Traveling with Stephy

The ultimate Hawaiian islands travel guide: a 1-month itinerary day by day

Since my earliest childhood, it had always been one of my biggest dreams to be able to explore the unspoiled nature of the Hawaiian island, located right in the middle of the Pacific ocean. Therefore, I feel so grateful that I had the chance to explore this preserved archipelago for a month. I hope I can inspire you to do the same and this is why I have created my ultimate Hawaiian islands travel guide that gathers everything you need to know to enjoy the archipelago at the fullest including a 1-month itinerary day by day.

The Hawaiian islands are composed of eight major islands: Oahu, Kauai, Maui, Big Island, Lanai, Molokai, Niihau, and Kahoolawe. Overall the archipelago has lots more isles and atolls, but the others islands are uninhabited. Each island is different and unique to the other with its scenery. The Aloha state, located 2’000 miles away from California coasts, has 1,4 million residents. English and Hawaiian are the two official languages.

Throughout the next chapters, you will find more details on:

  • Oahu
  • Kauai
  • Maui 
  • Big island (also called Hawaii)

When to visit the Hawaiian islands?

The Hawaiian islands can be visited all year round offering nice temperatures between 20°c and 35°c. However, some periods of the year are more propitious to visit with notably less risk of tropical storms. Consequently, I strongly advise you to visit the archipelago between May and June. In my opinion, this is the best time of the year to discover the islands as the weather is mostly dry and not too hot. Above all, the locals and the rest of the US are not on summer break just yet. Therefore, most of the famous places are not too crowded at this time.

“In case you cannot visit the Hawaiian islands during this period, just try to avoid April (spring break) as well as July and August (summer break).”

How long to stay on the hawaiian islands?

Alright, to discover the top attractions of the four main islands (Oahu, Kaui, Maui, and Big Island), I strongly recommend staying on the island for at least for one month. Indeed, there are so many things to do, you won’t get bored! Of course, if you can slowly travel, I would highly suggest spending 3 months around the archipelago to experience all the secret parts and hidden gems of the islands.

How to get around between the hawaiian islands?

Great news! The four main islands are conveniently accessible with short inter-island flights (approximately 25 minutes) with the local Hawaiian airline. The check-in process is super easy as you can do it yourself so you don’t need to come to the airport hours in advance. On top of that, I have never seen an airline so punctual! 

On the islands, the easiest way to explore the surroundings is with a rental car. However, if your budget does not allow it or if you have time to slow travel, the islands are well-served with public transportation.

“I highly recommend taking the first-morning flight every time so that you have a full day on your next paradise destination.”

Where to stay on the Hawaiian islands?

The archipelago offers various types of accommodation ranging from the most luxurious resorts to private rooms at the inhabitant’s home. During our journey, we mainly used the platform Airbnb to book either apartments or private rooms, and we were super happy about our stays! Feel free to send me an e-mail if you want more information about our accommodations.

Oahu

Waikiki is the place to stay since it is the perfect hub to explore any part of the islands with short rides. Moreover, you will be able to enjoy the city life that the island has to offer! What more could you ask for?

Kauai

Because the island is mostly uninhabited, Kapaa is one of the best places to stay since the location allows you to visit any part of the island with short rides. Furthermore, this small city has everything you need from a shopping center to beautiful beaches! 

Maui

Because Maui island is shaped like a butterfly, Kihei is a convenient place to stay as it is located in the middle of it, so you can easily travel to any part of the islands with short trips. 

Big island

Due to the big size of the island and with no access road at some point, Big island is the only one that I recommend staying at two different places during your journey, namely Hilo (East side) and Kona (West side). On top of that, these cities have their airport, so you can arrive on the Big island via one airport and leave via the second one.

ultimate Hawaiian islands travel guide

A 1-month itinerary day by day

My husband and I had the chance to spend an entire month around the Hawaiian archipelago and it was more than perfect! Therefore, I am happy to share the details of our journey with you! To simplify the reading of the itinerary, I have simply listed the activities to do per day. For all the details about the activities mentioned below, go to the “what to do” chapter to have accessed the complete travel guides for each island. 

TRAVEL JOURNEY OVERVIEW

DAY 1 – 5 : OAHU

DAY 6 – 11 : KAUAI

DAY 12 – 17 : MAUI

DAY 18 – 23 : BIG ISLAND

DAY 24 – 28 : OAHU

day 1 - oahu

  • Day of arrival at Honululu international airpot
  • Rest day

day 2 - oahu

  • Manoa falls
  • Waikiki

day 3 - oahu

  • Hanauma Bay Nature Reserve
  • Koko Crater trail

day 4 - oahu

  • Dive in cage less with sharks
  • Laniakea Beach Park

day 5 - oahu

  • Lanikai Pillbox trail
  • Hoomaluhia Botanical garden

day 6 - Kauai

  • Transfer from Oahu to Kauai with a inter-island flight (25 minutes) from Honululu airport to Lihue airport
  • Wailua falls
  • Kapaa

