Duval to Duval St: Jax to Key West

Duval to Duval St: Jax to Key West


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Trip Information

PointsAway reader Jillian wants to find a cheap Key West vacation traveling from Jacksonville, Florida. Flexible in her travel schedule, Jillian tries to make it down to Key West at least once a year to enjoy the day and nightlife on famous Duval Street, have some fun in the sun and enjoy various water-sports including skiing. She has one travel companion, so she’s looking for a way for two adults to make the trip while saving money.

Current Program Status

Jillian doesn’t currently hold any points or miles credit cards or have a significant balance with any points or miles programs, so this is a great opportunity for her to break new ground!

Our Take

Key West can be a great place to visit. I always love stopping at the Mel Fisher museum whenever I’m in town, and the large buoy marking the southernmost point in the United States is an iconic photo opportunity.

Although it’s in the same state, Key West couldn’t be much farther away from Jacksonville, and is a more than 8 hour drive. In fact, at 503 miles, it’s a longer distance from Key West to Jacksonville than it is from Jacksonville, North Carolina to Jacksonville, Florida!

In many circumstances, this might seem right at the distance threshold where flying makes sense, but many people don’t consider flying to Key West an option as airfare is notoriously expensive. This serves as a great opportunity to revisit Southwest’s program and introduce you and Jillian to British Airways Avios, a powerful points program that works well for this itinerary and even better for those looking to visit other short-distance, high-price locations like islands in the Caribbean. Let’s get started.

How to Fly

American Airlines Using British Airways Avios

The cash price to fly American Airlines to Key West from Jacksonville via Miami is extremely high, at $422 per passenger at its cheapest. This is the kind of pricing that makes the Keys a difficult destination for many flyers.

The most affordable redemption of American AAdvantage® miles for the flight is to utilize MileSAAver fares. MileSAAver fares take 12,500 points each way, or 25,000 points in total. For longer distance flights, this may make sense for travelers that fly domestically most often, but there’s a better option available given the short distance of this flight.

British Airways Avios allow distance-based redemption on American Airlines on flights where MileSAAver fares are available. Redemptions start at just 4,500 Avios for trips of 650 miles or less. Unfortunately, Avios bookings are by segment and not for a whole trip. This means a flight from Jacksonville to Key West, connecting in Miami, consists of two award bookings: Jacksonville to Miami and Miami to Key West. Each segment is 4,500 Avios since it’s under the 650 mile distance threshold. That equates to 18,000 Avios per passenger for the whole flight.

You can verify the number of Avios required for any flight segment using the Avios Calculator on BA’s website. Because Miami is an American hub, the airline offers many flights to exotic locations throughout the Caribbean, on which Avios may be used if MileSAAver options are available.

After checking for availability using AA.com, Avios award trips can be booked via BA.com. It’s best to search for the flights on BA’s website using a multi-city route as opposed to simply searching for a roundtrip itinerary due to the per-segment limitation of Avios, but you can also call them to place a booking if you have trouble with the website.

Chase Sapphire Preferred® is a great way to accrue the necessary amount of Avios for free, since its annual fee is waived for the first year. It features a bonus of 40,000 points after $3,000 in purchases. Points transfer 1:1 to British Airways, along with Southwest, Korean Air, United, Virgin Atlantic, Amtrak, Hyatt, Priority Club, Marriott and Ritz-Carlton. The card also pays a 7% annual points dividend on all points earned throughout the year, even those already redeemed. The card offers 2 points per $1 on travel and dining purchases and 1 point per $1 on all other expenses.

Chase British Airways Visa Signature® is a strong alternative, with a bonus of 50,000 Avios after $2,000 in purchases. Avios do feature transferability to other programs, but not at the advantageous rate offered by Ultimate Rewards, so they’re best put to use on flights with BA or partners like American.

Southwest Airlines

Unfortunately, Southwest doesn’t offer a route from Jacksonville to Key West, but they do offer a route from Orlando to Key West. Located just about 2.5 hours south of Jacksonville, flying out of Orlando can still save about 11 hours and 700 miles of roundtrip driving as opposed to footing it all the way down I-95 and US 1.

