Ka'anapali Beach in Maui Hawaii

Maui, Hawaii For First Timers

(Last Updated On: May 15, 2020)

Are you planning a trip to Maui, Hawaii? This post serves as a Maui for first timer’s guide. After reading through you will have a good understanding of the possible activities and places to eat while in Maui.

Maui, Hawaii seems to be a top bucket list destination for most people.

I know it surely was one of mine. For as long as I could remember I had always wanted to visit Hawaii. Even more than the Caribbean.

Growing up on the east coast, the thought traveling to Hawaii was so daunting. First you would need to travel all the way across the country, and then from the west coast you would need to take a nearly six hour additional flight to make it to the stunning beaches of Hawaii. So, for most folks, a trip south to Florida for some fun in the sun is a lot more affordable.

Statue on the Westin Resort & Spa Ka'anapali beach, Maui, Hawaii
Statue on the Westin Resort & Spa Ka’anapali beach, Maui, Hawaii

But when I moved to Portland six years ago, I realized that a trip to Hawaii is a lot more doable! It is certainly still a long flight, don’t get me wrong, but the trip is just about cut in half from what it would be if you were flying from Boston, New York, or any east coast state for that matter.

So back in March, my mom and I started talking about going on a possible trip to Hawaii.

View from our Hawaiian Airlines flight before we landed in Maui
View from our Hawaiian Airlines flight before we landed in Maui

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Before I jump into telling you all about my first trip to Hawaii I thought I would share a little about me incase you haven’t stopped by my blog before.

Hi! I’m Jane and I started Plain Jane Lifestyle as a fun creative outlet to write about food, travel and blogging!

If you are thinking about starting a travel blog, or any type of blog for that matter, here are a few of my most popular past posts that will help you get started: What Every Blogger Needs To Know About Blogging Legally and Start A Blog In Less Than 10 Minutes With Siteground (affiliate).

Okay back to Hawaii…

We decided to go in October when the height of the travel season was slower.

The fall is a great time to visit Hawaii/ One reason is that prices will be lower, school is back in session which means less families traveling together, which equates to more open lounge chairs poolside!

Arriving in Maui, Hawaii
Arriving in Maui, Hawaii

Our home while in Maui was at the Westin Resort & Spa Ka’anapali on the island of Maui. We stayed four nights and five days total.

We loved our hotel. The location was in my opinion the most optimal spot for what we were looking for, which was convenience, fun, relaxing and safe.

The Westin Resort & Spa, Ka'anapali beach, Maui, Hawaii
The Westin Resort & Spa, Ka’anapali beach, Maui, Hawaii

A lot of people decide to rent cars to explore the island.

For our first trip to Maui, we opted not to rent a car, but if I were to go back and visit I would be open to it. Our thought behind  not renting a car was that we only had limited time on the island, and we thought that we wouldn’t venture from the resort too much during this trip. There is also the extra costs of renting a car and paying for parking which can be around $35/day at most hotels. So for those reasons we decided against renting a vehicle.

But we met lots of people that did decide to rent cars and felt completely safe and had fun visiting neighboring towns as well as driving in the mountains.

Arriving in Maui, Hawaii before checking into the Westin Resort & Spa
Arriving in Maui, Hawaii before checking into the Westin Resort & Spa

What I enjoyed most about the Westin Resort & Spa

Was the expansive property the hotel was situated on. There must have been about five separate pools to choose from on the property as well as the ocean right in front of you to cool off in. There where two waterslides, waterfalls, an adults only pool area, coi fish ponds, and swans that roamed the property. It was honestly fun just lounging in the sun, mai tai in hand and relaxing!

One of the many pools on the Westin Resort & Spa propert
One of the many pools on the Westin Resort & Spa property

Shopping at Whaler’s Village

Next door to the Westin Resort & Spa was Whaler’s Village. Here you will find over 90 shops and restaurants in an outdoor mall like setting on the beach. My mom and I loved the café Island Vintage Coffee located among the vast labyrinth of shops and restaurants. In fact we came back to eat here a few times because it was delicious and well priced!

