel breakfast Β· pack bags (Big Island departure is tomorrow morning)
8:00 AMUber to North Shore β€” beautiful drive through Ko'olau Mountains (~1 hr)
No rental car on Oahu β€” Uber/Lyft is the way Β· mornings are cooler, less crowded, calmer ocean
9:00 AMArrive North Shore β€” 7 hours to enjoy! 🌿
Hale'iwa town shopping & coffee · Waimea Bay swimming · Giovanni's shrimp truck lunch 🦐 · Matsumoto's Shave Ice 🍧 · Sunset Beach walk
3:30 PMStart heading to Waimea Valley πŸ•“
Waimea Bay and Waimea Valley are very close, but Uber pickup on North Shore can run long β€” leave by 3:30 PM for comfortable arrival
4:30 PMWaimea Valley check-in
59-864 Kamehameha Hwy, Haleiwa β€” same road as the North Shore spots
5:00 PM βœ…Toa Luau at Waimea Valley 🌺 β€” Silver Seating
Flower lei greeting Β· kava ceremony Β· luau feast Β· full Polynesian show Β· fire knife dancing Β· ~3 hours
~8:00 PMLuau ends Β· Uber back to Waikiki (~1 hr)
Dress code: Casual to aloha wear β€” no swimsuits
NightBack at hotel · finish packing for Big Island tomorrow ✈️
Day 5
✈️ Oahu β†’ Big Island Β· Arrival in Kona
Tuesday, August 4, 2026
✈️ HNL β†’ KOA Β· 10:59 AM Β· Pick up rental car
β–Ό
Early AMHotel breakfast β€” eat early, bags packed the night before
9:15 AMCheck out of Hyatt Place Waikiki Β· Uber to HNL airport
⚠️ Standard checkout is 11 AM β€” request early checkout the night before. Flight is 10:59 AM Β· must be at HNL by 9:45 AM for checked bags Β· leave hotel by 9:15 AM
10:59 AMInter-island flight departs Honolulu (HNL) ✈️
Alaska as Hawaiian Airlines Β· AS 1068 Β· Boeing 717-200
11:46 AMArrive Kailua-Kona (KOA) β€” Big Island! πŸŒ‹
Quick airport, easy to get through
~NoonPick up rental car at KOA Β· load up and head to condo
4:00 PMCheck in to Kona condo 🏠
2BR/2BA β€” 10-min walk to Kailua Pier & restaurants
EveningGrocery run β€” KTA Super Stores in Kona πŸ›’
Stock the kitchen tonight so breakfast is ready before Kahalu'u Beach tomorrow morning
NightExplore the pier area Β· Ali'i Drive waterfront Β· first Kona dinner
Day 6
🀿 Snorkeling at Kahalu'u Beach
Wednesday, August 5, 2026
🐒 Sea turtles Β· 🍽️ Huggo's βœ… 7 PM Β· πŸŒ… sunset
β–Ό
MorningKahalu'u Beach Park β€” best easy snorkeling on Big Island 🐒
Sea turtles almost guaranteed Β· 5 min drive from condo Β· free entry
AfternoonKona town Β· Kailua Pier area Β· coffee shops Β· relax before dinner
7:00 PM🍽️ Farewell dinner β€” Huggo's on the Rocks βœ… Reservation confirmed (7:00 PM)
Oceanfront, $40–60/person Β· huggos.com Β· Ali'i Drive, walking distance from condo Β· ask for a sunset table πŸŒ…
EveningKona sunset from Ali'i Drive β€” spectacular views πŸŒ…
Enjoy from your dinner table or the seawall walkway after
Day 7
πŸŒ‹ Hawaii Volcanoes National Park
Thursday, August 6, 2026
πŸŒ‹ All-day Β· KΔ«lauea Β· Lava tube Β· Chain of Craters
β–Ό
Early AMEarly start! Pack snacks and water β€” long day ahead
~1.5–2 hr drive south from Kona
πŸŽ’ Pack lunch from condo or KTA β€” very limited food inside the park Β· don't leave without it!
Late AMArrive Hawaii Volcanoes National Park πŸŒ‹
$30/car entry Β· valid 7 days Β· stop at Visitor Center first
MiddayKΔ«lauea Iki Trail Β· Thurston Lava Tube Β· Crater Rim Drive
Kids love the lava tube β€” an actual tunnel through hardened lava!
AfternoonChain of Craters Road β€” drive to the coast Β· ocean entry lava shelf
Stop at the Holei Sea Arch before heading back
