Ask Oyster: Unique, friendly, winter escapes that won’t break the bank

by William on October 26, 2009

Question: Karen

I own a restaurant, the only time we get to take a vacation is when we close for the month of January. I would like to know where you suggest going and where to stay. Here are my requirements….SUN, WARM, FRIENDLY PEOPLE. Preferably not a lot of children. We don’t like to just throw away money so luxury is not required, but not uncomfortable. Here are some of the places we have been and enjoyed….Costa Rica, St. Thomas, St. Marteen(eh?), Belize, Florida Keys.

Answer: Will Begeny, Oyster’s Senior Editor

Karen, you sound like my kind of traveler. Presumptive sleuthing suggests that, since you own a restaurant, you care about food. As such, I’m going to rule-out the all-inclusives.

Consider Jamaica. It has the mountainous, exotic beauty of Costa Rica (without the foot-long insects and dangerous tap water), the convenient, well-developed comforts of St. Thomas (without the cruise ship claustrophobia), the distinct local culture of Belize (and more ways to indulge in it), and the good-natured, low-key fun of the Florida Keys (forgiving, partially, Jamaica’s socio-political homophobia).

The Cliffs, in Negril, Jamaica

The cliffs at Catcha Falling Star in Negril, Jamaica

In particular, in the incredibly laid-back hippie haven of Negril, there are a number of unique hideaways perched along its coarse rock cliffs—few of which allow children, for safety’s sake. Of these, take your pick: the Rockhouse Hotel; Tensing Pen; Catcha Falling Star (if the other two are booked). If you’d rather  be on the beach, check out the Negril Tree House (gorgeous beach) or Jake’s (cute, artsy hotel on the remote, uniquely beautiful, black sand beaches of the South Coast, near Floyd’s Pelican Bar).

The isolated beach at Natura Cabanas in Cabarete, Dominican Republic

The isolated beach at Natura Cabanas in Cabarete, Dominican Republic

Alternatively, in the Dominican Republic, there’s a lively, kite-surfing town called Cabarete, populated largely by European expats who bring excellent restaurants and great nightlife. Consider Natura Cabanas, a quaint, eco-boutique set along an isolated beachfront—its bathrooms are gorgeous and in January, don’t sweat its lack of air-conditioning (couldn’t help myself).

Or, if you’re willing to make up the cash spent on the flight by cooking your own meals, check out the Ke Iki Beach Bungalows in Oahu, Hawaii. As for Hawaii, the rumors are true: it is a tropical paradise, and the people do make hearts smile.

Have any other travel or hotel queries? Ask Oyster! Send your questions over to askoyster@oyster.com. We’ll select a few to answer and post ‘em up as part of our recurring Ask Oyster feature.

Previous post:

Next post: