Skip to Content

Your First Trip to Hawaii? Tips and Tricks for an Epic Vacation!

Taking your first trip to Hawaii? Find out which island is best for your first time in Hawaii, where to eat, where to stay, things to do on your first trip to Hawaii, and more!

Our first trip to Hawaii was epic. Seriously, what an incredible vacation! Hawaii, while it has gorgeous beaches, is so much more than a beach vacation. From hiking, to volcanoes, to wildlife, to sunsets, and more, there are so many things you can do for your first time in Hawaii.

Build the type of first time to Hawaii vacation that fits you! This post includes details about the Road to Hana, viewing Green Sea Turtles, coffee farm tours, Hawaiian historical locations, and more. I’ll give you tips on what to do and where to eat, along with a detailed Big Island and Maui itinerary.

How to Plan Your First Hawaiian Vacation - make your first trip to Hawaii, epic with these tips and tricks.

Disclosure: This page includes affiliate links.

First Trip to Hawaii

For our first trip to Hawaii, we decided to visit Maui and the Big Island. In this post, I’ll explain why we chose these two islands – and why we chose two islands versus one – for our first trip to Hawaii.

Planning your first Hawaii vacation can be overwhelming because you are:

  • unfamiliar with the size of the island,
  • unsure how long it takes to travel around the island, and
  • don’t know which things to do in Hawaii.

I’ll discuss how our first Hawaii trip went, what we learned, and what we would do differently next time. No matter what you decide, don’t stress, because I can assure you it will be an incredible vacation! Hawaii is beautiful, exciting, and relaxing – no matter exactly which things you decide to do.

Best Island to Visit in Hawaii for First Time

Prior to booking our trip, we researched which Hawaiian island is best for first-time visitors. To start, its best to understand the highlights of each island.

Hawaii Island (also known as Big Island)

The Big Island is the largest Hawaiian island (hence, its nickname!). Hawai‘i Volcanoes National Park is located on the island which includes two of the most active volcanoes in the world (Kīlauea and Mauna Loa).

Hawaii Island is know for diverse geography and climates, including: snow-capped mountains, black sand beaches, and lush rainforests. The Big Island also features the Kona coast, which is home to hundreds of coffee farms (several which offer kona coffee tours).

Woman taking photo in Kīlauea Iki Crater at Hawaii Volcanoes National Park


Maui is known for beautiful beaches, snorkeling, whale-watching, and the epic Road to Hana. It’s also home to the Old Lāhainā Lūʻau, which is consistently rated as one of the most authentic luaus in Hawaii.

Haleakalā National Park is located on Maui, which features a dormant volcano summit that offers an incredible sunrise and stargazing.

Wai’anapanapa State Park in Maui on Road to Hana from first trip to Hawaii


Oahu is home to Honolulu which is the largest city and capital of Hawaii. This island is known for the Pearl Harbor National Memorial and the Polynesian Cultural Center.

Oahu is also home to one of the most famous beaches in the world, Waikiki Beach. With Diamond Head set in the background, this beach is iconic for panoramic views, celebrity sightings, and surfing.


Kauai is the least-developed of the 4 most commonly visited islands (Hawaii, Maui, Oahu, and Kauai). It offers a more rural, secluded experience; with lush greenery and beautiful waterfalls.

The rugged Na Pali Coast is only accessible by boat, helicopter, or foot. Since 97% of the land is undeveloped, it offers some of the most advanced hiking trails in the state.


Molokai is a quiet island with no name-brand lodging options and no direct flight from the continental US. Therefore, the island is less popular with tourists and known for offering an authentic Hawaiian experience.


Lanai is an expensive, small island with luxury resorts and secluded beaches. Like Molokai, there are no direct flights from the continental US.

For most first-time Hawaii visitors, Big Island, Maui, Oahu, or Kuaui are going to be better options than Molokai and Lanai (due to accessibility and price).

Hale Halawai Park in Kailua Kona with palm trees, stone walls, lava rock, and crashing waves.

We skipped Oahu (though it is a popular first-time visit choice), because we weren’t particularly interested in the big city vibe of Honolulu. We live in a city and drive to cities for weekend trips trips (such as Cincinnati and Columbus). On this trip, we wanted to experience the remoteness of Hawaii.

While Kauai sounded beautiful and secluded, we were particularly interested in the Road to Hana and visiting the National Parks (and especially, seeing an active volcano with possible lava flow). Therefore, we selected Maui and Big Island for a first trip to Hawaii.

