Hawaii
Sailing Trips & Tours

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Our most recommended Hawaii Sailing Trips & Tours

From Lahaina: Sunset Dinner Cruise with Live Music

1. From Lahaina: Sunset Dinner Cruise with Live Music

Departing from Pier One in Lahaina Harbor, enjoy a relaxing sunset cruise with a delicious three course meal, listen to island-style music, and watch the sun go down while cruising the waves on a state-of-the-art catamaran. Once aboard you will be seated by our crew to tables assigned based on the size of your party. Once you’ve settled in, our table side service will begin, and the crew will bring you warm breadsticks and water. Your dinner cruise includes two free drinks, once the catamaran has motored out of the harbor, we will take your drink order. We typically serve local beers from Maui Brewing Company, Cabernet and Chardonnay wine, cocktails such as Mai-Tai's, Pina Colada's, Margarita's, Tequila Sunrise, etc., soda, juice, and water. Your meal begins with a crisp Caesar salad, homemade buttery croutons, shredded parmesan cheese, and warm breadsticks. For the main course, your options are rosemary garlic roasted prime rib, fresh Mahi-Mahi with lemon buttery caper sauce, or penne pasta with fresh Thai basil marinara sauce. On the side, enjoy freshly sourced vegetables sautéed and steamed white rice with shoyu sauce. For dessert delight in homemade double layer chocolate cake or New York-style cheesecake. Relax as the sun sets behind the distant Maui mountains, and keep an eye out for humpback whales while you enjoy your delicious dinner cruise.

Lahaina: Afternoon Turtle Town Snorkel Cruise

2. Lahaina: Afternoon Turtle Town Snorkel Cruise

Take in the beautiful scenery on an afternoon charter that takes you to Lahaina Turtle Town. Considered one of the best snorkel spots in Maui for its artificial reef, made from the remains of the Mala Wharf. Snorkel in the stunningly clear waters, and catch sight of the vibrant sea life. What makes this spot special is the artificial reef and its recreation among the destroyed Mala Wharf by a 30-foot surf during hurricane Iniki in 1992. Now it is a healthy reef and home to a vast array of sea life including Green Sea Turtles, Nenue (lowfin chubs), Goatfish, Octopus, Black Durgeon, Frogfish, and Parrotfish. Enjoy snorkeling in the translucent waters of Maui, sure to leave you in awe with abundant sea life and unreal clear visibility. Afternoon snorkels on Maui are a treat! There are very few options that do afternoon snorkel charters, which allows us to bring you to an exclusive area that will be little to no other tourism in the area - giving a unique experience you're sure to love. Lahaina Turtle Town is a very unique and highly desired snorkel location featuring turtle cleaning stations and an abundance of reef fish. This afternoon trip brings the possibility of experiencing an awesome boat snorkel charter without having to wake up at the break of dawn to get to the morning trips! Sleep in, enjoy the morning, and come for an awesome snorkel charter in the afternoon. Whale watch season officially starts December 1, 2021, so along with an awesome afternoon snorkel tour, you will have the opportunity to go Whale watching too. Humpback whales visit the Hawaiian Islands seasonally, so this is a combination of snorkeling at a beautiful reef as well as whale watching on the same tour. All snorkel spots are determined daily weather permitting. Please understand and respect the captain's decisions on the safest snorkel locations for the day. Where ever your captain takes you, the crew will provide you with snorkeling tips and gear. The catamaran has 2 restrooms and freshwater showers available for passengers. 

Big Island: Eco-Friendly Twilight Manta Ray Adventure

3. Big Island: Eco-Friendly Twilight Manta Ray Adventure

Experience an exciting 75-minute nighttime snorkeling expedition. Get up close and personal with stunning manta rays as they gracefully soar through the water. Your underwater adventure will take place in clear warm waters near protected reefs abundant with marine life.   After the sun sets, head off into the nighttime waters to see a fascinating "manta ray ballet" along the Kona coast near the mouth of Keauhou Bay. This point of departure is one of the island’s most successful and consistent manta ray viewing locations. Your snorkeling guide will outfit you with all the necessary gear needed to embark on your experience including snorkel gear, wetsuits, and flotation devices. After a quick safety briefing, plunge into the dark waters and be captivated by these graceful creatures as they feast on plankton. Grip onto the flotation swim ring with high-illumination blue water lights that attract the plankton on which the mantas feed. Soon afterward, rays will glide through the water almost at arm's length opening their enormous mouths to feast. After your remarkable underwater adventure, return to your boat and warm up with a nighttime snack of hot chocolate and cookies

