MorningLate Morning/Early AfternoonAfternoon/Late AfternoonEveningNotes
Day 1Breakfast at HomeFlightFlightLand at OahuHA has no free good entertainment options, bring some
Travel DayArrive at JFK for Flight to OahuLunch and Dinner on AirplaneFly to LihueThe flight can be long! Traveling from the east means you'll likely have a layover
Hawaii Airlines(HA)Pick up rental car at LihueHawaii airports are small and quick and moving between gates is easy
JFK to Oahu to Lihue(~15 hours)Drive to AirBnB in Poipu
Rental car kiosks are right outside of Lihue airport(10 minutes to deplane and get car)
Jeeps are not needed. I got one and hated how it drove so changed it.
The roads at night are DARK since there are no street lights on the island.
Day 2Walk to coast near AirBnBBrunch at Art Cafe Hemingway(7.5/10)Shopping on the main road in KapaaVisit Kukui’ula Village Shopping Center
This island has many chickens! Try the lemonade at Art Cafe Hemingway - delicious - great eclectic brunch
Kap'aaDrive to Lihue(through tree tunnel)Kapaa Beach Park walkwayOpaekaa Falls on the drive back to LihueDinner at Eating House 1849(8/10)
The walkway across the street from Art Cafe is really nice, flat and long and you can rent bikes to ride on it
Costco and more shoppingDrive to Kapaa for BrunchDessert at the Spot(6.5/10)Costco for groceriesKap'aa has some cool eclectic stores to check out but nothing amazing
Opaekaa falls has some nice overlooks of the falls and on the other side of the Waimea River
Costco is great for groceries and gas as both are EXPENSIVE on the islands
Eating House 1849 - highly recommended dinner spot but expensive
If you're in the Poipu area, you'll likely return to the Kukui'ula Village area many times - lots of good restaurants and dessert places
Day 3Breakfast at homeHike Maha'ulepu trails and visit the beachVisit HanapepeDrive home, recover from seasickness :)
Gillin's/Mahaulepu beach gate is closed due to filming of new THE ROCK movie until sometime in 2019(should be open as of November 2019)
Maha'ulepu BeachDrive to Gillin's beach but find the path closedVisit Makauwahi CaveCaptain Andy's Catamaran Dinner Tour(8.5/10)Ride near CJM stables gets you to Mahaulepu but it's a bit rocky and bumpy
Not Na Pali Coast* Catamaran TourDrive near CJM Stables to get to Maha'ulepuLunch at Anake’s Juice Bar(6.5/10)Maha'ulepu has amazing views and great hiking trails
Makauwahi cave is only open on weekends and requires you to crawl on your knees through a tiny entrance
Anake's Juice Bar has great reviews everywhere but I guess I'm just not an acai bowl person
Hanapepe was surprisingly dead for a saturday afternoon
Captain Andy's catamaran tour was great. We booked a Na Pali Coast tour but the weather was bad so we headed south.
They said we could get a refund, reschedule or just go south with them. We went south and it was worth it.
We had a group of spinner dolphins swim alongside our boat for 20 minutes, a once in a lifetime experience. Dinner was ok.
The way back is on sails so seasickness abounds(I know from personal experience)
Day 4Breakfast at homeATV Tour continued(~3 hours)Poipu Beach ParkDessert at Lappert's Ice Cream(8.5/10)ATV tour was great and surprisingly challenging yet still good for beginners.
ATV TourATV Tour with Kipu Ranch Aventures(8/10)Lunch at Da Crack(7/10)Spouting HornDinner at Home
Kipu allows you to change drivers at each stop and the trip takes about 3 hours. Main complaint is too many stops and slow pace.
Poipu Beach and Spouting Horn
Da Crack is a huge hit with locals as there's always a line. Portions are huge and it's a good KETO spot. It's a decent mexican spot.
Poipu Beach park has good beginner snorkeling and you'll see turtles and seals sunning themselves.
Spouting Horn is one of those stop it and check it out type of things. The spout is bigger when the waves are higher.
Lappert's ice cream is DELICIOUS and at Kukui’ula Village Shopping Center. We stopped here a few times during our stay.
Day 5Breakfast at homeLunch at Beach House Restaurant(6/10)Farmer's marketDinner at JO2 Restaurant in Kapaa(8.5/10)The open door helicopter ride over the island is amazing, pure amazing.
Open Door Helicopter RideJack Harter open door helicopter ride(10/10)Dessert at Waikomo Shave Ice(9/10)Snack at home(tropical fruits!)
I'm afraid of heights and my sweaty hands were clutching the seat but the views are unbelievable.MUST DO if you're on the island.
Shave IceWailua falls pit stop
Beach house has a great view but the lunch was mediocre for the price - maybe dinner is better
Waikomo Shave Ice near Da Crack is a small food truck that has the best shave ice I tried on any island
Farmer's markets pop up daily on Kauai. Try the various tropical fruits as they actually have taste here. Starfruit and dragonfruit were my favorite.
