The Caribbean’s reliable sunshine and tranquil, blue-green coast annually draw millions of visitors seeking tropical island relief and relaxation. It’s no surprise that high season in January and February also coincides with the highest prices for flights and hotels. But pushing your Caribbean visit into budget-friendly summer and fall runs the risk of hurricanes and tropical storms. Fortunately, there is a shoulder season sweet spot between late March and mid-to-late June that still affords favorable weather without the hefty price tag. While some Caribbean islands are generally spared the destructive force of tropical storms year-round, you’ll want to make sure to visit these 8 cheap islands before the onset of hurricane season.
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1. Puerto Rico
In September 2017, Hurricane Maria’s powerful winds and heavy rainfall wreaked havoc for more than 30 hours on Puerto Rico, destroying homes and damaging critical infrastructure, such as power lines and roads. The storm’s lasting impact is connected with a death toll of more than 1,000 people by the most conservative estimates. This knowledge is important to keep in mind when visiting, both out of respect for Puerto Rico’s hardship and also understanding that tourism helps fund recovery efforts.
Most visitors arrive via San Juan — Puerto Rico’s capital. The city’s historic Old Town constitutes the second-oldest European settlement in the Americas and still exudes colonial charm today. Cobblestone streets crisscross between picturesque plazas and pastel-hued buildings housing cafes and galleries. San Juan’s art scene continues outward into the Santurce area, home to the Puerto Rican Museum of Art and iconic street art and graffiti throughout the neighborhood. Visiting Puerto Rico’s stunning beaches and lush jungle are budget-friendly as well. Just outside San Juan, Condado offers excellent people watching along the resort strip, while Escambron is popular with families for its calmer waters and snorkeling. On the west coast, Rincón is one of the Caribbean’s premier surfing locations and Playa Sucia’s gorgeous crescent-shaped beach is popular with hikers and solitude seekers. Hikers should also seek out El Yunque National Forest, which features a trail system that takes in gushing waterfalls and raging rivers through the hilly rain forest terrain.
Roundtrip flights during shoulder season from New York and Chicago to San Juan can be had for just $241 and $347, respectively.
Our Puerto Rico Hotel Pick: Da House Hotel
Da House Hotel is a charming boutique hotel above the famous Nuyorican Cafe, in the heart of Old San Juan. The hotel only has 27 rooms that are purposefully unplugged with only high-power air-conditioning and telephones in the rooms for amenities. Rooms are spacious and eclectic, and some have balconies overlooking the cobblestone streets of Old San Juan.
Pricing for Da House Hotel
2. Dominican Republic
Hurricane Maria was still a category 5 storm when it made landfall in the Dominican Republic in 2017, but fortunately, the destruction and loss of life was significantly less than on Puerto Rico. Typically, Dominican Republic-bound travelers have their sights on Punta Cana for its idyllic white-sand beaches, shimmering sea, and all-inclusive deals. If a no-hassle beach vacation with user-friendly nightlife is what you’re after, then Punta Cana definitely fits the bill. For a greater dose of local culture or immersion in nature, you’ve gotta get away from Punta Cana. More pristine coastline awaits on the Samaná peninsula, which offers secluded beaches, waterfall hikes, and humpback whale sightings offshore. Most visitors base themselves in bohemian Las Terrenas or the more laidback fishing village of Las Galeras. Further afield near the Haitian border, Playa Bahia de Las Aguilas rewards visitors who make the journey with six miles of nearly deserted, white-sand beaches and stunning cliffs. The Dominican Republic’s capital, Santo Domingo, is replete with historic sites, including the oldest cathedral and military fortress in the Americas. The city’s historic center, known as Zona Colonial, is also teeming with cafes and bars where a Presidente beer will only set you back $1.50.
Direct flights during shoulder season from Chicago, Detroit, and New York to Punta Cana range between $400-$650 roundtrip. Meanwhile JetBlue flights to Santo Domingo from New York are a steal for $338 roundtrip.
Our Dominican Republic Hotel Pick: Casa Coson
Located on a secluded stretch of sand outside Las Terrenas, Casa Coson is an affordable option for travelers looking to unwind and unplug in a beautiful setting. The hotel also has a large pool, free breakfast, and includes private terraces and mini-fridges with all guest rooms. Don’t forget to schedule a morning massage and check out the yoga hut.
