10 places to travel in the Caribbean for less

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The Caribbean costs less than you think

No matter the season, the Caribbean is an alluring travel destination, but traveling during the off season can be a savvy way to avoid crowds and, more importantly, save money. While the thought of traveling during hurricane season may deter you, it shouldn’t necessarily stop you from considering that fall Caribbean vacay (after all, hurricane season technically runs from Jun. 1 to Nov. 30, spanning half the year). And with kids back to school, fall is a perfect time to plan that adults-only escape.

To help you save even more during this value travel season, we’ve crunched the numbers and found 10 Caribbean destinations where prices are down more than 10 percent for fall 2017, making a trip to paradise even more tempting. Pick your favorite and start planning that Caribbean getaway (on Cheapflights.com, of course).

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Havana, Cuba — Average airfare down 43% over last fall

Taxi in Havana, Cuba
Embark on a cheap Cuban holiday in Havana, Cuba. (Image: Havana, Pedro Szekely via Flickr CC BY-SA 2.0)

Just 90 miles from Key West, Fla., Cuba has been so close but just out of reach for many Americans. The United States imposed an embargo on Cuba in 1960 and broke diplomatic relations in 1961. Although the American embargo remains in place, many of the restrictions were lifted in 2015 which led to commercial flights between the U.S. and Cuba and more travel opportunities for Americans. Currently the U.S. Office of Foreign Assets Control issues general licenses that permit U.S. citizens to travel to Cuba, provided it falls within one of 12 categories like family visits, educational activities, or professional research. However, the President has recently indicated that restrictions would once again tighten. While the timing on this is uncertain, many Americans with hopes of visiting Cuba are doing so as soon as possible. With prices down for fall travel, this could be just the time to make the trip, although if doing so under the “people-to-people” travel category — the only one of the 12 impacted by the new restrictions — try for early September (before the 90 day period in which the Secretary of Treasury issues the new rules is up).

There are many hotels in Havana, but with the new restrictions placed on hotel options, it may be easier (and a more authentic experience) to stay at a casa, a locally run bed-and breakfast style accommodation. For an even more authentic experience, try eating at a palador; private, family-run restaurants in people’s homes that gained legal status in Cuba in the early 1990s. From riding in a classic car or Coco taxi (a motorized taxi) to touring a cigar rolling facility to people-watching along the Malecón, there is plenty to see and do. Don’t miss having a Daiquiri at El Floridita, famous as the local regular haunt of Ernest Hemingway. Today cantineros (bartenders) continue to serve the bar’s famous cocktails, including the Floridita Daiquiri (a blend of Havana Club rum, lemon juice, white sugar, ice and maraschino. Check out our guide to what Americans can expect traveling to Cuba.

La Romana, Dominican Republic — Average airfare down 43% over last fall

La Romana Beach, Dominica Republic
Secluded La Romana is one of the Dominican Republic’s best kept secrets. (Image: Christian Córdova, Paraíso Terrenal via Flickr CC BY 2.0)

Skip the more tourist-y Punta Cana and head to La Romana, a town on the Dominican Republic’s southeastern coast famous for sugarcane. Also known for its exemplary golf courses like that of secluded Casa de Campo, the beaches here beckon more and more bargain-hunting beach-goers each year. There are plenty of all-inclusive resorts here, which also helps drive down travel costs.

George Town, Cayman Islands — Average airfare down 38% over last fall

Wreck diver, Cayman Islands
Dive into fun in the Cayman Islands. (Image: Neil Rickards, GOPR0266 via Flickr CC BY 2.0)

George Town might be where cruise ship passengers disembark en masse, but it’s also where travelers touring the Caribbean stay for less. George Town has all the requisite Caribbean vacation features; beautiful beaches, sunny skies, moderate temps year-round, snorkeling and several points of interest. One such point is the Cayman Islands National Museum, a collection of cultural exhibits housed in the Cayman Islands’ oldest building, Seaman’s Monument, which honors those lost at sea, the ruins of Fort George and a collection of noteworthy restaurants like Blue by Eric Ripert, a contemporary restaurant with a menu focused on locally and responsibly caught seafood. Diners can try six- and seven-course prix fixe menus or à la carte dining by the famed chef.

