Island hopping isn’t as common in Hawaii as it is in places like the Caribbean (the islands are just so big and far apart!), but if you’re itching to check off another Hawaiian Island from your bucket list, I’ve got the PERFECT thing.

On my last trip to Maui, I finally did Trilogy’s Discover Lanai Tour. It’s their most popular tour, and I’ve been wanting to check it out for a while.

Here’s the scoop:

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Visit Lanai with Trilogy’s Discover Lanai Tour

Trilogy has a big legacy on Maui…they were the first company to offer sailing excursions on Maui and they just celebrated their 50th anniversary.

While they offer a bunch of different snorkel and whale watching tours around Maui, their flagship tour is their day trip to Lanai.

There are other companies that take you to spots off of Lanai to snorkel, but Trilogy is the only tour operator that actually lands on the island. And they’ve put together the PERFECT itinerary for a day of fun in the sun.

Discover Lanai Tour Itinerary

There are four options for this tour every day (an early morning and a late morning departure from both Kaanapali Beach and Maalaea Harbor).

Since I was staying in Kapalua (and still running on mainland time), I picked the early morning tour leaving from Kaanapali Beach.

The tour leaves from Kaanapali at 7AM, but you need to arrive by 6:30AM to check in.

They’ll validate your parking if you park in the Sheraton garage (you’ll still pay about $15), but at this hour it’s pretty easy to get one of the free parking spots in the public parking section of the garage (not the main section and you won’t go through a gate to park).

We met on the beach in front of the Sheraton (right near the public beach entrance) and got loaded up on the boat quickly and after getting settled and a quick safety spiel, we were off!

*This tour loads from the beach which means you have to wade through knee deep water to get to the boat’s ladder. They time each person’s entry with the waves so you shouldn’t get wet but I usually like to take off my shorts just in case.

It took just over an hour to cruise over to Lanai and it was smooth sailing. We were served warm cinnamon rolls, fresh fruit, and coffee pretty quickly after we boarded and then just before we got to Lanai, they brought out warm breakfast croissant sandwiches.

When we got to Lanai, we docked at Manele Harbor, gathered our things and did the quick walk (about ¼ mile) to Hulopoe Beach. The crew also had some golf carts if you’re not able to walk that far.

Once we got to the beach we had about 2.5 hours to spend on the island. They have a great set up on the beach with chairs, mats, plenty of shade and a snack and drink station.

The snorkeling is right off the beach and the crew is there to help you get your gear and time your entry in between waves. There are also a couple of crew members further out on surfboards to keep an eye on everyone.

I was actually pretty impressed with the snorkeling…I think it’s one of the better spots I’ve been to in Hawaii.

But what I really LOVED about this setup is that you can snorkel for however long (or little) you want and when you’re done, you’re on one of the best beaches in Hawaii.

There’s also a short hike you can do up past the tidepools for a great view of Pu’u Pehe Rock.

The time flew by (I could’ve stayed here all day) and a little before 11:30AM we packed up our things and walked back to the harbor for lunch.

If you’ve ever done a snorkel tour, most of the time “lunch” consists of a sandwich and bag of chips, but this is a BBQ lunch in a large pavilion overlooking the harbor.

We had salad, rolls, kiawe-wood grilled chicken, corn on the cob, and stir fry noodles all served at the table. And there was plenty for seconds!

They have adirondack chairs and corn hole set up on the lawn plus the general store down below has a great gift shop (with Trilogy and Lanai merch).

After lunch, we loaded back up on the boat to sail back to Maui. They opened the bar up plus we had ice cream sundaes just before we landed.

And we saw dolphins!

We were back on Kaanapali Beach by 2:30 PM and spent the rest of the afternoon shopping at Whalers Village and hitting Monkeypod for happy hour. What a great day!

***Want to save major $$$ on your trip to Hawaii? I get asked ALL the time how I’m able to travel so often to Hawaii and stay at really nice resorts. Well, my favorite travel hack is cashing in points to score free airfare and free nights at some of Hawaii’s most high end resorts. Read my full guide on the exact system I use to max out credit card rewards here. Seriously, it’s going to save you soooo much money.

Let’s Talk Numbers – Is It Worth It?

By now you’re probably thinking “sign me up.” But let’s talk numbers first…it’s definitely expensive. Everything in Hawaii is expensive now.

The tour is $289/adult ($255/teen, $190/child, 2 and under are free) before tax and tip. And it’s a little bit more if you leave from Maalaea.

For a family (even a couple), that’s a lot of money.

So is it worth it?

Everything is relative, but I would emphatically say YES. This is a HIGH VALUE excursion.

First of all, it’s 8 hours. In comparison, my other favorite snorkel trip on Maui is $279/person for a 3.5 hour trip.

Also, they’re basically feeding you all day. We had cinnamon rolls, fresh fruit, coffee and juice plus hot breakfast sandwiches on the boat over to Lanai. On the beach, they had water and popcorn set out (plus reef safe sunscreen to use). Lunch was pretty extensive (salad, bbq chicken, stir fry noodles, corn on the cob). And there was a top shelf open bar on the boat ride back (plus ice cream sundaes).

And the service is top notch. This really is a luxury cruise. You’re never standing in line at a buffet…everything on the boat and at lunch in the pavilion is served to you and they are ON IT.

But honestly, the biggest selling point here is the flexibility to do what you like to do. Because the snorkeling on this trip is all done from the beach, you can get in for as long (or as little) as you want and there’s plenty else to do.

Actually quite a few people on our boat didn’t even go out to snorkel at all. So if you have a mix of people in your travel group (some older, some younger, some who want to snorkel, some who don’t) everybody can just do what they want to do. Whereas when you go out on a snorkel boat to an offshore location, if you don’t want to snorkel you’re just stuck sitting on the boat.

And like I said, the beach here (Hulopoe Beach) is spectacular and there’s plenty of shade plus a great short hike if you’re not the type who likes to sit still.

So I would really think of this like an excursion to another island that also happens to have great snorkeling instead of just a snorkeling trip.

Trilogy’s marketing campaign for this tour says that “Discover Lanai is sure to become your favorite day of vacation!” and you know what? It was!

P.S. One of the reasons I’m able to travel to Hawaii so often is because I get free flights with my Southwest credit card AND I can fly someone with me for free with my Companion Pass.

I have this Southwest Premier Rapid Rewards Visa card through Chase. The current sign up offer is 50,000 points. Depending on where you live and fly from, that’s at least one completely FREE ticket to Hawaii and it could be two depending on the time of year (or more if you catch a crazy sale).

But the real pro travel hack is getting the Southwest Companion Pass.

If you acquire a certain amount of annual points with Southwest (either through flying or credit card spend), you get a companion pass where you can bring someone with you on every flight you take FOR FREE for the entire year. I can’t tell you how many thousands of dollars I save using this every year.

What makes this doable is that the sign up bonuses from Southwest credit cards goes towards the point requirement.

By far the quickest way to qualify for the companion pass is by signing up for a personal AND business card through Southwest.

**Besides being a business owner, if you’re self-employed, a freelancer or contractor, a gig economy worker, if you own rental properties, etc…you qualify for a business card.

And you’ll be most of the way towards qualifying for a Companion Pass PLUS you’ll have 110K points to book flights to Hawaii. That’s enough points to book 3-4 flights to Hawaii! AND you can take someone with you for FREE.

P.P.S. Here’s one more really important thing you need to know before your Hawaii trip…

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii and a lot of state and national parks have instituted reservation systems at some of the island’s most popular spots to help manage the crowds and make things a little more sustainable.

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan.

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too.
Get that info >> HERE