Help me choose...please!

Question

Hi. Our daughter is getting married on Kauai and we are coming to Maui for five nights after. We are looking for rest, relaxation, beautiful property and to be pampered (after all of the wedding hoopla). We are also celebrating our 30th anniversary, so we want it to feel super special!

We have five nights and are between Hotel Wailea, the Fairmont, and Grand Wailea. I usually am drawn to smaller boutique resorts, but I'm not sure Hotel Wailea is the right choice since not on the beach? I'm not opposed to hearing other suggestions in the same category. We are also considering the first night at Paia Inn so that we can start the Road to Hana early the next morning. But I also am not sure it's worth the hassle of moving hotels?

Thank you in advance and these forums are always so helpful when planning somewhere you've never been!

Answer

First — congratulations on your 30th anniversary! That’s a wonderful reason to make your Maui stay after the Kaua‘i wedding feel extra-special. All three of the resorts you’re considering — , , and — have their strengths. Which is “best” really depends on what kind of anniversary-style vibe you want (quiet & romantic, resort-luxury & beach, or full-on resort indulgence). Below I compare them — plus thoughts on the separate idea of staying one night at to start the Road to Hana early.

How the three main resorts compare for a 5-night “celebration / pamper / relax” stay

Hotel Wailea — Boutique, romantic, and ideal if you want a quieter, more intimate, “grown-up” atmosphere. It’s adults-only and tends to attract couples rather than families, so chances are you’ll have more peace and tranquility rather than pool-noise or kids running around. The vibe is relaxed, refined, and suitable for a milestone anniversary where you want to unwind, enjoy your privacy, and maybe a fine dinner or spa-style relaxation. Some guests note the tradeoff is that it doesn’t sit right on the beach, so you may need to rely on shuttle or hotel transport if you want full beach access. If you value serenity over “resort buzz,” this could be the most special and low-key choice.
Fairmont Kea Lani — A good middle ground: a large, well-appointed resort with comfortable rooms, good amenities, and beach access, but less overwhelming than Grand Wailea. If you want convenience, comfort, and a nice balance of resort services without the sometimes hectic vibe of a mega-resort, this could be a strong fit. It may offer more privacy and calm than Grand Wailea, while still giving you resort-style comforts.
Grand Wailea Resort & Spa — The “go big or go home” choice. This is a massive, luxurious, amenity-packed resort right on Wailea Beach. It offers lush grounds, multiple pools, a full-service spa (in fact one of Maui’s largest), many dining and entertainment options — ideal if by “pampered” you mean spa days, gourmet meals, beach-front lounging, and no-stress resort living. The scale, variety, and convenience make this great if you want to settle in, be taken care of, and treat yourselves to the full luxury resort experience. On the flip side: because it’s big and popular, the atmosphere can be less intimate; pool areas may be crowded; and resort fees + dining + extras add up. Some guests say the size and crowds take away from a “private, romantic” feel.

Which to pick, depending on what you want

If you want a quiet, romantic, intimate, couple-focused spot, minimal fuss, and a sense of peace — go with Hotel Wailea.
If you want comfort, convenience, moderate luxury, beach access, but without mega-resort scale, consider Fairmont Kea Lani.
If you want full resort luxury, spa & pampering, resort amenities, beach-front comfort, and lots to do just on site — choose Grand Wailea Resort & Spa.
If you aren’t sure which vibe you’ll prefer, think about how much time you’ll actually spend on-property. If many of your days will be out exploring Maui (hikes, beaches, sightseeing), a boutique or mid-size resort (Hotel Wailea or Fairmont) may give the best balance. If you plan to mostly relax, unwinding at the resort itself, Grand Wailea might deliver more “luxury for downtime.”

What about staying at Paia Inn the first night, then moving to Wailea for the rest?

This idea has its merits — it allows you to start the Road to Hana early with minimal driving from Paia, which makes the drive and early-morning start more manageable. However, it also introduces extra logistics: packing up after travel, moving lodgings, checking in somewhere else, and possibly feeling rushed or tired. For a 5-night stay, moving after just one night may feel like a hassle (especially after a wedding and during an anniversary trip), which could undercut the restful, relaxed vibe you’re aiming for.

If it were me — wanting a restful, celebratory 5-night stay after a wedding — I’d prefer to unpack once at a dream-resort base (Wailea) and use a rental car or day trip for Hana — especially if I’m not ultra-driven to make the early start. The stress of moving hotels might outweigh the benefit of the early-morning Hana advantage. That said, if seeing Hana early is a top priority, the one-night at Paia Inn could work — just know it adds a bit of friction to an otherwise restful plan.

Other suggestions / alternatives to consider

If you like the idea of a boutique-style resort but with easier beach access or slightly different vibe than Hotel Wailea, there are other smaller or mid-size resorts around Wailea / south Maui worth a look — sometimes with better balance of luxury + intimacy.
Consider what matters most: adult-only / quiet vs. full-resort amenities vs. beach-front. If spa, pampering, and “resort as destination” is key, Grand Wailea and Fairmont stand out. If privacy, simplicity, romance matter more — Hotel Wailea shines.
Because you’re celebrating something special (30th anniversary), it’s worth splurging a little more for atmosphere, comfort, and ease rather than trying to over-optimize every dollar. Memories from such a milestone trip often come more from how the stay feels than a strict “value” calculation.

My Recommendation: If I were you…

I would book 5 nights at Hotel Wailea — it matches your stated desire for rest, relaxation, beautiful property, intimacy, and a feeling of “being pampered” (though in a quiet, boutique way rather than busy-resort style). I’d skip the one-night move to Paia — instead use a rental car or guided tour for a relaxed Road to Hana day (so you don’t disrupt the ease of your vacation). If as I suspect, much of your time will be spent relaxing, watching sunset, maybe spa or a nice dinner — Hotel Wailea delivers a great balance. That said — if you’d rather more resort-style pampering, with beach access and maximal convenience, then Fairmont Kea Lani would be my second choice (or even Grand Wailea if you want all-out luxury and don’t mind more bustle).