ReturnPunalu'u Black Sand Beach πŸ–€ β€” 45–60 min stop on the way back to Kona
Stunning jet-black sand Β· sea turtles often rest on the beach Β· natural stop on Hwy 11 heading north β€” no detour needed
EveningDrive back to Kona Β· dinner at the condo or local restaurant
Day 8
🀿 Two Step Snorkeling + πŸ¦… Manta Ray Night Snorkeling
Friday, August 7, 2026
βœ… Manta Ray Snorkel β€” 7:00 PM BOOKED
β–Ό
MorningTwo Step / Hōnaunau Bay β€” morning snorkeling 🀿
~30 min south of Kona Β· exceptional coral, sea turtles, spinner dolphins Β· arrive before 9am for best conditions
MiddayBack to Kona Β· lunch Β· relax at the condo
AfternoonRest up Β· rinse off after morning snorkeling
5:00 PMDinner 🍽️ β€” Umekes Fish Market recommended (best poke in Kona)
74-5435 Kaiwi St, Kailua-Kona Β· eat before the tour β€” no heavy meal
6:45 PMDrive to Honokohau Marina (10 min from Kona town)
After turning into the harbor, take the very first road to the RIGHT β†’ pass boat storage and Sea Store & Deli on the left β†’ TURN LEFT β†’ meet crew under the pavilion next to the brown-roof restrooms
7:00 PM βœ…Manta Ray Night Snorkel β€” Hang Loose Boat Tours πŸ¦…
Check-in is your start time Β· gear, wetsuit top & floatation device provided Β· light snacks & water on board
Day 9
πŸ–οΈ Hapuna Beach + ⛰️ Mauna Kea β€” Northern Loop
Saturday, August 8, 2026
πŸ–οΈ Hapuna Beach Β· 🍽️ Waimea lunch Β· ⛰️ Mauna Kea stargazing
β–Ό
MorningHapuna Beach State Recreation Area πŸ–οΈ
~30 min north of Kona Β· one of Hawaii's best white sand beaches Β· wide beach, calm water
MiddayDrive to Waimea 🍽️ (~25 min) β€” lunch in this charming upcountry town
Known for farm-to-table dining Β· cooler mountain climate Β· good rest stop between the coast and Mauna Kea
AfternoonContinue toward Mauna Kea via Saddle Road ⛰️
~45 min from Waimea Β· bring jackets β€” 30–40Β°F colder at the summit! Β· free parking
EveningSunset at Mauna Kea Visitor Information Station (9,200 ft) πŸŒ…
NightfallMauna Kea stargazing πŸ”­
Milky Way visible with the naked eye Β· volunteer astronomers with telescopes Β· one of the best stargazing spots on Earth
NightDrive back to Kona (~1.5 hrs) Β· pack up the condo Β· remember checkout tasks for tomorrow morning
Day 10
β˜• Kona Coffee Country + ✈️ Fly Home
Sunday, August 9, 2026
β˜• Coffee farm Β· ✈️ KOA β†’ ORD Β· 9:06 PM Β· πŸ›‹οΈ SEA Lounge
β–Ό
By 11 AMβœ… Check out of condo (complete checkout tasks!)
Dishwasher, towels in washer, trash to dumpster, lock up
11:30 AMKona Coffee Country β€” farm tour β˜•
Coffee tasting Β· beautiful mountain views Β· ~2 hours Β· ~$25/person
1:30 PMLunch in Kona town 🍽️
3:00 PMLast beach time or souvenir shopping πŸ›οΈ
6:00 PMReturn rental car β€” Budget KOA
8:00 PMAirport · check in for flight ✈️
9:06 PMDepart Kailua-Kona (KOA) β€” Delta Airlines ✈️
KOA β†’ SEA β†’ ORD Β· overnight flight
+1 Β· 6:00 AMArrive Seattle (SEA) β€” 4h 35m layover Β· check gate for Delta 637
6:30 AMπŸ›‹οΈ Lounge split β€” no cost
Wife + 1 kid β†’ United Club (Explorer pass Β· Gate A10 area Β· ⚠️ verify location)
You + 18yr old + 1 kid β†’ The Club SEA (Priority Pass Β· Gate A11)
β˜• Hot breakfast Β· WiFi Β· comfortable seats after overnight flight
9:45 AMMeet at departure gate · board Delta 637 ✈️
10:35 AMDepart Seattle β†’ Chicago
4:43 PMArrive Chicago O'Hare (ORD) 🏠
Home sweet home! (Monday, August 10)
Waikiki Beach, Oahu

