3 days you’ll remember in Kailua, Hawaii.
Kailua is where Hawaiian dreams slow to a sun-kissed whisper. Located on Oʻahu’s windward coast, this laid-back town blends crystalline waters with lush mountain views and a strong sense of local pride. Think beach picnics under swaying palms, sunrise kayaking to the Mokulua Islands, and bites of island-fresh poke after a barefoot stroll.
This Foresyte itinerary was crafted to help you experience the best of Kailua—three days of ocean air, off-the-beaten-path gems, and true island tranquility.
Let’s take it from the top.
Itinerary inspired by the Foresyte community.
📍 Sippin’ on Sun
Day 1: Snorkel With Manta Rays
“Start with the island’s most magical nighttime adventure, floating under the stars as gentle manta rays glide beneath you. It’s equal parts serene and surreal.”
Day 1: Dinner @ Surf and Turf Dinn
“Treat yourself to a seaside feast of fresh-caught mahi and grilled steak under tiki torches. The soundtrack? Crashing waves and ukulele strings.”
Day 2: Sail and Snorkel
“Set sail for a coastal snorkel tour where coral gardens, spinner dolphins, and turquoise waters welcome you into their world.”
Day 2: Lunch @ Da Poke Shack
“No frills, all flavor. This local favorite dishes out unbelievably fresh poke bowls just steps from the beach, spicy, sweet, or shoyu-style.”
Day 2: Luau Nights
“Fire dancers, kalua pork, and flower leis. Attend a sunset luau for that unforgettable dose of aloha spirit, island storytelling, and rhythm.”
Day 2: Dinner @ Ultimate Burger
“Sometimes you just need a burger, and this one’s got Kona coffee BBQ sauce and island slaw piled high, local and legendary.”
Day 3: Brunch @ Big Island Farms
“Take a tour of this lush, sustainable farm nestled in the hills. You’ll leave with a deeper appreciation for the flavors on your plate.”
Day 3: Kona Brews
“Chill out at a local brewery with a cold Big Wave golden ale or tropical IPA. Bonus if there’s live music and a sunset view.”
Day 3: Bites @ Summit Views
“Make the trek to Mauna Kea’s summit at golden hour. Watching the sky shift from gold to indigo above the clouds? Otherworldly.”
Day 3: Dinner @ And of Course…
“Let yourself live slow. Morning swims, hammock naps, roadside shave ice, and that salty breeze in your hair, Kona is a vibe.”
Kailua Itinerary FAQ.
What are the best things to do in Kailua for a weekend trip?
The best things to do in Kailua include relaxing on Lanikai Beach, kayaking to the Mokulua Islands, hiking the Lanikai Pillbox trail, shopping in Kailua Town, and enjoying local bites from the farmer’s market.
When is the best time to visit Kailua for a weekend getaway?
The best time to visit Kailua is from April to October when the weather is warm, the ocean is calm, and there’s less rainfall—perfect for beach days and outdoor exploring.
Where should I stay in Kailua for a weekend vacation?
Vacation rentals are popular in Kailua, offering a more residential and local experience than resorts. Stay near Kailua Beach for direct access to sand and surf.
Is Kailua safe for tourists on a weekend trip?
Yes, Kailua is considered very safe for visitors. The town has a peaceful vibe, friendly locals, and a strong community presence—just be respectful of the area’s residential nature.
What is Kailua known for among weekend travelers?
Kailua is known for its breathtaking beaches, laid-back charm, water sports like kayaking and paddleboarding, and a quieter, more authentic feel compared to Waikiki.
How do I get around Kailua during a short stay?
Renting a car is the best option for getting around Kailua and exploring the rest of Oʻahu. Within town, biking and walking are popular and scenic ways to move between beaches and shops.
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