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Oahu Itinerary & Trip Recap



This was my third time in Hawaii, second in Oahu, first time with Sofia. We chose Maui for our baby moon exactly two years ago today, because it is a more relaxing baby moon island (read my baby moon tips here) so we chose to go to the island of Oahu for the first time in Hawaii with Sofia, because there's just so much to do.


It's funny because our baby moon in Maui in 2017 was exactly the same days we went to Oahu this year 2019, and honestly these first set of weeks in November are just PERFECT for weather and to avoid crowds. But there are so many good times to visit Hawaii, read about it here.


We decided on going 10 whole days (you already lose 2 days traveling since the flight takes 6 whole hours even from LA, read about the best airlines to fly to Hawaii here), and honestly it was just perfect. Not too long, not too short, we had time to relax yet explore the WHOLE island. If you are traveling with kids, I would def recommend a minimum of 5 nights in Hawaii.


Since we had 10 days to enjoy and explore, I booked three different hotels. Mainly so we could stay in three different areas and explore nearby those. And the second reason, so we had a different vibe, typically by the 3rd night in one hotel, with the same views, same breakfast, same pool, same beach, it gets repetitive. Changing hotels and areas makes it more fun too, a new pool to explore, new nearby restaurants, new views to wake up to. You get the point!


For the first leg of our trip we stayed at the Four Seasons Oahu. This five star resort is located in Ko Olina, a really tranquil area of the west side of the island, a great place for both families and couples, very secluded and laid-back, exact vibe to Maui.


The lagoons make the waters as calm as they can be, perfect for Sofia to swim and play in the water. There are tons of water activities to do in this area, one of the best dolphin and snorkel tours, you'll also find a great golf course & hike nearby, but overall this area is the most relaxing one, which is why we chose to stop here first, to get the first three days of relaxation by the beach & pool at a luxurious hotel we could enjoy, before exploring Oahu.


The resort in particular is amazing and offers so much for the whole family, as you know we love the Four Seasons because it's one of the most kid-friendly luxury resorts out there, and it's always a safe choice to go to. They offer a complementary kids club for kids ages 5 to 12, open from 9a to 5p, so if your kids are old enough, you can leave them there during opening hours (don't worry they offer tons of activities through the day) and you can go relax at the adult-only pool, get a pampering SPA treatment, or go do an adult activity. The other 2 pools are kid-friendly, we enjoyed a cabana by the pool that overlooks the ocean and it was just perfect, plus it has a shallow area with rocks that Sofia loved to play at. The room views were also unbeatable, and the room & bathroom made us happily order room service every night. It was the best choice for the first relaxing part of the trip.


And see my tips on how to get the best deal at this luxurious hotel here.


Our second stop was The Moana Surfrider in prime Waikiki! Widely known as the "First Lady of Waikiki," this historic hotel opened doors in 1901 and is a beautiful blend of Victorian elegance and contemporary & renovated comfort.

We loved it’s unbeatable beachfront location (which made it relaxing and gorgeous beach vibe) yer in the heart of the city, within all the shopping, dining and entertainment. Perfect to walk in the evening and grab bites in nearby restaurants, to enjoy the famous Waikiki beach, and get that city-beach vibe. Personally, I feel like staying in this area is also a must if you visit Oahu.


Our room was the “Tower Ocean Suite”, a 1 Bedroom Suite with straight up ocean-front views. For those traveling with kids who need a dark & separate room, this suite is great because the sofa turns into a bed and they also provide cribs, so you can have the babies/kids sleep in the living room which turns pitch black too, and is completely separate from the bedroom. Sofia is used to sleeping in hotel rooms with us but just a great alternative for those needing two full rooms. And the views are unbeatable. Win win.

Plus, with our room we got access to The Beach Club Lounge, an oceanfront lounge that offers complementary appetizers and beverages all day (perfect for the minis who constantly get hungry) breakfast every morning and cocktails every evening.


This time, we went out for early sunset dinner (around 430/5p) every night, and it was just perfect. My favorite restaurants (kid friendly approved) in Waikiki are:

1. Dukes: a must go-to classic, ocean-front.

2. Surf-Lanai, another classic at the iconic Royal Hawaiian.

3. Top of Waikiki, unbeatable views from the top of the building, great at sunset or night.

4. La Mer, open-air dining a with a high-end fixed-price French menu & ocean views.

5. Aloha Table, laid back, fresh breeze, local Hawaiian cuisine.

6. Veranda, simply classic and gorgeous, with the best ocean front views


If you ever need a kid-activity to get a break from the beach & city while in Waikiki, check out the Honululu Zoo, it's walking distance.


The only baby/toddler friendly activity in the Waikiki waters is a sail boat that leaves at 3pm and cruises around for an hour. They accept kids these ages. Just be careful of the sun. Ask your hotel front desk, or directly approach the boats.


While in the city, you should also visit two great city viewing spots!


- Drive up to Puu Ualakaa State Park, and there's a parking on top. You will be able to see the city from behind and it's just stunning, and a great drive too! Easy and comfy to do with kids, and you can even have a picnic up there with them if it's a foggy day and not too hot.


- Go up to Diamond Head. You can't drive up all the way, you can drive up to the parking lot where you will be able to either take the bus that goes to the top, or hike up. Honestly if you have kids it's def easier to take the bus, but if you are in shape and have babies or toddlers than can put in the carrier, you can def hike up too! The hike takes about 45 minutes to reach the top. You'll want to allow at least 1.5-2 hours to really relax and enjoy the hike and the scenery.


And while in Waikiki, you should also pay a visit to historic Pearl Harbor, just outside Waikiki.


Our third and final location was Alohilani Resort, completely different vibe from the other two as well! A modern oasis, when you walk in you find an open-air lobby that is one the most breathtaking I’ve seen. It includes a captivating 280,000 gallon Oceanarium which Sofia was obsessed with and you could see from the breakfast area too, which by the way, it was my fav buffet, wow! We had a direct ocean-front view (room 1221 by the way, my birthday ha! If you have a chance, ask for this room or a similar one, such a crazy view!) and it was brand new and just spotless. So comfy to come back to after exploring nonstop.


We took advantage being there and visited a ton of nearby beaches that are some of the best of the best in Oahu, if you go there, you can't miss them. And since we woke up early, and these beaches were just 30min away from this final location, we were able to always come back to the room for Sofia to take her nap properly and take a break from the sun.


Hawaii has epic beaches, some of the most crystal clear waters I have ever seen:

1. Lanikai Beach

2. Kailua Beach Park

3. Waimanalo Bay Beach Park

4. Waikiki Beach

5. Malaekahana Beach

6. Kailua Beach

7. Makaha Beach Park

8. Ala Moana Beach Park

9. Sandy Beach

10. Sunset Beach


Hawaii is also great for hiking, not baby and toddler friendly, but here are the best hikes:

1. STAIRWAY TO HEAVEN

2. KAAU CRATER HIKE

3. SEVEN FALLS HIKE

4. PALI NOTCHES

5. THREE PEAKS/OLOMANA TRAIL

6. TOM TOM TRAIL

7.  WILIWILINUI RIDGE TRAIL

8. KOKO HEAD STAIRS

9. PINK PILLBOX HIKE/MAILI PILLBOX HIKE

10. CROUCHING LION HIKE

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