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Design Lifestyle Travel

Travel Guide: Maui, Hawaii

June 23, 2017

I’ve been so fortunate to have grown up with Hawaii as a common travel destination for my family over the years. While I’ve gone to almost all of the islands, Maui is probably my favorite; that said, they are all so beautiful, and each has so much to offer. Maui is great for couples but also perfect for getting the whole family together for a vacay. The Mr. and I just returned from the island where we spent 8 days with my side of the family; we also went there back in September right after our wedding for our honeymoon part 1 — part 2 is an upcoming trip to Italy.

With all my travel guides, I highlight the highs and the lows — what to look out for and what to expect — even in terms of cost. If you have additional questions or feel that you need another category added, I’d love to hear from you!

Where to Stay

Luckily, I’ve stayed in what seems like most all of the hotels, each differs but are great options at the end of the day, though it all depends on your needs. There are two main areas of the island that you will want to look at for accommodation; the west side and the south side. The West (Kaanapali) side is more beautiful in my opinion, with lush green mountains, and is very close to Lahaina (fun historic tourist town with shopping, restaurants and boat harbor). The south side has the advantage of slightly less rain in the winter, and Wailea (the luxury area of the south side) is a quieter area than Kaanapali.

{ White sheets, comfy bed, great view, just steps from the beach, and someone who cleans my room twice a day = my kind of paradise. }

Shop the look of this tropical must haves:

Favorite Places To Stay For a Couple

Grand Wailea $$$ – This hotel is at the top of my list; it’s got it all. A beautiful beach, privacy, groomed grounds, and a fantastic pool – both an adult only one and a sand bottom one, if your heart desires. It also offers easy access to the beach and every amenity that you could want. The Grand Wailea Spa is one of my favorites.

Four Seasons $$$$ – I love staying at The Four Seasons; however, it’s not the cheapest on the island. I recommend that if you can’t make it work for your budget, try to make it there for an amazing brunch.

Sheraton $$ – The Mr. and I stayed here in September and were pleasantly surprised. That being said, unless it’s whale watching season, stick to the buildings close to the pools; the other buildings will require you taking three elevators which can be a pain when you want to head back to the room to grab your phone or book. It’s not as updated at the Westin {see below}, but the pool is fantastic and the distance to prime snorkeling and a beautiful beach to lounge on can’t be beaten.

The Westin $$ – Stylishly updated hotel compared to its neighbor the Sheraton, but you share the same beach – head towards Black Rock for easy access to gentle snorkeling right off the beach with a high chance of turtle sightings. Be warned; while great for couples, it is also very kid friendly — maybe more so than the Sheraton — keep in mind they do have an adult only pool which the Sheraton does not. Right next to the Westin is Whalers Village, offering shopping at both high and low-end retailers as well as a number of restaurants situated on the beach walk.

Camping $– yep, I’ve done this too. If you are an adventurous couple, I highly recommend it! Remember, you don’t have to do this the entire trip — mix in a couple nights. Rent your gear here.

Favorite Place to Stay For a Group Trip:

Honua Kai – While the hotels listed above are, of course, accommodating for a group, I loved staying in a condo on our last trip. Each of the condos that we rented included two sizable bedrooms, a shared kitchen, and a living room — perfect for two couples. We got two condos for four couples on the ground floor — making it super easy to run back and forth from the rooms to the pools (and for my little niece to run around). When selecting a condo, I wanted a pool that one might expect from a hotel, and this one has it. Lazy river {check}, multiple pools {check}, bar {check}, great beach {check}, and it has a Dukes restaurant right on the property {check}. We couldn’t have been happier. Plus there are lots of bbq’s which made for fun, relaxing dinners without breaking the bank while allowing some solid family time.


Biking, surfing, snorkeling, scuba, hiking, or even hang gliding – the island is your oyster. That being said, nobody would blame you if your idea of an activity is turning the page of a good book while catching some rays.

