Massimo Sport Hawaii Tours
About
When you're looking for someone who truly gets what makes Oahu special, Massimo Sport Hawaii Tours is where locals would point you. This Honolulu-based outfit has figured out how to share the real Hawaii – not just the postcard version – through adventures that dig into both our incredible landscapes and the stories that make this place home.
What sets them apart is their range. Want to see all of Oahu in a day? Their private Circle Island tours hit spots most visitors never find. Need to pay respects at Pearl Harbor? They handle the logistics so you can focus on the experience. Craving some water time? Their SUP tours around Lanikai and the Mokulua Islands will have you paddling through some of the clearest water you've ever seen.
The family angle is solid too. Whether you're bringing keiki (kids) along for jet skiing thrills or parasailing adventures, or planning something more mellow, they know how to make everyone happy. That's not always easy when you're dealing with different ages and energy levels.
But here's what really matters – these folks care about keeping Hawaii, well, Hawaii. They run their tours with respect for the land and ocean, which means a lot when you live here year-round. You'll leave knowing more about our culture and natural world than when you arrived, and that deeper connection tends to stick with people long after they head home.
It's that combination of local knowledge, genuine care for the islands, and ability to create memorable experiences that keeps visitors coming back to Massimo Sport Hawaii Tours.
Activities (17)
South Shore Aloha Friendly Tour
Want to see Oahu's south shore like a local? The South Shore Aloha Friendly Tour All Ages delivers an intimate 3-4 hour journey to our island's most breathtaking coastal spots. With groups limited to up to six people per group, you'll experience personalized exploration of Diamond Head, world-famous Kailua Beach, and hidden gems that make our coastline legendary. Your private guide starts at Diamond Head's volcanic crater lookout, where panoramic views sweep across Honolulu to the endless Pacific. We'll cruise through Kahala and Hawaii Kai's luxury neighborhoods—home to celebrities and stunning beachfront estates—before stopping at Koko Head Lookout for panoramic views of Hanauma Bay and the Pacific Ocean, with a clear look at the Koko Head crater. At Hanauma Bay's crystal-clear nature preserve, enjoy stunning viewing of this world-renowned location, then visit Sandy Beach Park to witness powerful shore breaks creating dramatic coastal theater, before heading to Makapu'u Lookout for sweeping views of rugged lava rock cliffs with an optional short walk on the Makapu'u Lighthouse Trail. The real magic happens at Waimanalo Beach's soft white sand and turquoise waters, followed by visits to Kailua Beach Park and postcard-perfect Lanikai Beach with its offshore Mokulua Islands. Your knowledgeable local guide weaves Hawaiian history and insider stories throughout the journey while you capture photos at our most scenic locations. Flexible stops mean we can customize the experience to your group's interests—maybe swinging by Leonard's Bakery for Hawaii's famous malasadas or adding short walks at scenic lookouts. This South Shore Aloha Friendly Tour welcomes all ages 100 and under. Private vehicle transportation includes Waikiki hotel pickup and drop-off, plus fuel surcharge and local taxes. The meeting point is in Waikiki, with 72-hour cancellation policy and stroller accessibility. Food, drinks, and gratuities aren't included, though we can arrange local culinary stops. Book your private south shore adventure with MS Hawaii Tours from $150 and discover why these beaches and coastal landscapes continue to captivate visitors for decades.
