Hi there, we are planning our summer trip and have narrowed it down to Maui or Anguilla.
I’ve heard the beaches of Anguilla are among the prettiest in the Caribbean, which has the snorkeler in me salivating. On the other hand, I’ve read that Maui – while there are nice beaches – is more of an adventure.
Does anyone have any experience with either of these, recommendations, etc.?
The Maui fire happened the day we were supposed to arrive, so we pivoted and went to Kauai which I would highly recommend.
Our plan in Maui was to do the road to Hana in two days, and just hang out at a resort near Lahaina. It’s not adventure in the zip line/rafting sense (I think) but a lot of waterfalls and interesting beaches, I think.
One thing to think about is the weather, and possibility of hurricanes in the Caribbean.
My vote is Caribbean for a winter trip and Hawaii for a summer visit (beautifully calm waters).
Have you been to either Hawaii or the Caribbean before? If not, then I can give some general thoughts. If so, then disregard these ramblings.
While not these two places specifically, I have spent time in both Hawaii and the Caribbean. I love both. And both will give you amazing beaches, great snorkeling, and an overall fabulous vacation - you really can’t go wrong. I have a slight preference for the Caribbean - the water feels warmer and a bit more inviting to me, and I like Caribbean culture. But again - Hawaii also has beautiful water and a fascinating culture, so there is no wrong choice. Honestly, the way I would choose is if you are on the East Coast, then the Caribbean, if you are on the West Coast, Hawaii, just for the sake of easier travel. And check overall costs, if that is a concern - Hawaiian hotels tend to be very pricey.
Kauai is wonderful and greet snorkeling - we did a sea turtle snorkeling trip there which was fantastic.
This is an excellent point. I did once get caught in a hurricane during an October trip to the Caribbean which killed about 2 days of the trip while we sheltered in place - but at a fantastic bed and breakfast so it still wasn’t too bad.
Never to Hawaii, but to the Caribbean several times: Culebra (twice), San Juan, St. John, Cancun, Cozumel
Ah go to Hawaii then 
If I lived on the east coast I’d go to Anguilla.
West coast, Hawaii.
All the east coast people I know think it’s just easier to go to the Caribbean. But if you’ve never been to Hawaii and can spring for business class, then go for it.
Maui has prettier scenery than Anguilla. Anguilla is very small and I don’t remember the snorkeling being as good as the snorkeling off Maui. Maui is mountainous. Anguilla is flat.
Anguilla is less touristy and less crowded. Of course, Maui lost Lahaina in the fires which was a great and historic spot.
If I recall correctly, you’re not on either coast?
It kind of depends on what you like to do.
If you go to hang out on the beach, enjoy the water, and not a lot else, then the Caribbean is fine. We own a timeshare on Grand Cayman, so we’ve been there many times. We’ve also been to other islands.
In Maui there is a lot more to do. We like to go to both Maui and Kauai. We live on the east coast so we go for 2 weeks.
We haven’t used them for years, but there are some blue Books, I think one is called Maui Revealed, which are pretty good and taking a look might give you a sense of all there is to do on Maui.
You also do have to worry about hurricanes in the Caribbean in the summer.
I’m in Davenport. It’s about $200-$300 more per ticket to fly to Hawaii – not insurmountable. We’ll fly out of MLI (Moline – local, across the river)
This would be a 1-week trip.
The last few times in the Caribbean have been in the summer, and there have been clouds and brief spats of rain, but no hurricanes.
Snorkeling is my favorite activity – we pack lunches and go beach-hopping, then go out for dinner.
Maui has awesome snorkeling, including (hopefully) seeing big sea turtles and lots of them.
I swam with a turtle off Tamarindo Beach on Culebra. It was a really cool experience.
I had some time between jobs earlier this fall and my wife and I went to Maui for a few days and did the Road to Hana. It was my first time to Hawaii, and — maybe I’d built it up too much in my mind — but for the first day or two (before we did the road to Hana; we were just in the Wailea area) it felt a little underwhelming, in a “did we pick the right island?” kind of way.
