5 Best Islands for Starting Over in 2016

July 23, 2015

Ditch the car. Walk to the beach. Stay for the sunset. This could be your new routine.

Best Islands for Starting Over | Isla Holbox Mexico
Isla Holbox, Mexico Shutterstock

Just a two-hour drive and a ferry ride from hectic Cancun lies an island that feels like the other side of the planet, with a few hammocks (invented by the Maya here in the Yucatan — de nada) and 20 miles of white beach, a handful of low buildings comprising “downtown” and clear water for miles. Peaceful but impressive whale sharks visit ofshore in some seasons. Tourists also visit the island, but mostly for the same reasons people live here: warmth and peace.

Best Islands for Starting Over | Dominican Republic
Dominican Republic Shutterstock

One of the largest countries in the Caribbean, the DR has a distinctive culture with its own cuisine, literature and dance, which means living here feels less like a permanent vacation and more like real life in a real place. Working in the island’s varied economy (with longer- term work visas available) will integrate you even more. The DR has strong ties to the States and regular nonstop fights, in case you don’t want to start over completely.

Best Islands for Starting Over | Raratonga, Cook Islands
Raratonga, Cook Islands Shutterstock

Picturing a new life on a tropical island? You’re probably picturing Rarotonga — remote and quiet at Muri Beach with its iconic lagoon, or more remote and even quieter on Manuia Beach on the sunset side. Spend evenings chatting with fishers and pearl farmers. Getting here can be pricey as fights are few, but once here, the cost of living is low relative to other South Pacific islands, making this strand of paradise an even better deal.

Best Islands for Starting over | Thailand
Koh Samui, Thailand Shutterstock

On Thailand’s second-largest island, there’s always something going on, with a thriving local arts scene, sailing regattas, religious festivals and vibrant nightlife. If there’s a slow moment, get a Thai massage (not your average back rub) and enjoy the local version of Thai cuisine. The supportive expat community eases transitions and homesick- ness. Varied parts of the island suit various moods — hopping Chaweng for urban action, more secluded bays like Laem Sor on the southern coast for serenity.

Best Islands for Starting Over | Madeira

This Portuguese island of the coast of Morocco has warm summers and mild winters, a climate close to perfect. People walk for transportation and recreation on a network of trails (about 600 miles worth) used to service irrigation canals called levadas that run through the mountainous interior. Tell what month it is here by what flowers are blooming — poinsettias in May, orchids in December. The sweet wine that shares the island’s name is available year-round.


More Destinations