How many Islands should I visit?

One island is plenty for a first time trip to Hawaii. There is enough to do on either Maui or the Big Island to keep you busy for an entire week.

However, two of our top things to do were on separate islands: Hawai‘i Volcanoes National Park (Big Island) and the Road to Hana (Maui). Therefore, we visited two islands in order to hit our two highest priorities.

While one island is just fine, it’s also very manageable to visit two islands. I was concerned we’d feel rushed or wish we’d stuck to one, but that wasn’t the case at all. I’m so glad we visited both Big Island and Maui. Plus, the tiny “island hopper” plane was an adventure all in itself.

Island hopper plane in Hawaii. Decide which islands to visit for first time in Hawaii. Fly between islands to visit more than one.

In the rest of this post, I’ll explain how we broke up our time between Maui and the Big Island, including where to stay, things to do, places to eat, and a detailed itinerary for each island.

Where to Stay in Maui

Most people stay in either west or south Maui. West Maui includes the towns of Lahaina, Kaanapali, Honokowai, and Kapalua. South Maui includes the towns of Kihei, Wailea, Makena, and Maalaea.

You could also choose to stay along the Road to Hana or in Kahului (near the airport), but this is the wetter side of the island. West and South Maui are dryer and sunnier.

For our first trip to Hawaii, we chose Kihei primarily due to budget and location. Kihei is less expensive than some of the other options, and a nice, central location. It was about a half hour drive to the Road to Hana, the airport, and Lahaina town (where the Old Lāhainā Lūʻau is located). Our ocean view hotel was steps from the ocean for morning and evening walks in the sand.

5 Things to Do in Maui

1. Haleakalā National Park

While it is most popular as a sunrise destination, sunset is also a spectacular view. We decided to visit the summit at Haleakala for sunset on the evening of our arrival. After a quick bite to eat near the airport, we took the 1.5-2 hour drive to Haleakala. Literally above the clouds at 10,023 ft, the views are incredible and it was the perfect way to start our Hawaii vacation.

Haleakalā National Park at Sunset, things to do on your first trip to Hawaii
Haleakalā National Park at Sunset, things to do on your first trip to Hawaii

2. Road to Hana

Download the Shaka app and purchase a Road to Hana tour (we did Road to Hana and the backside loop). Leave early and drive to Paia town to grab a quick snack or breakfast, before you embark on the Road to Hana. We chose Cafe Mambo for coffee and a smoothie.

If you’ve got kids, take a road trip scavenger hunt to entertain them on the way. They’ll be plenty of stops along the way, but a game will help keep them engaged during the longer stretches of driving.

Below, I’ve listed each stop we made along the Road to Hana. The Shaka app will suggest even more stops, but you’ll have to pass up some Road to Hana stops if you’ve only got one day for the drive. Do not skip the Road to Hana, it is a must-do if you are in Maui for your first trip to Hawaii.

Na'ili'ili-haele Falls in Maui on Road to Hana from first trip to Hawaii

Road to Hana Things to Do (pictures of each stop, labeled below)

  1. Bamboo Forest and Na’ili’ili-haele Falls – Short hike through bamboo to waterfalls (now closed).
  2. Nua’ailua Bay Scenic Viewpoint – Roadside scenic viewpoint.
  3. Ke‘anae Peninsula – Old Hawaiian village with taro fields and a historic lava rock church.
  4. Ching’s Pond – Swimming hole with cliff jumping.
  5. Ke‘anae Peninsula Overlook – Roadside overlook of Ke‘anae Peninsula.
  6. Halfway to Hana – Quick stop that is popular for banana bread and shaved ice.
  7. Waikani Falls (3 Bears) – A set of 3 waterfalls visible from the road.
  8. Lower Puohokamoa Falls – Incredible 200 ft waterfall.
  9. Wai’anapanapa State Park – Black sand beach set along dramatic volcanic coastline.
  10. Backside of Road to Hana – Remote drive along the coast with dirt roads and cliffs.
  11. ‘Ohe‘o Gulch – Also called “Seven Sacred Pools” and part of Haleakalā National Park.

3. Kihei Craft Fair

The Kihei Craft Fair is an open-air market on Kihei Rd. We made a quick stop to purchase souvenirs and check out goods made by local artisans. You can grab shaved ice here, too.