{ So nice to get out of the gym and get into some other activities. }

Biking/Flying down Haleakala is a must-do in my book. I really recommend doing this at the beginning of your trip as you will be getting a very early start, and this is much easier when you are haven’t adjusted to the time zone. For those fearful of the ride, it’s pretty easy and it’s pretty much downhill – there are those that like to ride a bit faster than others, but you can take your time on either a self-guided or small group tour ride. If you are still not up for it, don’t miss out — head to the top of Haleakala to simply take in the sunrise. For those who want more of a thrill, try hang gliding {my father did and it gave him bragging rights as the rest of us were far too fearful}. Check out the Haleakala Bike Co. for additional information and advance bookings.

The Road To Hana – this is a must if you haven’t done it before — just be sure to start in the morning.  That said, I don’t really recommend making the drive all the way around. Be sure to stop in the surfer town of Paia on your way {see a Plantation home tour in Paia here} for some light shopping and a bite at Paia Fish Market.

Nakalele Blowhole – If you are looking for a hike but not wanting to commit the full day as you do for the road to Hana, I recommend visiting the Nakalele Blowhole. I use the term “hike” lightly here but depending on which way you take, you can do some climbing up and down in parts.  The sheer force and height that the waters reach are impressive.

Surfing while Maui may not have the barrels of the North Shore, there are waves that you can chase. You can also take lessons right off the beach in front of Whalers Village – rates vary.

Snorkeling is one of my favorite activities to do in Maui. With so many beaches to choose from, there are typically great spots just steps from your hotel. There are some other beaches and coves that you can access a   nd are worth checking out {see beaches below} You can typically find stores nearby or at your own hotel that rent snorkel gear, but I purchased mine a few years back {find them here} and love having my own set. See below for the best snorkeling spots.

Beaches and Coves

Whether you want to lounge, surf or go snorkeling, here are my favorite spots to visit – be sure to catch a sunset or sunrise, they are magical!

{Watch the turtles from the rocks at Napili Bay the water is so clear you won’t even need

to get in, though I recommend it.}

{ Black sand beach during the road to Hana. }

{ Sunsets that you will never forget. }

Ka’anapali Beach is a beautiful stretch of soft sand and beautiful clear water. Find your spot near black rock {directly in front of the Sheraton} which is perfect for easy access to some pretty good snorkeling, though I recommend getting there early to avoid crowds.  Say hi to the turtles for me — there’s no doubt that you will see them there. Surfing lessons, parasailing, and rentals can all be found on the beach directly in front of Whalers Village.

On the western edge of Maui on Ka’anapali Beach situated in front of the Ritz-Carlton {shown above} – arrive in the early am {around 7am} and try to catch the dolphins playing in the surf.  Enjoy a quiet beach despite being in front of the hotel.

Napili Bay – {see below in the “eats” section for an amazingly tasty treat in the area – The Gazebo}. This was a great place to stop and swim after indulging in a great breakfast. The long strip of sandy shore makes it easy to set up camp for snorkeling, and it’s fantastic at both ends of the beach.

Honolua Bay – I include this one due to the beauty of the beach and the easy access to snorkeling. The only trouble is, this is when you are likely to burn on your trip. It’s easy to loose track of time and before you know it your back and legs have been exposed to the sun for far too long.  Tour boats make their way here but you won’t find yourself bumping into others if you get there early enough. On your way there or back, keep an eye out for Coconut Caboose – see below for review.

Black Sand Beach – while on the road to Hana you will most likely make your stop here. The black sand beach provides a beautiful contrast against the turquoise water. Plan to spend 30 minutes here as there is much more to see along your journey but it will provide you a rare opportunity to experience a beach like this.

Where to Eat: 

There are endless options but here are a few of my favorites.

{ image above taken on our last visit to Frida’s Beach House – love this palm leaf print wallpaper! }

Shop the look with these palm wallpapers:

{ Pictured above: The Gazebo – make sure to get macadamia nut pancake with banana – hey, you are on vacation! }
{ Fleetwood’s on Front Street is a must – grab a signature cocktail at the rooftop bar. }

Fleetwood’s on Front Street $$$ – Hands down my favorite place, owner Mick Fleetwood of Fleetwood Mac is the owner {love love love Fleetwood Mac}. I recommend going early on in your trip as you likely will want to go back. Make a reservation for the rooftop – I suggest going early to catch one of the two guests that make an appearance at approx 5:30 pm. One is a bagpipe player and another is a local fish farmer. They both have incredible stories that they share, adding to the whole experience. If you arrive early, grab one of their delicious and inventive cocktails at the bar. Live music can often be found on the second floor – my family danced the night away on our last visit after an amazing birthday dinner for my mum.

