One Month In Hawaii: The Best Oahu Travel Itinerary
Ready to go steady in Oahu? If you’re looking to spend one month in Hawaii, the island of Oahu is your perfect match. Oahu offers so much more than the popular tourist attractions of Honolulu and Waikki. This island has stunning beaches, waterfalls, hikes, and natural landscapes that will make you fall in love with Hawaii.
We spent 5 weeks working remotely and exploring Oahu, and below we share everything we learned during our stay. From where to stay in Oahu, to how much money it costs to spend a month in Hawaii, we’ve tried our best to answer any question you might have.
North Shore, Oahu, Hawaii
Tantalus Lookout, Oahu
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Table of Contents
A note about responsible travel in Hawaii
We tried our best to create a sustainable travel guide that encourages visitors to minimize their environmental impact in Hawaii. We do this by equipping you with recommendations to support the local economy, learn about the local culture, and appreciate the natural beauty of the Hawaiian Islands.
If you choose to travel, you have a responsibility to be a self-aware visitor, doing your best to leave a place better than you found it. Please pick up your trash, wear your reef safe sunscreen, don’t use plastics, don’t touch animals, the list goes on. We travel to fall in love with our world and its people, and we care for and protect the things we love.
Please also do your own research at the time of your visit on which hikes and beaches are open or closed. The ocean has strong tides and hikes across the island vary widely in difficulty. This article is for informational purposes only, we are not liable for any damages resulting from the use of this information.
Can you spend a month in Hawaii?
Absolutely. If Hawaii has long been on your bucket list, an extended stay is the best way to get the most bang for your buck, to experience all that the islands have to offer. Plus, slow travel is a more sustainable alternative, allowing you to immerse yourself more fully in a destination, and support the local economy. With an extended stay, the most expensive part of your trip will be flights and accommodation – but certain accommodations offer discounts for extended stays, which we’ll get into below.
Hiking in Oahu, HI
What is the Best Hawaiian Island for a month long stay?
If you’re planning to spend a month in Hawaii, we recommend going steady with the island of Oahu. With more than 125 miles of coastline, Oahu has an endless amount of beaches to explore. Plus, there’s more to this island than most people realize. While Honolulu and Waikiki are widely visited, the less explored regions of the island hold the most beauty. This is where you’ll spend the majority of your time.
Other islands like Maui and Kauai are more popular for traditional vacations, making them more expensive and a bit more remote for an extended stay in Hawaii. Of course, you can easily take a short flight from Oahu to any of these destinations for a reasonable price. But do consider the additional carbon emissions associated with traveling between the islands, rather than choosing to go steady on Oahu. If you choose to travel, offset your carbon emissions and try your best to fly eco-friendly airlines.
Secret Island Beach, Oahu
Tantalus Lookout, Oahu
Get to know Oahu
Use a platform that compares multiple airlines and prices, like Wayaway or Google Flights. Purchasing a travel credit card is also a great way to get flight points and fly for free.
Outsite is a co-living community, a.k.a. a stunning shared home that is perfect for your extended stay in Hawaii. You’ll have your own room and bathroom, with all the amenities of a home away from home.
Rent from Baba Rentals – a small, local business on the island that offers great customer service and affordable cars.
The longer you travel, the more you need travel insurance. We recommend Visitors Coverage, which offers a variety of plans based on your individual needs.
Sustainable travel is non negotiable, and it’s the best way to respect the places you explore. Read our specific sustainable travel tips for Hawaii before you go to find the best eco tours and local eats.
Honestly, anytime. We went in April/May and had amazing weather. There is something happening on the island throughout every season. Decide what’s important to you (ex: whale watching or seeing surf competitions) and research flights during that time of year.
Hiking in Oahu
Beaches in Oahu
How much does a month in Hawaii cost?
We can tell you EXACTLY how much one month in Hawaii costs, because we just finished up our trip.
