Island Hop or Stay in One Spot?

Planning a trip to Hawaii can be very exciting and it all starts with deciding what island to visit. It’s really a personal preference and depends on how much time you have in Hawaii. We wanted to visit multiple islands and explore as much as we could without having to check in/out of our accommodations every other day. We decided to split our two weeks between Maui and Kauai and if I were to do it all over again, I wouldn’t change a thing.

It was the perfect amount of time to split between two islands. We spent 6 days in Maui (all at the same condo) and then 6 days in Kauai. We split up our time in Kauai and stayed a night near the airport and 5 days near the beach. I highly recommend staying in one spot on each island, this will save you the time and hassle of checking in and out of your accommodations and save money on multiple cleaning, service, and other reservation fees.

2-Weeks in Hawaii

We split our time and spent the first week in Maui and the second week in Kauai. Here is a list of my favorite spots we traveled to on each island.


  • Ka’anapali Beach
  • Black Rock Beach
  • Nakelele Pt. Blow Hole 
  • Lipoa Point Lookout
  • Maluaka Beach (Waile)
  • Haleakala National Park
  • Road to Hana
  • The Bay Golf Course, Kapalua


  • Waimea Canyon
  • Awa’awapuhi Trail Hike
  • Poipu Beach
  • Hanalei Bay
  • Sunsets in Princeville
  • Napali Coast
  • Ha’ena State Park
  • Kalalau Trail
  • Ke’e Beach
  • Tunnels Beach
  • Helicopter Tour through the Napali Coast

One Week in Maui

We started off our trip to Hawaii in Maui. Flew into OGG airport, rented a hardtop jeep, and headed to the west side of the island. We stayed the entire time in Kaanapali. We loved this part of the island and each night we found a new beach to relax and watch the sunset. We also felt we were close to the main activities, top beaches, and other attractions on the island. If you want to venture to other areas around the island its just a quick drive to the south or east side.

Sunset in Kaanapali, Maui

We thought Maui had some of the best snorkeling we have ever experienced. For more details on sunset locations, the best snorkeling spots, and top things to do in Maui, check out One Week Itinerary in Maui, Hawaii for recommendations a complete itinerary!

One Week in Kauai

Kauai- also known as the “garden island” is one of my favorite islands in Hawaii. This island is so peaceful, lush, colorful, and has the perfect mix of relaxation and adventure. Kauai has gorgeous sunsets, a plethora of beaches to relax and snorkel, canyons, valleys, plenty of hikes, and awesome happy hour specials. 

Hanalei Valley Lookout- taken on our drive from Princeville to Hanalei Bay

We spent 7 days in Kauai and it was the perfect amount of time for us. For a full itinerary, complete list of major spots we hit, excursions, happy hour specials, best place to catch a sunset, secret turtle spots, and more check out One Week Itinerary in Kauai for more details!


Rent a car. If you talk to anyone who has been to Hawaii they will recommend that you rent a car and it is totally worth it! This will give you the freedom and accessibility to travel the island on your own time. There are so many sights to see in Hawaii and you don’t want to miss out because you are on someone else’s transportation schedule.

Is it worth the extra money for a Jeep or Convertible? 

Many people have asked this question, and although I am all for saving money, I think that its worth renting a convertible when in Maui. The road to Hana was unbelievable and the drive is a totally different experience with the top down… We actually tested this out, we kept the top on our jeep for some of the ride because we didn’t feel like taking it on and off every time we stopped to get out. Then the road back to our condo we kept the top off the entire drive and it was awesome! 

We reserved a 2-door jeep because it was cheaper, but we learned that most car rental places only have 4-door so they give you a free upgrade when you arrive. If you are traveling with just 2 of you then I highly recommend trying this!

Another reason you should rent a car… Due to the time change (we are from Michigan) we ended up waking up at 6am most mornings and would drive to a different beach everyday. This was awesome because we were the only ones on the beach for a couple of hours. I can’t say this would have been the same if we had to reply on public transportation to get us there.

Where to rent a car? 

I found that Discount Hawaii Car Rental was cheaper than every other car rental place I researched. It was about half the price compared to other well known rental car companies. They work with multiple rental car companies to get you the best rates.

Tips to save money

I understand that everybody has different travel styles and some of you might not agree with my next statement, but our travel style is more about activities and exploring and less about eating out. We found that a great way to save money was to eat out less and cook meals in the condo. If you plan on grocery shopping then I highly suggest finding a store right when you land because food is usually cheaper by the airport and main towns compared to the touristy areas.

During our trip we shopped for food to make meals at the condo, and alcoholic beverages to pack in our cooler during the day. Most days we packed sandwiches and snacks to bring to the beach or in our backpacks while we were hiking. Another tip is to try and hit Happy Hour at nearby restaurants to save on food and drinks while still getting to experience some of the best local joints on the island.

Where to stay

This depends on your travel style, some people prefer a resort where they don’t have to cook or clean, while others prefer a vacation unit such as a house or condo. We stayed in a rental condo on both islands. 

On Maui there are multiple places to stay all over the island and it is divided into multiple regions. I would say the most popular are Kihei, the south region, and Lahaini and Kaanapali on the west side of the island. In Kauai most people usually stay on the north side of the island near Princeville or Hanalei Bay, or the south side near Poipu Beach. Each region on each island offers a unique atmosphere and vibe and you should consider your travel style, desires, and budget before deciding. Below is a summary of the popular spots to stay on each island.