JO2 restaurant is a good asian fusion restaurant in a strip mall in Kap'aa. Expensive but highly recommended.
Day 6Breakfast at homeCanyon Trail at Pu’u Hinahina LookoutPihea Vista Trail at Puu o Kila Lookout Dinner at home
Waimea Canyon is beautiful and filled with plenty of hikes - plan to spend a whole day here, maybe two if you love hiking as we barely scratched the surface.
Waimea CanyonWaimea Canyon Drive and OverlookLunch at Porky's in Waimea(8/10)
It takes about an hour to get to the overlook from Poipu, the roads from the foot are slow and winding.
Definitely go all the way to the top and do the first part of the Pihea Vista trail, the views are incredible.
Prepared to be tired after a trip here and bring a jacket since temperatures do drop a bit.
Porky's is a solid sausage dog place and is conveniently located right when you come down the canyon for good post hike eating.
Day 7Breakfast at homeLunch at the Lanai(7/10)Move from Poipu to Princeville AirBnBDinner at Kauai Ono(9/10)
The Maha'ulepu beach ride at CJM stables was a letdown as you barely saw the beach.
Horseback RidingBeach Horseback ride at CJM Stables(5.5/10)Dessert at Lappert's Ice Cream again
Not many great views and the ones you see, we already saw during our day 3 hike. I'd recommend skipping it.
Move to PrincevilleCostco for Gas(2.99 versus 3.99+ elsewhere)This was our last day in the south as we moved up north to Princeville.
Outdoor Dinner
Kauai Ono was a fantastic dinner experience. It's a 5 course menu served under an outdoor tent at princeville ranch.
Not for the picky eater as there is no choice and it is expensive at $60 per person but totally worth it.
Bring bug spray and note they only serve dinner on Tuesday and Wednesday.
Day 8Breakfast at homeExplore Hanalei/Ching Young Village ShopsHanalei BeachWalk down to explore/see Princeville Resort
The road to Hanalei and beyond has one lane bridges, custom is to let ~7 cars pass then go
Explore Hanalei and PrincevilleDrive to HanaleiLunch at Three Brothers Deli(6.5/10)Princeville Foodland for GroceriesDinner at home
Hanalei is a cute little town with a ton of stores and plenty of restaurants and food trucks
Dessert at JoJo's Shave Ice(3.5/10)Ice Cream at Lappert's
Lunch was just ok, don't recommend. JoJos shave ice wasn't good, flavors tasted fake, pass on this one
Hanalei beach showed the damage from the 2018 storms but still a very nice beach, decent area for surfing
The road past Hanalei is now open but visiting the beach at the end of the road requires a reservation(
While closed, it limits what you can do to the north as there's a lot of great hikes/beaches past the blocked areas.
Foodland is the main supermarket on the island and has great poke and tons of SPAM.
Princeville resort isn't as fancy as impressive as the Grand Hyatt down south but just as expensive - has a nice private beach though that you can visit even if not staying.
Day 9Breakfast at homeBeach time and snorkelingLunch at Coconut's Fish Cafe(8.5/10)Smith's Family Luau(6/10)The princeville resort beach isn't amazing and the snorkeling is just OK there.
SnorkelingWalk to the Princeville Resort beachDrive to Kap'aa for lunch/shoppingDessert at Hee Fat Shave Ice(8/10)
Hideaways beach which is behind the tennis courts before the resort is better but harder to get to and neither have good parking in the area.
LuauCoconut's Fish Cafe(also locations in Maui) has the best fish tacos - SO GOOD.
Hee Fat General Store has a shave ice place with solid shave ice - get the real fruit flavors!
Smith's family luau was fine. You get to walk around their big garden then eat a buffet style meal. I probably wouldn't do a luau again on any island - just not my type of thing.
The pork was pretty good but everything else was rather bland and didn't taste homemade and it takes to long from arrival to dinner to the show.
Day 10Breakfast at homeKauai Escape Room(8.5/10)Kap'aa walking around(beach paved trail)Dinner at home
There's so many farmer's markets in Kauai daily. At this one we got some Rambutan(tastes like grape)
Escape Room in LihueFarmer's market in KilaueaLunch at Gaylord's at Kilohana(7/10)Wailua Shave Ice(8/10)Packing
We also got a sugar loaf frosty. Delicious, check out Banana Joe's if you can't find a frosty at a farmer's market for a similar treat.
Last day in Kauai :(
The Kauai Escape Room is surprisingly good and we've done a dozen+ in various cities. This one compares well to the big city ones.
Gaylord's at Kilohana has some stores and is on an old plantation. Food was ok but the area is neat and worth checking out.
Kap'aa has some cool chic stores we came back to and a lot of solid food places plus there's always the beach side walking trail.
Wailua Shave Ice is solid and apparently they have a location in San Diego and Portland, OR too.
