Hawaii has always seemed like a bit of an anomaly to me, as you travel a huge distance and it feel worlds away from home, yet don’t need to pack your passport. I spent three consecutive Januarys in Maui soaking up the sun, salt water, and sand, and would travel back there again in a heartbeat. Maui truly feels like paradise found, and is worth every second of the long (and often costly) flight. I would recommend booking a minimum of 7 days to make the travel worth it, and leaving plenty of open time in your itinerary to soak up all of the beautiful, natural offerings that this lush paradise has to offer. Read on for my Maui, Hawaii travel guide.
Where To Stay
There are different stretches of beach within the island that each have their own flavor and personality, and are all excellent options for residing during your trip. Kaanapali, Wailea, and Kapalua are my top picks for areas, and I stayed for three years at the Kaanapali Alii. This condo-style hotel has a beautiful pool, is directly on the beach, and was an easy home base for exploring the island.
What To Eat
Lahaina Grill – In the “downtown” area of the island, this classic spot is consistently on the “best” lists for dining, in both the Hawaiian Islands and the US as a whole. The food is fantastic, year over year, and the ambiance feels like a blend of Hawaii and old-world Charleston. From grilled fish to foie gras, you can’t go wrong with anything here, especially for a special occasion dinner.
Merriman’s – Hand’s down my favorite restaurant on Maui. Located on the premises of the Ritz Carlton residences in Kapalua, this feels like the ultimate manifestation of Hawaiian farm to table dining. Go early, and sit on the terrace overlooking the cliffs and ocean next to the fire pits for the perfect sunset experience. Don’t forget to make a reservation here.
Spago at the Four Seasons – Wolfgang Puck’s quintessential Maui eatery at the Four Seasons is gorgeously designed, open to the ocean air, and home to one of my favorite dishes on the island – the spicy ahi tuna poke in sesame-miso cones. We’ve literally ordered these to-go before and eaten them sitting in the lobby of the hotel.
Kula Lodge – No upcountry trip (see details in the next section) is complete without a lunchtime stop at Kula Lodge. The view itself would be reason enough to stop here, but the food is also simple and lovely. We had a mung bean curry that the owner came out and told us all about, as well as some lovely grilled fish.
Ono Gelato Company – No vacation is complete without ice cream! Stop off at Ono in the heart of Lahaina to get your sweet tooth-fix.
What To Do
Depending on where you stay, hotels tend to offer a myriad of options for activities. We did paddle boarding, snorkeling, and a sunset whale watch during migration season, which was absolutely incredible. Here are a few other favorite options:
Surfing Goat Dairy – Charming and whimsical, we visited this dairy and sampled goat cheese flights and goat cheese truffles to our heart’s content.
Upcountry Drive – If you love a good road trip, take the winding road “upcountry” to Haleakala Crater, the highest point on Maui. Stop at Kula Lodge en route for a relaxing lunch, and check out the lovely little shops along the way, ending at Haleakala National Park.
Spa day at Grand Wailea – As if laying on the beach isn’t relaxing enough. If you really want to paper yourself, book a spa afternoon at the Grand Wailea. This stunning spa is absolute heaven. Bonus points: it’s next door to the Four Seasons, so stop there for a cocktail on your way out.
My favorite of the Hawaiian islands, Lanai is a short ferry ride away from Maui, but feels like another world. This island does not have the concentration of people (especially tourists) that Maui or some of the other islands do, as it was formerly and primarily used for pineapple plantations by the Dole family. There are two Four Seasons resorts on the island – one on the beach, and one at the highest point of the island, up in the clouds. Both are stunningly beautiful, remote, and worthy of your time. The higher Four Seasons boasts expansive grounds, a quiet croquet court, beautiful golf course, and is the perfect place for horseback riding at sunrise. The lower Four Seasons is perfect for its remote beachside, lovely pools, and sunset cocktails overlooking the water.