day 7 - kauai

  • Hanalei

day 8 - kauai

  • Kayak on the river
  • Kuilau Ridge trail

day 9 - kauai

  • Anini Beach Park
  • Napali coast cruise

day 10 - kauai

  • Waimea Canyon
  • Awa awa pui trail

day 11 - kauai

  • Sleeping giant trail

day 12 - maui

  • Transfer from Kauai to Maui with a inter-island flight (25 minutes) from Lihue airport to Kahului airport
  • Iao Valley State Park

day 13 - maui

  • Road to Hana
  • Waianapanapa State Park
  •  Pipiwai trail

day 14 - maui

  • Kayaking and snorkeling with green sea turtles 

day 15 - maui

  •  Haleakala National Park

day 16 - maui

  • Hookipa Beach

day 17 - maui

  •  Waihee Ridge trail

day 18 - big island

  • Transfer from Maui to Big island with a inter-island flight (25 minutes) from Kahului airport to Hilo airport
  • Akaka Falls State Park

day 19 - big island

  • Hawaii Volcanoes National Park

day 20 - big island

  • Waipio Valley lookout
  • Hapuna Beach

day 21 - big island

  • Polulu Valley

day 22 - big island

  • Swim with dolphins tour
  • Puuhonua O Honaunau National Historical Park

day 23 - big island

  • Magic Sand Beach Park
  • Snokeling with manta rays tour

day 24 - oahu

  • Transfer from Big Island to Oahu with an inter-island flight (25 minutes) from Kona airport to Honolulu airport
  • Waimanalo Bay Beach Park

day 25 - oahu

  • Kualoa Ranch tour
  • Byodo-in temple

day 26 - oahu

  • surf lesson at Haleiwa Beach Park
  • Dole plantation

day 27 - oahu

  • Diamond Crater Head trail
  • Pear Harbor

day 28 - oahu

  • Day of departure from Honululu international airport

What to do on the Hawaiian islands?

As mentioned, the Hawaiian islands have so much to offer for all tastes! To get all the details from the activities mentioned above, read the following full travel guides for each dedicated island. 

Oahu

Read my full Oahu travel guide here to get all the details on what you should do during your stay. 

hawaiian islands travel guide oahu travel guide
hawaiian islands travel guide oahu travel guide
hawaiian islands travel guide
hawaiian islands travel guide oahu travel guide

Kauai

Read my Kaua’i travel guide here to get all the details on what you should do during your stay. 

hawaiian islands travel guide
kauai travel guide anini beach hawaiian islands travel guide
hawaiian islands travel guide kauai travel guide

Maui

Read my Mau’i travel guide here to get all the details on what you should do during your stay. 

Iao valley park Maui travel guide hawaiian islands travel guide
Haleakala National Park Maui travel guide hawaiian islands travel guide
bucket list experiences Maui travel guide
hawaiian islands travel guide Maui travel guide

Big island

Read my Big island travel guide here to get all the details on what you should do during your stay. 

hawaiian islands travel guide big island travel guide
hawaiian islands travel guide big island travel guide
hawaiian islands travel guide big island travel guide

What bucket list activities can you do on the hawaiian islands?

The Hawaiian islands are the ideal place to check once-in-a-lifetime experiences off your bucket list! From swimming with wild dolphins to snorkeling cage-free with sharks, animals, and ocean lovers are prepared for an unforgettable time!

swimming with wild dolphins in the open ocean

Have you ever been dreaming of swimming with wild dolphins in the open ocean? 

Read here all the details to check this memorable adventure off your list!

swimming with wild dolphins open sea
wild dolphins

snorkelink with manta rays at night

Do you want to experience the exceptional adventure of snorkeling with manta rays in the middle of the ocean? On top of that, do you want to do it at night?

All the details here to check this amazing adventure off your list!

snorkeling with manta-rays-in-Hawaii

snorkeling cage free with sharks

Do you want to experience one of the craziest adventures of all time by swimming with sharks in the middle of the ocean? On top of that, do you want to meet these amazing creatures cage free? 

Read the details here to check this wild experience off your bucket list!

swim with sharks cage free Oahu travel guide

kayaking and swimming with green sea turtles

Do you want to experience a special encounter with green sea turtles in the open ocean?  I have the perfect activity for you! 

Check out all the details here.

bucket list experiences Maui travel guide
Maui green sea turtles

In conclusion

In summary, the Hawaiian island is the perfect place to enjoy great island vibes with memorable bucket list experiences! Most importantly, the archipelago is an amazing location for nature lovers, adventure enthusiasts, and animal lovers! 

That is to say, I hope I have inspired you to visit the Hawaiian islands someday soon and that you will enjoy your journey as much as we did!

Finally, feel free to contact me at any time if you have any questions. It would be a great pleasure to share with you!

Sending you lots of Love, 

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