Bridgetown, Barbados — Average airfare down 23% over last fall

St Nicholas Abbey, Barbados
See how rum is made during a bargain trip to Barbados. (Image: bixentro, St Nicholas Abbey, Barbados via Flickr CC BY 2.0)

Bustling Bridgetown, Barbados, boasts a yacht club, off-shore shipwreck diving and duty-free shopping. The charming commercial hub is one of the most beautiful cities to explore on foot in the Caribbean thanks to its British colonial architecture. Popular pastimes include sunbathing on the pristine beach at Carlisle Bay and touring the 350-year-old St. Nicholas Abbey to see how its famous rum is produced. Don’t miss a stroll through Cheapside Public Market for Bajan fruits, vegetables, plants, spices and handicraft souvenirs and dinner at the lively (and delicious) fish fry in Oistins held each Friday night.

Marsh Harbour, Bahamas — Average airfare down 25% over last fall

Marsh Harbour, Bahamas
The Bahamas is a boater’s paradise. (Image: Michael McKechnie, Sailboat silhouette via Flickr CC BY 2.0)

Located in The Abacos, a 120-mile island chain comprised of the main islands of Great Abaco and Little Abaco plus smaller islands and cays in the northern Bahamas, Marsh Harbour is a laid-back settlement that attracts folks who come to swim, snorkel, shop and boat far from the crowds. With regular ferries to other nearby islands, it’s easy to get even further off the beaten path. The area’s calm waters make it one of the world’s top boating destinations, and its close proximity to the U.S. make it easy to reach by plane or boat.

St. George’s, Grenada — Average airfare down 17% over last fall

Seven Sisters Falls, Grenada
Seven Sisters Falls is one of Grenada’s most popular attractions. (Image: Jason Pratt, Seven Sisters Falls via Flickr CC BY 2.0)

Grenada — the 120-square-mile island in the eastern Caribbean, 100 miles north of Venezuela — is packed with plenty of things to do on the main island and it’s smaller sister islands Carriacou and Petite Martinique. Dubbed the “spice islands of the Caribbean,” Grenada offers beautiful beaches, diving among colorful coral and charming island hospitality. Dive sites include an underwater sculpture park in the Molinere Beauséjour Marine Protected Area and the 600-foot Bianca C, a cruise liner that caught fire and sank off the coast in 1961. In the capital St. George’s, there are several forts to explore, including Fort George, the Grenada National Museum, which displays historical artifacts and exhibits on the island’s nautical history, River Antoine Rum Distillery, the oldest functioning water-propelled distillery in the Caribbean, and the picturesque St. Margaret’s Falls or Seven Sisters Waterfall, a succession of seven waterfalls accessible after a short hike.

Oranjestad, Aruba — Average airfare down 16% over last fall

Beach in Aruba
Have an ah-mazing getaway for less in Aruba. (Image: Phil Comeau, Oranjestad beach via Flickr CC BY 2.0)

With a near-constant temperature of 82 degrees Fahrenheit year-round, lower prices to Aruba are yet another reason to visit the island known for its pink sandy beaches. Located 15 miles north of Venezuela, the 70-square-mile island offers endless options. The capital Oranjestad is a harbor city popular with cruise ships. There is a tram that runs from the cruise ship terminal to the center of town, making six stops along the way, including the House of Parliament, Archaeological Museum and Fort Zoutman, Aruba’s oldest building built in 1798 to protect the city from pirates. Dine at the family-run Driftwood, where charter boats bring in fresh catch daily, and Red Fish, a casual spot for home-style classics like sopi di jambo (okra soup) and conch stew. If you time your visit right, don’t miss the Bon Bini Festival every Tuesday evening, which showcases the island’s music, dance, crafts and food.

