Massimo Sport Hawaii Tours
Activities (17)
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South Shore Aloha Friendly Tour
The South Shore Aloha Friendly Tour picks up guests directly from Waikiki hotels and travels along Oahu's south and windward coastline in a private vehicle with a personal driver and guide. The route takes in the Diamond Head scenic lookout, the Kahala and Hawaii Kai neighborhoods, the Koko Head lookout with views over Hanauma Bay, Sandy Beach Park, the Makapu'u lookout, Waimanalo Beach, Kailua Beach Park, and Lanikai Beach. Food, drinks, and gratuities are not included. Pickup and drop-off at a Waikiki hotel are included, and pickup from other locations is available for an added fee. The tour suits travelers who want a relaxed, flexible way to cover a long stretch of Oahu's southern coastline without arranging their own transportation. Stroller accessibility is available, making it a practical option for families with young children.
Family-Friendly Private Circle Island Tour of Oahu
This private circle island tour of Oahu picks up guests at their Waikiki hotel and travels the island with a personal driver and guide in a dedicated, air-conditioned vehicle. The itinerary is flexible, so stops can be adjusted to match the group's interests. The tour suits families, couples, and anyone who prefers a private experience over a shared shuttle. Child safety seats are provided for young children as required by Hawaii law. Bottled water, hotel pickup and drop-off within Waikiki, fuel charges, and local taxes are all included. Food, gratuities, and personal purchases are not included, though the guide can arrange stops at local spots serving shrimp plates, poke, shaved ice, and other Hawaiian foods. Pickup outside Waikiki can be arranged in advance for an additional fee. Comfortable footwear is practical for outdoor stops throughout the day.
Family-Friendly Pearl Harbor Tour With Private Transportation
The tour begins with hotel pickup in Waikiki, where a personal guide arrives in a private vehicle reserved for the group alone. A ferry ride then brings the group to the USS Arizona Memorial, built over the sunken battleship and honoring the sailors and marines who lost their lives there. On the return trip, an optional stop in downtown Honolulu includes the King Kamehameha Statue and Iolani Palace. Admission to the memorial, reserved boat tickets to the USS Arizona Memorial (subject to Navy operations and availability), hotel pickup and drop-off, and the private guide are all included. Complimentary child safety seats are available for younger children. Food, beverages, and gratuities are not included. Pickup outside Waikiki is available for an additional fee.
Large Group Private Luxury Tour of Oahu Island
This private tour of Oahu lets a group set its own itinerary. Travelers can choose the stops they want, or share their interests with the guide and let local knowledge shape the route. Admission to several North Shore beaches is covered, including Waimea Bay, Banzai Pipeline, Sunset Beach Park, Turtle Bay Beach, and the broader North Shore area. Hotel pick-up and drop-off from the Waikiki area are included at no extra charge, and hotels outside that area can arrange pick-up for an added fee. Drop-off at a different location from pick-up can be arranged for a small fee. Water, towels, sunscreen, and a personal driver and guide are all part of the package. Gratuity is not included but is welcome. Note that the tour is not wheelchair compatible. Be accurate about group size when booking, as it affects preparation for the day.
Large Group Oahu Friendly Hiking Experience
This private hiking tour lets a group choose which Oahu trail to tackle, rather than following a fixed route. Options include Manoa Falls, Maunawili Falls, Diamond Head State Monument, Koko Crater Railway Trail, Koko Crater Botanical Garden, Makapuu Lighthouse Trail, and Kuliouou Ridge. Some trails pass waterfalls, some move through rainforest, and some lead to viewpoints overlooking Honolulu and the east side of the island. Pick-up and drop-off from Waikiki area hotels are included. Hotels outside that area can arrange pick-up for an added charge, and a different drop-off location can be arranged for a small fee. The tour includes water, towels, sunscreen, a personal driver and guide, fuel surcharge, and local taxes. Gratuity is not included. The tour is not wheelchair compatible, and conditions can be affected by weather. When booking, note the hotel address and be accurate about group size so supplies and transportation are arranged correctly.
Private Luxury Tour of Oahu Island
This private tour of Oahu lets travelers shape their own itinerary. Tell the guide where to go, or share what interests you and the guide will plan a route using local knowledge of the island. Pick-up and drop-off from a Waikiki area hotel are included, and admission to several North Shore stops is covered as well, including Waimea Bay, Banzai Pipeline, Sunset Beach Park, Turtle Bay Beach, and the North Shore area. Water, towels, sunscreen, and a fuel surcharge are also part of the package. The tour is not wheelchair compatible, so travelers who require that accommodation should look at other options. Note the hotel information at checkout so the guide can plan accordingly. Gratuity is not included in the price but is appreciated.
