Get Two-For-One On Your Next Caribbean Break With This New Charter Flight Route

Caribbean island hopping can be long-winded. Routes between neighboring islands are elongated by stops in other, farther countries. Interisland ferries exist only in small patches of the region. Plane tickets can rise to incredibly high prices, considering the distance traversed. A shift towards increasing the accessibility of Caribbean travel is being made in 2025, with airlines increasing their routes across the region. One such introduction was the official launch of Charter Air Direct in December 2024, which opened up a direct 30-minute flight route between San Juan, Puerto Rico and the island of Anguilla. Wrapping two Caribbean tourist destinations you should have on your radar into one vacation package, a new charter route is offering a two-for-one experience of the lively culture and pristine beaches of the islands.

San Juan, Puerto Rico's colorful capital, serves up a lively slice of Latin culture within close proximity to the continental U.S. Travelers curious about the history of the region, the contemporary art and music of the Caribbean, or the exceptional food dished up by the Boricuas can indulge their cultural curiosities on the first leg of the charter route. Traveling onwards to Anguilla, sunseekers can splay out on white Caribbean shores, kept pristine by the island's limited international connections. Pack the whole family for a trip that will suit everyone's idea of an idyllic Caribbean break.

Beneath bougainvillea-laced through the balconies' white filigree, a stroll through the pastel painted streets of San Juan transports travelers immediately into the Caribbean. Sun soaks the ultimate holiday destination to escape cold temperatures year round, where a cobblestoned maze of scenic streets leading out towards the imposing fortress that flanks the city's fore. The centuries-old cityis packed with historical sites and cultural intrigue.

500 years of history are wrapped into the protected San Juan National Historic Site, incorporating two of the most impressive sites still standing in Old San Juan. Oversee crashing Caribbean waves from the sentinel city walls of Castillo San Felipe del Morro and Castillo San Cristóbal, or visit tour the halls of historical homes and museums dedicated to contemporary island art or San Juan's sporting prowess.

Taste the influence of the Spanish, African, and native Taíno populations on the island by indulging in classic Puerto Rican dishes. Rub shoulders with the locals at the island's oldest diner, Cafeteria Mallorca, or splash out on a fine dining experience oriented around fresh-caught seafood at 1919.

While in the original home of genres like reggaeton, bomba, and plena, culturally-inclined travelers should also partake in a night of music and dance in San Juan. Switch between high-paced salsa swinging and cocktails in one of the world's best bars in La Factoría, where secret passages link a diverse range of dancefloors and bars.

One short flight hop later and you'll be laid out on some of the world's best ranked beaches, enjoying the clear waters of this tranquil Caribbean paradise. Anguilla, a tiny British overseas territory which foregoes gigantic resorts and crowded sun loungers in favor of pristine shores and luxurious hotels, is quintessentially Caribbean. Recover from a culture-fueled romp around San Juan by immersing yourself in Anguilla's untouched natural surrounds.

There are 33 beaches to choose from on the island. Seek out the ultimate seclusion by setting out for Little Bay, cloistered by cliffs and accessible only by boat. Rest under the tamarind trees and wade out into the turquoise waters that fringe Meads Bay. Watch the white shores slowly stain pink as the sun sets, champagne in hand, on a sundowner sailing cruise, or spy the only inhabitants of Prickly Pear Cays, the flitting bananaquit birds.

The water temperature around Anguilla hovers between 70- and 80-degrees Fahrenheit and are only gently rocked by the docile waves, creating ideal conditions for casual swimmers, snorkelers, and divers. Bobbing over waves underlaid by low-lying coral, set out off shore from Shoal Bay Beach and plunge into the midst of schools of blue tangs over a web of colorful coral and gliding eagle rays. Divers should head to Ram's Head to plunge into a maze of tunnels and caves or explore the wreckage of an 18^th century Spanish Galleon now serving as an underwater museum.