Day 11Breakfast at homeFlight from Lihue to MauiAirBnb check in/unpackDinner at The Mill House(7.5/10)Inter island travel isn't long BUT it is tiring and does waste a good portion of a day.
Travel from Kauai to MauiCheck out of AirBnbCostco for groceries
However, it's difficult to pack a lot of stuff in on travel day even though it's a short trip between islands so keep that in mind when planning vacations. It is a less than ideal day.
Shopping at Hanalei
The airports are small and quick so you can arrive 45 minutes before a flight and be fine especially if you have TSA PreCheck.
We stayed in Kihei which is a central location and a solid starting point for any day trips.
The Mill House was good, not great but it's worth it because the location and setting is awesome
Day 12Lahaina front street walkMaui Escape Room(7/10)Dessert at Island Cream(9/10)Dinner at Lahaina Grill(9/10)
Lahaina is a great walking area with plenty of stores but was mostly closed in the early morning.
Lahaina/Western Maui DayWhaler's Village shopping centerLunch at Hula Grill(7/10)2nd Maui Escape Room(IT WAS HOT)
Whaler's Village shopping center is close to the Kaanapali resorts and will validate parking for 3/4 hrs depending on purchase. We got 3hrs from the escape room or 4hrs from the restaurant.
Kaanapali Beach walking path
Otherwise parking is $4/30 minutes so expensive but the beach areas are nice and have a beautiful walking path.
Lahaina front street/Banyan Tree
Maui escape room was fun but not as good as the one on Kauai. However, it was 95 and we wanted some air conditioning so we did two of them. The military themed one is better than the tesla one.
Island Cream was some of the best ice cream/gelato I've ever had - well worth going out of your way to the random strip mall location.
The Kaanapali beach walking path is great and long - passes by all of the major hotels in the area. Ululani's shave ice hsa a location here and they're pretty good.
Lahaina front street is a tourist hot spot towards the late afternoon/evening. Parking is expensive but there is a small amount of free parking on the side of the road and on the south part of the street.
Front street has the banyan tree(a cool old big tree) and a ton of cool art galeries with local artists and some neat shops.
Lahaina Grill was fantastic with impecable service but quite expensive($30 apps, $50 entrees) and there's no view which is a shame for the area - definitely a recommendation if you can afford it.
Day 13Visit Haleakala(9/10)More time at HaleakalaKamaole Beach ParkDinner at home
Haleakala is AMAZING - otherwordly place with awesome views and unique landscapes.
Haleakala CraterLunch at South Maui Fish Company(8/10)PackingWe didn't have time to do the Road to Hana(NEXT TIME) as we fly out tomorrow.
South MauI Fish Company has pretty good fish tacos - my favorite are still at Coconut's Fish Cafe which has locations in Maui too.
Lots of great beaches in Maui including Kamaole.
Having a kitchen at home is a great money saver as we could just eat left overs from Lahaina and Mill House(still delicious).
Day 14Breakfast at homeHumpack Whale National Sanctuary(6/10)Land at Kona, drive to AirBnb areaRelax at home
Ululani's is good, not the best shave ice I had but had to try it since I was on Maui and it was said to be the best.
Flight to the Big IslandCheck out of AirBnBAirport/FlightLinner at Foster's Kitchen(5.5/10)
The Humpback Whale Sanctuary visitor's center is cute but nothing amazing, they were doing some work on it while we were there.
Snack at Ululani's Shave Ice(8/10)Check into AirBnB
The flight from Maui to the Big Island is short(40 minutes) and the airports are both a breeze so you can arrive 45 minutes before flight.
Snack for airplan at Sugar Beach Bake Shop(7/10)Foster's Kitchen has a nice view but the food there is bland.
Flying between islands is easy but it is tiring(and made me slightly sick!)
Day 15Drive from Kona to Volcanoes National Park(~2 hrs)Volcanoes National Park(9/10)Driving back through Chain of Craters RoadRoute 200 home, mountain viewsWe came here simply for the volcano!
Volcanoes National ParkStop at Paradise Meadows to buy some giftsHikingTaking the long way back home through HiloShopping at Waikoloa
The drive from Kona to Volcanoes National park is about 2hrs each way but it has cool varied landscapes on the way.
Punaluu Black Sand BeachDriving down Chain of Craters RoadDinner at Pineapples Island Fresh Cuisine(4/10)Packing
There's some neat stops along the way. Paradise meadows is a local farm that sells honey, coffee and awesome chocolate nuts.
Punaluu black sand beach is a beautiful beach with black sand(duh) where you can see turtles quite often.
Volcanoes National Park was closed in spots but still awesome. There was no live lava in the park when we went there.
The sulfur vent trail was really cool and chain of craters road was neat as well.
We chose to take a longer route home to see Hilo and the other part of the island. Pineapples Island Fresh Cuisine had good yelp reviews but the food was very disappointing.
Day 16Flight to PortlandFlightLayoverFlightFlying the other way sucks :(, all day event!