Playover on Oahu

Formed approximately 300,000 years ago at the eastern edge of the Waikiki coastline, Diamond Head is one of Honolulu’s most iconic sights. Get an early morning start at the trailhead and hike to the top (560 feet) of this volcanic tuff cone for sweeping views of downtown Honolulu and Oahu’s south shore.

Rent a car and head to the north shore (about 45 minutes from downtown Honolulu) for some serious eats at Giovanni’s Shrimp Truck, located at 66-472 Kamehameha Highway in Haleiwa. We can vouch for the scampi, which comes with a dozen shrimp marinated in olive oil, chopped garlic, lemon butter and two scoops of white sticky rice.

For unrivaled sunsets, make reservations for the 5:30 p.m. sailing aboard Na Hoku II, which pushes off from Waikiki Beach (right near Duke’s Barefoot Bar). The cost is $30 per person and it’s all-you-can-drink (beer, mai tais, wine, etc.) for the 90-minute cruise; if you’re visiting during the winter, be on the lookout for humpback whales.

When you’re ready for some sun and sand, skip Waikiki’s crowded scene, pack some sandwiches and drive over to Kailua Beach – it’s less than 30 minutes from Honolulu and its cerulean waters are ranked among the best beaches in the country. The beach’s prime location on Oahu’s eastern coast makes it a popular place for water sports such as wind surfing, parasailing and kayaking.

Dole Whip, the plantation’s signature soft serve pineapple ice cream is a must-try when in Hawaii. Grab a cone and get lost in the over three-acre maze or hop aboard the Pineapple Express, a narrated 20-minute ride that tells the history of this famous fruit and its importance to Hawaii.

Catch a wave with the premier Hawaiian Fire Surf School where – you guessed it – Honolulu’s firefighters are your instructors. Two-hour lessons (in groups of 10 to 12) take place on the southwestern end of the island at Ko Olina Beach and start at $119 for trainees 11 and over.

Stop by the Kapiolani Community College Farmers’ Market in parking lot C on Saturdays from 7:30 to 11 am. The well-known market offers locally sourced treats such as fresh island poke made with local ahi from Hibachi, burgers from North Shore Cattle Company, macadamia nuts from Ahualoa Farm and honey products from the Hawaii Beekeepers Association.