4. Old Lāhainā Lūʻau

Can you take a first trip to Hawaii without going to a luau? Of course not. A luau is a must-do for your first time in Hawaii! The Old Lāhainā Lūʻau is not only the highest rated Maui luau, it is also one of the highest rated in the entire state.

Known for its authenticity, we got dressed up and really enjoyed this luau, all with the sun setting in the background.

Old Lahaina Luau - the Best Luau on Maui for your first trip to Hawaii

5. ‘Īao Valley

A state monument, ‘Īao Valley is located in rainforest. This state park includes a botanical garden and 0.6 mile walk to view the ʻIao Needle. The ʻIao Needle is a 1200 foot tall natural feature which rises up from the valley floor.

Iao Needle in Maui, things to do on first trip to Hawaii

5 Places to Eat in Maui

1. Da Kitchen – We liked it so much that we ate there twice! It appears the Kahului location has closed, but there is a new location in Kihei.

2. Cafe Mambo – This cafe was bustling for breakfast, but we only grabbed a coffee and smoothie to go for the Road to Hana.

3. Nalu’s South Shore Grill – After a long day on the Road to Hana and the backside loop, we ate a late dinner with live music at Nalu’s.

4. South Shore Tiki Lounge – A lover of tiki decor, I had to check out this tiki lounge. My husband and I both enjoyed the casual vibe, outdoor seating, and the food.

5. Akami Coffee Co. – This clean, bright, modern aesthetic coffee shop has locally grown coffee and great reviews.

Crab on Lava Rock Keanae Peninsula in Maui, Road to Hana

Maui Itinerary (3.5 Days)

Day 1

  • 2:00 PM – Arrive in Maui and Pickup Rental Car
  • 4:00 PM – Early Dinner at Da Kitchen
  • 5:00 PM – Head to Haleakala Summit for Sunset
  • 7:30 PM – Sunset
  • 8:00 PM – Head to Hotel (Kihei)

Day 2

  • 7:00 AM – Continental Breakfast at Hotel
  • 7:30 AM – Leave for Paia Town / Road to Hana
  • 8:00 AM – Arrive in Paia Town, Get Coffee and a Smoothie
  • 8:30 AM – Travel Road to Hana
  • 9:00 PM – Late Dinner at Nalu’s South Shore Grill

Day 3

  • Morning – Rest and Relax at Hotel
  • 1:00 PM – Lunch at South Shore Tiki Lounge
  • 2:00 PM – Coffee at Akami Coffee Co.
  • 2:30 PM – Kihei Craft Fair for Souvenirs
  • 3:30 PM – Return to Hotel, Get Dressed for Luau
  • 5:45 PM – Old Lāhainā Lūʻau
  • 8:45 PM – Head Back to Hotel

Day 4

  • Morning – Walk Kihei Beach, Pack, Checkout
  • 12:30 PM – ‘Īao Valley
  • 2:30 PM – Late Lunch at Da Kitchen
  • 6:00 PM – Fly to the Big Island
  • 7:30 PM – Arrive in Kailua-Kona, Pickup Rental, Head to Condo
  • 9:00 PM – Late Dinner at Foster’s Kitchen

Where to Stay on the Big Island

Visitors typically choose to stay on the Kona side (east) or Hilo side (west) of Hawaii Island. The Hilo side is wetter, full of waterfalls, and closer to Hawai‘i Volcanoes National Park. The Kona side is dryer, sunnier, and has better beaches than the west side of the island.

For our first trip to Hawaii, we chose Kailua-Kona on the Kona side due to the drier weather and sunshine. I didn’t spend time in Hilo, so I can’t speak to the town’s vibe; but I absolutely loved the walkability and atmosphere in Kailua-Kona.

Where to stay on Big Island for your first trip to Hawaii, Kohea Hai in Kihei

10 Things to Do on the Big Island

1. Ali’i Garden Market Place

We visited the Ali’i Garden Market Place on our first full day in Kailua-Kona. Since we had traveled from Maui the evening before, this was a relaxing morning with shopping, coffee, and lunch all available at the market. A great spot to start the day!

2. Kona Coast

Download the Shaka app and purchase the Kona Coast tour. This leisurely drive along the coast offers incredible views, Big Island history, bee farms, and architectural points of interest. Below, I’ve listed each stop we made along the Kona Coast.

