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Take a Caribbean Vacation for Under $1,000. Yes, Really.

Aug. 24, 2017
Managing Money, Personal Finance, Planning a vacation
Take a Caribbean Vacation for Less Than $1,000
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You’re lounging on a white-sand beach, sipping a brightly colored drink served by a man in a crisp, white uniform. He adjusts the umbrella so the sun just misses your eyes. Reggae music bounces in the background.

It’s a fantasy that comes at a premium. But with a few adjustments — a cooler in arm’s reach, sunglasses and your earbuds — you don’t need a fortune to make it a reality.

With proper planning, one person can take a Caribbean vacation for less than $1,000. You won’t be staying at a 5-star resort or dining in the top restaurants, but on these islands, living like a local can provide a richer experience at a fraction of the price.

Destination: Consider all costs

Cheap airfare doesn’t tell the whole story. You’ll want to balance the cost of getting there with the expenses you’ll incur once you arrive. Research the cost of airfare, lodging, food and activities in several locations. The following locations typically cost less than others, though you’ll want to explore prices specific to your point of origin and travel dates:

  • Cancun
  • San Juan, Puerto Rico
  • Puerta Plata, Dominican Republic
  • Turks & Caicos
  • Negril, Jamaica

» MOREEverything you need to plan your next vacation

Travel dates: Take an offseason risk

You can save hundreds on accommodations and flights if you travel in the offseason, generally mid-April through mid-December. You might have a few days of rain — and the chance of a hurricane — but the savings are worth the risk, according to travel blogger Matt Kepnes, better known as Nomadic Matt.

“True, you may go and there might be a hurricane,” says Kepnes, who suggests watching the weather beforehand and buying travel insurance if you’re particularly concerned. “Or nothing might happen and you’ll get the beaches to yourself!”

Flights: Start early and be flexible

For the best flight deals, start looking early and be flexible on dates, travel times and airlines. Sign up for alerts from websites such as Kayak and SkyScanner.

You should be able to find offseason round-trip tickets from Chicago to several Caribbean destinations for less than $400 and from New York to the islands for less than $300. You’ll pay less to fly out of a city like Miami, which is much closer to the destination, and more to fly from the West Coast.

Housing: Opt for hostels, vacation rentals

You don’t have to sleep on the beach to keep your lodging expenses in check. Use services like Airbnb or HomeAway to find rooms or even entire homes for less than you’d pay to stay in a resort. And don’t count out hostels — these aren’t the flophouses you might imagine. Check Hostelworld for hostel reservation options along with reviews.

Smaller resorts are a possibility, too, especially if you’re not traveling alone. “I found an amazing little resort located right next door to the home my friends were all staying in, for only $260 per person [total] for myself and my fiance,” says Nikol Drapeau, a social media manager in Redondo Beach, California, who recently traveled to Jamaica with a group of 15 other friends.

Food and drink: Dine like a local

It’s easy to overspend on food, particularly if you limit yourself to tourist-filled restaurants. Branch out for both a better value and more authentic local cuisine. “Walk five blocks in any direction away from the tourists, and then find a place to eat,” Kepnes advises. “If the menu is in multiple languages or there are no locals there, it’s not local food.”

And don’t forget: Not every meal needs to be a restaurant meal.

“We were able to find a Costco-like store close and stock up on groceries,” says Brie Tabios, who works as a senior designer in San Francisco and was part of Drapeau’s group of friends in Jamaica. “We had eggs a few different ways for breakfast and chicken a few different ways for dinner, and then had money left over to splurge on other [meals].”

Fun: Opt for free activities

You’re in the Caribbean — the main attractions are mostly natural and often free.

“Sure, you can pay to have someone take you to a famous waterfall or on a must-see hike,” says Kepnes, “or you can just ask someone if there is a waterfall or a nice mountain nearby and do it yourself.”

If you want to splurge on a guided activity, there’s no harm in haggling. Once off resort grounds, Drapeau and Tabios found most prices to be negotiable. As a group, they had even more bargaining power and were able to pay just $20 per person to have a tour guide take them to the Blue Hole, a waterfall site in Ocho Rios.

More savvy travel tips from NerdWallet


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