πŸ–οΈ Oahu β€” Waikiki

July 31 – August 4, 2026 Β· 4 Nights

🏨 Hyatt Place Waikiki Beach

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.

πŸ“…
Jul 31 – Aug 4
4 Nights
πŸ›οΈ
2 Queens + Sofa Bed
Sleeps 5
πŸ“
427 sq ft
Room Size
πŸŒ†
City View Premium
Room Type
🍳 Free Breakfast Daily πŸ“Ά Free WiFi πŸŒ† City View βœ… Fully Refundable πŸ›‹οΈ Sofa Bed πŸ™οΈ Prime Waikiki Location
βœ… Fully refundable before Friday, July 24, 2026.
⚠️ Destination fee and deposit are due at the property β€” see private notes for amounts.
ℹ️ No car needed in Waikiki β€” everything is walkable or a short Uber ride.
🌺 βœ… BOOKED Β· Mon Aug 3 Β· 5:00 PM

Toa Luau at Waimea Valley

Silver Seating Β· ~3 hours Β· Haleiwa, North Shore

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.

βœ… Included: Waimea Valley admission Β· flower lei greeting Β· kava ceremony Β· luau feast Β· full Polynesian show Β· fire knife dancing Β· traditional cooking demos Β· 1 Mai Tai or Aloha Juice per adult (Silver tier)
⚠️ No hotel pickup β€” must arrive on your own. Uber from Waikiki ~1 hr. Pairs perfectly with a North Shore morning!
πŸ“ Toa Luau Β· 59-864 Kamehameha Hwy, Waimea Valley, Haleiwa
πŸ‘” Dress code: Casual to aloha wear β€” no swimsuits
πŸ–οΈ

Waikiki Beach

Steps from the hotel

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.

βœ… Free to access Β· try a surfing lesson β€” this is where surfing was born!
πŸ—»

Diamond Head State Monument

Day 3 Β· Sunday Aug 2 Β· 7:00–8:00 AM entry slot

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.

1.8 mi round trip
560 ft elevation gain
60–90 min total time
🟑 Moderate Β· All ages βœ…
πŸŽ’ Bring: water bottle per person Β· sneakers (no flip flops) Β· reef-safe sunscreen Β· phone for photos Β· QR code confirmation
⏰ Morning plan
7:00 AM β€” Uber from Hyatt Place (~10 min Β· ~$15)
7:10 AM β€” Enter crater, start hike
8:30 AM β€” Done, back at entrance
8:45 AM β€” Uber back to hotel
9:00 AM β€” Hotel breakfast βœ…
βœ… $5/person Β· timed entry β€” book the 7:00–8:00 AM slot for cooler temps and smaller crowds
⚠️ Tickets open exactly 1 month before β€” buy on July 3 at 6:00 AM Chicago time (Hawaii day starts then)
πŸ”— gostateparks.hawaii.gov/diamondhead
🦐

North Shore Day Trip

~1 hr drive β€” gorgeous scenery

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.

βœ… Best by Uber or rideshare β€” no rental car on Oahu in this trip.
πŸ›οΈ

Ala Moana Shopping Center

World's largest open-air mall

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.

