David Elliott and Nat Bletter debuted Madre Chocolate in 2010, preaching bean to bar. Madre specializes in single origin bars from the Big Island and South America. A blackboard map of Big Island cacao farms that Madre sources from includes Hawi, Crillo, Likao Kula Farm in Holualoa, and Hart Farm in Paukaa. I particularly enjoyed the sweet-tart Lilikoi bar; Coffee & Cardamom with 70% dark chocolate from Pangoa, Peru; and Triple Cacao featuring 70% Dominican dark chocolate. Their salted coconut truffle also hit.

Dylan Butterbaugh debuted Manoa Chocolate in 2010, sourcing direct from farmers as part of the company’s regenerative approach to chocolate production. My favorite chocolate bars included lilikoi 50% dark milk chocolate and strawberry white chocolate mac nut from Manoa’s “Flavors of Hawaii” series. 70% dark chocolate from Kealakekua (Big Island) and 70% dark chocolate from Waiahole (Oahu) were highlights from their “Hawaiian Grown Cacao” series. Sea salt chocolate covered mac nuts are also habit forming. Manoa’s shop and tasting bar also serves hot chocolate tea made with shells and sells a refreshing carbonated cacao spritzer.

Chef Moké Warren and wife Teri opened their first Moké’s Bread & Breakfast in 2004 on a Kailua side street. Their son Keola and daughter Leilani helped the family expand to Japan in 2013 and to Kaimuki in 2019. Moké’s serves one of Oahu’s best breakfasts, including fluffy pancakes topped with cascading lilikoi (passion fruit) sauce or mango cream sauce and tangy li hing mui (salted plum) powder. Their loco moco is also a knockout, especially the version with ribeye instead of a hamburger patty.

Jennifer Lobendahn and husband Nik opened this popular brunch spot and bakery in 2016 and added Easy ‘Que in 2019. Signature Kailua eggs feature Portuguese sausage, rice, Over Easy’s namesake eggs, and bacon cabbage broth poured tableside. Other creative options include custard French toast, coconut shrimp burgers, and the BLT inspired ABC special. Bakery items include a flaky, volcano-shaped guava cream cheese “crater” and the house bacon & cheese wrap made with a supple scallion pancake.

Longtime coffee pro James Musselman moved to Kailua with his wife, island girl Amy Martin-Anacleto. I enjoyed my two visits to their cart, which parks on Sundays at Lokahi Kailua Market. The name RUBYVIOLET references bookend colors in the rainbow and their two rescue dogs. Their climate friendly concept smartly skips refrigeration, opting for shelf stable powders, syrups and oat milk. Delicious lattes display exquisite artistry. I loved my beet latte with rainbow peppercorn syrup and iced ube latte spiced with ginger.

A wine shop felt like an unlikely place to find premium poke, but Tamura’s warrants attention for over 20 different preparations. I particularly enjoyed “Island Inamona” ahi seasoned with crushed kukui nut, “Island Ninja” ahi amped up with chile flake, and Smoked Salmon Belly swimming in soy sauce. Punchy garlic King crab shoulders featured sweet meat that pulled easily from shells.

Nani Nikcevich and chef-partner Nick “Bear” Yamada have run Uahi Island Grill in downtown Kailua since 2007, in their largest space yet since 2016. Uahi translates from Hawaiian as “smoke.” Uahi serves some of the best plate lunches in town. Garlic Chicken features crispy boneless thighs. Juicy Kalua pork is oven-braised and sautéed with kale. Red Curry Grilled Fish features the catch of the day. During my visit, that meant flaky white shutome (broad-bill swordfish) fillets in mild Thai red coconut curry, topped with green papaya salad. For dessert, purple sweet potato haupia pie isn’t the sweetest option, but is your best bet.

Sunrises and sunsets on the beach at Kailua and neighboring Lanikai are equallly spectacular. Thanks to the time difference between Hawaii and the mainland, I was up before dawn most days and spotted fishermen casting their reels in the consistently tame surf.

Koko Head, about 40 minutes from Kailua, poses quite a challenge. Especially in hot weather. So arrive early. The U.S. Army originally built a tramway up a steep mountain during World War II as a lookout with concrete pillboxes. The tram is long gone, but railroad ties remain for hikers to climb. The peak provides spectacular panoramic views.

Lanikai Pillbox trail, which runs along Ka’iwa Ridge, is much less grueling than Koko Head. Sit atop the graffiti coated, World War II era pillbox and enjoy Pacific Ocean views, before descending into the beachfront neighborhood.

Makapu‘u Point Lighthouse, located in Waimanalo on Oahu’s eastern tip, dates to 1909. Makapu‘u Point Lighthouse is 30 minutes from Kailua and easily accessible with a paved path. Of course Pacific Ocean views are plentiful.