@baggagegirls Curious how much it costs to spend one month in Hawaii? Here’s exactly how much money I spent exploring Oahu! Traveling to Hawaii, I knew that this was going to be an expensive trip. It helps to realize that I would have incurred a lot of these expenses anyway for a normal month, whether I was in Hawaii or not (food, gas, shopping, etc.) FLIGHTS: I got my flight mostly paid for by credit card points but it would have been about $600 roundtrip. #baggagegirls #whatispent #travelexpenses #hawaiitraveltips #travelcost #traveltips @Outsite @Baba Rentals LLC
♬ Summer day - TimTaj
TOTAL: $4108
Keep in mind that some of these costs are simply fixed costs of living, that we would have incurred no matter where we were. Groceries, gas, shopping, and eating out are things we spend money on no matter where we are in the world!
Of course, things were more expensive in Hawaii. But we’ve also had the reverse, traveling to a destination where the cost of living is actually cheaper than our lives at home!
For Cheap travel destinations:
Bali Budget Itinerary: 2 Months For $2000
Is Costa Rica expensive? How To Travel Costa Rica On A Budget
How to save money traveling in Hawaii
Here are 3 key ways to make your trip to Oahu more affordable:
- Stay at a co-living house: Outsite has a stunning house in Hawaii where you can stay with others who are traveling in Hawaii. The accommodation offers discounts for extended stays and you’ll have access to a full kitchen. Plan to cook some meals here each day to save money.
- Explore free activities: Oahu has SO many free things to do, that you don’t need to spend money on activities. Explore countless beaches and hikes that don’t cost a single dollar (see our favorites below!).
- Rent a car through a local company: Baba Rentals is an amazing and affordable car rental company on the island that will save you money and allow you to put your money into the local economy of the place you visit.
@baggagegirls Interested in working remotely from Hawaii? We just published a Digital Nomad Travel Guide for Oahu on Baggagegirls.com 🫶🏼✈️ This travel guide has all our best tips from where to stay to what to do in Oahu! To get you started with some inspo, here’s a little Oahu Travel Vlog 💌 ••• #oahutraveltips #oahutravelguide #baggagegirls #exploretheworld #hawaiitravelguide #traveltips
♬ vlog, chill out, calm daily life(1370843) - SUNNY HOOD STUDIO
Where To Stay In Oahu
Outsite is our top recommendation for where to stay in Oahu. We stayed at Outsite Wailupe for 5 weeks, and wrote a full review of our experience here to answer all your questions about this up and coming accommodation style.
We are kind of obsessed with this company and the idea behind coliving homes for those who work remotely and travel. Staying with Outsite offers you the best chance to build a community of fellow travelers in Oahu.
Outsite Wailupe, Oahu
Outsite Wailupe, Oahu
Oahu’s Regions
Honolulu
The busy city and hub of tourism in Oahu. You’ll find hostels, a variety of restaurants, and nightlife here. Waikiki Beach is a popular spot for beginner surfing.
North Shore Oahu
East side Oahu
The East side has the best views from the car, so be sure to ride down the rocky coastline. Explore the Lanikai beach and pillbox hike, and work your way up Koko Crater. Also check out Kailua, a town with great shops and a local farmers market on Sundays.
Central Oahu
The more residential area of the island. You can visit Pearl Harbor in Central Oahu.
West side Oahu
The West side of Oahu is more residential, but it has some beautiful hikes and beaches. Be cautious with your belongings in all areas, and leave nothing in your car, this area is known for break ins. You’ll find the best sunsets here. Be sure to do the Pink Pillbox hike at sunset!
One Month In Hawaii: week by week breakdown
Week 1 in Oahu: One Month In Hawaii
Spend your first week adjusting to the time zone and exploring the surrounding area. If you stay at Outsite, you don’t have to go far to find amazing hikes and beaches.
- Hike Kokohead
- Relax at Cromwell’s Beach
- Watch the sunset at China Walls
- Get a month long membership at Sun Yoga Hawaii (we got 11 days for $11!)
- Swim from the oceanfront dock at Outsite
- Hike Manoa Falls
Outsite Wailupe, Oahu
Koko Crater Stairs, Oahu
Week 2 in Oahu: One Month In Hawaii
After a relaxing week, you’ll be ready for an adventurous week 2 on the North Shore. Spend time this week exploring the famous North Shore & Kailua, a town on the east coast of Oahu.
