Are baggage fees included in regional flight prices?

Usually, no. Regional carriers are notorious for charging fees for any bag exceeding 15-20 lbs. Assume you will pay $30-$50 at the counter for a standard checked bag.

Should I book a round trip or two one-ways?

Book two one-ways. Regional island-hopping schedules change frequently due to weather or aircraft availability; having separate tickets makes it easier to manage cancellations without voiding your entire itinerary.

Finding Cheap Inter-Island Flights in the Caribbean

Avoid regional hubs whenever possible and use the ITA Matrix to compare multi-leg itineraries. Booking separate one-way tickets on regional carriers like LIAT or InterCaribbean often beats the price of a single through-ticket from major legacy airlines.

Use ITA Matrix to find base prices. Do not start on Expedia or Kayak. Use the ITA Matrix tool to search for specific city pairs. Set your search to 'calendar of lowest fares' to identify which days of the week are cheapest to fly between specific islands.
Identify the regional carriers. Major US airlines (American, Delta, United) often charge high premiums for island-hopping. Look for regional specialists like InterCaribbean, Caribbean Airlines, Silver Airways, and Winair. Search their individual websites directly, as they often do not show up on major OTA aggregators.
Leverage hub-and-spoke logic. If you are flying from a smaller island to another, check if a flight through a major hub (like Barbados, Antigua, or San Juan) is cheaper. Sometimes a flight from 'Island A' to 'Hub' and 'Hub' to 'Island B' booked as separate tickets is $200 cheaper than a direct charter.
Book at the right time. For Caribbean regional flights, the sweet spot is 4–6 weeks out. Unlike domestic US flights, last-minute deals here are non-existent; prices skyrocket as seats on these small planes fill up.

Are baggage fees included in regional flight prices?: Usually, no. Regional carriers are notorious for charging fees for any bag exceeding 15-20 lbs. Assume you will pay $30-$50 at the counter for a standard checked bag.
Should I book a round trip or two one-ways?: Book two one-ways. Regional island-hopping schedules change frequently due to weather or aircraft availability; having separate tickets makes it easier to manage cancellations without voiding your entire itinerary.