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Trip Report

Hawaii 3 Week Vacations. Oahu Maui Big Island Itinerary

Three weeks on three islands - best hikes in Hawaii Big Island, fresh pineapple, hula dancing, black sand beaches and whales!

by wishingoceansAbout Me:Hi, my name is Oriana! I like working in and exploring the best that nature has to offer - hiking, trekking, climbing, diving, swimming, paddle boarding, and volunteering on farms. read more

North AmericaUnited States21 days / December 2020

Highs & Lows

The three peaks hike gives the most amazing views you may ever see!

Hawaii is extremely expensive, in every way.

Itinerary Overview

  • 7 Nights: Maui
    Black and red sand beaches, waterfalls, and Mars-esque volcanic scenery.
  • 7 Nights: Island of Hawai'i
    Volcanoes, green sand beaches, whales and night-diving with manta rays.
  • 7 Nights: O‘ahu
    Beaches, hiking, nightlife

Q & A

  • What would you have changed?

    I wish I had spent more time on Oahu, and taken an extra week to visit Kauai. Although Oahu has a reputation as the most "touristy" island, the tourism is well-deserved as this island boasts some of the best views and the most fun you can have anywhere in the world. For sure, this is the island to visit if you can only pick one.

  • Anything go wrong during the trip?

    Petty theft can be common on the islands, tourist-heavy Honolulu in particular, so never leave your bags left out unattended. Lock your passport and other valuables up in your lodging as soon as you arrive, and only bring however much money you need when going out. Be sure to bring a waterproof holder for your phone to protect it during all the water activities!

  • How was the food?

    The local food and the Thai food are both spectacular.

  • What tips would you give a friend?

    You must, must, must visit a Luau! These showcases of Hawaiian culture, from hula dancing to fire dancing and traditional roasts, give you amazing insight into the island nation which will allow you to appreciate the land that much more. The shows are absolutely spectacular and will keep you on the edge of your seat! It's also a great idea to visit the local farms. Cacao, vanilla, coffee, sugarcane, and pineapple are all very big here, and it's great to support the local farmers and learn about the production process. Plus, you will get to taste and take home fresh vanilla beans and cacao! Because Hawaii is so expensive, there are only really two economical ways to visit: either bring a group of 3-5 friends to split a car and airbnb, or utilize couchsurfing and camping. It's very difficult to find affordable food, but you can mostly utilize the farmer's market/grocery store, and a lot of the best activities to do on the islands (hiking and exploring the beaches) are all free or extremely cheap! I also recommend you buy a sarong - sarongs are the traditional dress of Hawaii, and they are extremely cheap (only $10 at the local convenience store) and extremely functional!! I use mine as a dress, skirt, shorts, top, cover-up, scarf, blanket, beach towel, bath towel, bag, you name it I've used a sarong for it! It's also extremely common (and easy and pretty) for women to wear sarong dresses everywhere around Hawaii. Just tie one on and out the door you go! Be sure to go snorkeling here - there are sea turtles everywhere!...Read More

  • Packing tips?

    You will need many swimsuits! Make sure to bring some secure, stable swimsuits that can hold up to jumping into waterfalls, surfing, and other water sports. Ideally, bring some rashguards to protect your skin during long days in the water and surfing. You will also want plenty of hiking clothes, a sunhat, and dresses/nice clothes for going out at night. Don't worry too much about your packing, as anything you need can easily be bought on the islands.

  • Transportation Tips?

    In Hawaii, the rental car is king. There is very little in the way of public transportation/taxis. Uber and Lyft are both very accessible, but expect to pay high prices. Rental cars are, however, also expensive, so the ideal is to bring a group of friends and all split the costs. DEFINITELY ensure you have very good insurance for the rental car - on every single island, we ended up with some sort of dent or ding within the week. The roads can be rather treacherous, so do not skimp on the insurance and bring your rental car back to the airport early to give yourself enough time to possibly fill out the paperwork for a dent you may not have noticed....Read More

  • Any surprises?

    Some restaurants in Hawaii are cash-only, so be sure to bring some cash on you. Hawaii only allows the use of reef-safe sunscreen (most sunscreen in mainland USA is not reef-safe) so leave your sunscreen at home and buy some when you're in Hawaii.


  • Airbnb. Nice and quiet, very spacious, plus a pool and laundry machines.

  • Airbnb, lots of good options in the Big Island, but you will end up driving a lot every day as the island is quite large and there are things to see all over. So, I recommend spending some time at an airbnb at one side of the island, then a few days at an airbnb on the other side.

  • The Beach Waikiki Boutique Hostel - it's expensive for a hostel (think: $45+/night), but boasts a relaxing rooftop terrace with hammocks and a small kitchen, plus a very social and friendly ambiance. Excellent place to meet other travelers, and the location is very nice, only a few minutes walk to the beach and local restaurants.