Trip Information

Aimee wants to travel from Jacksonville to Jamaica with her fiancé. They’ve never been before and would love to experience a nice vacation in a place like Montego Bay. Aimee would like to travel this September, and is new to miles and points, with no balances to speak of on hand.

My Take

This is a great opportunity to explore the options for vacationers not only from Jacksonville, but from across Florida and beyond to save big on travel to a popular Caribbean destination.

Given the small size of the island, after arriving in Montego Bay or Kingston, the locations of Jamaica’s international airports, it’s possible to drive to other popular destinations in Jamaica like Ocho Rios within just a few hours. That means finding an affordable flight solution opens us up to all Jamaica has to offer, and not just one small part of the country. However, our solution might just be different from what you expect. Let’s get started!

Best Route From Jacksonville to Jamaica

Often when plotting trips to the Caribbean, I turn instinctually to using Avios. As mentioned in our guide to using Avios for flights on American, flights from Miami to many destinations in the Caribbean – including both Jamaican destinations – can be had for just 4,500 Avios each way.

Avios award bookings are calculated on a per-segment basis, so a total of 9,000 Avios would be needed per person each way for a theoretical trip from Jacksonville to Miami and then Miami to Montego Bay. American charges 17,500 miles during peak travel times and a reduced 12,500 miles from September 7th to November 17th each way for this same route.

Since Aimee would be coming from Jacksonville, using Avios instead of AAdvantage miles makes the most sense. Indeed, even if she were traveling from farther away – up to 1,151 miles from MIA, using Avios would still make sense. Since Avios redemptions are based on distance, flights farther than that would require more Avios than American will miles in their own program, making the flat rate a better prospect.

Searching for two passengers, we see that award dates are good in June from Jacksonville to Montego Bay:

Availability for the flight home is less impressive but still fair:

However, if we look at the details for this itinerary, we see it actually routes through Dallas! This is fine when using American miles, but remember that Avios are distance-based, so connecting in Dallas instead of Miami means a much higher number of Avios would be necessary. Because of that, it just doesn’t seem like using Avios is going to be a good choice in this case. That got me looking for alternatives.

To Fly, First Drive

When I look for new ways to approach a booking, I often go to the Wikipedia page for the destination airport. Why? These pages are kept relatively up to date and have a simple, uniform list of carriers and destinations served by that airport. Most flights go both ways, of course, so if a flight is listed in one direction, I can typically take advantage of that route coming or going.

In this case, Southwest and JetBlue’s list of destinations from Montego Bay shared something in common:

Catch it? Both offer service to Montego Bay from Orlando. That’s a lead worth investigating, given Orlando is a relatively painless drive from Jacksonville, at around 2.5 hours. It’s a drive I’ve made on several occasions in order to save big on a flight.

Turns out this was a lead worth investigating! Flights from Orlando to Montego Bay on both JetBlue and Southwest are very affordable. JetBlue and Southwest have revenue-based points programs, meaning the cheaper a flight is, the fewer points will be required. Take a look at JetBlue’s rates from Orlando, for example:

Southwest’s redemptions offer even better value:

As you can see, Southwest’s rates are about half those of JetBlue’s from a points perspective, and are consistently so across the full month, while JetBlue’s prices vary upwards on many other days in September.

However, notice also the taxes and fees seen on the Southwest ticket. If you’ve looked at many Southwest award fares before, you’ll know that seeing taxes and fees totaling a mere $2.50 each way is what most award tickets require. However, special taxes and fees associated with this international redemption mean fees of $46.50 per person on this redemption. That means those 3,290 Rapid Rewards Points only absolve us of $78.50 of each ticket. That’s still a good deal; a similarly priced flight with lower taxes and fees would require more points, so the extraordinarily low number of miles needed mean this flight remains the best option.

The return trip on Southwest brings additional taxes and fees, but the number of points required remains extremely low consistently through September:

Using a mere 6,580 Southwest Rapid Rewards Points, we cut the cost of this trip to just $106.82 in taxes and fees, compared to a minimum cash price out of Orlando on Spirit Airlines of $257.

Southwest, however, includes two checked bags, while Spirit would tack an additional $40-$50 on for one bag each roundtrip, and even more for a second. That makes the Southwest trip the clear winner for anyone able to travel out of Orlando.

Roundtrips out of Jacksonville start at $477 since Avios isn’t a viable option for this itinerary, highlighting the value of driving to Orlando.

Even if Aimee pays cash for her tickets and skips using points entirely, she’d still save $225 each on the roundtrip for flying out of Orlando instead of Jacksonville.

Finding The Miles

At 3,290 points each way, Aimee would need 6,580 points per person roundtrip. She can get the first 1,250 Rapid Rewards points for each passenger for free in just a few clicks.

Free Southwest Points

First, Southwest offers 500 bonus points just for opening a free Rapid Rewards frequent flyer account. Next, you can tie together your AirTran and Southwest frequent flyer accounts to earn an extra 750 points. Don’t have an AirTran account? No problem! You can still make one for free here!

Ultimate Rewards

Ultimate Rewards is one of our favorite programs for earning Southwest points, given that the points can also be transferred to a variety of other programs when they prove more convenient.

If Aimee would like to start earning free travel on everyday purchases she’s already making, she should consider the Sapphire Preferred, which offers 40,000 bonus points after $3,000 in purchases in the first three months. She could instantly transfer a few thousand of these points to her account and that of her husband in order to cover the rest of the points needed.

Dining & Shopping

Additionally, she could sign up for Rapid Rewards Dining or Rapid Rewards Shopping, both of which would allow her to earn miles without requiring a particular type of credit card. In fact, Rapid Rewards Dining offers an extra 1,000 bonus points just for creating an account and spending $25 at a participating restaurant! There’s even more ways to earn points with Rapid Rewards Dining, which we’ll be covering soon.

If Aimee would like to start earning free travel on everyday purchases she’s already making, she should consider the Sapphire Preferred, which offers 40,000 bonus points after $3,000 in purchases in the first three months. She could instantly transfer a few thousand of these points to her account and that of her husband in order to cover the rest of the points needed.

Buy Points

Aimee can always buy the last few points she’d need to cover at least a one-way, but we wouldn’t recommend that given the other earning options that exist.

Wrapping Up

This trip shows how much money can be saved sometimes from flying through an airport relatively near home. Prices on flights to Montego Bay and several other Caribbean and Central American locations from Orlando are particularly low right now as Southwest places a high priority on promoting flights that once belonged to merger partner AirTran and JetBlue defends its “focus city” designation for Orlando.

By comparison, flights from elsewhere in Florida, except out of Miami, are much more expensive. Given Orlando’s central location in the state, it’s pretty easy for folks as far flung as Tampa and Jacksonville to take advantage of this deal. The deal just gets better when Aimee puts Southwest points, so easily earned, to work covering this flight.

Happy travels!

Happy travels!