Barbados Itinerary: Five Days of Things to Do

There aren’t a ton of flights to and from Barbados. But if you’re in NYC, JetBlue does an easy one from JFK that’s about four and a half hours. It’s pretty comfortable. Once you arrive, the airport itself is tiny, so it’s really easy to find your way around and out. But you will notice that you can easily get outgoing flights to any other Caribbean island, Canada, and a lot of different parts of Europe. One year, after we had spent Christmas in Barbados, we all went to Reykjavik, where New Year’s is a really big deal. If you’re looking to have a hot Christmas and a cold New Year’s, there’s really no better way you can do it.

The main reason I’ve started going to Barbados is because my friend’s family has had a house there for a long time. He’s spent a lot of summers and holidays there. The house is on the water next to Gibbes Beach, which is my main tip: Stay on the water. If you’re there to surf, stay on the East Side, next to the ocean. But if you want those waters to be calm and chill, like I do, stay on the Caribbean Sea side, the West of the island. It should be pretty easy to rent a house on either side, through something like Vrbo or a luxury service like Altman Real Estate, throughout the year that is basically on the beach. If you would prefer to stay at a hotel, there are great ones there. The biggest luxury one is Sandy Lane (Sandy Lane St. James, BB24024, Barbados), where Tiger Woods got married. I’ve heard it’s nice, but you have an equally good experience if you just stay at a beach house. Plus, all the houses have a house staff and someone who is managing the property. They’ll cook for you, clean for you, give you recommendations for things to do, and connect you with people who can help you do them.

Altman Villa Rentals Royal Villa 26

Sandy Lane Resorts

In my experience, most of those houses also come with a driver. which is great; Barbados isn’t a big place, but it can be tough to get around without a car. There is a bus system, which I’ve taken into downtown, but it doesn’t run that frequently. The driver on staff at Miles’s house was able to take us everywhere we wanted to go during the trip. If you can’t hire someone through your house, Airbnb, or hotel, you should be able to get one either through the staff of your house or through one of the many car services available on the island, like Terrvette Tours, Five Star Fast Track, and Ambitious Tours and Taxi.

I’m not a big vacation shopper; I’m just super-meticulous about what I require and buy. One thing that’s nice is that the dollar is like, two to one, so the island isn’t that expensive. Everything is really fucking cheap. So we did buy a lot of provisions at this organic food shop called Gourmet Shop (#5 Chattel Village, Highway 1 It’s the place on the island to buy nicer wines, cheeses, special vinegars. It’s like a foodaholic’s dream. That’s where we’d get any of the expensive shit you want that you might be used to in New York, if you’re craving something specific.

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