Pricing for Casa Coson
Famous for its reggae beats, gorgeous beaches, and welcoming locals, Jamaica is a budget-friendly destination across the board. For starters, Jamaica’s often-overlooked capital, Kingston, has a wealth of free and low-cost activities. Fleet Street’s vibrant murals and graffiti and the grounds of the Devon House — a Georgian-style mansion built by Jamaica’s first black millionaire, George Stiebel. Touring the mansion’s interior requires joining a group tour for a modest cost. Jamaica’s second city, Montego Bay, sees most of the islands visitors and cruise ships for its expansive beaches, all-inclusive resorts, and nightlife. The grittier city center and resort area are divided by the Hip Strip and Doctor Cave’s Beach, home to cheap jerk restaurants and low-cost accommodation. For more natural surroundings, Ochos Rios on Jamaica’s northern coast is a great launching point for jungle treks, zip-line tours, and waterfall hikes. There are a handful of scuba operators, so be sure to do a price comparison and negotiate your price if visiting during shoulder season.
Non-stop flights from Boston and New York Montego Bay run for about $432 and $550 roundtrip, while roundtrip tickets to Kingston costs just $393 from New York.
Our Jamaica Hotel Pick: Doctors Cave Beach Hotel
The Doctors Cave Beach Hotel puts guests in the heart of Montego Bay’s nightlife and within easy walking distance of the famous beach that it’s named after. There’s also an on-site bar, pool, and hot tub.
Pricing for Doctors Cave Beach Hotel
Located between Guadeloupe and Martinique, Dominica is one of the Caribbean’s most under-the-radar destinations. The island’s rugged mountain interior holds pristine rain forest, a geothermal lake, active volcano, and numerous waterfalls. Much of these landscapes are protected within reserves, such as Morne Trois Piton National Park. The 115-mile Waitukubli National Trail takes in much of the island’s natural beauty and remote corners. Shorter hikes are plentiful too, such as the Titou Gorge and Trafalgar Falls, which both lead to scenic swimming holes. Dominica’s numerous public beaches don’t cost a thing to enjoy. Soufriere Bay Beach’s underwater hot springs keep the shoreline fairly warm, perfect for easing sore feet after a long hike. Due to volcanic activity, Dominica also has several black-sand beaches. The northerly village of Calibishie is bookended by black-sand Number One Beach to the west and the Red Rocks cliffs on the east side. Public transportation is limited, so renting a car for at least a portion of the trip can help you cover more ground. QB Vehicle Rentals charges just $49 for renting a compact SUV for the day, while six-day rentals average out to $38 per day.
Roundtrip flights from New York average around $725 and require a stopover in San Juan, Puerto Rico.
5. Isla de Vieques
Like its big sister island, Isla de Vieques was also hit hard by Hurricane Maria back in 2017. The island’s residents include a significant number of US expats, which helped financially fuel the recovery efforts. Additionally, Vieques doesn’t possess much infrastructure to be damaged in the first place since the island only housed a US Navy base until 2003. Fortunately, the base was converted into a wildlife refuge after its closing, so there’s still plenty of pristine wilderness and coastline to explore. Vieques’s most remarkable natural attraction is undoubtedly Bahía Bioluminiscente — a bioluminescent bay home to a thriving population of tiny phosphorescent dinoflagellates. Come nightfall, these creatures transform the bay into a mosaic of fluorescent-blue lights. Due to its protected status, accessing the bay can only be done through organized kayak or electric boat tour (and it’s most amazing on full moons). Other highlights include Vieques National Wildlife Refuge, which contains some of the Caribbean’s most untouched white-sand beaches along its southern coast. If traveling via San Juan, booking a connecting flight with Air Flamenco will make for the smoothest journey. There are also 30-minute ferry connections from Ceiba, a port city that’s roughly one hour east of downtown San Juan.
Our Vieques Hotel Pick: Bravo Beach Hotel
Although its beach isn’t Vieques’s finest, the Bravo Beach Hotel offers free breakfast, two pools, and balconies with excellent ocean views. Furthermore, the property is within short walking distance of the ferry from mainland Puerto rico and cafes and shops in Isabel II. Guests can borrow coolers, beach chairs, and water toys to take to the beach.
Pricing for Bravo Beach Hotel
6. St. Kitts
The larger territory of this dual island nation, St. Kitts receives a modest 115,000 visitors annually. These low visitation numbers are certainly not for a lack of gorgeous beaches nor tropical beauty. The island’s less populated southern reaches hold some of the most picturesque white-sand beaches in the region. Cockleshell Beach sees the occasional influx of visitors when cruise ships dock at the adjacent port. Otherwise, visitors can have idyllic stretches of sand like Banana Bay Beach and Major’s Bay all to themselves. St. Kitts sits within a submerged volcanic mountain range, exemplified by its mountainous terrain rising quickly from the shoreline. The highest peak, Mount Liamuiga stands at 3,792 feet above sea level. Most hikers can tackle the five-mile summit hike in 4 to 6 hours roundtrip. There are more leisurely hiking trails that take in the lowland rain forest, bat caves, and gushing waterfalls. To enjoy the island’s lush scenery in comfort, visitors can hop aboard the St. Kits Scenic Railway for a three-hour tour for a premium of $89. The journey carries passengers at a leisurely pace along tracks that formerly connected the island’s sugar plantations to processing facilities in Basseterre.