βœ… Don't miss the Makai Food Court β€” excellent local and Asian food options.

πŸ’‘ Waikiki Tips

πŸš•No rental car on Oahu β€” use Uber, the Waikiki Trolley, or TheBus. Everything in Waikiki is walkable.
πŸŒ…Waikiki faces south β€” beautiful afternoon light but not a traditional "sunset beach." Head to Magic Island or Ala Moana Beach for sunset views.
🧴Hawaii requires reef-safe sunscreen β€” oxybenzone and octinoxate are banned. Pick up reef-safe sunscreen before leaving Chicago (cheaper than buying in Hawaii).
🍳Take advantage of the free hotel breakfast every morning β€” it saves money and time, especially on beach days.
πŸ’§Tap water in Hawaii is safe to drink. Bring reusable water bottles β€” single-use plastic isn't sold at many Hawaii beaches.
πŸ•Hawaii Standard Time (HST) is UTC-10 β€” no daylight saving. That's 5 hours behind Chicago in summer. Expect to be up early the first couple days!
πŸ“±Download the Uber app and make sure it works in Honolulu β€” you'll use it constantly with no rental car.
🌊Waikiki water is calm and great for kids β€” much more sheltered than North Shore. Perfect for little ones.
Big Island, Kailua-Kona

πŸŒ‹ Big Island β€” Kailua-Kona

August 4 – 9, 2026 Β· 5 Nights Β· With Rental Car

🏠 Kailua-Kona Condo β€” 2 Bed / 2 Bath

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.

πŸ“…
Aug 4–9, 2026
5 Nights
πŸ›οΈ
2 Bed / 2 Bath
Private Condo
⏰
3 PM / 11 AM
Check-in / Check-out
🚢
10-min walk
To Pier & Restaurants
🍳 Full Kitchen 🚿 2 Bathrooms 🌊 Near Ocean πŸ›οΈ Near Kailua Pier 🍽️ Walk to Restaurants βœ… All Fees Included
βœ… All fees included in the total β€” no surprise charges at checkout.
⚠️ This is NOT all-inclusive β€” plan for groceries, dining, and activity costs.
πŸ›’ Stock up at KTA Super Stores in Kona on Day 6 β€” breakfast and lunch from the condo saves a lot over 5 days.
🐒

Kahalu'u Beach Park

Best easy snorkeling on Big Island

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.

βœ… Free entry Β· rent gear on-site for ~$10–15 Β· arrive before 10am for calm water
πŸ¦… βœ… BOOKED Β· Fri Aug 7 Β· 7:00 PM

Manta Ray Night Snorkel

Hang Loose Boat Tours Β· Honokohau Marina

Giant manta rays (10–14 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.

βœ… Included: Snorkeling gear Β· jacket-style wetsuit top Β· floatation device Β· bottled water Β· light snacks Β· professional guide Β· live commentary
⚠️ Not included: Gratuities Β· GoPro rental (call to reserve) Β· no hotel pickup β€” drive yourself to the marina
πŸ“ Meeting point: Honokohau Marina, 74-381 Kealakehe Pkwy
Into the harbor β†’ first road RIGHT β†’ pass Sea Store & Deli on left β†’ TURN LEFT β†’ brown-roof restrooms β†’ meet crew at pavilion
View tour on Viator β†’
πŸŒ‹

Hawaii Volcanoes National Park

~1.5–2 hr drive south Β· $30/car

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.

βœ… $30 entry per car Β· valid 7 days Β· start early β€” it's a full day trip from Kona
⛰️

Mauna Kea Visitor Center

9,200 ft Β· Free Β· Bring jackets!

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.

βœ… Free Β· rental car allowed Β· whole family can go including 8-year-olds Β· jackets essential!
⚠️ Summit (13,796 ft) requires a guided tour β€” rental cars not permitted above visitor center level.
πŸ–οΈ

Hapuna Beach

~30 min north Β· One of Hawaii's best

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.