The road to Hana, though, was great, in part because we rented a great Jeep (via Turo; highly recommend one that has a roof that opens up) and we used an AMAZING audio tour on our iPhone from GuideAlong (this one). The app knows where you are (because of the phone’s GPS) and the narrator chimes in with this awesome, confident voice and great suggestions for exactly where to stop. Like, he tells you where to look for coconuts, and you park and look around, and, sure enough: coconuts! And you open one up and drink/eat it right there on the beach. He points out several "must stop"s along the way, as well as things that are best skipped.
We did the drive across two weekdays (staying in Hana in between). The stay in Hana was underwhelming as well, but it was a good idea to split the drive up across two days, and I don’t want to think about what the drive would be like on a weekend during the busy season. The app was $15, and was easily the best purchase of the trip.
Oh, if you’re into hiking, I also recommend the Pīpīwai Trail at Haleakalā National Park (don’t forget your annual National Parks Pass if you have one!). We did that the morning after we stayed in Hana, before driving back.
I’m the hiker; she loses interest after about a mile. hehe. So usually we rent a vehicle (golf cart on Culebra…) and get around that way.
I am so glad we made the effort this summer - all the way from the east coast.
We took a day flight and economy plus was plenty comfortable to read, watch movies, etc. and upgraded on the red-eye return.
Lots of little hikes in Hawaii - a mile or two to a waterfall, or even shorted to a hidden beach. Happy compromise
We also used an app (the Shaka Guide one) and it was great. We discovered lots of spots we would not have seen otherwise.
If feels like a big commitment trip since its so far, and you have the time, I recommend hitting several islands. We flew into Honolulu so stuck around to explore Oahu for a couple of days, then the Big Island (which personally I feel, been there done that, but we were happy to take the kids - missed the lava flow 
) and Maui turned Kauai bc of the fire. Anyway, the point I was going to make is, if all you have is carry-on luggage and TSA pre check, hoping islands was as easy as riding a bus.
We will be back for Maui and more of Kauai for sure.
You’ve narrowed your choices to two very different islands in my opinion. I spent a day trip in Anguilla about 20 years ago and from what I recall, the beach I visited, Shoal Bay, was amazing. I can’t speak to snorkeling since I am not a swimmer but I was staying in St Barts and I think people interested in that part of the Caribbean (Anguilla, St Barts, St Martin) suggested Saba for the best snorkeling. Saba isn’t too far from Anguilla so doing a day trip there shouldn’t be a problem.
I just so happened to have visited Maui this past summer returning a few days before the Lahaina fires. This was my second time there and Maui is fantastic for snorkeling, among many other things. My kid loves to snorkel and wanted to swim with Sea Turtles and was able to do exactly that without much effort. In fact, I was able to be a few feet from them myself at the Black Rock Beach, where some came within a few feet from the shore where I was standing in shallow water. Absolutely incredible to witness! Maui offers so much natural beauty that I would definitely pick it over Anguilla if you want more than just the typical beach relaxation experience. You can drive to the top of Haleakala and watch an amazing sunset (I recommend this over the sunrise which requires too early start time), see some beautiful waterfalls and surf! I am on the east coast so making the trek to Hawaii takes much more effort but since you are not on the coasts, traveling to either place would be a wash I suspect. Feel free to DM me with any specific questions.
The last time we were on Culebra, there was some construction, so we couldn’t take the usual hiking trail to Carlos Rosario Beach – IMO the prettiest beach on the island and some of the best snorkeling. So we decided to try to hike up the west coast starting at Tamarindo. We made it over and around several huge boulders and all sorts of smaller rocks, about two-thirds of the way there… and then she decided to stop. I was incredulous. lol. “We’ve come so far!” We could see the point separating Tamarindo Grande from Carlos Rosario… and while it looked daunting, I wish we at least would have tried it. lol, next time the normal trail will surely be open.
Something else to keep in mind, depending on the length of your vacation, is the time it takes to fly to Hawaii (11hrs) if you’re traveling from the East Coast versus going to the Caribbean.
When I went for my honeymoon the jet lag was more than I expected. Fortunately I was there for over 2 weeks but coming home was the same in reverse 
.