Discover the serene beauty of Oahu with a private hiking experience designed for all levels. Enjoy personalized guidance, stunning views, and hidden trails that showcase Hawaii’s lush landscapes in a relaxed setting.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2–4 hours
Fitness Level
Suitable for most fitness levels, including beginners with some light walking ability
Wildlife
History
The trails you explore feature areas historically significant for ancient Hawaiian settlements and lookout points used during wartime.
Conservation
This experience emphasizes Leave No Trace principles, ensuring the preservation of Hawaii’s fragile ecosystems for future generations.
Massimo Sport Hawaii Tours
Discover the serene beauty of Oahu with a private hiking experience designed for all levels. Enjoy personalized guidance, stunning views, and hidden trails that showcase Hawaii’s lush landscapes in a relaxed setting.
Massimo Sport Hawaii Tours is a Hawaii-based tour operator that runs tours across Oahu. The company offers private, family-friendly, large-group, luxury, and eco-friendly options. Tour categories include private luxury island tours, private circle island tours with snorkeling, large-group circle island and snorkeling experiences, family-friendly Pearl Harbor tours with private transportation, South Shore Aloha friendly tours, off-road adventure tours on Oahu’s North Shore, hiking experiences, and surfing and stand up paddle board lessons.
The Off-Road Adventure Tour uses a Ford Raptor F150 to access a private wildlife sanctuary where guests can encounter monk seals, sea turtles, and seasonal humpback whales, and view secluded beaches and dramatic coastal scenery. The South Shore Aloha Friendly Tour provides a private half-day route that highlights landmarks such as Diamond Head and Lanikai Beach. The Family Private Pearl Harbor Tour includes exclusive transportation and visits the USS Arizona Memorial and associated museums.
Other listed offerings include a Lanikai to Mokulua Islands stand up paddle board tour, eco-friendly island tours, and multiple large-group and private hiking and luxury tour configurations. Tour names indicate availability of private transportation and options tailored to families and large groups. Massimo Sport Hawaii Tours operates on Oahu and presents a variety of island experiences focused on sightseeing, marine wildlife encounters, and water-based activities. Prospective guests can review specific trip descriptions to confirm amenities, transportation details, and activity level for each tour. Full itineraries, booking requirements, capacity limits, and pricing details are available on the business listing and individual tour pages online today.
Tours Offered
16
Varied private and group options
Private Transport
Available
Private transportation on select tours
Wildlife Viewing
Monk seals & turtles
North Shore sanctuary sightings
Tour Types
Family, Luxury, Eco, Adventure
Options for families and groups
Compare trips, confirm inclusions, and reserve private transportation or group experiences on Oahu.
Wear sturdy, comfortable shoes
Proper footwear will ensure stability and comfort on uneven terrain and dirt trails.
Bring plenty of water
Stay hydrated throughout the hike, especially in Hawaii’s warm climate.
Apply reef-safe sunscreen
Protect your skin from the sun while keeping Hawaii’s environment safe.
Carry a small backpack with essentials
Bring a snack, hat, and camera to enhance your experience and capture memories.
Hiking shoes or sturdy sneakers
Provides support and grip for uneven terrain and trail surfaces.
Light hat or cap
Protects your face and head from the sun during hikes.
summer
Reusable water bottle
Keeps you hydrated throughout your outdoor adventure.
Light rain jacket or poncho
Prepares you for unexpected showers and keeps you comfortable.
spring|fall|winter