Island Vintage Coffee, Whaler's Village, Maui, Hawaii
Island Vintage Coffee, Whaler’s Village, Maui, Hawaii

The stores range from small boutique shops to your chain high end stores such as Louis Vuitton. Whaler’s Village has a nice small playground for young toddlers in the middle of all the shops. It’s a nice spot for families to enjoy some Hawaiian shaved ice, sit on a bench and let their little ones play and burn off some energy.

Whaler's Village, Maui, Hawaii
Whaler’s Village, Maui, Hawaii

Snorkeling Excursion

During our five day stay we knew that we wanted to book at least one excursion that got us out onto the ocean via boat.  There are lots of informational booth kiosks along the beach walkway with sales professionals that can explain all of the various tours available.

After looking through lots of brochures and asking questions we decided to take a three hour catamaran boat ride to snorkel with fish and sea turtles as well as have a nice lunch onboard with a few cocktails included. Out of the many options we booked with Teralani Sailing Charters.

Our experience was unforgettable! We boarded the catamaran directly from the beach in front of nearby Whaler’s Village. This was so convenient for us, as we did not need to worry about taking an Uber anywhere to start this excursion.

Our catamaran sailing boat the Teralani
Our catamaran sailing boat the Teralani

The staff of the catamaran went over safety rules, and then we set off on our sailing adventure. We encountered a pod of dolphins that performed jumps and twirls mid air! We must have seen about 40 dolphins!

Next we made our way to our snorkeling spot along an old shipping port, that has since turned into a spot for coral to grow and where sea turtles love to hang out. We saw about three very large sea turtles on our snorkel venture. The sea turtles are a federally protected species and we always had to make sure we gave them about five feet of space at all times.

We ended the trip with some deli sandwiches, chips and a beverage of our choice while enjoying our sail back to Ka’anapali beach.

Stunning sunset from the beach in front of the Westin Resort & Spa, Maui, Hawaii
Stunning sunset from the beach in front of the Westin Resort & Spa, Maui, Hawaii


Going to a Luau in Hawaii is a must do while visiting, especially if this is your first time to Hawaii. We went to the Luau performed at our hotel, the Westin Resort & Spa. Among the many luau’s that are performed along the beach we mostly selected this one because it was in our hotel. But, as it turns out this is one of the most well attended Luau’s on the beach.

I was so excited for the food alone. But I must say my expectations were blown out of the water. This luau was part comedy show, part dance performance and part history lesson.

Luau at the Westin Resort & Spa, Maui
Luau at the Westin Resort & Spa, Maui

We had purchased our tickets online about a few months prior for “premium seating”.  This meant that you would have an assigned spot close to the front and would get to eat first.  This was well worth it because the line to get into the luau was about a mile long, and there is a chance that if seating is filled than you will not be able to get a seat at all.

We sat with other nice couples who were on vacation from Chicago and New York. It was fun talking with them over a meal before the performance started.

Hawaiian dancer at the Luau
Hawaiian dancer at the Luau

We ate buffet style and had pulled pork, BBQ chicken, rice, and macaroni and potato salad.  Dessert was also offered after dinner that included Starbucks coffee, tea, chocolate cake, cheesecake and a pineapple tart. Overall the food and show were both excellent!

Morning walks on the property

My mom and I were both early risers each day of the trip. Part of this can be attributed to the time change we were experiencing, but regardless we both prefer to get up early.

Walking path along Ka'anapali beach
Walking path along Ka’anapali beach

Along the beach in front of our hotel there is a nice walking/running path that goes on for miles and miles. You feel completely safe venturing out on it as there are so many people getting their morning workouts in or walkers enjoying a cup of coffee while gazing out at the ocean.

View of the stunning skyline on a morning walk
View of the stunning skyline on a morning walk

One particular morning we took a walk west on the walking path and eventually we wound up by the Royal Lahaina Resort which had a beach front restaurant serving a delicious looking breakfast. We decided to stop there to eat and opted for the breakfast buffet as opposed to ordering off the breakfast menu. It was delicious!

If I went back to Hawaii…

and I would most certainly love to go back, here are the places and things on Maui that I would like to do:

Surfboards on Ka'anapali beach, Maui, Hawaii
Surfboards on Ka’anapali beach, Maui, Hawaii

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