Vieques, Puerto Rico — Average airfare down 14% over last fall

Rocky coastline in Vieques, Puerto Rico
Escape to inexpensive Vieques for vacay. (Image: Steven Isaacson, Rounding the tip of the point., via Flickr CC BY-SA 2.0)

Eight miles off the coast of Puerto Rico, the island of Vieques might be tiny (it’s roughly 20 miles long), but it’s an off-the-beaten-path alternative to bustling San Juan. The Malecon is the island’s main restaurant, bar and shopping strip, and the sparkling, sparsely populated village of Esperanza has one of the most popular beaches. The island has a lively street food scene with food trucks and stands selling pinchos (savory chicken and beef skewers). Getting around the island is easy – rent a car, hop on a publica (a public van that traverses the island), or go by horse (there are 3,000 wild horses that roam the island, descendants of those brought by Spanish explorers from the 15th to 19th centuries). Don’t leave without eating mofongo, a Puerto Rican fried plantain dish filled with vegetables or meat, at El Quenepo in Esperanza.

Providenciales, Turks and Caicos — Average airfare down 12% over last fall

Providenciales beach, Turks & Caicos
Provo is perfect. (Image: John Sawicki)

The British territory of Turks and Caicos is known for its signature turquoise water. It’s pristine, picture-perfect beaches beckon visitors year round. Less crowded than other Caribbean cities, Providenciales, or Provo as the locals call it, is a great stopping off point for diving and avoiding the cruise ship passengers in Grand Turk, the capital island. The beaches of Grace Bay are a big draw and the perfect way to spend the day soaking up the sunshine and sipping on rum punch. Dive for souvenir conch shells steps from beach bar da Conch Shack, which serves cracked conch, conch salad, curried conch chowder and conch fritters. Try Johnny Fries (Turks & Caicos salted French fries drizzled with black bean and pepper gravy) or island staple rice and peas, but save room for the rum cake garnished with rum raisins.

Philipsburg, Sint Maarten — Average airfare down 11% over last fall

beach in Sint Maarten
Soak of the sun in Sint Maarten. (Image: St. Maarten Tourist Bureau)

The capital Philipsburg, on the southern portion of the divided island of Sint Maarten (the northern portion of the island is French and the southern portion is Dutch) is a popular cruise ship stop as well as vacation destination for longer stays. Located on the northern end of the Lesser Antilles, European sophistication meets a laid-back Caribbean vibe. Unlike some islands where attractions are timed to the arrival and departure of cruise ship passengers, Sint Maarten offers 24/7 entertainment, including numerous casinos. Unique attractions include the 12 Metre Challenge, which lets boating enthusiasts actively participate in head-to-head challenges in a yacht that won the America’s Cup (you can also sit back and enjoy the ride), and the chance to navigate a catamaran where the Atlantic Ocean and Caribbean Sea meet. A trip here is all the more tempting for shoppers as the island is tax free and duty free.

Overall, fall temperature in the Caribbean vary by only a couple degrees compared with the rest of the year, and satellite weather predictions can give you a heads up on the chance of storms in your area. For those with weather worry, protecting your trip with travel insurance is also an option. Here are 10 reasons why you shouldn’t be afraid to book a trip during hurricane season.

Which Caribbean island is calling your name? Share with us in the comments and search for flights to the destination of your choice on Cheapflights.com (or better yet, compare prices of a few different islands to get the best deal).

*Data is based on average round-trip flights from all U.S. departure points for September and October 2017 found on Cheapflights compared with same dates last year.

10 places to travel in the Caribbean for less was last modified: June 26th, 2019 by Lauren Mack
Author: Lauren Mack (163 posts)

Lauren Mack has traveled to 40 countries on five continents, including Cuba, New Zealand, Peru and Tanzania. For many years, she called China, and then Taiwan, home. Countries at the beginning of the alphabet, particularly Antarctica, Argentina and Australia are on her travel bucket list. Lauren is a multimedia travel and food journalist and explorer based in New York City.