Discover amazing Kailua activities and premium in-home experiences.
Kailua is a picturesque destination in Oahu, where you'll find crystal-clear snorkeling spots, waves perfect for surfing. Whether you're seeking relaxation, exploration, or local flavor, this vibrant spot has something for everyone.
Self-guided kayak to Mokoli'i (Chinaman’s Hat) with gear and a quick safety demo
Paddle to Kailua’s twin islands, snorkel coral reefs, and hike Moku Nui with an expert guide
Discover top North Shore snorkel spots with provided gear and local tips
Customize your Kailua beach day with quality kayaks, boards and accessories ready for easy pickup
Paddle a calm rainforest river and bay with all gear supplied for an easy adventure
Explore a lush rainforest river at your pace on a delivered stand-up paddleboard, perfect for all ages.
Paddle Kaneohe Bay at your own pace and snorkel vibrant coral reefs with included gear
Paddle to the Kaneohe Sandbar for reef views and a rare mid-ocean sandbar experience at your own pace
Pick up a kayak in Kailua and paddle to Chinaman’s Hat at your own pace
Paddle at your own pace to the Kaneohe Bay Sandbar with gear, demo, and safety talk
Explore Kahana Valley’s rainforest river with easy pickup and included transport pads
Paddle Kailua Bay to Mokulua or Popoia with included gear and easy car-top transport
Paddle sheltered Kailua Bay to Popoia Islet at your own pace with tandem gear provided
Paddle from Kailua to the Mokulua Islands for an all-day ocean kayak and hiking experience.
Guided paddle to Popoia Island for beginners with optional snorkeling and wildlife viewing
Paddle East Oahu’s reef-protected routes at your own pace with all gear included
Ride an e-bike through Kailua with 3 tasting stops and a local guide
Paddle to Popoia Island with a guide, snorkel Kailua Bay, and enjoy beach gear for the afternoon
Ride an e-bike through Kailua with food tastings and beach time
Learn SUP and explore Popoia Island with a friendly guide in Kailua
E-bike your kayak to Kailua Beach, then paddle to Moku Nui with a guide
Guided e-bike and kayak trip to Popoia Island with optional snorkeling
E-bike to Kailua Beach, then kayak to Popoia Island with a guide
Explore land and sea at your own pace with an e-bike ride, Pillbox hike, and Lanikai snorkeling
Snorkel Electric Beach with a lifeguard-certified guide
Ride a versatile midlength for speed, carves, and control across varied waves
Sample six honeys with a charcuterie board in a relaxed 45 minute tasting
Kayak to Popoi’a Island with a guide, then snorkel and relax on Kailua Beach
Paddle and snorkel Kailua Bay at your own pace, with lunch included
Kayak to the Mokulua Islands with a guide and snorkel the coral reef
Relax at Kailua Beach with snorkeling, boogie boarding, and lunch included
Learn paddle techniques then enjoy beach time with gear and lunch included along Kailua’s scenic coast
Paddle calm streams and protected bays at your own pace with gear and island permits included
Enjoy beach gear, facilities, and free parking steps from Kailua Beach with easy access to Lanikai
Sample six natural wines and learn the winemaking process in a friendly, educational setting
Sample six OENO wines and tour the production facility
Savor locally grown O‘ahu wine and chocolate in a guided pairing led by the winery team
Explore the whiskey-making process with a distiller and enjoy a guided tasting
Build your own private Oahu tour with 8–10 stops in about 7 hours
Kailua is a picture-perfect beach town on Oahu’s windward coast, where turquoise waters, soft sands, and lush mountain backdrops come together in harmony. Just 30 minutes from Honolulu but a world apart in feel, Kailua invites you to slow down, dig your toes in the sand, and truly embrace island time.
Begin your day with sunrise at Lanikai Beach -- one of the most photographed beaches in the world -- then explore nearby hiking trails like the Pillbox Hike for sweeping views of the ocean and Mokulua Islands. In town, browse boutiques, grab fresh poke, or join a local canoe club for a taste of community spirit.
Kailua’s magic lies in its balance of natural beauty and authentic local life. Through Greetwell, guests can enjoy private beach yoga, guided snorkeling adventures, in-home massages, and chef-prepared meals highlighting island-grown ingredients. It’s an ideal base for couples, families, or solo travelers seeking both comfort and cultural connection.