Updated: Dec 2, 2022
The Gypsea Traveller is a Hawaii Travel Agency. The Owner, Libbi is a travel agent that lives in Hawaii. she has visited all of the Hawaiian Islands and lives on Oahu. This blog has a ton of recommendations based on first hand experience living in Hawaii.
Oahu has the largest population out of all of the Hawaiian Islands. Almost 1 million residents call Oahu home. Oahu is where Honolulu and Waikiki are. It's famous for Pearl Harbor, Waikiki Beach and the North Shore. When you stay in Waikiki you can easily walk to many restaurants and shops and enjoy the variety of nightlife. Oahu also has more local parts of the island on the East Side/Windward Coast, the North Shore and the West Side/Leeward Coast. Visitors can enjoy surfing on the North Shore, seeing dolphins on the Westside, visiting Lanikai and Kailua Beach on the Eastside of the island or exploring the many beautiful beaches. You can do almost anything on Oahu that you can do on the other Hawaiian islands, while keeping busy and being close to shops, restaurants and nightlife.
I highly recommend booking your excursions as soon as you book your vacation. Excursions are booking up months in advance. I can help recommend the best ones and make sure you book them ahead of time.
Snorkeling Shark Cage Snorkel Snorkel with Wild Spinner Dolphins Wreck and Reef Dive Shallow Reef Dive - No experience necessary
Pearl Harbor You can do Pearl Harbor on your own or through a tour. If you want to do it on your own you'll need to reserve tickets for the USS Arizona ahead of time here. You can also show up at 7:00am and get in the standby line to be put on the next available boat out to the USS Arizona. You can also do it by a tour listed below.
Check out my blog on How to Visit Pearl Harbor The Full Pearl Harbor Tour Pearl Harbor + USS Arizona+ City Tour
Island Tours Island Tour with Pearl Harbor
Hidden Gems of Oahu
Private Oahu Island Tour
Catamaran Tradewind Sail Afternoon Delight with Mai Tai's
Sunset Mai Tai Sail
Surf or SUP Surf Lessons SUP Turtle Tour
Kualoa Ranch/Jurassic Park Jurassic Adventure Tour 2 Hour ATV Tour
Hollywood Movie Sites
It's very popular for the fire show.
Great for families with kids. They have activities before the luau you can participate in
A fun party atmosphere with good drinks. Lately I've been recommending Chief's over Germaine's though.
A smaller luau with only 60 people vs 300+. It's educational.
All luau's offer transportation and can be found in the excursion link below (except Nutridge-book direct).
Don't see an excursion you're looking for? Click here for more options!
Diamond Head Diamond Head is a crater that was formed over 300,000 years ago during a volcanic explosion. The hike is only 0.8 miles one way, but you'll gain 500 feet in elevation. The views from Diamond Head are very beautiful. Diamond Head is open 6 days a week (closed on Wednesdays) from 6am-6pm, although you can't arrive after 4pm. The hike is really popular trail as it's very close to Waikiki. You can Uber there or drive a rental vehicle. It's $10 to park if you drive and $5 per person to hike. Kids under 3 are free.
Aiea Loop Trail Aiea Loop Trail is a beautiful hike. It's one of the few hikes that does have shade. The views from the hike are amazing. You'll get to experience walking in the trees, but you'll also have great views of the mountain ranges. The hike is 5 miles long and is a loop. The elevation gain is 1309ft but it doesn't feel that bad as you have a longer time to reach that elevation unlike some of the shorter hikes. There is parking available and the hike is free.
East Side of Oahu
Koko Head Crater Koko Head is a trail for more advanced hikers due to the trail having no shade and the need to hike uphill over 1000 stair steps. The steps are actually old railroad ties. They are not easy to climb. The trail is around 1.6 miles but remember half of that is uphill. The elevation gain is around 885ft. The views from the top are beautiful! I'd suggest going early in the morning as there's no shade and it can get very hot. There is parking available and the hike is free.
Makapu'u Lighthouse Makapu'u Lighthouse is an easier paved trail. Like most hikes in Hawaii there isn't shade. The hike is 2.5 miles long with an elevation gain of 505 ft. The view from the hike is very beautiful. During the winter months, you can often see whales from the hike. There is parking available and the hike is free.