Off-Road Adventure Tour On Oahu’s North Shore
Here's what you won't find anywhere else on Oahu: exclusive access to a private wildlife sanctuary that regular tourists never see. This off-road adventure tour on Oahu's North Shore takes you deep into protected territory aboard a powerful Ford Raptor F150, far from the usual crowded attractions. Your 4 to 6-hour expedition starts with Waikiki hotel pickup, then heads straight for the North Shore's restricted natural preserve. Inside this sanctuary, you'll encounter Hawaii's most elusive wildlife—Hawaiian monk seals lounging on remote beaches, sea turtles basking in pristine coves, and majestic albatross in their nesting grounds. Winter visitors (December through April) get the added bonus of humpback whale watching from exclusive clifftop vantage points where you'll witness these giants breaching just offshore. The real thrill comes as your expert local guide navigates rugged terrain most people never experience. You'll barrel through hidden valleys, cruise along dramatic coastal cliffs, and discover secret beaches that make for incredible photo opportunities. Between the adrenaline rushes, you'll hear fascinating stories about Hawaii's conservation efforts and local legends that have shaped this land. Small groups of 4 to 6 people mean you get personalized attention throughout the journey. We'll even stop at authentic North Shore food spots so you can taste real island flavors—not the tourist trap versions. This off-road adventure tour on Oahu's North Shore Honolulu welcomes all ages (100 and under) and includes your private vehicle with expert driver/guide, Waikiki hotel pickup and drop-off, plus all fuel surcharges and local taxes. Food, drinks, and gratuities aren't included, though we can arrange meal stops on request. Hotel pickup outside Waikiki costs extra. With 72-hour cancellation and stroller accessibility, this exclusive sanctuary access offers a once-in-a-lifetime chance to discover Oahu's hidden natural treasures.
Family-Friendly Private Circle Island Tour of Oahu
After three decades of showing families around our island, I can tell you this family-friendly private circle island tour of Oahu delivers everything that makes our home special. Your group of up to six gets picked up right from your Waikiki hotel for a completely customizable 5-6 hour journey around the island with your own guide and air-conditioned vehicle. We start at Diamond Head Scenic Lookout for those postcard views, then head to Halona Blowhole where the ocean puts on a show, shooting water geysers through ancient lava tubes. The peaceful Byodo-In Temple in Valley of the Temples offers a serene contrast before we explore Kualoa Ranch's lush landscapes—you'll recognize these backdrops from Jurassic Park, Lost, and Hawaii Five-O. Our agricultural stops at macadamia nut and coffee farms let you taste what we grow here while learning about local farming traditions. The North Shore is where things get exciting with world-famous surf spots like Banzai Pipeline, where winter brings those massive waves and pro surfing competitions. Waimea Bay's crystal-clear waters tell the story of big-wave surfing history. Turtle Beach (Laniakea Beach) is always a family favorite—watching Hawaiian green sea turtles in their natural habitat never gets old. Kids love the Dole Plantation for pineapple history and Dole Whip tastings. Throughout the day, we'll hit local food spots serving authentic Hawaiian specialties: kalua pork, fresh shrimp, shaved ice, and haupia chocolate pie. This private circle island tour of Oahu Honolulu welcomes participants aged 100 and under, with strollers easily accommodated. Your package includes private transportation, personal driver/guide, Waikiki pickup and drop-off, bottled water, plus all fuel surcharges and local taxes. Food, drinks, gratuities, and personal expenses are separate, though we're happy to arrange meal stops. With our 72-hour cancellation policy and completely customizable itinerary, every family-friendly private circle island tour of Oahu becomes your perfect island adventure, enriched with genuine Hawaiian cultural stories I love sharing.
Family-Friendly Pearl Harbor Tour With Private Transportation
Having lived here for years, I can tell you that this family-friendly Pearl Harbor tour with private transportation Honolulu offers something most visitors miss—the luxury of experiencing this sacred site without the usual crowds and time constraints. Your group of two to six travels in a dedicated vehicle with your own guide, making it perfect for families who want to explore at their own rhythm. The 2.5 to 3-hour experience starts with pickup from your Waikiki hotel, whisking you straight to Pearl Harbor National Memorial. Once there, you'll settle in for a powerful 23-minute documentary filled with actual wartime footage from December 7, 1941. It's an eye-opening introduction before you dive into the two comprehensive museums, where artifacts, photographs, and short videos bring that pivotal day to life. The heart of your visit is the ferry ride to the USS Arizona Memorial. Built directly over the sunken battleship, this memorial honors the final resting place of over 1,100 sailors and marines. It's a profound moment that gives families time for quiet reflection and meaningful photos. On your way back, consider the optional downtown Honolulu sightseeing. Your guide can show you the Statue of King Kamehameha—Hawaii's legendary unifying ruler—and ʻIolani Palace, America's only royal palace and former home of Hawaiian royalty. This family-friendly Pearl Harbor tour with private transportation Honolulu welcomes everyone from infants to centenarians (up to age 100) and easily accommodates strollers. Everything's included: hotel pickup and drop-off from select Waikiki locations, Pearl Harbor admission, reserved USS Arizona Memorial boat tickets (subject to availability and Navy operations), plus plenty of time for exploration and photos. Just remember to cancel at least 72 hours ahead if plans change. Your guide will call the day before to confirm pickup details, ensuring everything runs smoothly for your family's visit to this remarkable piece of American history.
