How to Travel to the Caribbean on a Budget

The Caribbean has many islands, airports and hotels to choose from, which is great for cost-conscious travelers.
Sally FrenchMar 10, 2021

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White sandy beaches provide a restful reprieve from daily stresses. Secluded shores and remote islands encourage natural social distancing. And, if you’re coming from the U.S., you’ll get to explore a new region without too much jet lag.

For these reasons, plus a high level of affordability, the Caribbean makes a solid choice for a budget-friendly vacation in 2021.

Given the many airports and wide range of hotels for every price point, your Caribbean vacation might not even cost you a ton out of pocket. Here’s what you need to know about traveling to the Caribbean on a budget with points and miles — whether you're planning a soon-ish vacation or a post-vaccine getaway.

Most Caribbean islands have reopened to international tourism, and many hotels are trying to make pandemic era travel more enticing and less stressful by offering . Plus, the U.S. Virgin Islands and Puerto Rico are U.S. territories. This means not only that travelers to these areas can leave their passports at home, but also that they won't need proof of a negative test to board their return flight.

There are more than two dozen countries and territories to explore in the Caribbean, and hundreds of islands within them to explore. Thrill-seekers might zoom down the waterslide and splash into the 141-acre waterscape at the Atlantis Paradise Island in the Bahamas. Foodies might munch on mofongo — a fried plantain-based dish — while in Puerto Rico. Underwater adventurers might spot migrating humpback whales while scuba diving the U.S. Virgin Islands.

Snowbirds tend to flock to the Caribbean between December and April, which is also the region’s dry season. Consider traveling during the shoulder season for the best of both worlds — visiting in May, June or November promises mostly good weather, plus fewer crowds and lower prices.

According to the National Oceanic and Atmospheric Administration, the official Atlantic hurricane season runs from June 1 through Nov. 30. Budget travelers might visit in the summer to benefit from the lowest prices, but it could be a risk.

Lodging in the Caribbean can range from rugged charm to modern luxury. There are tranquil, adults-only retreats and vibrant, family-focused resorts. Whatever your budget and priorities, there’s likely a Caribbean hotel that can meet your needs.

Here are some hotel sweet spots for an island vacation, with tips for booking with points.

Escape the crowds at the Zemi Beach House, a boutique hotel that has just 76 rooms and suites, yet spans the six acres of Shoal Bay East, Anguilla’s famous beach. Soak in views of the stunning turquoise ocean waters from the pool. You won’t have to travel far to take advantage of ocean sports, boat tours and snorkeling.

Hilton La Romana is an all-inclusive family resort on the pristine Bayahibe Beach. The hotel has its own waterpark, casino and fitness classes, plus multiple dining options, including French, Italian and South American restaurants.

Nightly rates at the Hilton La Romana this spring can cost less than $200. And since it’s all-inclusive, you might not spend an extra dime on food and entertainment, either. You can also find all-inclusive rooms for as few as 48,000 points per night.

The Hyatt Regency Grand Reserve has an ideal location on the beach, yet it’s not far from the El Yunque rainforest, where you might spot the endangered Puerto Rican Parrot. Or head to the historic town of Old San Juan, where you can meander down the colorful, umbrella-lined Fortaleza Street.

Finding somewhere to stay is only one part of the equation though. Unless you’re coming from South Florida by boat, you’ll likely be flying into your Caribbean destination.

Some of the biggest airports in the Caribbean include:

Generally speaking, it's best to fly into one of the bigger airports — you’ll have better odds of finding a direct flight and/or flights that you can book with airline miles. Bigger airports also tend to mean more lounge access, which can easily be gained by holding certain and can prove a solid money-saver on airport meals.

Here are some airfare sweet spots to inspire your award flight booking to the Caribbean.

doesn't publish an award chart, and the costs to book their flights in points are generally tied to the fare prices in cash. That makes it easy to spot good points redemptions; if you see a cash fare sale or a low-cost flight, you know you’re getting a deal when booking on points, too.

Southwest flies to many airports in the Caribbean, including:

For example, you could fly from Chicago’s Midway Airport to San Juan, Puerto Rico for $83 one-way (or about 3,800 Rapid Rewards points) this spring.

Not to mention, there are relatively few additional fees on Southwest (fares include two free checked bags, no change fees and complimentary snacks).

If you like to fly in style, look to United. NerdWallet spotted cross-country Business Saver Award fares on United this spring for flights from San Francisco to Nassau for as low as 30,000 miles each way.

American is one of the largest airlines serving the Caribbean, so it’s not hard to find a flight to your destination that fits your schedule. MileSAAver off-peak award flights between the contiguous 48 U.S. states or Canada and the Caribbean cost 12,500 points in the main cabin (or 15,000 points for regular MileSAAver fares).

You’ll likely find a cheaper cash fare if you’re flying from a U.S. hub city relatively close to the Caribbean, such as Miami or Dallas. But good luck finding a cheap cash fare flying from the West Coast. If that’s you, you’re better off booking with American Airlines miles.

Once in the region, you might not want to restrict yourself to just one island accessible by major airlines. Smaller airlines make island hopping possible.

One of the largest providers of inter-island flights is aptly named interCaribbean Airways, which operates small aircraft. Flights are fairly affordable, generally starting at about $50.

Alternatively, Cape Air operates multiple flights throughout the Caribbean and has certain codeshare flights in partnership with American, JetBlue and United.

Once you feel safe returning to travel, consider a budget-conscious trip to the Caribbean as an easily accessible destination. Use your hotel points at places like the above examples, where you can stay at a high-quality resort for a reasonable amount of points. Book your flights with airlines that both service the area regularly and can be booked with points or miles to get there cheaply.

As with all COVID-19 era travel, be sure to check travel restrictions and health recommendations from U.S. agencies, as well as local authorities at your destination before booking and traveling. Consider as well.

As vaccines roll out, whether you’re planning a getaway for later this year or into 2022, you can combine the serenity of warm, sunny beaches and pristine reefs with easy-to-come-by deals. The Caribbean could prove to be an excellent — not to mention budget-friendly — post-vaccine vacation.

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