βœ… Free to visit Β· paid parking ($10) Β· arrive early for the best spots
🀿

Two Step / Hōnaunau Bay

30 min south Β· Local favorite

Arguably the best snorkeling on the Big Island β€” exceptional coral, incredibly clear water, sea turtles, spinner dolphins. Right next to Pu'uhonua o Hōnaunau National Historical Park (worth a visit too).

βœ… Free snorkeling Β· small parking area fills up fast β€” arrive before 9am
β˜•

Kona Coffee Country

The only US-grown coffee

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.

βœ… Free farm tours Β· pick up authentic Kona coffee as a souvenir (much cheaper than airport)
🍺

Kailua-Kona Town

10-min walk from condo

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.

βœ… Watch for spinner dolphins from the pier β€” especially 7–9am

πŸš— Rental Car β€” Kailua-Kona

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-UpTuesday, August 4 β€” ~Noon (after flight arrives at 12:16 PM)
Drop-OffSunday, August 9 β€” by 8:00 PM (before 9:06 PM flight)
Duration5 days
LocationKailua-Kona β€” near KOA airport
MileageUnlimited
Booked viaCostco Travel
InsuranceUse Chase Sapphire card (primary CDW coverage) β€” see private notes
ℹ️ Costco app booking: Shop β†’ Travel β†’ Rental Cars.
⚠️ Rental cars are NOT allowed above the Mauna Kea Visitor Center (9,200 ft). The summit requires a guided tour.
βœ… You CAN drive to the Visitor Center (9,200 ft) in your rental car β€” no restriction below the summit.

πŸ—ΊοΈ Key Driving Distances from Kona

🐒 Kahalu'u Beach Park~5 min south · 3 miles
πŸ–οΈ Hapuna Beach~30 min north Β· 25 miles
🀿 Two Step / Hōnaunau~30 min south · 20 miles
⛰️ Mauna Kea Visitor Center~45 min Β· 35 miles
πŸŒ‹ Volcanoes National Park~1.5–2 hrs south Β· 97 miles

βœ… Condo Checkout Tasks

Check-out is by 11:00 AM on Sunday, August 9. Please complete the following before leaving:

🍽️Load and start the dishwasher β€” all dishes in, running before you leave
🧺Put used towels in the washing machine and start it β€” host specifically requests this to help housekeeping (machine is small)
πŸ—‘οΈTake trash to the dumpster β€” in the enclosed area by the entrance to the parking lot
πŸ“¦Remove all personal items β€” check under beds, in drawers, bathroom shelves, charging spots
πŸ”’Lock all doors before leaving
⚠️ Host notes that failure to complete these may result in a negative review. Pack the night before to make morning checkout stress-free!

πŸ’‘ Big Island Tips

πŸ›’Stock the condo kitchen on Day 1 β€” KTA Super Stores in Kona is the best grocery option. Budget ~$200–300 for 5 nights of breakfast + lunch supplies + snacks + drinks.
🧴Reef-safe sunscreen only β€” Hawaii law bans oxybenzone/octinoxate. Buy it before leaving Chicago β€” much cheaper at home.
🌑️Kona is hot and sunny (85–90Β°F) but bring layers for Mauna Kea β€” it can be 30–40Β°F at the Visitor Center, even in August.
🌊Respect the ocean β€” check conditions daily. Red flags = no swimming. Always snorkel with a buddy.
🐒Sea turtle rule: Stay 10 ft away from sea turtles β€” it's federal law. They'll often swim right up to you, but don't reach out or block their path.
πŸ’§Bring lots of water for long driving days β€” the volcano and Mauna Kea trips are full days with limited stops. Pack a cooler.
πŸ“·Lava tube tip: At Thurston Lava Tube in Volcanoes NP, there's also a second, unlit lava tube nearby β€” bring flashlights for an adventure!
β˜•Kona coffee is the only US-grown coffee β€” buy it at a farm (Greenwell Farms, Kona Joe) for authentic quality at better prices than souvenir shops.
πŸŒ‹Volcanoes NP strategy: Start with the Visitor Center film, then walk the KΔ«lauea Iki Trail, then do Chain of Craters Road in the afternoon when lighting is best for photos.
🌟Mauna Kea stargazing tip: Volunteer astronomers bring telescopes every clear evening (weather permitting). No reservation needed β€” just show up after sunset.

