The slogan Maui No Ka Oi! means, “Maui is the Best.” Conde Nast Traveler readers have agreed, voting this beauty as “Best Island” for 20-plus years. The historic whaling town of Lahaina is a perennial “must do,” with galleries, cafes, Friday Night art walk, and harbor bustling with snorkeling, whale watching and sunset dining excursions. 

Castle features accommodations on West Maui’s Kaanapali Coast and South Maui’s Kihei. Both are prime springboards for exploring artsy upcountry towns en route to the majestic summit of Haleakala. Or tackle the serpentine road to Heavenly Hana, where waterfalls, rainforests and stunning coastline overwhelm the senses. 

If you’re into snorkeling, hiking and windsurfing, the 734 sq. mile “Valley Isle” has you covered with lush rainforests and powdery beaches to eclectic Upcountry towns like Makawao. From December through April, this humpback playground often delivers close encounters during whale watching excursions.