Kona Coast Things to Do (pictures of each stop, labeled below)

  1. End of the World – Short walk to 30ft cliffs along the ocean (popular for cliff-jumping).
  2. Kealakekua Bay State Historical Park – Site of the Captain Cook monument and a popular bay for snorkeling.
  3. Big Island Bees – Bee farm tours and honey tastings.
  4. Painted Church – Historic church on the hillside with painted walls and ceilings.
  5. Monago Hotel – Hotel built in 1917 on the slopes of Mauna Loa overlooking Kealakekua Bay.

3. Kailua-Kona

Downtown Kailua-Kona is easily walkable, filled with restaurants, bars, coffee shops, food trucks, shops, and more. We spent several evenings and an afternoon exploring the area.

Hale Halawai Park in Kailua Kona with palm trees, stone walls, lava rock, and crashing waves.

4. Snorkeling

Snorkeling was on our list of possible things to do in Hawaii, but we didn’t book the excursion until after we arrived. We popped into a booth along the sidewalks in Kailua-Kona and booked a half-day snorkeling catamaran tour (with lunch included).

Snorkeling tour on Big Island, things to do on first trip to Hawaii

The ocean air, boat ride, clear waters, and scenic views were incredible. The snorkeling and fish were interesting, but there may be better spots to snorkel (such as Kealakekua Bay).

Snorkeling tour on Big Island, things to do on first trip to Hawaii

5. Stargazing at Mauna Kea

This was an interesting activity, to say the least. We drove to the Mauna Kea Visitor Information Center for stargazing, leaving our hotel around 5:30 pm (sunset was around 7:00 pm). The visitor center is at 9000 ft elevation and you can only drive beyond that point with four-wheel drive (plus, safety awareness related to the drop in atmospheric pressure and oxygen).

Therefore, our plan was to drive to the visitor center, stargaze, and then head back. Unfortunately, it was a cloudy evening on the mountain (you can see the clouds setting in above the Gilbert Kahele Recreation Area. After we returned to the base of Mauna Kea, away from the clouds, the clear sky was filled with stars.

At the visitor center, it was uncomfortably cold and windy. Paired with the darkness, the wind was quite unnerving. We spent about 15 minutes (mostly sitting in our car because walking was made difficult by the wind), before we decided to make the descent back down Mauna Kea.

All that being said, the drive to Mauna Kea was peaceful and beautiful as we watched the sun setting over the Hawaiian landscape.

Sunset on Big Island
Near ascent up Mauna Kea, the Gilbert Kahele Recreation Area

6. Hawai‘i Volcanoes National Park

The national park is a bit of a drive from Kailua-Kona, but don’t skip it. The scenery is other-worldly and well worth the trip. The wide array of terrains and climates in a Hawaii is what most amazed us on our first trip to Hawaii.

Download the Shaka app and purchase the South Island Epic Coastal Journey which will include a few stops along the way to the national park (such as a coffee farm and black sand beach). Pair that tour with the Volcanoes National Park tour, and switch to it when you arrive at the park entrance.

Once you enter the park, there are plenty of sites to see. Below, I’ve listed several things to do in Hawai’i Volcanoes National Park.

Hawai’i Volcanoes National Park Things to Do (pictures of each stop, labeled below)

  • Lava Tree Molds – Quick stop, with parking, near the entrance of the park.
  • Kilauea Visitor Center – Stop in for bathrooms, an overview of the park, and trail maps.
  • Sulphur Banks Trail – Easy, flat, 1.2 mile round-trip on raised boardwalk through sulphur banks.
  • Kilauea Overlook & Steam Vents – Massive. Photos do not do Kīlauea caldera justice. Near the overlook are many steam vents.
  • Kīlauea Iki Trail – Moderate to challenging hike with a 400 ft descent into an incredible, scenic, other-worldly crater – a highlight of our entire trip. There are several ways to do the Kīlauea Iki hike (as a loop, adding on Thurston Lava Tube, etc.). We chose the out-and-back option which travels from the Kīlauea Iki Trailhead, down into the crater, and then back up to the trailhead.

7. Punalu’u Black Sand Beach

One of the most famous black sand beaches in Hawaii, Punalu’u is a great stop to make between Kailua-Kona and Volcanoes National Park. Any first-time visit to Hawaii must include a visit to an iconic black sand beach.

Pack a snack or early lunch with a blanket, and enjoy the scenery. You might see some Green Sea Turtles, too!