- Snorkel Sharks Cove
- Beach day at Waimea Bay
- Explore Haliewa town
- Hike the North Shore Pillbox
- Explore Kailua
- Hoʻomaluhia Botanical Gardens – you can go early and walk the gardens or drive through after 9 am
- Kailua Farmers Market – support local vendors on Sundays!
Hiking in Oahu
North Shore Pillbox hike, Oahu
Week 3 in Oahu: One Month In Hawaii
Now that you’re more comfortable with your surroundings, explore Oahu’s less widely visited spots. Spend your third week checking out the east and west sides of the island, which are lesser known by tourists who come for short stays.
East Side
- Hike the Makapu’u lighthouse trail
- Visit Alan Davis beach
- Drive the east windward side for stunning views of the coastline and mountains
- Hike Crouching Lion
West Side
- Visit Yokohama Beach
- Hike the Pink Pillbox
- Go on a Swimming with Dolphins Eco Tour
Eastern shore, Oahu
Pink Pillbox hike, Oahu
Week 4 in Oahu: One Month In Hawaii
If it’s your last week on Oahu, you’re going to want to spend some time revisiting one or two of your favorite spots. We went back to Cromwells beach time and time again – and we frequented Raised by the Waves for the amazing healthy food options. For your last week, make sure you plan to drive around the island and stop off at different beaches and picture spots that you find along the way. Here are a few recommendations below.
- Hike Lulumahu falls – it’s easy to get lost on this hike, try to bring a map of the route in case you don’t have service on the trail
- Visit Kualoa Ranch – nature reserve offering tours
- Visit Secret Island Beach – right by Kualoa Ranch, so you can do both on the same day
Secret Island Beach, Oahu
Lulumahu Falls, Oahu
Best Beaches in Oahu
- Cromwells (10 minute drive from Outsite)
- Sharks Cove (North Shore) – bring your mask and snorkel!
- Waimea Bay (North Shore)
- Sunset Beach (North Shore)
- Alan Davis Beach (East side)
- Secret Island Beach (East side)
Eastern shore, Oahu
Eastern shore, Oahu
Best Hikes in Oahu
- Koko Head (10 min drive from Outsite)
- Manoa Falls (15 min drive from Outsite)
- Crouching Lion
- Pink Pillbox
- LaniKai Pillbox
- Lulumaku Falls
- North Shore Pillbox
- Diamond Head
Diamond Head hike, Oahu
Koko Crater Stairs, Oahu
Cultural experiences and local festivals in Oahu
Our best recommendation to find local festivals and cultural experiences taking place during your stay is to check with your Outsite Community Manager. These individuals are employed by Outsite to help you during your stay, and they are local to the area!
You can also search for experiences on Get Your Guide. This is the tour operator that we primarily choose when traveling.
Swimming with dolphins eco tour
Swimming with dolphins eco tour
Eating Out in Oahu
We recommend eating out at local food trucks rather than fancy restaurants, to save money and enjoy a more authentic food experience. Below we’ve listed a few of our favorite spots that we recommend.
- Farm to Barn
- Raised by the Waves
- Ono Yo
- Pig & the Lady Honolulu
Sunrise Shack, North Shore, Oahu
Grocery Shopping in Oahu
On the island of Oahu, two grocery stores are most popular – Foodland and Safeway. Foodland is the pricier of the two, but offers more health food options. Safeway is a bit more affordable and we tried to shop here as much as possible. Both grocery stores are a short drive from Outsite, and Foodland is walking distance.
Wrap It Up: One Month In Hawaii
This is everything you need to spend one month in Hawaii, falling in love with the island of Oahu. If you plan to working remotely while traveling to Hawaii, we recommend checking out these other posts:
- The Ultimate Digital Nomad Travel Guide for Oahu
- 10 Remote Work & Travel Tips To Get You Started TODAY
If you have any further questions about how to go steady in Hawaii, drop them in the comments below!
xoxo,
Baggage girls