Lanikai Pillbox is a short hike. It's not too difficult but also isn't easy as you need to climb the ridge which can be slippery, muddy and difficult. Bring shoes with good grip. The hike is only 0.9 miles but the elevation gain is 406ft. When you get to the top you'll see the old pillbox which is a WWII bunker. You'll also be able to see Lanikai beach and the Mokulua islands. Lot's of people like doing this hike early in the morning to experience the sunrise. We like to hike it and then eat breakfast at Cinnamon's afterwards. There is parking available although it can be difficult to find and the hike is free.
West Side of Oahu
Ma'ili Pillbox The Ma'ili Pillbox hike is an intermediate hike as there is no shade, and you'll have to hike uphill. The hike is only 1.6 miles with half of that being uphill, but the elevation gain is 679 feet. The views from the top are beautiful. During the winter months, this hike is a great place to spot whales. You'll also get to see the old WWII bunkers at the top. There is parking available and the hike is free.
Kaena Point Kaena point can be accessed from the West side/Waianae or from the North Shore/Wailua. The hike is around 5 miles and is pretty flat. There is no shade and it sometimes rain due to the mountain range being right there. In the winter the hike is great for spotting whales. At the end of the hike there are tidepools where 99.9% of the time I've seen an endangered Hawaiian Monk Seal. There are only 1000+ left in Hawaii. Bring lots of water for this hike. There is parking available and the hike is free.
Kaena Point Kaena point can be accessed from the West side/Waianae or from the North Shore/Wailua. The hike is around 5 miles and is pretty flat. There is no shade and it sometimes rain due to the mountain range being right there. In the winter the hike is great for spotting whales. At the end of the hike there are tide pools where 99.9% of the time I've seen an endangered Hawaiian Monk Seal. There are only 1000+ left in Hawaii. Bring lots of water for this hike. There is parking available and the hike is free.
Safety Tips -remember to bring lots of water -start your hike early due to many hikes not having shade -rain may occur and the trails can become slippery so bring good shoes
-never leave anything valuable in your vehicle.
Break-ins occur regularly at hiking trailheads. If you must leave things in your vehicle, put them in your trunk and do this before you get to your final destinations as people will watch you and see you put stuff in your trunk at the trailhead. I lived there and never had my vehicle broken into, but I also never left a thing in my car. We also left our car unlocked to avoid a broken window.
I highly recommend making reservations anywhere you want to eat. Some places are only taking reservations. We found eating at some local spots at around 4-5pm wasn't at busy and we usually didn't have to wait.
Sweet E's Cafe for Breakfast I love their french toast and Egg's Benedict
Barefoot Beach Cafe Great little beach cafe on the water in Waikiki. Very casual. They have breakfast, lunch and dinner
Deck at Queen Kapiolani Hotel They have great views of Diamond Head
Duke's at Outrigger Waikiki Duke's is on the water in Waikiki
Yard House for Happy Hour They have awesome Poke Nachos and 1/2 off happy hour Monday-Friday for a budget meal
Longboards in Ko'Olina It's right on the water. They have amazing drinks like key lima colada, guava lava, mai tai and more!
Beach House by 604 in Waianae and at Pearl Harbor This restaurant is on the water. They have great foods and the best sunsets. They have another location called Beach House by Pearl Harbor that's also on the water.
Island Vintage Shave Ice This is the BEST shave ice on the island! Trust me! I've tried them all! I love their lilikoi'i flavor. All of their flavors are natural. I recommend getting ice cream on the bottom and sweetened condensed milk on the top.
Leonards Malasadas Malasada's are fried doughnuts but are not like a normal donut. Leonards has the best ones! There's locations in Waikiki and others around the island.
Giovanni's Shrimp Truck We always stop at Giovanni's on the North Shore for some of their famous shrimp.
La Tour They are located in cafe and have good sandwiches as well as yummy macaroons!
Located in Kapolei, Waimanalo and Kailua. There dinner menu is especially good with local fish.
If you've been dreaming of a Hawaiian vacation, but don't know where to start to plan your vacation, book your free 30 minute consultation with The Gypsea Traveller to learn more. Libbi can help you book a vacation package that includes your flight, the perfect resort for you, car rental or airport transfers and insurance. She can also custom design an itinerary for you based on excursion and restaurant recommendations.
Libbi lives in Hawaii and has visited all of the Hawaiian Islands. She loves helping clients book their dream vacation to the Hawaiian Islands. You can visit www.thegypseatraveller.com and click on "Schedule Consult" to choose a date/time to zoom with Libbi, The Gypsea Traveller