Punalu'u Black Sand Beach on the Big Island
Closeup of sand at Punalu'u Black Sand Beach

8. Ka’u Coffee Mill

Like Punalu’u, the Ka’u Coffee Mill is a great pit stop between Kailua-Kona and Volcanoes National Park. We had enough time to take the short 20-minute free tour to learn about how they produce their version of the famous Kona Coast coffee bean.

9. Kailua Pier and Kamakahonu Beach

Located side-by-side, the Kailua Pier and small Kamakahonu Beach are a great spot for a short afternoon swim or wade in the water. Right off the beach is a restaurant (attached to the Marriott) and a surf shack to rent kayaks, paddle boards, and more. Plus, it’s nestled right in downtown Kailua-Kona with food, drinks, and shops only steps from the beach.

If you like visiting historical buildings, take the short walk over to Hulihe‘e Palace. Formerly the vacation home of Hawaiian royalty, it now houses a museum and gift shop ran by the Daughters of Hawai‘i. We didn’t take the tour, but popped into the gift shop and walked the grounds of this historic property.

Huliheʻe-Palace near Kailua Pier and Kamakahonu Beach on Aliʻi Drive in Kailua Kona

10. Hale Halawai Park

Hale Halawai Park is a simple beachfront park located right in downtown Kailua-Kona. Along with being a nice walk and pretty views, we saw Green Sea Turtles along the rocks each time we were in the park. Viewing Green Sea Turtles in their natural habitat is another must-do for your first trip to Hawaii.

4 Places to Eat on the Big Island

1. Foster’s Kitchen – We ate here for our first evening in Kailua-Kona. The food was delicious, and the seating, right on the ocean, was the perfect intro to this seaside town full of shops, restaurants, and bars.

2. Keoki’s Ono Fish and Chips – This fish and chips joint with lovely garden seating in the back, appears to have closed.

Keokis Ono Firh and Chips Big Island places to eat

3. Daylight Mind Coffee Company – We had coffee and brunch at this expansive restaurant with plenty of seating (located right on the ocean). Everything was delicious, but unfortunately it appears to be permanently closed.

4. Coffee Shack – This quaint little coffee shop has incredible views, due to its location on the hillside, overlooking the coast.

Coffee Shack on Kona Coast overlooking Kealakekua Bay

Big Island Itinerary (3.5 Days)

Day 1

  • Morning – Rest and Relax at Condo
  • 11:00 AM – Lunch at All’i Garden Market Place
  • 12 Noon – Explore Kona Coast
  • 1:00 PM – End of the World
  • 2:00 PM – Kealakekua Bay
  • 2:30 – Big Island Bees
  • 4:00 PM – Painted Church
  • 4:30 PM – Monago Hotel
  • 5:00 PM – Dinner at Ono Fish and Chips
  • Evening – Walk Kailua-Kona Downtown, Coffee at Daylight Mind

Day 2

  • 8:00 AM – Body Glove Snorkeling (lunch included)
  • 1:00 PM – Rest at Hotel
  • 5:30 PM – Head to Mauna Kea for Stargazing
  • 7:00 PM – Arrive at Base of Mauna Kea for Ascent

Day 3

  • 9:30 AM – Travel to Hawai‘i Volcanoes National Park
  • 10:00 AM – End of the World
  • 11:00 AM – Coffee Shack
  • 12:30 – Ka’u Coffee Mill
  • 1:30 PM – Punalu’u Black Sand Beach
  • 3:00 PM – Tree Molds at Volcanoes National Park
  • 3:30 PM – Kilauea Visitor Center at Volcanoes National Park
  • 4:00 PM – Sulphur Banks Trail at Volcanoes National Park
  • 4:30 PM – Kilauea & Steam Vents at Volcanoes National Park
  • 5:30 PM – Kīlauea Iki Trail
  • 9:30 PM – Late Dinner in Kailua-Kona Downtown

Day 4

  • Morning – Rest and Relax at Condo
  • 11:30 AM – Kailua Pier and Kamakahonu Beach
  • 12:30 PM – Hale Halawai Park
  • 1:30 PM – Lunch and Coffee at Daylight Mind
  • 6:00 PM – Head to Airport

If you liked these Hawaii travel ideas, you might also like:

Want to save this Hawaii Itinerary for later? Pin it!

How to Plan Your First Hawaiian Vacation - make your first trip to Hawaii, epic with these tips and tricks.