Maui: West vs South

West Maui- Lahaini, Kaanapali, and Kapalua

West Maui is home to some of the most gorgeous and famous beaches in the world. This area offers a wide variety of restaurants and accommodations leading it to be one of the most popular places to stay on the island. Lahaini is an old whaling village that now offers a fun atmosphere and a variety of dining and shopping. The Kaanapali area has multiple world class beaches that expand along the shore line. Kapalua is known for some of the best golfing in all of Hawaii. We spent one day golfing at Kapalua Golf – The Bay Course and it was a dream come true for my husband, a previous collegiate golfer. This course isn’t cheap but I tagged along just for views!

Kapalua Golf – The Bay Course

West Maui is a great place to stay and you will not run out of options for dining, accommodations, beaches, and excursions. The west also has the best sunsets on the entire island!

South Maui- Kihei and Wailea

The southeast part of Maui is not nearly as busy as the West side. Kihei is a great place to stay if you are looking for budget-friendly accommodations. If you are looking for luxurious and upscale resorts then check out Wailea, this is home to the famous Four Seasons Maui, Hotel Wailea.

We took a day trip to Kihei and Wailea to check out a few beaches and snorkel. We stumbled upon Maluaka Beach and this was my absolute favorite beach in all of Maui! I wish we would have discovered this beach earlier in the trip because I would have gone back to snorkel with the turtles again. It is also worth checking out Oneuli Beach, this is one of the dark sand beaches on Maui.

Maluaka Beach, South Maui
Oneuli Beach, South Maui. Oneuli means “dark sands”

Kauai: North vs South

North Shore Kauai- Princeville and Hanalei

The northern region of Kauai includes Princeville and Hanalei and this is one of the most scenic areas in all of Hawaii. We loved the northern region for many reasons including, beautiful sunsets overlooking Hanalei Bay, amazing food trucks with budget-friendly prices, less developed, and it felt like we were on ‘island time’ with no schedule. There are a few luxury accommodations available in the Hanalei Bay Area if you are interested

Sunset from Princeville (Northern Region Kauai)
Hanalei Bay, North Shore Kauai

South Shore Kauai- Poipu, Koloa, and Lawai

The south side of Kauai definitely offers sunnier and better weather and has an abundant amount of resorts, shops, and restaurants, offering more of the ‘resort’ feel. We noticed there were more fine dining options compared to local dive bars and food trucks in the northern region. Poipu Beach and Shipwreck Beach are two of the most popular beaches in Kauai and both located in the southern region, definitely worth checking out.

Staying in the southern region of Kauai means that you are closer to Waimea Canyon State Park and this is a great park to visit if you want to check out scenic overlooks, explore the state park, or do some hiking. To shorten our drive time and avoid rush hour traffic we stayed a night near the south so that we could wake up early and head to Waimea Canyon State Park.

Waimea Canyon State Park

Total Cost for 2-weeks in Hawaii

This cost vary based on your accommodations, amount of people, flights, excursions, food and dining budget, shopping, and overall travel style. I can give you a general idea of what ours cost. I am a budget traveler who likes to plan and guess how much we will spend ahead of time. What that being said once I am on vacation I will often find myself saying “treat yourself” or “ohh who cares how much it costs, we are on vacation” or “just book it, when will we be back here?” Make sure to keep that in mind when you see our total cost.

  • Flights: Round trip from Michigan (flew into OGG on Maui, flew home from LIH on Kauai) we used our Delta miles (63,000 each person round trip) and if we were to pay that would have cost us roughly $800 each ticket. Note- I am not including this in the total since we used our miles.
  • Food and Drinks: we spent a decent amount on groceries, cooked in our condo, and ate mostly at food trucks (which is some of the best local food). We did go to a nice restaurant a few times. Our food estimate was roughly $500
  • Accommodations: A week in Maui for a 1 bedroom condo: $1,400. In Kauai we stayed at two different condos totaling just around $1,000.
  • Excursions: We did not do any excursions in Maui because there was enough to do on our own, our main adventure in Maui was The Road to Hana and all we had to pay for was gas along the drive. In Kauai we did a Napali Coast Boat Tour ($150 for both of us) and Helicopter Tour ($300 for the both of us)
  • Rental car: Maui our total was $175, Kauai was around $230, so $405 total for the two weeks. I highly recommend shopping around for the best rates because some places we looked at were double the price
  • Shopping: We bought a few souvenirs, clothing items, and gifts $400
  • Extra we forgot to budget for: $500
  • Entertainment: We did not do a Luau (wish we would have) but instead we played golf at Kapalua on Maui. My Husband said this was the nicest course he has ever played, and he golfed in college. We had a connection at the course so that helped a little but just for him to play was $300.

Grand Total for 2 Weeks in Hawaii for 2 People: $4,955 and this was the best money we have ever spent!

About Author

Hi, I'm Sierra, a world traveler with an adventurous spirit. I love all things coffee, my dogs, the outdoors, and spur of the moment adventures.

If you are looking for travel inspiration, destinations and itineraries, or budget-friendly vacations, then you came to the right place! I know planning a trip can be incredibly time consuming and stressful but don’t worry, I’ve made is easy for you!

You might also enjoy:

Leave A Comment

Your email address will not be published. Required fields are marked *