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Sailing the Hawaiian Islands

Have you ever been sailing? Let us paint a picture for you. There’s something so exciting and adventurous about jumping on a boat for the day (or even longer) and heading out into the ocean to explore, spotting coastal and marine wildlife, and making stops to snorkel, investigate a hidden beach, or simply take in the views. Not to mention that lazing in the sun on board a catamaran, cocktail in hand, is the absolute epitome of luxury! What better place to enjoy this experience than Hawaii?

The art of sailing is a deeply rooted tradition in this archipelago, connecting the eight islands long before airplanes were in the sky. It’s certainly one of our favorite ways to get to know Hawaii; read on to see which sailing experience you want to add to your own bucket list!

Learning the tricks of the trade

Whether you’re already a sailing fanatic, or simply a novice with a taste for adventure, why not devote some time to learning or improving the craft against the gorgeous backdrop of the Hawaiian landscape? Sail Hawaii International is based in Honolulu, Oahu, and offers training courses in navigation and sailing for complete beginners and seasoned sailing veterans alike.

These certified courses range from introductory 3-hour lessons and coastal navigation and cruising sessions for beginners and intermediates to advanced week-long immersive education adventures such as the Pacific Offshore Challenge. These often-demanding courses are the perfect learning opportunity for advanced sailors; spending 7 days and 6 nights living and sleeping on board the Gemini sailing yacht. You’ll depart from Honolulu and enjoy a jam-packed sailing itinerary between the Hawaiian Islands, coming face-to-face with wildlife and unforgettable views! Hawaii is the perfect place to learn sailing as a brand-new skill or hone it as an existing craft!

Tours in and around the Hawaiian Islands

If you’re not keen on taking on the task of actually being in control of the sailing yourself, there are still many ways for you to soak in the joys of being out on the open water!

The simplest (and cheapest) way to do this is aboard one of the Hawaiian passenger ferries! There aren’t many ferries running between the islands, which makes island-hopping tricky, unless you’re prepared to take a flight! However, there are two passenger ferry routes, both departing from Lahaina, on the island of Maui! The first route takes you to Lanai in 45 minutes, and runs 5 times a day, while the other ferry runs twice a day to Molokai, with the journey taking around 90 minutes. However, if you’re in search of something a little more memorable that will take up a whole day in your itinerary, we recommend one or more of the boat tours listed below...

Snorkel and picnic on the Na Pali coast
with Captain Andy’s Sailing Adventures

Head to Kauai’s Port Allen, where your enormous and opulent catamaran awaits you! Dig into a continental breakfast as the boat sets sail alongside the famously breathtaking Na Pali coast! You’ll see rushing waterfalls, lush green valleys, dramatic cliffs and lava tubes, all narrated by your knowledgeable and friendly crew, who will fill your ears with tales of history and legend as you take in the spectacular views! You’ll stop at a tropical reef, where you’ll have the chance to snorkel and see the brightly colored world beneath the surface of the ocean, working up an appetite for a deli lunch picnic and a refreshing beer back on deck. This is a fantastic day to remember, topped off with Hawaii’s excellent cuisine, and well worth including in your holiday itinerary!

Island-hop aboard a luxury yacht
with AdventureSmith Explorations

Place yourselves in the trustworthy hands of travel experts AdventureSmith Explorations for a mini eight-day cruise around the archipelago, embarking from Molokai and concluding at the Big Island, with stops at Lanai and Maui along the way. Greet each day with morning yoga sessions, out on the deck, followed by fruit and freshly-baked pastries. Your days will be brimming with activities such as visiting significant museums and cultural sites, snorkeling, paddle-boarding, kayaking, whale watching, and hiking to waterfalls and volcanoes. After each busy, fun-filled day you’ll head back to the boat for the evenings to unwind with a complimentary massage before a delicious dinner and a glass of wine – does it get any better than that?

A day trip to Molokini

One of our favorite sailing adventures to enjoy in Hawaii, this day trip is cherry-picked from our dreamy 2-week Hawaii itinerary, and is a perfect addition to your vacation if you plan on staying in Maui at any point. Molokini is a small, half-moon shaped volcanic crater, partially submerged just off the coast of Maui, now teeming with tropical wildlife both above ground and below the water, including a huge number of gorgeous seabirds that call Molokini their home. You’ll be sailing there on the Malolo catamaran from Maui’s Maalaea Harbor, stopping in multiple spots for some snorkeling, including a visit to Turtle Town, where you’ll find yourself amongst the rare green turtles! You’ll enjoy breakfast and lunch onboard the Malolo as well, and you’ll be back at your vacation rental by the evening to put your feet up and have dinner after an exciting day at sea!

Enjoy a Friday night dinner and fireworks
aboard the Makani catamaran

Oahu is mainly known for being a surfing hotspot, but there are some awesome sailing opportunities here as well! This Waikiki evening cruise is without a doubt one of the best ways to see the Honolulu skyline, lit up by its traditional Friday night firework display. You’ll be whisked away on the Makani catamaran, where you can spot turtles and dolphins, and in some seasons, humpback whales! Out on the open ocean, you’ll see some of the most amazing sights that Oahu has to offer, including the majestic Ko’olau mountains and Diamond Head Summit. Bask in an exquisite Hawaiian sunset before taking your seats in the open-air dining area for a tasty, island-style dinner buffet and then kicking back to watch the impressive fireworks display!

Discover a Hawaiian location of your choice
on a Sail Trilogy island tour

We’re concluding our guide to sailing the Hawaiian Islands with this magnificent choice. Sail Trilogy mainly operates out of Maui and has been consistently voted as the number one sailing company in Maui for the past 45 years! However, it does also boast a vast range of tours to various destinations, each with an extraordinary itinerary! Simply pick the tour that sounds perfect for you and go from there! Some Sail Trilogy highlights for us include the Discover Olowalu tour, where you’ll spend the day in Maui’s ‘mother reef’ getting acquainted with all the brightly-hued corals and tropical marine life that live there, or the 2-hour deluxe Ma’alaea sunset whale watch, where you can witness these amazing creatures frolicking in the waves during the golden hour. Or, what about spending the day getting to know the lesser-known island of Lanai on Sail Trilogy’s flagship Discover Lanai Tour? You’ll have the chance to swim, snorkel and play volleyball in the beautiful Hulupo’e Bay, hike through Lanai’s natural paradise landscapes, and take a historic island tour. The cherry on top: a mouth-watering BBQ lunch, a staple of the Sail Trilogy Tours. Don’t forget your camera – this day will be full of moments you’ll want to capture!

Feeling intrigued by the idea of sailing the Hawaiian Islands, or just feeling inspired to plan your next vacation in these incredible islands? Ready to take the plunge? Head over to our rentals page to find your perfect vacation rental for your trip to Hawaii, and check out our blog to discover our incredible 2-week Hawaii itinerary!

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