Caribbean island-hopping works because of private aviation. Plain and simple. Many islands are separated by short distances but limited by ferry schedules, airline connections, and small airport infrastructure. Turboprops and light jets solve this by flying direct routes, using shorter runways, and accessing airports that commercial airlines often bypass.
Instead of planning around hubs, travelers can move from point to point between islands in under an hour. This makes multi-island itineraries practical, whether the goal is to combine resort destinations, reach quieter islands, or avoid congested terminals.
Based on historical data, our charter team has prepared the most common island-hopping routes, along with flight times, pricing ranges, and destination highlights.
Bahamas to Turks & Caicos
Route: Nassau (MYNN) to Providenciales (MBPV)
Aircraft: Light jet
Flight time: About 1 hour 10 minutes
One-way charter price: From USD 12,000
Nassau International Airport is an airport of entry with customs available and no slot requirements. Providenciales is also an airport of entry, although slot coordination is required, especially during peak travel periods.
This route is popular with private jet travelers combining urban island infrastructure in Nassau with the resort-focused environment of Turks & Caicos.
Nassau highlights
Nassau offers a mix of cultural sites and marine attractions. Clifton Heritage National Park is known for its snorkeling trails and historic plantation ruins. Downtown Nassau features colonial landmarks such as Parliament Square and Fort Charlotte. Paradise Island attracts visitors with large marinas, beachfront resorts, and entertainment complexes.
Providenciales highlights
Providenciales is centered around Grace Bay Beach, known for shallow waters and reef protection zones. Boat charters to the Caicos Cays are common day trips, including Little Water Cay and Half Moon Bay. Scuba diving and snorkeling remain core activities due to the island’s marine park system. Luxury villas and low-density resorts dominate the accommodation market.
Puerto Rico to U.S. Virgin Islands
Route: San Juan (TJSJ) to St. Thomas (TIST)
Aircraft: Turboprop
Flight time: About 30 minutes
One-way charter price: From USD 7,000
Luis Muñoz Marín International Airport operates 24 hours per day, provides customs services, and does not require slots. Cyril E. King Airport in St. Thomas is also an airport of entry and does not require slots, but it does not operate around the clock.
This route is often used by travelers combining Puerto Rico’s cultural attractions with the beach-focused experience of the U.S. Virgin Islands.
San Juan highlights
Old San Juan is known for preserved Spanish colonial architecture and historic fortresses such as El Morro and San Cristóbal. Condado and Isla Verde remain popular for beachfront resorts and dining. Many travelers also plan excursions to El Yunque National Forest, the only tropical rainforest in the U.S. National Forest system.
St. Thomas highlights
Magens Bay is one of the most visited beaches on the island due to calm water conditions and sheltered access. Yacht charters to nearby St. John are common, offering access to protected beaches inside the Virgin Islands National Park. Charlotte Amalie remains a duty-free shopping hub.
St. Maarten to St. Barts
Route: Princess Juliana (TNCM) to St. Barthelemy (TFFJ)
Aircraft: Turboprop only
Flight time: About 30 minutes
One-way charter price: From USD 4,500
St. Barts runway restrictions limit operations to turboprop aircraft such as the PC-12 and Caravan. Both airports operate with limited daily schedules and are not open 24 hours.
This route is widely used by international travelers arriving at St. Maarten who want a fast and direct connection to St. Barts.
St. Maarten highlights
Simpson Bay functions as the island’s marina and nightlife center. Grand Case is known for French-Caribbean dining and boutique restaurants. Maho Beach remains a popular attraction due to aircraft arrivals directly over the shoreline.
St. Barts highlights
Gustavia Harbor attracts large yacht traffic during peak season. Colombier and Gouverneur beaches are among the island’s most visited natural sites. Seasonal dining events and luxury shopping shape the island’s winter tourism profile.
St. Maarten to Anguilla
Route: Princess Juliana (TNCM) to Clayton J. Lloyd (TQPF)
Aircraft: Turboprop only
Flight time: About 25 minutes
One-way charter price: From USD 4,500
Anguilla relies on turboprop access due to runway limitations. Neither airport operates 24 hours, and no slots are required.
This route is often chosen by travelers seeking a quieter resort experience after arriving internationally through St. Maarten.
Anguilla highlights
Shoal Bay East and Meads Bay consistently rank among the Caribbean’s top beaches. The island is known for independent dining venues and beachfront restaurants. Boat trips to Sandy Island and Prickly Pear Cays remain popular half-day excursions.
St. Barts to Anguilla
Route: St. Barthelemy (TFFJ) to Clayton J. Lloyd (TQPF)
Aircraft: Turboprop only
Flight time: About 30 minutes
One-way charter price: From USD 4,500
This route connects two premium leisure destinations and is frequently used by travelers dividing time between social stays in St. Barts and resort-focused stays in Anguilla.
Both airports operate with limited daily schedules, making advance planning important.
Aircraft options
Turboprops dominate short Caribbean routes due to runway performance and operating efficiency. The PC-12 and Caravan are widely used for flights under one hour. Light jets are more common on longer sectors such as Nassau to Providenciales.
Aircraft selection is usually driven by runway restrictions, passenger count, baggage volume, and scheduling preferences.
Planning tips
Private island hopping still requires customs clearance at designated airports of entry. Some destinations operate only during daylight hours, which affects late arrivals and early departures. Seasonal weather patterns can also influence flight windows.
Allowing buffer time between flights and hotel check-ins improves itinerary reliability.
Final thoughts
Island hopping in the Caribbean only works when access, timing, and local knowledge come together. Short runways, limited airport hours, customs requirements, and seasonal congestion mean that routing between islands is rarely straightforward.
This is where experience matters. An established private jet charter provider like Icarus Jet understands which aircraft can operate safely into smaller airports, how to manage slot approvals, how to coordinate customs clearance, and how to align flight schedules with resort arrivals.
For travelers planning multi-island itineraries, working with a provider that specializes in Caribbean operations helps turn a complex routing plan into a smooth travel experience. The right partner does not just arrange a flight. They help design the entire island-hopping journey, so time is spent exploring destinations rather than managing logistics.
FAQs
How far in advance should island hopping flights be booked?
Peak season travel between December and April should be booked weeks in advance. Off-season flights may be available with shorter notice.
Are turboprops commonly used for private charters in the Caribbean?
Yes. They are widely used because they perform well on short runways and are efficient for short flight segments.
Can more than two islands be visited on one trip?
Yes. Many itineraries include three or more destinations depending on schedule and aircraft availability.
Is customs clearance required on private inter-island flights?
Yes. International movements still require passport control and customs clearance even when flying privately.
When is the busiest island-hopping season?
Demand is highest from December through April, especially around holidays and major regional events.