From Lahaina: Lana'i Coast Maui Sail and Snorkel Trip

4. From Lahaina: Lana'i Coast Maui Sail and Snorkel Trip

Start the tour by boarding a brand new luxury catamaran at the dock in Lahaina. Set off on your incredible adventure along the spectacular coastline of Lana'i. Onboard the vessel, enjoy a continental breakfast of tropical fruit, freshly baked banana bread, and locally roasted coffee. Head towards the pristine reefs along Lana’i’s south shores where you'll discover stunning sea cliffs, uncrowded snorkeling sites, and expansive island views. Get geared up with the snorkeling equipment provided and plunge into the warm waters to discover an array of local marine life.  This relaxed tour does not have a set destination, so the experienced crew can select the best locations based on sea conditions, and visit multiple snorkel sites when time and weather allow. After swimming and snorkeling, sit back with a drink and enjoy a full lunch while trying to catch a sighting of Lana’i’s famous spinner dolphins. Finally, return to the dock where your memorable day at sea concludes.

Waikiki: Turtle Canyons Snorkel Excursion

5. Waikiki: Turtle Canyons Snorkel Excursion

Experience the magical underwater world of sea turtles. Dive under the waves with a snorkel and see the rainbow of tropical fish. Connect with the wide array of stunning marine life on this two-hour tour. Start off with a cruise along the coast, where you can potentially spot spinner dolphins and humpback whales during the wither months. Once at the Turtle Canyons, you’ll get a brief lesson on snorkeling and your snorkeling equipment.  Snorkel alongside the sea turtles and tropical sea life under the supervision of a certified lifeguard, returning to the boat whenever you please to relax with complimentary refreshments.

Maui: Deluxe Sunset Sail from Lahaina

6. Maui: Deluxe Sunset Sail from Lahaina

Enjoy stunning sunset on the coast of Maui on a catamaran cruise from Lahaina. Lay back on the forward trampolines or sit under the covered cabin space while savoring mouth-watering cold hors d’oeuvres and sipping on chilled drinks. Keep an eye out for whales as you sail.  Depart from Lahaina and set sail in the waters of Maui. Admire breathtaking views of the verdant and dynamic shores as the sunset paints the sea in a golden glow. Have a refreshing cocktail or snack on a delicious selection of hors d’oeuvres.  From December to May, enjoy the thrill of watching the humpback whales as they make their yearly journey to Hawaii. During the rest of the year, keep your eyes peeled for graceful seabirds and the black-finned Māui dolphin.  Return to your meeting point in Lahaina at the end of your cruise. 

Maui: Molokini Snorkel & Performance Sail with Lunch

7. Maui: Molokini Snorkel & Performance Sail with Lunch

Discover Molokini aboard a fast-sailing catamaran, where your trip includes a continental breakfast on the leisurely sail across Ma’alaea Bay. Take in the stunning landscape that makes Maui special, and during whale season (December – May), spot the humpback whales as they swim nearby. While at Molokini, swim, snorkel, and rinse off with a freshwater shower. After snorkeling, indulge in a full lunch buffet and refresh with a variety of beverages, including wine and local beer. Maui’s afternoon trade winds can really get the boat going, so join the friendly crew at the helm and try your hand at sailing the high seas! 

Big Island: Captain Cook Historical Dinner Cruise

8. Big Island: Captain Cook Historical Dinner Cruise

Step aboard and step back in time… Join for an enchanting Hawaiian history lesson from the experts on Kona’s one and only Historical Sunset Dinner Cruise. This 3-hour family adventure departing from the Kailua Pier is narrated by a local historian tour guide, who will reveal secrets, tell stories, and share legends related to the numerous landmarks along the 12 miles of magnificent Kona coastline. Unwind to Captain Cook’s Monument at Historical Kealakekua Bay (only accessible by boat or hiking) with a complimentary cocktail from a fully stocked, premium bar. Begin your delicious dinner starting with Mauna Loa Big Island Macadamia Nuts (Vegan/GF) appetizer. Enjoy a salad starter of Kealaola Farm mixed salad greens, Waimea grape tomatoes, Japanese cucumber, and red onion (Vegan/GF), served with house-made Maui Onionvinaigrette dressing (Vegan/GF). Choose your main course from a selection of Thai coconut curry with Hamakua sweet potatoes, Hawaiian breadfruit, carrots, and bell peppers (Vegan/GF), or steamed jasmine rice (Vegan/GF) with Kiawe mango barbecue pork short ribs served with a papaya salsa (GF) and island baked coconut dinner rolls served with butter (Vegetarian). Your dessert is a cheesecake with a local Lilikoi glaze (Vegetarian). Keep an eye out for dolphins, turtles, manta rays, and seasonal humpback whales throughout the evening. Enjoy live music from some of the Big Island's best entertainers performing slack key Hawaiian Style music. Catch the sunset on the water and make sure to look for the famous Green Flash, a fleeting glimmer of intense emerald light that appears on the horizon just after sunset. Other highlights include the Ahu’ena Heiau, the Holua Slide, and the famous Kuamo’o Battlefield, just to name a few.

