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.
Paddle at your own pace to Mokoli'i and hike for panoramic Oahu views
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
Explore Mokoli'i at your own pace with gear, demo, and route tips
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
Taste local favorites and explore Kailua by e-bike with a knowledgeable guide and exclusive shop discounts
Paddle to Popoia Island with a guide, snorkel Kailua Bay, and enjoy beach gear for the afternoon
Ride electric bikes through Kailua, taste local favorites, and explore beaches and hidden gems with a guide
Learn SUP and explore Popoia Island with a friendly guide in Kailua
Explore Moku Nui by kayak with e-bike transport and expert guides; lunch and shave ice included
Ride e-bikes to Kailua Beach, then kayak and snorkel around Popoia Island with a guide
Guided paddle to Popoia Island with e-bikes to tow kayaks, snorkeling, and beach time included
Explore land and sea at your own pace with an e-bike ride, Pillbox hike, and Lanikai snorkeling
Experience Oahu’s Best Snorkeling With a Lifeguard Certified Guide
Paddle to Popoiʻa Island with a guide, then enjoy snorkeling, lunch, and free time on Kailua’s sandy beach.
Explore protected waters, snorkel reefs, and picnic at your own pace with gear, lunch, and guidance included
Learn paddle techniques then enjoy beach time with gear and lunch included along Kailua’s scenic coast
Paddle to the Mokulua Islands for snorkeling, wildlife encounters, and a picnic lunch on secluded shores
Paddle calm streams and protected bays at your own pace with gear and island permits included
Enjoy turquoise waters with included snorkel gear, boogie boards, and a tasty lunch.
Protect Hawaii's marine life and enjoy 2.5 hours of kayaking or SUP on turquoise waters
Explore Kailua's reefs on a 3-hour traditional Hawaiian sailing canoe and hear local stories from expert watermen
Sample six natural wines and learn the winemaking process in a friendly, educational setting
Savor locally grown O‘ahu wine and chocolate in a guided pairing led by the winery team
Discover Hawaii’s whiskey-making process and enjoy a guided tasting in an active distillery.
Connect through hands-on Hawaiian traditions, farm-to-table dinner, and panoramic views in a small-group luau
Guided 2.5-hour snorkel with gear included and a marine conservation option
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.