Island Guide

I’ve had so much fun sharing my photos from my trip to Maui with you that I thought I would do a comprehensive post on a guide to the island including where to stay, shop and eat! Hopefully you’ll find it useful when planning a trip to the most beautiful place on earth!

Wailea Beach Marriott Resort & Spa: 3700 Wailea Alanui Drive
One of the four amazing hotels located in Wailea featuring a gorgeous ocean front infinity pool (shown in the image above). This was the hotel where we held our reception and stayed around our wedding. It’s in the perfect location in Wailea and is located next to the Shops at Wailea (a total bonus)!

Pineapple Inn: 3170 Akala Drive
This is the best bed and breakfast in Wailea! We spent our first three days on the island here and we absolutely loved it. The gardens are gorgeously landscaped and the ocean view from the pool and hot tub were to die for! Perfect for enjoying a glass of wine and watching the sun set.

Kamaole Sands2695 South Kihei Road
If you’re looking for a more budget friendly option, I’d recommend renting a condo in the Kamaole Sands. The grounds are beautiful and the complex is located directly across the street from the beach in South Kihei.

Ho’oilo House: 138 Awaiku Street, Lahaina
This has to be the most beautiful place to stay on the entire island! The house was designed specifically as a bed and breakfast and each room is prettier than the next. It’s located on the hillside above Lahaina offering beautiful ocean views.

The Shops at Wailea3750 Wailea Alanui Drive
This is my favorite place to shop on the island; it has a number of designer shops including Tiffany & Co, Louis Vuitton, Gucci, Baron & Leeds, Bettega Veneta, St. John, BCBG and Coach. It’s also home to a couple delicious ice cream shops and a general store that has everything you could possibly want.

Whalers Village2435 Ka’anapali Pkwy
Located in Ka’anapali has a great mix of high end boutiques and local shops. It’s also home to a couple wonderful restaurants that sit directly on Kaanapali Beach. The only downside is that parking is extremely limited considering the shops are very popular with tourists, not to mention it’s very expensive unless you make a purchase at which point you can have your parking ticket validated.

Front Street: Front Street, Lahaina
Front Street offers an ocean front backdrop to numerous surf shops, jewellery stores and eclectic art galleries. It’s the best place to find souvenirs to bring home for friends and family (or just for yourself).

The Gazebo Restaurant5315 Lower Honoapiilani Road
This topped my list of restaurants to check out while we were on the island and it did not disappoint! It’s hands down the best place for breakast with a gorgeous ocean front location on Napili Bay. You get a beautiful view of the surf, the neighbouring island of Molokai and in the winter months humpback whales from your table! I had the white chocolate and macadamia nut pancakes (which were absolutely delicious) and my husband had the cheese omelet (which he loved). Make sure you arrive early though, it’s very popular, we waited about 45 minutes to be seated.

Old Lahaina Luau1251 Front Street, Lahaina
In my opinion this is the best luau on the island. We did a ton of research before deciding which one to go to since there are so many to choose from. It’s definitely not cheap but this is one of those circumstances where you get what you pay for. We were so happy we decided on this one as the food was delicious (my meal is pictured above), all alcoholic beverages were included and the show was wonderful.

Joy’s Place1993 South Kihei Road
This was my favorite find on the island! Tucked away on a side street in Kihei it’s the cutest breakfast and lunch cafe you’ve ever seen. All of the food is made from organically grown fresh produce and the sandwiches are made to order. They also have a selection of delicious and healthy fruit smoothies.

Maui Tacos2411 South Kihei Road
A favorite among locals and tourists alike and for good reason, they have an amazing selection of delicious tacos at a bargain price (which is often hard to come by on Maui where food is a little more expensive than at home). They have locations all over the island making it easy to always enjoy a yummy taco.