πŸ’° Budget to Plan For

πŸ›’Groceries β€” ~$200–300 for 5 nights (breakfast + lunch + snacks)
🍽️Dining out β€” budget for 5+ dinners and some lunches in town
πŸŒ‹Volcanoes NP β€” $30/car entry
β›½Gas β€” Hawaii gas is expensive; budget more than you'd expect for the driving days
🎁Souvenirs β€” Kona has great local shops; buy koa wood items, Kona coffee, and macadamia nuts
πŸŒ™ July 31 late arrival: Hotel restaurant will be closed at midnight. Grab snacks at ABC Store near baggage claim at HNL before leaving the airport β€” water, snacks, and light food for the kids.
βœ… Hotel breakfast is included every morning at Hyatt Place Waikiki β€” no groceries needed for Oahu!
🌊

Day 2 Β· Aug 1 β€” Waikiki

First full day

Lunch: Makai Food Court at Ala Moana Center β€” excellent local Hawaiian food. Teriyaki chicken, fresh fish, Asian options. ~$12–15/person.

Dinner: πŸ₯‚ Anniversary Dinner β€” Earl's Kitchen + Bar βœ… BOOKED, 8:00 PM Β· Modern, lively Β· ~$40–60/person.

🍧 Grab shave ice anywhere on the strip β€” kids will love it!
πŸ—»

Day 3 Β· Aug 2 β€” Diamond Head

Hike morning, beach afternoon

Breakfast: Hotel breakfast before or after the hike (back by 9 AM βœ…).

Lunch: Marukame Udon 🍜 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 🍽️ β€” beachfront, lively, kids menu. Great sunset views at Outrigger Waikiki on the Beach.

πŸ“ Leonard's Bakery Β· 933 Kapahulu Ave Β· Marukame Udon Β· 2310 Kuhio Ave Β· Duke's Waikiki Β· Outrigger Waikiki on the Beach
🌿

Day 4 Β· Aug 3 β€” North Shore + Luau

Full day out

Lunch: Giovanni's Shrimp Truck 🦐 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 βœ…

πŸ“ Giovanni's Β· 56-505 Kamehameha Hwy Β· Matsumoto's Β· 66-111 Kamehameha Hwy, Haleiwa
Day 5 Β· Aug 4Ali'i Drive restaurants β€” explore Kona on arrival night
Day 6 Β· Aug 5Farewell dinner β€” Huggo's on the Rocks βœ… 7:00 PM reservation confirmed Β· Ali'i Drive, oceanfront
Day 7 Β· Aug 6Cook at condo β€” you'll be exhausted after Volcanoes Β· pasta or rotisserie chicken from KTA
Day 8 Β· Aug 7Early dinner 5 PM before manta ray tour β€” Umekes Fish Market or Ali'i Drive
Day 9 Β· Aug 8Lunch 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 9Lunch in Kona town before heading to airport
🐟

KTA Super Stores β€” Poke Bar

Any day Β· Best value poke in Kona

Fresh poke made daily β€” tuna, salmon, and octopus options. ~$12–15/lb. Pack in the cooler bag for beach lunches. Stock up here on Day 5 arrival evening.

βœ… Tuna and salmon are pork-free Β· perfect beach lunch Β· grab a rotisserie chicken too
🐠

Umekes Fish Market

Best poke in Kona Β· Day 8 pre-manta dinner

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.

βœ… All poke options pork-free Β· 74-5435 Kaiwi St, Kailua-Kona
πŸ•

Kona Brewing Company

Any afternoon Β· Casual bite or beer

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.

πŸ“ 75-5629 Kuakini Hwy, Kailua-Kona Β· ~$20–30/person
πŸŒ…

Ali'i Drive Waterfront Dining

Day 5 arrival Β· Day 6 farewell dinner

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.