Private Luxury Tour of Oahu Island
Here's your chance to explore Oahu like never before with this private luxury tour of Oahu island Honolulu, crafted exclusively for your group of up to six people. Over five to six hours, you'll discover the island's most spectacular destinations with complete flexibility and your own dedicated driver-guide who knows every hidden corner of this paradise. The North Shore awaits with its legendary beaches—Waimea Bay, the world-famous Banzai Pipeline, Sunset Beach Park, and Turtle Bay Beach. All admission fees are covered, so you can focus on soaking up the magic. Want to hit specific spots? Perfect. Prefer to let your local guide create the ideal itinerary based on what catches your interest? Even better. This private luxury tour of Oahu island adapts to you, revealing both iconic landmarks and secret gems that showcase the island's incredible diversity. From pristine swimming coves to legendary surf breaks, the North Shore delivers experiences you'll remember forever. We've got your comfort covered too—fresh towels, sunscreen, water, fuel surcharge, and local taxes are all included. Hotel pick-up and drop-off comes complimentary for all Waikiki accommodations, with service available outside Waikiki for an additional charge. Need to be dropped somewhere different than your pick-up location? We can make that happen for a small customization fee. Whether you're traveling with family, your partner, or a group of friends, this private luxury tour of Oahu island Honolulu welcomes all ages and creates those exclusive moments you came to Hawaii for. Just note that the tour isn't wheelchair compatible, and you'll need to provide your hotel details at checkout for smooth transportation logistics. Pack your sense of adventure—we'll handle everything else for this personalized journey along Oahu's most captivating coastline.
Large Group Oahu Friendly Hiking Experience
Looking to explore Oahu's incredible hiking scene with a group? This large group oahu friendly hiking experience Honolulu adventure accommodates seven to eleven people of all ages for an unforgettable five to six-hour journey from $XX. The beauty of this experience lies in its variety of trail options. You might find yourself chasing waterfalls on the two-hour Manoa Falls trail or pushing your limits up the Koko Crater Railway Trail for those jaw-dropping views of Honolulu and the east side. Diamond Head State Monument delivers those classic panoramic shots of Waikiki and Koko Head Crater that'll make your Instagram followers jealous. If you're visiting during whale season, the Makapuu Lighthouse Trail becomes prime whale-watching territory with spectacular coastal vistas. For serious waterfall hunters, the three-hour Maunawili Falls hike showcases some of our most stunning natural scenery. Nature enthusiasts will love the Koko Crater Botanical Garden – an easy two-hour stroll featuring diverse local plants and every variety of plumeria tree you can imagine. The Kuliouou Ridge Hike takes you deep into our lush rainforest for three hours of pure tropical immersion. What makes this large group oahu friendly hiking experience stand out is the variety of trail options available for your group adventure. Your personal driver and guide handles all the logistics, including complimentary pick-up and drop-off from Waikiki hotels (outside Waikiki available for additional charges). Water, towels, sunscreen, fuel surcharge, and local taxes are all covered. Keep in mind this tour isn't wheelchair compatible, and you'll need to provide your hotel details at checkout. Want a different drop-off location? That's possible for a small fee. This comprehensive hiking experience lets you explore Oahu's beautiful trails with the convenience of professional guidance and transportation.
