Traveling to Wailea 12/28-1/4

Question

My husband, teenage daughter and I will be staying at the Fairmont in Wailea at the end of the year. It is our first time in Maui and would love to hear about any local favorite restaurants, bars, shopping, beaches that we need to see. We love to eat, wander around, but mostly we like to hang out at the beach. Would appreciate your recommendations as I know it will be a busy time of year for tourists.

Answer

That sounds like a wonderful trip — staying at gives you a great home base in Wailea. End-of-December through early January is a busy time, but also a beautiful time to enjoy Maui’s beaches, restaurants, and vacation vibe. Below are my top picks — for beaches, eats & drinks, shopping / wandering, and a few bonus ideas — all mindful of a family with a teen and beach-loving plans.

🌊 Beaches & beach-side fun near Wailea

Ulua Beach — A calm, family-friendly beach just a short walk from many Wailea resorts. Great for swimming and, when conditions are good, snorkeling — there’s a reef not far offshore. Facilities are decent (parking, showers, restrooms), which makes it easy for a beach day without too much planning.
Keawakapu Beach — A beautiful stretch of sand near the border of Wailea and Kihei, often less crowded than bigger resort beaches. It’s ideal for a relaxed beach afternoon and sunset strolls.
Makena Beach (Big Beach) — If you’re up for a short drive south of Wailea, Makena Beach delivers expansive golden sand, lots of space, and a wild-Hawaiʻi beach vibe. It’s a great place for sunbathing, sandcastle-building, and beach games — though ocean conditions can be rough, so check surf advisories before swimming.
Take a walk (or bike) along the Wailea Beach Path — a paved coastal path that stretches roughly 1.5 to 2.9 km depending on where you start. It’s perfect for early-morning strolls or sunset walks, and links many of the beaches, resorts, and public-access points.

🍽️ Restaurants, bars & local eats — family-friendly and fun for teens

— A laid-back but lively spot known for good food, wood-fired pizzas, island-style salads, and cocktails (and non-alcoholic drinks) — a nice mix if you want something casual after the beach. Great for families and offers a fun vibe.
(at The Shops at Wailea) — For a more modern, island-inspired meal, Lineage offers creative dishes drawing on local flavors and comfort-food style cooking. It’s especially nice if you want something trendier and slightly more elevated than pizza or burgers.
— If you’re up for a more scenic, special-occasion dinner, Ferraro’s (at the nearby Four Seasons) offers oceanfront dining and a romantic, elegant atmosphere. Sunsets here are especially lovely — worth at least one splurge night.
For a quick & easy bite or to pick up supplies: the eateries and market-style vendors at The Shops at Wailea — good if you want flexibility (grab-and-go breakfasts or snacks between beach days, or a casual lunch after shopping).

🛍️ Shopping, wandering & laid-back exploring

The Shops at Wailea — an open-air shopping center with boutiques, art galleries, souvenir shops, and a variety of restaurants. Great for an afternoon or evening stroll when you want a break from the beach.
Use the Wailea Beach Path for beach-hopping or just easy walking — early morning or sunset strolls along the coast are a nice way to soak in Maui’s vibe without relying on cars.

📅 Some bonus ideas & tips considering your travel dates (12/28–1/4)

Because this is peak season, beaches and popular restaurants may be crowded — go early to secure a good beach spot, and make dining reservations when possible (especially at spots like Ferraro’s or Lineage).
Switch it up between chill beach days (Ulua, Keawakapu) and at least one day drive south to Makena Beach for a different vibe and lots of beach space.
For convenience and flexibility — when you don’t want to commit to a full sit-down meal — use The Shops at Wailea for quick meals or snacks, especially useful with a teen.
Balance beach time with a nice dinner out (e.g. Monkeypod for casual + fun, Ferraro’s for a splurge). A mix can keep the trip relaxed but also special.
Don’t forget some downtime: early-morning beach walks on the path, sunset watching, and letting your daughter explore — sometimes those unplanned moments end up being the best memories.

In short — you’re in a great spot. With a base at Fairmont Kea Lani, you’ll have easy beach access, and there are enough options nearby to keep each day varied: a mix of chill beach lounging, good eats, casual shopping, and a special night out or two.

Mahalo — and you’re going to love Maui!

Traveling to Wailea 12/28-1/4

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