Sansei Seafood Resturant and Grill – $$-$ – If you love sushi then make sure to add this one to your list. They offer two happy hours an early and a late one – if you plan to go to the early hh there is actually a line so keep that in mind.  There are a few locations and one doesn’t seem better than the other, this is a great stop for a group or a couple. They have creative rolls and the fish options are amazing.

Burger Shack $$ – is part of the Ritz Carlton and as you can guess expensive for a burger shack {burger is $25} but it was delish and the Mr. and I split it while taking in the spectacular view.

The Gazebo $ – My older sister insisted that we come here for breakfast. Greeted by a long line we were tempted to skip but she kept insisting. The line moved quickly and we were so happy we stayed. You can’t beat the view of this casual dining spot and the macadamia nut pancakes with coconut syrup are a must as well as the fried rice – I definitely recommend sharing and only order a half order of the rice! It’s adjacent to the Napoli Bay beach and part of the Napili Shores Maui Condos.

Coconut Caboose $ – A mobile spot that serves up organic shaved coconut ice that offers lots of all natural flavors that is not to miss, on the way to or from {or both} from Napoli Bay.

Paia Fish House $-$$ – There are three locations but I recommend making a stop at the Paia location on your way to or from your trip to Hana. They are known for the Ono burger, which is delish but you really can’t go wrong with their menu.

Island Fresh, Paia $ – We stopped here by chance when we had some time to burn before our flight home and we were so glad we did. The service is great and each item we ordered was delicious but I am in love with their fresh smoothies.

Aloha Mixed Plate $ – we stopped here after a day of surfing and were really in need of a cold beer. Situated right on the beach and offers up great food and drinks and a welcome price point break from all the pricey spots on the island.

Frida’s Beach House $$ – Situated right along the ocean front – right next to Aloha Mixed Plate, Hanu and Mala Ocean Tavern {see below} this Latin fusion restaurant is one not to miss. Fresh fish and over 40+ tequilas on the menu this is great for couples or a group. Try one of their tequila flights!

Mala Ocean Tavern $$$ – Run by the same owners of Friday’s Beach House a sister restaurant, Hanu. Definitely not the largest restaurant on the island, so a reservation is best, especially to snag a seat on the outdoor patio. Make sure to get the salsa with edamame salsa while taking in the sunset.

The Lahaina Grill $$$ – Another favorite and the Mr. adores this place. The downside, no view to speak of. Upside, memorable dishes, fantastic service, and when you are done – head out to front street and meander from shop to shop.

Where to Shop

While I don’t consider Maui to be a shopping mecca you can definitely make your suitcase heavier by stopping at the following locations.

 { Front Street, Lahaina is beautiful day and night. }

{ It’s rare that I don’t find something when traveling – you never know when you will find that perfect piece you didn’t know you had to have. }

Shop my favorite natural summer bags

{ A colorful fence in the town of Paia – a beautiful and quaint surfer town. }

Whalers Village – Situated right along the beach, you can find stores ranging from Billabong to Louis Vuitton and some great swimwear shops – of course.

Paia Town– Again on your way to or from Hana, schedule some time to shop in the little boutiques that line the streets. I stopped in shops that ranged from swimwear to a little antique shop.

Front Street, Lahaina – Perfect for window shopping and picking up trinkets and souvenirs to take home. Restaurants are found in between boutiques making it a great opportunity to scope out dinner options.

Shops at Wailea – a small shopping center but perfect for grabbing all necessary beach items to splurging on a special item – you are on vacation, treat yourself!

I hope you enjoyed this manicured, travel guide to Maui, HI.


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