Because Jillian is flexible with her travel days, Southwest’s flight from Orlando to Key West can be had for a very low number of points. Availability at the $91, or 4,800 points, level is widely available through the end of the year, with availability only tightening up consistently towards Christmas.

Because Wanna Get Away® fares are available for both legs of the trip, the itinerary comes in at just 19,200 points + $10 for 2 adults, a good deal compared to the $363.60 cash price.

Chase Sapphire Preferred® is once again a great option with its bonus of 40,000 points after $3,000 in purchases. Points transfer 1:1 to Southwest, along with the other programs mentioned above, in increments of 1,000 points. Because there’s no annual fee for the first year, this represents the cheapest Southwest option.

Southwest offers 750 free bonus miles just for signing up for their frequent flyer program, Rapid Rewards®. This means Jillian would only need to transfer 19,000 miles instead of 20,000 if she took advantage of Ultimate Rewards, since its transfers take place in 1,000 point increments.

Where to Stay

Key West is a challenging destination for hotel award bookings. A Hyatt, Westin, Crowne Plaza and Marriott all exist and offer an excellent stay, but each requires a steep points price. The Hyatt is a Category 6 location, their highest, requiring 22,000 points per night, the same as their finest locations in London and Paris. When applied in London or Paris, however, they represent tremendous value compared to rates that are often $700 or more per night. In Key West, Hotels.com has a room at the Hyatt quoted at $260 per night. So, this doesn’t represent a particularly good redemption value.

The same holds true for the Westin, Crowne Plaza and Marriott. Even Fairfield Inn, a typically budget-oriented property, is listed as a Category 7 property on Marriott’s award chart, requiring 35,000 points per night. Therefore, this is one of the rare cases where we recommend simply paying for a stay and choosing to earn miles rather than use miles.

Hotels.com has a great value at the Parrot Key Hotel & Resort, a 4-star property for just $139 per night early in October. Hotels.com bookings also earn WelcomeRewards™, which give customers a free night for every 10 they book. With enough travel, this can effectively serve as a 10% discount. Paying with a credit card that offers a category bonus for Hotels or Travel (see our Sign-Up Links page for some of the best) will also net points that can be used more effectively on other itineraries in the future.

Image courtesy: Hotels.com

Our Recommendation

This itinerary shows that not all trips are created equal, and that sometimes using cash in conjunction with points is the best way to maximize value. By combining, for example, nearly all of the promotional sign-up points offered by Chase’s Sapphire Preferred® with the Hyatt® Visa Signature’s 2 free award nights at any property, it’s possible to create a truly free itinerary back and forth from Jacksonville.

However, in this case, I’d recommend a more conservative approach, flying in and out of Orlando and utilizing less than half of the Sapphire’s promotional points on the Southwest flights while paying for accommodations at the best cash rate possible. Accommodations could even be booked using Sapphire via Hotels.com while earning 5 points per $1, by utilizing the Ultimate Rewards Mall, and this expense could be used in helping to meet the card’s minimum spend requirement.

Everyone values points differently. In this case, I’d personally prefer to use some judiciously while earning more and saving them toward another trip in the future.

Trip Component Cash Price Points + Cash Savings
Southwest: MCO to EYW Roundtrip, 2 Adults: 10/07-10/09 $363.60 19,200 Rapid Rewards Miles (19,000 UR Points Transferred) + $10 flight fees $353.60
Parrot Key Hotel & Resort 3 Night Stay, 2 Adults: 10/07-10/09 $367.62 1,390 UR Points Earned at 5x/$1 (valued at 2¢ each), WelcomeRewards™ equal to $42 earned towards a free room after 10 booked nights through Hotels.com $69.80
Total: $731.22 17,610 Ultimate Rewards Points + $377.62 $423.40 including future savings

Even better, this does not include the minimum 24,000 Ultimate Rewards points Jillian has left over even before considering the points she earned in booking the hotel. That’s more than enough to repeat the trip next year!

Happy travels!

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Casey Ayers is a consultant and entrepreneur with a passion for travel. After amassing enough miles and points to travel anywhere in the world for almost free in less than six months, he developed PointsAway as a way to help others make travel dreams big and small come true.
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