Non-stop flights from New York and Charlotte to Basseterre can be had for approximately $490 and $635 roundtrip.
Our St. Kitts Hotel Pick: Royal St. Kitts Hotel
The Royal St. Kitts Hotel grants easy access to the golden sands of Frigate Bay Beach without breaking the bank. The property’s modern apartment-style units with kitchens are well-suited to families and groups of friend traveling together. Self-service laundry facilities make an extended stay convenient.
Pricing for Royal St. Kitts Hotel
7. St. Croix
The largest of the U.S. Virgin Islands, St. Croix sits more than 40 miles south of its sister islands and any other Leeward Islands. This distance has resulted in less tourist traffic, especially from cruise chips, thus creating a more authentic atmosphere. As a U.S. territory, visitors don’t have to calculate exchange rates or suffer international fees, thus helping save further travel money. Much of the island’s coastline is public access, so there’s no need to splurge on a beachfront hotel. Isaac Bay’s remote location on St. Croix’s eastern tip requires a 20-minute trek that’s well worth the effort for deserted beaches and offshore snorkeling. More snorkeling and hiking awaits just offshore at Buck Island Reef National Monument — a thriving 19,000-acre coral reef system swarming with marine life. Snorkelers are guided by a marked underwater trail off the island, which features a guided walk past sea turtle nesting grounds. The main city of Christiansted houses the canary-yellow Fort Christiansvaern compound comprising the Christiansted National Historic Site. Touring the facilities, which include its dungeon and citadel will only set you back $7. The fort protected the city from pirate sieges and hurricanes during the 18th and 19th centuries. St. Croix’s second city, Frederiksted is home to an art museum, fort, and Cruzan Distillery, where visitors can witness how rum has been made on the island since 1760.
Getting to St. Croix isn’t as easy as other destinations on this list. Most flights require a connection in San Juan or St. Thomas, though Spirit airlines operates direct flights out of Fort Lauderdale for roughly $350-400 roundtrip.
Our St. Croix Hotel Pick: Cottages By The Sea
Cottages By The Sea is great choice for budget-conscious travelers who prefer a pristine beach and swimmable seas to plush amenities. The beach is one of the longest and loveliest on St. Croix. That being said, the family-owned property is within walking distance of shops and restaurants in Frederiksted and offers free water sports equipment and snorkeling gear.
Pricing for Cottages By The Sea
This overseas French territory presents visitors with a wide selection of free nature-based activities and an incredible blend of French and Creole culture. The island’s southern portion holds some of the French Antilles’ finest beaches, namely Plage des Salines — a magnificent strand of sand backed by a salt pond and swaying palms. The pastoral villages of Les Anses d’Arlet in Martinique’s southwestern peninsula embody quintessential Caribbean charm and are surrounded by equally extraordinary beaches. Both Anse Mitan and Anse Noire are ideal for snorkeling, though the latter stands out for cliff jumping and black sand. Martinique’s northern coast is craggier and defined by seaside cliffs clad in jungle. The pastel-hued fishing village of Grand-Riveière is the start of a superb, but challenging hike that travels 12 miles to the village of Le Prêcheur. Here, you’ll find another trailhead, which takes the most gradual ascent up imposing Mount Pelée. The 4,583-foot peak is visible from all corners of the island, and thankfully, hasn’t erupted since destroying Martinique’s former capital in 1902 and claiming the lives of most of the island’s 30,000 residents.
Unfortunately, Norwegian Air has stopped service to Martinique’s Fort de France airport for the time being. Thus, the only direct flight from the mainland U.S. is from Miami, which comes out to $736 roundtrip with American Airlines.
Our Martinique Hotel Pick: Residence Hoteliere Les Cayalines
The Residence Hoteliere Les Cayalines provides sufficiently comfortable rooms enhanced kitchenettes and furnished balconies. Grounds feature tropical gardens and swaying palms. Guests can laze by the lovely pool or make the short walk to nearby Sainte Luce beach.
Pricing for Residence Hoteliere Du Golf
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