Large Group Private Luxury Tour of Oahu Island
This large group private luxury tour of Oahu Island caters perfectly to parties of seven to eleven people who want the island experience on their own terms. What sets this five to six-hour adventure apart is the flexibility. Come with a wishlist of spots you've been dying to see, or let your local guide take the wheel—literally and figuratively. Your guide will take you wherever you want to go, or you can tell them what you like and they'll set a course using their own local knowledge of the island. Your journey includes admission to some of Oahu's most breathtaking coastal destinations: Waimea Bay, the Banzai Pipeline, Sunset Beach Park, and Turtle Bay Beach. The North Shore portion alone is worth the entire trip. The logistics are handled seamlessly. Complimentary hotel pick-up and drop-off covers all Waikiki area accommodations, while those staying elsewhere can arrange transportation for an additional fee. Need a different drop-off location? That's available for a small charge. Beach essentials like towels, sunscreen, and water come included because nobody wants to haul that stuff around. This large group private luxury tour of Oahu Island welcomes all ages, though it's not wheelchair compatible. Your dedicated personal driver and guide ensures every moment of these five to six hours counts. Fuel surcharge and local taxes are included so you can focus on soaking up paradise. Just bring your sense of adventure and prepare for an Oahu experience crafted exactly how your group wants it. From $XX per group.
Large Group Family-Friendly Private Circle Island Tour of Oahu
Here in Oahu, families know the best way to explore our island is at your own pace, not rushing through cookie-cutter stops. This large group family-friendly private circle island tour of Oahu puts your ohana first, accommodating seven to twelve people for a five to six hour adventure that's completely tailored to what excites your kids. Your personal driver and guide becomes your local connection, working with you to craft the perfect day. Got marine life enthusiasts in the group? We'll prioritize the best snorkeling spots. Love dramatic vistas? We'll hit the scenic lookouts that'll have everyone reaching for their cameras. Prefer hands-on cultural experiences? Just let us know in the comment section when booking, and we'll design an itinerary that keeps every family member engaged. What sets this experience apart is the freedom from rigid schedules. While other tours herd groups through standard highlights, you'll have quality time at each location. No rushing, no stress – just your family discovering Oahu's diverse landscapes together. We handle the logistics so you don't have to. Complimentary pick-up and drop-off from Waikiki area hotels is included, along with water, towels, sunscreen, fuel surcharge, and local taxes. Need a different drop-off location? We can arrange that for a small additional fee. Hotels outside Waikiki can also be accommodated with additional charges. This large group family-friendly private circle island tour of Oahu welcomes all ages, though it's not wheelchair compatible. With transportation and sun protection covered, your family can focus entirely on creating those personalized memories that reflect your unique interests and travel style.
Large Group South Shore Aloha Friendly Tour
The Large Group South Shore Aloha Friendly Tour Honolulu offers one of the most comprehensive ways to experience Oahu's spectacular coastline. This five to six-hour adventure takes seven to eleven guests on an journey through iconic beaches, dramatic cliffs, and upscale neighborhoods including Diamond Head, Kahala, and Hawaii Kai. Starting with convenient Waikiki hotel pickup, you'll wind through Diamond Head's prestigious streets, the upscale Kahala area, and Hawaii Kai's stunning residential enclave. The tour hits all the must-see spots: romantic Lanikai Beach, Sandy Beach Park with its dangerous cliffs and powerful shore break, and the scenic Hawaii Kai Lookout with its sweeping coastal panoramas. The Large Group South Shore Aloha Friendly Tour provides the perfect blend of natural beauty and local culture. You'll sample Leonard's malasadas in Hawaii Kai during your stop. Plus, you'll explore world-renowned Hanauma Bay, experience the pristine stretches of Waimanalo and Kailua Beach Park, and tackle the Makapuu Lighthouse Trail for scenic shots of the rugged eastern coastline. Your driver doubles as your tour guide, sharing information about the scenic world famous beaches and surf breaks, and Hollywood film industry's shooting grounds that have made these locations famous. The tour welcomes all ages and covers everything—water, towels, sunscreen, fuel surcharge, and local taxes. Complimentary pickup and drop-off from Waikiki hotels is included, with custom arrangements possible for different locations at additional charges. Note: this tour isn't wheelchair compatible. Book this Large Group South Shore Aloha Friendly Tour Honolulu from $XX and discover this scenic drive around Oahu's south shore.
