Maui Activities Update: Boss Frog’s Calypso and Malolo Offering Safe (and amazing!) Ocean Adventures

Maui • December 14, 2020

Opening in 1989 as a small shop at Anchor Square, Lahaina, Boss Frog’s has grown into Hawaii’s leading full-service rental business, with shops on Maui, Kauai, and the Big Island. 

“I came to Maui on our first catamaran, the Frogman, from Santa Barbara in 1987,” says owner Phil Kasper. “My son Chris and I lived in a garage in Lahaina. I worked on the Frogman during the day. At night, I waited tables.”

From these humble beginnings came not only multiple stores on Maui, Kauai and the Big Island, but three owned and operated ocean adventure boats- the Calypso Maui, the Malolo, and the Quicksilver. 

The Calypso Maui

The Calypso operates like a spacious, floating amusement park, and her double hulls are built for stability. It is equipped with a glass-bottom viewing area, water slides, jumping off points and freshwater showers.

The boat launches from Ma’alaea – the most easily reached, centralized harbor on the island. Guests choose from the morning Molokini Snorkeling Tour, the sunset Dinner Cruise, the seasonal Whale Watch (mid-December through mid-April; for more on Whale Watch see below), and – for super special occasions, the Private Charter! The views from Calypso Maui are better than any other boat for miles, because she is the only vessel on the island that has three decks.  

The Malolo

Boss Frog’s is also operating the Malolo , a 55-foot comfortable, stable catamaran. The Malolo visits both Molokini and Turtle Town, two of the best snorkeling locales in Maui- and the world. Guests have approximately one hour of snorkeling at each site, usually plenty to see all the marine life and have a great time. The overall trip time is approximately 5 hours. 

The Malolo is equipped with easy access stairways into the water on both the front and rear of the boat. There are also two restrooms, trampolines to lay out on and a friendly, experienced captain and crew. A continental Breakfast and deli lunch are included as is all snorkeling gear. The boat is equipped with flotation devices such as foam noodles, body boards and float vests for guest use. Optional wet suits and high quality 16 mega pixel Olympus underwater digital cameras are available to rent.

Molokini has a well earned reputation as being one of the most spectacular snorkeling locales in the world. The visibility inside this volcanic crater is incredible. At times, you can see up to 100 feet. All kinds of tropical fish love this marine preserve. Amazing seabirds hang out on and around the crater, too. There is no fishing or fish feeding which allows the natural ecosystem flourish. Our snorkel vessels are all unique to accommodate our equally remarkable guests. 

Whale Watch Season is Here!

The two-hour Calypso whale watch is a thrilling, family-friendly Maui activity. From December 24th through April 15th, climb aboard the Calypso, Maui’s only catamaran with three decks. All of Calypso’s 360-degree ocean views are “fin-tastic”, even from the inside when a break from the sun is preferred. The first and second decks have spacious cabins with tinted windows. The windows make for excellent viewing through the water’s surface, regardless of the sun’s glare. Comfortable seating throughout this stable vessel ensures a relaxing time on the water while guests marvel at these incredible marine mammals. There is even a bar and snack area. 

“The onboard naturalist, captain, and crew are just as excited as guests to see humpbacks,” says Chris. “The 45-foot  cetaceans  inspire awe, delight, and excitement with their very existence, and whenever they come over to our 65-foot catamaran – wow, oh wow!”

“Whenever the boat is stopped for a while, you can go down to the underwater viewing room. If the whales choose to swim beneath the vessel, you’ll be able to see them through the glass panels in the bottom of the hull! That is one of the most awesome things about the Calypso whale watch.”

Dinner Cruises: The Calypso also offers an exceptional evening Maui dinner cruise.

Guests sit back, relax, and enjoy great food and great company as they glide along the coastline. Watch the sun set over  Lanai.  Leave the navigation to the excellent captain, leave the dishes to the fabulous crew, and keep a light watch for dolphins while you sip your mai tai.

Boss Frog’s also offers a dinner cruise aboard the Quicksilver, which depart from Lahaina Harbor.

Enjoying a dinner cruise on this motor catamaran is a lot of fun. Live music plays as you board the floating restaurant. You and your party find a place to sit. You choose indoor or outdoor seating, and you meet your fellow passengers sitting nearby. The Quicksilver cruises north along the West Maui coastline. The amazing crew serves all your drinks and your dinner, so you can take your time watching the sunset. And during whale season, there is a very good chance that you see a whale or two before dessert.

The dinner is delicious.  You can view the most current dinner menu on Quicksilvermaui.com. Beer, wine, mai tais, and other mixed drinks are available. 

Whether it’s snorkeling, whale watching or enjoying a sunset dinner cruise, Boss Frog’s is open offering world class ocean activities on Maui. 

For more information, go to bossfrog.com.

 A person scuba diving next to a large school of fish in clear blue water, learn how to start scuba.
By Cheryl Lee January 21, 2026
Learn how to start scuba diving in Hawaii with clear steps, beginner essentials, top islands for training, safety tips, and what to expect on your first dives.
The peak of Mauna Kea on the big island of hawaii covered in snow
By Cheryl Lee January 19, 2026
It snows on Hawaii - and this post is here to break down the where, when, why, and how. Learn more about Hawaii’s snowfall and unique geography.
By Cheryl Lee January 16, 2026
Snorkeling in Hawaii is one of those experiences that stays with you long after you’ve dried off. The islands’ warm, clear waters are home to coral reefs teeming with tropical fish, sea turtles, and a variety of other marine life. Whether you’re a beginner testing out your first mask or a seasoned snorkeler chasing reef walls, Hawaii offers some of the best snorkeling conditions in the world. But before you grab your fins and jump in, it helps to understand what makes each island unique, how to snorkel safely, and how to protect the fragile ecosystems beneath the surface. Read our complete guide to making the most of snorkeling during your visit to the Hawaiian Islands.
1966 and 2026 This Week Hawaii magazine cover image
January 8, 2026
Discover the evolution of This Week Hawaii, from its 1966 founding to becoming Hawai‘i’s most widely read visitor magazine and digital travel resource.
Nene geese, what Hawaii  is known for.
By Cheryl Lee November 12, 2025
Discover what makes each Hawaiian Island unique, from Oahu’s surf culture to Kauai’s lush beauty and Maui’s luxury resorts. Learn more about what every Hawaiian island is about.
driving down a one way road on the coastline of hawaii with a view of the ocean and neighborhood
By Cheryl Lee October 27, 2025
Learn essential Hawaii driving etiquette and rules. From speed limits to local customs, here’s what you need to know for safe, respectful travel.
A kii statue in Puuhonua O Honaunau National Historical Park in Hawaii
By Cheryl Lee October 19, 2025
Looking to learn more about Hawaii’s history during your visit? This is our full guide to some of Hawaii’s best historical locations to visit during your stay!
Discover the best time to visit Hawaii.
By Cheryl Lee October 16, 2025
Plan your Hawaii trip smart! Learn the best months for sunny weather, fewer crowds, and good deals—plus insider tips from local island experts.
What Hawaiian Island Should You Visit? First-Timers Guide
By Cheryl Lee September 15, 2025
Planning your first Hawaii trip? Compare Oʻahu, Maui, Big Island & Kauaʻi in this guide to help you choose the best island for your perfect vacation.
By Cheryl Lee September 7, 2025
From farm-to-table fine dining and fresh island seafood to local shave ice and hidden roadside gems, Maui’s culinary scene offers something for every taste.