🍽️ Great for Day 5 arrival and Day 6 farewell dinner
πŸŒ‹

Volcanoes Day β€” Pack Lunch!

Day 7 Β· Aug 6 Β· No restaurants in the park

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 1.5–2 hr drive each way.

⚠️ No restaurants inside the park · pack enough for a full day
β˜•

Kona Coffee Shops

Any morning Β· Day 10 farm tour

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.

βœ… Kids can usually get Kona hot chocolate at farm tours!
πŸ“ KTA Super Stores, Kailua-Kona β€” stock up on Day 5 (Aug 4) evening after checking into the condo. Budget ~$200–250.
πŸŒ…

Breakfasts (5 mornings)

β–‘Eggs (dozen)
β–‘Bread + butter
β–‘Cereal or granola
β–‘Milk + yogurt cups
β–‘Fresh fruit β€” mangoes & bananas
β–‘Orange juice
β–‘Keurig pods (condo has Keurig)
πŸ–οΈ

Beach & Day Trip Snacks

β–‘Granola / protein bars
β–‘Trail mix
β–‘Chips + crackers
β–‘String cheese
β–‘Apples + oranges
β–‘Peanut butter + crackers
β–‘Fruit pouches for kids
β–‘Cookies / treats for kids
πŸ’§

Drinks

β–‘Large water bottles Γ— 5 (reusable)
β–‘Sports drinks (Gatorade for beach days)
β–‘Juice boxes for kids
β–‘Sparkling water
β–‘Beer + wine for adults 🍷
🍽️

Easy Condo Dinners (2–3 nights)

β–‘Pasta + jarred sauce
β–‘Rotisserie chicken (KTA has daily)
β–‘Sandwich ingredients
β–‘Salad mix + dressing
β–‘Frozen pizza (easy night)
β–‘Rice (condo has rice cooker!)
🧴

Supplies

β–‘Reef-safe sunscreen Γ— 2–3
β–‘After-sun / aloe lotion
β–‘Dish soap
β–‘Ziplock bags (for beach snacks)
β–‘Reusable grocery bags
β–‘Cooler bag for beach days 🧊
πŸ’°

Food Budget Estimate

Airport snacks (Jul 31)$30–50
Oahu lunches + dinners (4 days)$400–500
KTA grocery run (Aug 4)$200–250
Big Island restaurant dinners$400–500
Plate lunch / lunch spots$200–300
Snacks + drinks ongoing$100–150
Total estimate~$1,330–1,750
ℹ️ All options below are pork-free or have easy pork-free versions you can order.
🐟

Poke

Fresh raw fish with rice Β· tuna or salmon

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.

βœ… Tuna and salmon always pork-free Β· ~$12–15/lb at KTA
🍳

Loco Moco

Rice + beef patty + fried egg + gravy

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.

βœ… Ask for beef gravy (not pork) β€” most places accommodate easily
🦐

Garlic Shrimp

North Shore specialty Β· Giovanni's Truck Β· Day 4

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.

βœ… 100% pork-free Β· cash preferred
🍧

Shave Ice

Matsumoto's Hale'iwa Β· Day 4 North Shore

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.

πŸ“ Matsumoto's Β· 66-111 Kamehameha Hwy, Haleiwa Β· Day 4 North Shore
🍩

Malasadas

Leonard's Bakery Β· 933 Kapahulu Ave, Honolulu

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.

βœ… ~$1.50 each Β· not pork-related at all Β· kids will love these
🍱

Plate Lunch

Hawaii's fast food β€” but actually good

Two scoops of rice + mac salad + protein. Order teriyaki chicken, fish, or beef. ~$12–15/person. Found everywhere in Kona town and Waikiki. Filling and affordable.

βœ… Order teriyaki chicken or fish β€” always pork-free
πŸ₯­

Fresh Local Mango

August is peak mango season in Hawaii

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.

βœ… Look for Hayden or Rapoza varieties Β· much cheaper at KTA
β˜•

Kona Coffee

Only US-grown coffee Β· buy beans at the farm (Day 10)

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.

βœ… Kids can usually get Kona hot chocolate at farm tours!