What's the cheapest way to island-hop?

Fly into one hub like Barbados or Puerto Rico, then take budget airlines like InterCaribbean or LIAT. Avoid flying back to your original island - book an open-jaw ticket instead.

How far in advance should I book inter-island flights?

6-8 weeks minimum. Small regional airlines have limited schedules and fill up quickly during peak season (December-April). Some routes only run 2-3 times per week.

Can I take ferries between islands?

Limited options. Fast ferries run between some islands like St. Lucia-Martinique, Dominica-Guadeloupe, and within the Grenadines. Check L'Express des Îles for French territory routes. Most require advance booking.

Should I book hotels in advance?

Yes, especially December-April and during local festivals. Small islands have limited accommodation. Book 2-3 months ahead for peak season, 4-6 weeks for shoulder season.

How to Plan a Caribbean Island-Hopping Itinerary

Start with 2-3 islands within the same region (Eastern or Western Caribbean) for a 10-14 day trip. Book inter-island flights 6-8 weeks ahead and spend 3-4 nights minimum per island to avoid constant packing.

Pick your island cluster. Choose either Eastern Caribbean (Barbados, St. Lucia, Martinique, Dominica) or Western Caribbean (Jamaica, Cayman Islands, Cozumel) to minimize flight costs and time. Don't try to cover both regions in one trip.
Plan 3-4 nights minimum per island. Less than 3 nights means you'll spend more time traveling than exploring. For a 2-week trip, stick to 3-4 islands maximum. Factor in half-day losses for each island transfer.
Book flights in logical order. Fly into your northernmost or southernmost island first, then work your way through the chain. Check LIAT, InterCaribbean Airways, and Seaborne Airlines for inter-island routes. Book 6-8 weeks ahead.
Research entry requirements per island. Each island has different rules. Some require proof of onward travel, others need yellow fever certificates if coming from certain countries. French territories use euros, British use Eastern Caribbean dollars.
Pack light with quick-dry everything. Baggage weight limits on small planes are strict (often 40-50 lbs). Pack one carry-on and one checked bag maximum. Bring reef-safe sunscreen since many islands ban chemical sunscreens.

What's the cheapest way to island-hop?: Fly into one hub like Barbados or Puerto Rico, then take budget airlines like InterCaribbean or LIAT. Avoid flying back to your original island - book an open-jaw ticket instead.
How far in advance should I book inter-island flights?: 6-8 weeks minimum. Small regional airlines have limited schedules and fill up quickly during peak season (December-April). Some routes only run 2-3 times per week.
Can I take ferries between islands?: Limited options. Fast ferries run between some islands like St. Lucia-Martinique, Dominica-Guadeloupe, and within the Grenadines. Check L'Express des Îles for French territory routes. Most require advance booking.
Should I book hotels in advance?: Yes, especially December-April and during local festivals. Small islands have limited accommodation. Book 2-3 months ahead for peak season, 4-6 weeks for shoulder season.