Other wonderful restaurants:

Pineapple Grill: 200 Kapalua Drive
Cheeseburger in Paradise: 811 Front Street
Hula Grill: Whalers Village
Merriman’sOne Bay Club Place, Lahaina
Mama’s Fish House: 799 Poho Place 
Haliimaile General Store900 Hali’imaile Road, Makawao

Big Beach: South Makena Road
Big Beach, whose Hawaiian name is Oneloa meaning “long sand,” is my favorite beach on the island. At 3,300 feet long, you won’t find a bigger, more beautiful beach on the island. Located in Makena about a 10 minute drive south of Wailea, it’s rarely busy and even if it is, it doesn’t feel like it since it’s so massive. It offers amazing views of Molokini and Kahoolawe and if you climb up the lava rock wall at the north end of the beach you get an amazing view of the entire beach (which is where I took the above photo).

Polo Beach: Look for shoreline access sign on Wailea Alanui Drive
Polo Beach in Wailea is located in front of the Fairmont Kea Lani Hotel and is one of the best beaches to watch the sunset. It’s the quietest of all the beaches that front the four major hotels in Wailea making it perfect to watch the sun slowly sink into the Pacific Ocean.

Waianapapana State Park: Mile Marker 32 on the Hana Hwy
which is home to the amazing black sand beach, seen here, is my top pick if setting foot on a black sand beach is one of the things on your bucket list. It’s located just outside of Hana on the Eastern side of the island. It’s also home to some amazing lava tubes and an active blow hole.

Keawali Congregational Church5300 Makena Road 
Banyan Tree
: 649 Wharf Street, Lahaina
Tedeschi WineryHwy 37, Kula
‘Ahihi-Kina’u Natural Area Reserve: Makena Rd, South of Big Beach
Honolua Bay: 20 minutes north of Lahaina on the Honoapiilani Hwy
Kealia Pond National Wildlife Preserve: Mile Marker 2 on Hwy 31
Molokini: 2.5 Miles from Makena State Park
Hui No’eau Visual Arts Center2841 Baldwin Avenue, Makawao
Jaws – During the winter: Off Hana Highway at Hahana Road
Hookipa Beach: Mile Marker 9 on the Hana Highway
Haleakala National ParkHaleakala National Park, Crater Road
Keanae Peninsula: Between Mile Marker 16 &17 on the Hana Highway 
Oheo Gulch: 8 Miles past Hana on Hwy 31

If you’ve missed any of my previous posts about Maui, you can see them here.


  1. says

    I love this, Jen! I’ve been wanting to go to Hawaii for forever, so if I ever convinced my parents, I’ll now have all the info I need. Your trip sounds like it was incredible–I’ve really enjoyed seeing all of your pictures! xo

    • says

      Thanks Alyssa! I’m so happy you’ve enjoyed my photos! I was so glad to be able to share all the info that I learned during my trip. I think it’s always great to talk to people who’ve actually been somewhere because they have first hand knowledge about the best places to stay and eat which is much better than just reading about it online. xo

  2. says

    Hawaii is on my list of must-visit places in my lifetime, so this post is awesome!!! You did a great roundup and have me wanting to visit even more now. And your pictures are totally beautiful.


    • says

      Thanks Stephanie! It was on the top of my list as well and it didn’t disappoint so you’ll love it when you go! I’m glad I could share a bunch of the stuff that I learned throughout the trip with you so you have a better idea when planning your trip! Thanks for the compliment about my pictures, you’re so sweet!! xo

  3. says

    Great tips! I wish we would have went to the Old Lahaina Luau while we were there but we didn’t get the chance. When my husband and I go back we are definitely making reservations.

    • says

      Thanks Krystle! It was amazing, I would highly recommend it if you’re deciding between a couple different luaus. The ocean front setting is beautiful for the show and offers an amazing view of the setting sun! Definitely make reservations well in advance as family members decided they wanted to go once we had arrived on the island and had to be put on a cancellation list and be available to go any night.

      xo jen

  4. cae129 says

    Thanks for all the tips and photos and recommendations. This will be really helpful! Just curious though, would you recommend splitting your time between the Marriott and Ho’oilo House and if so, which one would you stay at first? I’m just trying to figure out the best way to spend our time on the island. Thanks!

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