I figure we might lose a day in overall flight time. On the other hand, based on half an hour’s research, it looks like there are a couple of hefty layovers going from Moline to AXA (Anguilla). So it may be a case of… six of one, half-dozen of the other.
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Absolutely! I have been to Anguilla as well, and it is a gorgeous island with amazing beaches, snorkeling and water, but the planes, trains and automobiles to get there would have me thinking twice before going again. And I’m not a fan of those little planes you sometimes have to take to island hop. 
I think Hawaii is fun if you’re someone who likes to be active on vacation. There’s definitely more to do.
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Some others have commented here, but it can depend on where you live…it takes a LOT less time to get to Hawaii from the West Coast then from the East Coast or Midwest. That said, it takes a long time to get the Caribbean from the West Coast, especially if you’re in a city that’s not well connected.
As for being adventurous, Maui can be as adventurous or non-adventurous as you’d like. As for Anguilla, I’d say it would be a little less adventurous than Maui, but it depends on you and your preferences and what you like to do. Both places do offer the chance to lie on the beach and stay at a fancy resort…compared to Anguilla I wouldn’t say Maui is more of an adventure, unless you’re very outdoorsy…
Also, keep in mind…Hawaii is a state, so you just need your driver license to travel there…
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We were thinking about a Florida vacation this winter. But now you all have me thinking about Hawaii or Carribean
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If you decide on (and haven’t been to) Culebra or St. John, those are fresh in my mind – feel free to DM questions.
We loved St. John, but that was 20+ years ago. I’m afraid it’s changed.
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Do let us know your decision.
If it helps at all, my son went to Maui and Kauai on his honeymoon, and they would say they liked Kauai more. To be fair, they stayed in a fancy place in Kauai and not so much in Maui, and they LOVED the helicopter tour over Kauai.
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If you’re looking for snorkeling, of all the Hawaiian islands, Maui offers a greater selection of off beach snorkeling. I’ve extensively stayed on them all, lived on Big Island, and go to Maui about 2x annually.
I’ve snorkeled the Caribbean, but other than Roatan (the second largest barrier reef in the world), I’ve been disappointed by the experience. The water is divine though!
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Have not been to Kauai or Molokai; Maui and the Big Island are tied as faves for me.
The thing about snorkeling - I’ve snorkeled extensively in both Caribbean and Hawaiian waters: The water is clearer in Hawaii because of the “newer” sand/ocean floor (lava). Not as much bio life stirring things up.
If that’s your major vacay jam, I’d opt for Hawaii. Snorkel the Molokini volcano crater, if it’s still accessible (most of the boats that take you there left from Lahaina) - also there are small Zodiac boat tours of lava caves and such where some snorkeling can be included.
Road to Hana is great, there are things to do when you get there (standing under a towering waterfall, Lindbergh’s grave, some cool hikes like through a bamboo forest, a hidden red sand beach, etc etc - all easily accessible and not overrun with people, at least not when I went). Sunrise on Haleakala is amazing. Bring a warm hoodie!
That said, the day you lose coming and going is intense - big time change and jet lag involved, at least for me. I wouldn’t go to Hawaii for just a week. Can you extend?
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I think it’s absolutely beautiful, but man, the driving was white-knuckle. Up, down, 180-degree curves, driving on the left, narrow roads.
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I could try – maybe work some days off to make up the time. PTO kind of sucks, unfortunately.
Maui is my fave of the 4 largest hawaiian islands. Tons to do there.
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We love Maui. We go every years for several weeks. We go in the winter tho so don’t know much about Maui in the summer. I believe that there are dolphin watch cruises whereas we go on whale watches.
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Yes, we did go on a whale watching cruise on Maui and DID see some whales. It was in the spring, I believe. Whales are generally there from September until April or May, and then they head up to Alaska.
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I think the best time for whales is Jan - Mar.
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You’re probably right about the BEST time, but whales are spotted before and after that window and whale watching cruises help provide information to one another to help their customers spot any whales that may be around.
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For Maui, it does seem like the Lahaina / Kaanapali area with the resorts is the popular place for tourists to stay. However, it is not in a very convenient place on the road network if you want to explore the island. The road network basically has a short road between Kahalui (where the airport is) and Kihei, then roads radiating out from there, one of which goes to Lahaina / Kaanapali.
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Actually, Wailea and Kihei are fine places to stay as well as closer to the airport. We have stayed there as well as at Kaanapali (on different trips over the years).
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Which of those would you say has the calmest, clearest beaches?
Wailea has very calm lagoons right outside the gorgeous and expensive Four Seasons hotel (we stayed in cheaper hotel next door). I’m not familiar with the other beaches as I’m not much of a beach person.
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