The Paths to Diamond Head Are Paved with Good Luncheons

Diamond Head, also known by its Hawaiian name Lē‘ahi,  is one of Oahu’s leading attractions.  The 300,000 year old crater rests on the eastern edge of Waikiki’s coastline, and is known for its historic trail which leads hikers to stunning coastal views of the cerulean Pacific Ocean, and possibly some humpback whale sightings in the winter from 560 feet above the crater floor.  The hike is just 0.8 miles from trailhead to summit, but if you decide to make a half day out of it and walk from Waikiki, you will be rewarded with a number of amazing dining options along Monsarrat Avenue or Kapahulu Avenue.  Here are some of our favorite picks.



Sunny Days

Sunny Days embraces health and good taste amidst paradise.  The casual cafe and restaurant along Monsarrat Avenue seeks to satisfy people’s appetites but also their feelings with a sense of slow living in Hawaii.

sunny days interior

Patrons are offered delicious and healthy Hawaiian meals, replete with fresh vegetables and fruits.  There is even a Mega Pancake, but it takes a lighter approach to the traditional pancakes with an airy, souffle-like texture that still maintains the toothsome attributes of hotcakes. 

sunny days mega pancakes, eggs benedict, acai bowl, egg toast

Sunny Days >> Get a special offer!
Location: 3045 Monsarrat Ave. Ste 6
Phone: (808)867-3257
Hours: 8am-3pm (Last Call 2pm) *Closed Thu


Aloha Cafe Pineapple

Another casual eatery on Monsarrat Avenue is Aloha Cafe Pineapple, a plate lunch outfit that offers delectable local flavors.  From breakfast items such as Berry Berry French Toast and Chocolate Banana French Toast to more mid-day appropriate meals as Mochiko Chicken & Garlic Shrimp Plate and Grilled Chicken Plate, both locals and visitors will find appreciation for the take away meals offered.

Be sure to try the Loco Moco, a 100% beef patty nestled atop a generous scoop of rice and slathered with a luxe demi-glace sauce crafted with pineapple juice and some farm-fresh local eggs for a taste of the tropics.

Aloha Cafe Pineapple >> Get a special offer!
Location: 3212 Monsarrat Ave.
Phone : (808) 739 – 1630
Hours: 7am-3pm (L.C. 2:30pm) *Closed Tue



A popular gathering spot on Monsarrat, Bogart’s offers taste-tempting other breakfast dishes and satisfying lunch plates.  A mainstay in the Diamond Head neighborhood, regulars love everything from the perfect cup of coffee to tropical fruit smoothies, Benedicts to waffles, specialty sandwiches to fresh salads, and famous fried rice to acai bowls.

If you are seeking to replenish some energy or gain some on the uphill climb, try the Mama’s Fried Rice with sauteed fresh mushrooms, spinach, asparagus, corn, and scrambled eggs incorporated into the fragrantly fried grains.

3045 Monsarrat Avenue, Honolulu, HI
Phone:  (808) 739-0999
Business hours:  Sun-Sat, 7am – 3pm


Pioneer Saloon

The original location of the popular high-quality plate lunch spot, Pioneer Saloon on Monsarrat Avenue offers a rustic casual experience for dining in.  The eatery founded in 2009 by Nori Sakamoto offers flavorful takes, sometimes even elevated, on local favorites such as Chicken Katsu Curry, Korean Beef, Tonkatsu, Ginger Pork, Garlic Ahi Steak, Miso Butterfish, Garlic Cajun Shrimp, Loco Moco, Tofu Avocado Salad, and Ribeye Steak Bowl.  A few things to try include the Furikake Salmon featuring filets of salmon seasoned with Japanese seaweed for a burst of umami, the Mochiko Chicken, tender marinated morsels of chicken steeped in a slightly sweet soy-based sauce that are battered in a rice flour and deep-fried to a beautiful crisp, and the Hamburger Steak, a tender, juicy patty grilled and bathed in a demi-glace sauce with onions.

Pioneer Saloon
3046 Monsarrat Avenue, Honolulu, HI
Phone:  (808) 732-4001
Business hours:  Sun-Sat, 11am – 8pm


Kaimana Farm Cafe

If you decide to take Kapahulu Avenue to and/or from Diamond Head, consider a stop at Kaimana Farm Cafe.  The charming spot is committed to provide meals that are good for the body and for the Hawaii community.


Sourcing its all-natural ingredients locally, Kaimana Farm Cafe crafts high quality, well-balanced vegetable-rich meals served with kindness and aloha.  One of the most popular meal options is the Power Bento, a full meal that offers a choice of a main dish among Dijon Chicken, Pork Kakuni (braised pork), Hamburger Steak, Vegan Hamburger, Garlic Shrimp, or Croquettes (potato, sweet potato, curry risotto, cheese, or shrimp); a choice of five sides among kale salad, Molokai sweet potato, curry potato, yuzu carrots, spicy tofu poke, rainbow hijiki, Japanese lotus root, soba salad, Brussels sprouts, Spanish olive pasta, beets & orange, and Japanese potato; and brown rice/white rice or a house green salad.

Kaimana Farm_Power Bento

Kaimana Farm Cafe >> Get a special offer!
Location : 845 Kapahulu Ave (Right in front of Safeway)
Phone : (808) 737-2840
Wednesday-Friday 8:30am-3:00pm. 5:00pm-8:00pm
Saturday 7:30am-3:00pm. 5:00pm-8:00pm
Sunday 7:30am-3:00pm 


These eateries offer some of Hawaii’s finest casual flavors, so while you may be tempted to swing by one of them for breakfast on the way up to Diamond Head, we recommend you definitely enjoy a meal on your way down.  If you have the willpower to fight off a food coma, then maybe do one on the way up and another on the way down.

Oahu's Best Coupons