Jet Skiing/Parasailing
Looking for an adrenaline rush? This ultimate jet skiing/parasailing experience will have you skimming across turquoise waters and soaring above the coastline. This one-hour aquatic adventure accommodates up to ten people, perfect whether you're traveling with family, friends, or that special someone. What sets this service apart is their extensive network of the island's top parasailing instructors and jet ski rental companies. They've done the legwork to connect you with the most reputable operators, so you get expert guidance every time. Want to feel the spray as you race across pristine waters? Or maybe you're drawn to that incredible bird's-eye view of the coastline? Either way, you're in for a treat. The beauty of this jet skiing/parasailing adventure lies in its flexibility. They work directly with your group to customize the experience based on your size and schedule preferences. No cookie-cutter approach here—they handle all the coordination so you can focus on the fun ahead. Looking to spice up your vacation? They've got you covered. Here's the best part: this experience welcomes participants of all ages. Whether you're bringing grandparents or teenagers, everyone can join in on the action. Starting from $250 for the one-hour session, you're getting exceptional value for access to premier water sports. Ready to make some waves? Give them a call to check availability and secure your spot. Their knowledgeable team will take care of all the details, leaving you free to anticipate the adventure that awaits on spectacular waters.
Private Circle Island Tour And Snorkeling Experience
This Private Circle Island Tour and Snorkeling Experience offers a completely customizable adventure for up to six people that lets you experience Oahu at your own pace. Your personal driver-guide crafts the perfect itinerary based on what excites you most. Want to spend time snorkeling at the North Shore's Turtle Beach and Sharks Cove? Interested in exploring the historic Haleiwa town, then heading to coffee farms and pineapple plantations? Your guide makes it happen. You'll visit actual filming locations from Jurassic Park and Hawaii Five-O, standing where these iconic scenes were shot in dramatic Hawaiian landscapes. This private circle island tour and snorkeling experience runs five to twelve hours and adapts to your interests. Your guide handles all the logistics while you explore Oahu's diversity. Everything's included – water, towels, sunscreen, local taxes, and fuel surcharge. Pickup and drop-off from Waikiki area hotels comes complimentary, though other locations can be arranged for additional charges. Different drop-off points are also possible for a small fee. This all-ages adventure works for everyone, though it's not wheelchair compatible. Your personal driver/tour guide shares knowledge and handles the details so you can focus on experiencing this customizable island tour. From $XX per group.
Eco-Friendly Aloha Island Tour
Here's what makes this eco-friendly Aloha Island tour special – it's nothing like those crowded bus tours you see everywhere. Suitable for all ages, you'll join just two to five other travelers for an intimate five to six-hour journey that reveals the real Hawaii most visitors never see. We take you straight to working farms and plantations where local families have been growing food sustainably for generations. You'll watch sustainable farming practices in action and understand how these methods help protect Oahu's natural beauty and wildlife. It's fascinating to see how island farmers maintain their agricultural traditions. Your personal driver doubles as your guide, sharing stories and insights you won't find in any guidebook. They know these back-country roads like their own backyard and love showing off hidden corners of the island. The tour works perfectly for families – kids get excited exploring working farms, while adults appreciate learning about Hawaii's agricultural heritage. Pick-up from Waikiki hotels comes included, though they can arrange transport from other areas for a small additional fee. Same goes if you want to end somewhere different than where you started – they're pretty flexible about customizing the experience. Everything's covered: water, towels, sunscreen, fuel surcharge, and local taxes. Just bring comfortable walking shoes since you'll be exploring actual working farms. Please note that this tour is not wheelchair compatible. What sets this apart from typical tourist activities is the focus on supporting local sustainable farming while giving you authentic insights into island life. You're not just sightseeing – you're contributing to the community that keeps Hawaii's agricultural traditions alive.