Maui: Sunset Catamaran Cruise with Dinner and Drinks

9. Maui: Sunset Catamaran Cruise with Dinner and Drinks

Watch the glow of the sunset on the Kahalawai Mountains, Lanai Island, and the Molokini Crater on this sunset catamaran cruise from Ma’alaea. Keep an eye out for humpback whales while listening to Hawaiian music. Savor a gourmet dinner and relax with two drinks from the bar. Depart from the Ma’alaea Harbor and set off into the waves on a catamaran. After exiting the harbor, enjoy a complimentary drink before the dinner service kicks off. Explore the alcoves of the boat, gaze out over the ocean, and snap photos. While soaking up the tropical views, listen to island-style music. For dinner, chef Keoni will serve the succulent Hawaiian prime rib, Mahi Mahi, teriyaki chicken, ribs, steamed vegetables, white rice with soy sauce, and more. As you dine, take in views of Kaho’olawe and Lanai in the distance, as well as the top snorkeling location, Molokini Crater. Gaze out at the Kahalawai Mountains of Maui extending toward the sky. You are likely to see humpback whales visiting the islands from Alaska along with other marine mammals.

From: Ma'alaea Harbor: Afternoon Snorkel to Coral Gardens

10. From: Ma'alaea Harbor: Afternoon Snorkel to Coral Gardens

Exploreone of Maui’s most impressive sites on this relaxing afternoon catamaran cruise to Molokini Crater or Coral Gardens. Dive into the rich marine biodiversity of the reefs in this partially submerged volcanic crater. Head to the meeting point at Maalaea Harbor for your check-in before boarding the Malalo catamaran. Set sail and admire the beautiful Pacific coastal views as you cruise towards your snorkel site. Stop at the ideal snorkeling location for that day. Have the option to purchase food and drink aboard. Jump into the pleasant water and look for colorful fish like parrot fish, yellow tang, and cornet fish. Keep your eyes peeled for the elusive spotted eagle ray. Feel free to rent wetsuits, digital underwater cameras, and prescription masks on the day of your activity to enhance your aquatic experience. After your unforgettable swim, relax with a drink (available to purchase) on deck as you return to your boarding point.

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What people are saying about Hawaii

Overall rating

4.5 / 5

based on 1,221 reviews

This is a MUST experience to have. The crew were above and beyond helpful, informative, and professional. Our 4 year old enjoyed this, our two teens enjoyed this, my wife and I all enjoyed this. We’re still talking about it. I read many of the other reviews “Too many people, otherwise good”… not this tour. The ship is the perfect size, not too many other passengers but just the right amount. The sailing was one of the “unforeseen” winners of this tour. Captain Greg and his crew shared their love and passion with everyone on board. WHEN we come back, this is top of our list of things to do again. Oh yeah, and did I mention you get to snorkel at the Crater?! You do and it’s awesome!!! Hope this helps. Good and drinks are great too. I think I’ve covered it all but you won’t go wrong with this adventure tour.

The activity was so much fun! The boat was fast, making it fun to ride. Our guide was fantastic (Lauren, I believe). She was extremely knowledgeable about the history about the island and her enthusiasm was great! We weren’t able to snorkel at Captain Cook due to low visibility but it ended up being great because we went to an area without anyone else and were able to see plenty of fish and coral. We saw a ton of the island’s natural beauty and even saw manta rays on the ride back. Snacks were fruit, chips/cookies, and juice or water. I highly recommend this tour—you won’t regret it!

This was one of the highlights of our trip to the Big Island. Great crew, so friendly and helpful, and the boat was spacious and comfortable. The captain gave us some interesting history as we cruised along the coast. We saw dolphins, flying fish and had a great time snorkeling. They provided breakfast and a BBQ lunch, both were great! We would do it again in a heartbeat, and wish they had an all-day trip, 1/2 day was too short!

Captain Anthony and crew run a top rated sunset cruise experience in a personal and engaging atmosphere.

The crew was a lot of fun! Great views. Mahi & drinks were tasty!