5 Day Travel Itinerary And Cheap Tips – Oahu, Hawaii


Who writes itineraries for a vacation in paradise? Not me. Well, not until today. I rather spend most of my time laying on the beach and the rest of the time eating. (If you didn’t know, Hawaii has REALLY good food.) All the time, I have Hawaii-virgins asking me where all the hot spots are in Oahu, and every time, I send them the exact same email, a list of activities and a list of restaurants. So I decided create an itinerary specifically for this post. I’ve also thrown in a few budget tips for those of you broke from the hotel and airfare. The itinerary is based on 5 days in Oahu. Enjoy!

Cheap Travel Tips:

  • Transportation: You don’t necessarily need a car in Oahu. You can pretty much get around taking the bus system. Adult fares are $2.25 per ride, or you can get a 4-day pass for only $25. You can even take this bus from Waikiki to North Shore.
  • Souvenirs: If you have a Costco card, get your gifts here. They’re cheaper and you can buy in bulk. It is located at 525 Alakawa Street.
  • When to travel: Go in the off-season like in March or September. Tourism will be down during those times, so travel companies will adjust the costs to get you to come.
  • I’ll say it again, rent a condo! There you can have a kitchen to use, so you don’t have to eat every meal out.

Itinerary and photos after the jump.


Day 1
8:00am Rise and shine!
9:00am Arrive at the Hawaii Nature Center to begin the Makiki-Manoa Cliffs hike
12:30pm Lunch: Side Street Inn (1225 Hopaka St)
3:00pm Hang out at nearby pool/beach
Day 2
7:00am Breakfast: Wailana Coffee House (1860 Ala Moana Blvd)
8:00am Go to Yamas Fish Market (2332 Young Street) to pick up some spam musubis (spam sushi)
9:00am Surf lessons at Kailua Beach Park
12:00pm Lunch: spam musubis
1:00pm Walk over to Lanikai Beach
4:00pm Back to hotel
7:00pm Dinner: Alan Wong’s Restaurant (1857 South King Street)
Day 3
(Fit for a Wed,
Sat or Sun)
9:00am Breakfast: Zippy’s (601 Kapahulu Avenue)
10:00am Aloha Stadium Swap Meet (junk, but fun to look at) – $1 per person
12:00pm Lunch: Food stands at the stadium (you can find some good stuff here)
2:00pm Pearl Harbor and the USS Arizona Memorial
4:00pm Ala Moana Mall
7:oopm Dinner: Curry House (cheap) or Longhi’s (expensive) at Ala Moana
9:00pm Dessert: Cream puffs at Liliha Bakery (515 North Kuakini Street)
Day 4
9:00am Breakfast: Eggs ‘N Things (343 Saratoga Road)
11:00am Drive to North Shore
12:00pm Lunch: Giovanni’s Aloha Shrimp (59-618 Kawoa Pl)
1:00pm Snack: Shaved Ice w/Ice Cream at Matsumoto’s Shaved Ice (Try to say you’ve had once. Wailoa Bakery has better shaved ice, but it’s by Diamond Head.)
2:00pm Polynesian Cultural Center
5:00pm Drive back
7:00pm Dinner: Jimbo Restaurant for hand made udon (the best)
Day 5
9:00am Snorkeling in Hanauma Bay
1:00pm Lunch: Puka Dog (2301 Kuhio Avenue / Nahua Street)
1:00pm Relax on Waikiki Beach
5:00pm Snack: Shaved Ice at Waiola Bakery (3113 Mokihana St)
6:00pm Dinner: Koterri Ramen at Tenkaippin (617 Kapahulu Ave)

Other Activities:

Restaurants I also recommend:

2 Responses to “5 Day Travel Itinerary And Cheap Tips – Oahu, Hawaii”

  1. Meagan says:

    Great recommendations! I’ll let you know where we end up going!

  2. Ann says:

    A tip: Fly out on Tues or Wed flights are cheapest then. What are some good condos in Oahu?

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