Large Group Family-Friendly Private Circle Island Tour of Oahu
This private tour of Oahu is built around what a family actually wants to see, not a fixed route of standard stops. Before the day begins, families share their interests in the booking comments, and the guide shapes the itinerary around those preferences. That flexibility means kids and adults spend time at places that suit them rather than moving through a predetermined schedule. Pick-up and drop-off from a Waikiki area hotel are included. Hotels outside that area can be accommodated for an additional charge, and a different drop-off location can also be arranged for a small fee. Water, towels, sunscreen, local taxes, and a fuel surcharge are included in the experience. A personal driver and tour guide accompanies the group throughout the day. This tour is designed with families in mind, including children. It is not wheelchair compatible, so travelers who require that accommodation should look elsewhere. When booking, providing an accurate group size is important because it determines how the tour is prepared. Gratuity for the guide is not included but is welcomed.
Oahu Friendly Hiking Experience
The Oahu Friendly Hiking Experience is a private, customizable hiking tour on Oahu where travelers choose their own trail from a list of options. Pickup and drop-off from Waikiki area hotels are included, and the tour comes with water, towels, sunscreen, and a personal driver and guide. Manoa Falls and Maunawili Falls both lead to waterfalls. Diamond Head State Monument sits close to Waikiki and offers views of Honolulu and Koko Head Crater. Koko Crater Railway Trail provides views of Honolulu and the east side of Oahu. Koko Crater Botanical Garden is an easier walk featuring local plants and flowers, including a wide variety of plumeria trees. Makapuu Lighthouse Trail leads to a lighthouse and serves as a whale-watching spot. Kuliouou Ridge Hike passes through rainforest. Hotels outside the Waikiki area can arrange pickup for an extra charge. The tour is not wheelchair compatible. This experience is weather dependent, so plans may shift based on conditions. Gratuity for the guide is not included in the price.
Large Group Private Circle Island Tour And Snorkeling Experience
This private circle island tour picks up guests directly from Waikiki area hotels and travels across Oahu, stopping at places such as Haleiwa town, Turtle Beach, and Sharks Cove on the North Shore, as well as a coffee farm, pineapple plantations, and filming locations from Jurassic Park and Hawaii Five-O. The route and stops can be adjusted with the guide to match what the group wants to see, so the itinerary is flexible from the start. Snorkeling is part of the experience, and towels, sunscreen, water, and a personal driver and tour guide are all included in the price. This tour suits large private groups looking to cover a wide range of Oahu highlights in a single outing. Hotel pickup and drop-off within the Waikiki area are complimentary; guests staying outside that area should expect an added charge. Drop-off at a different location from pickup can also be arranged for a small fee. The tour is not wheelchair compatible, so guests with mobility equipment will want to keep that in mind. Gratuity for the guide is not included.
Large Group Family-Friendly Pearl Harbor Tour With Private Transportation
Large Group South Shore Aloha Friendly Tour
This tour covers the south shore of Oahu, traveling through a stretch of coastline that includes beaches, surf breaks, cliffs, and neighborhoods associated with film locations and well-known residential areas. Suggested stops include Diamond Head, Kahala Beach, Hanauma Bay, Sandy Beach Park, Makapu'u Lighthouse Trail, Waimanalo Beach, Kailua Beach Park, and Lanikai Beach, along with local food spots such as Leonard Malasadas in Hawaii Kai. Pickup and drop-off from Waikiki area hotels are included. Hotels outside the Waikiki area can be accommodated for an added charge, and a different drop-off location can be arranged for a small fee. The itinerary is described as customizable, so noting hotel details and group size at checkout helps the operator prepare accordingly. Snacks, water, towels, sunscreen, and a personal driver and guide are included. The tour is not wheelchair compatible. Gratuity for the guide is not included but is welcomed.
About
Massimo Sport Hawaii Tours, based in Honolulu, runs a range of guided experiences across Oahu for families, couples, and small groups. Transportation picks up from Waikiki area hotels for several tours, making logistics simple from the start.
On land, the company offers a circle island tour that takes in natural landmarks, cultural sites, and locations used in film productions. A separate eco-friendly tour visits local farms and plantations, stepping away from the usual tourist corridors.
On the water, the company arranges stand-up paddleboard outings from Lanikai toward the Mokulua Islands, a route described as known mainly to locals. Jet ski rentals and parasailing can also be arranged through connections with operators the company works with, though advance notice is required.
Massimo Sport Hawaii Tours is based in Honolulu, Oahu. Do Oahu lists 17 activities from Massimo Sport Hawaii Tours.
Categories: Volcano Tours, Kayaking and Circle Island Tours.
Listings include South Shore Aloha Friendly Tour; Off-Road Adventure Tour On Oahu’s North Shore; Family-Friendly Private Circle Island Tour of Oahu; Family-Friendly Pearl Harbor Tour With Private Transportation; Large Group Private Luxury Tour of Oahu Island; Large Group Oahu Friendly Hiking Experience; and 11 more.
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