How to Travel to the Caribbean on a Budget with Points

The Caribbean has many islands, airports and hotels to choose from, which is great for cost-conscious travelers.
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Written by Sally French
Lead Writer/Spokesperson
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Edited by Kevin Berry
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White sandy beaches provide a restful reprieve from daily stresses. And, if you’re coming from the U.S., you’ll get to explore a new region without too much jet lag.

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.

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

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.

Visiting the Caribbean from the U.S.

The U.S. Virgin Islands and Puerto Rico are U.S. territories. This means that U.S. travelers to these areas can leave their passports at home.

When to visit the Caribbean

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.

Staying in the Caribbean

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.

Anguilla: Zemi Beach House by Hilton

Photo courtesy of Hilton

Escape the crowds at the Zemi Beach House by Hilton, 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.

This Hilton-owned hotel is typically pricey, with rooms easily costing over $700 per night. But if you have a Hilton free night certificate (or two), that’s a surefire good use of it. Zemi Beach House is also a great way to spend points, as it generally runs about 95,000 Hilton Honors points per night, which is a solid deal for a $700 room.

Dominican Republic: Hilton La Romana All-Inclusive Family Resort

Image courtesy of Hilton

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.

Puerto Rico: Hyatt Regency Grand Reserve Puerto Rico

Photo courtesy of Hyatt

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.

Standard room rates easily run over $450 per night. Luckily, it’s a Category 3 hotel, which makes it a great use of Hyatt free night certificates, which are relatively easy to obtain. Holding a Hyatt-branded credit card or reaching Hyatt elite status milestones can help you earn free night certificates more quickly.

Booking with World of Hyatt points also makes a great redemption. Rates start at just 9,000 points per night for off-peak bookings, which at NerdWallet's valuation of 2.3 cents per point, means it'll cost about $207 in points — a far better deal than paying cash on most dates.

Getting to the Caribbean

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:



Major airlines served

Lounges available

Lynden Pindling International Airport

Nassau, The Bahamas

American, Delta, JetBlue, Southwest, United

Priority Pass

Las Americas International Airport

Santo Domingo, Dominican Republic

American, Delta, JetBlue, Southwest, United

Priority Pass

Pointe-à-Pitre International Airport

Pointe-à-Pitre, Guadeloupe

Air Canada, Air France, JetBlue

Air France lounge (accessible with Delta Sky Club membership), Priority Pass

Luis Muñoz Marín International Airport

San Juan, Puerto Rico

American, Delta, Frontier, JetBlue, Southwest, United

Priority Pass

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 travel credit cards and can prove a solid money-saver on airport meals.

Flying to the region

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

Southwest Airlines

Southwest 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:

  • Aruba (AUA).

  • Grand Cayman (GCM).

  • Havana, Cuba (HAV).

  • Montego Bay, Jamaica (MBJ).

  • Nassau, Bahamas (NAS).

  • Punta Cana, Dominican Republic (PUJ).

  • San Juan, Puerto Rico (SJU).

  • Turks and Caicos (PLS).

United Airlines

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 Airlines

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. American uses dynamic award pricing now, so award rates will change based on demand.

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.

Island hopping in the Caribbean

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.

The bottom line

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 travel insurance as well.

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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