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Editor’s note: Chase provided the author with 100,000 Southwest points for use on this trip. The opinions expressed below are entirely his and weren’t subject to review by Chase or Southwest.
The first credit card I ever got was a Southwest Airlines credit card.
As with many college students, my parents encouraged me to open it in order to start building my credit and I had no idea about anything points- or miles-related. I just knew that, like TPG’s 10 commandments of good credit dictate, I should pay off my balance on time and in full every month.
I missed my first payment.
However, I haven’t missed a single payment since then, and I still carry the Southwest Rapid Rewards Premier Credit Card to this day.
I also remain a loyal Southwest flyer. I mostly grew up and still live in Austin, Texas, so Southwest has always been my main airline.
In fact, before I flew other carriers regularly, I thought you always had to check in exactly 24 hours in advance so you could secure good seats on your flight. I also thought you had the option to pick whatever open seat you wanted once you set foot on the plane. I was always the window-seat kid, though my brother would always veer toward the bulkhead to stretch his legs and fall asleep before the flight attendant announcements.
Since then, I’ve gotten to fly on a lot of different airlines, but Southwest will always have a special place in my heart. I appreciate how lovely their employees always are, and how easy they make flying for the average traveler thanks to customer-friendly ticket change and cancellation policies, not to mention the two free checked bags every person gets.
Given my history with Southwest, I jumped at the opportunity to use 100,000 Rapid Rewards points for some fun fall trips, and I was surprised to find just how many destinations the airline now flies to that I wasn’t even aware of before.
If earning 100,000 Southwest points for yourself sounds out of reach, remember that all three personal Southwest credit cards are currently offering introductory bonuses that can get you there quickly when you apply using these application links:
- Southwest Rapid Rewards Premier Credit Card.
- Southwest Rapid Rewards Plus Credit Card.
- Southwest Rapid Rewards Priority Credit Card.
Each card currently offers new cardholders 50,000 points after they spend $2,000 on purchases in the first three months from account opening. Plus, they can earn 50,000 more points after spending $12,000 on purchases in the first 12 months from account opening.
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Table of Contents
Surprising Southwest destinations
After searching the Southwest Airlines route map, I settled on Portland, Maine (PWM), and San Juan, Puerto Rico (SJU).
The first would be perfectly timed to take full advantage of the Northeast’s colorful fall foliage. As for the latter, I looked forward to spending a few relaxing days by the pool and beach in the Caribbean.
By sticking to the U.S., I could also avoid the restrictions and potential snafus of trying to visit another country during a COVID-19 surge.
Because I was booking weekend trips at fairly busy times, my tickets cost a bit more — both in terms of paid fares and redeeming Rapid Rewards points — than my award travel with Southwest usually does.
My round-trip itinerary from Austin to Portland cost 17,803 points plus the standard $11.20. My flights to and from San Juan were another 28,801 points with the same taxes and fees. Finally, I tacked on a car rental in Puerto Rico through Southwest’s partner redemption page for another 20,607 points, which saved me several hundred dollars. All told, I spent 67,211 of my 100,000 Rapid Rewards points, so I have some left over for more trips in the future.
Before I knew it, it was time to start charging up my camera batteries and packing for my trip.
Fall foliage in Portland
My first stop was Portland. I had never been before, but I mentioned it to some friends who had, and they said I was in for a treat, especially as I’d be there to see the leaves changing color at the end of September. Or so I thought.
Suffice it to say, Mother Nature had other plans. The weather was still pleasantly warm, and the leaves were not as vibrant as I had hoped. I was still able to get out and explore parts of Portland itself, though, including the historic center.
I even made my way up north to Acadia National Park for a full-day trip and was blown away by the scenery — enough to decide that I have to go back and actually see the fall foliage (assuming I have better luck next time).
The park is about a three-hour trek from Portland, and the drive itself is very beautiful. I took the scenic route along coastal Route 1 and was able to stop at quaint towns on the way. Because I had decided to make the journey on the spur of the moment, I did not realize you had to make a reservation to climb Cadillac Mountain for sunset. The park was out of passes for the day, though they said they had openings for the following day, so I’d recommend planning (just slightly) ahead if you plan to venture there yourself. You can easily reserve a spot online. I spent the rest of my time up there driving around the park and stopping for impromptu photo shoots.
As for my time in Portland, I decided to pull a true TPG move and check out some of the city’s best points hotels. I spent the first two nights at the relatively new Canopy by Hilton Portland Waterfront, which just opened right along the water in June 2021, near the pier from which the ferry departs to Peaks Island.
My room was spacious and, though not fancy, made for a great workplace when I had to attend to TPG business on the road. The top-floor gym was also a welcome sight … especially given how well I was eating.
The hotel was also right in the heart of the city and within walking distance of some fantastic restaurants. My first stop was Luke’s Lobster for a lobster roll. The ones they serve are filled with succulent meat on toasty, buttery rolls. Having another one would be reason enough to make a repeat visit to Maine.
I spent my final night nearby at the Press Hotel, which is located right off bustling Congress Street and is a member of Marriott’s Autograph Collection. The hotel took up residence in the former Portland Press Herald newspaper building, part of which dates back to 1923. Cheeky references to that past can be found throughout, including an entire wall of antique typewriters in the lobby and plenty of newspaper-clipping decorations in the bar area along with framed typesetting blocks.
Of course, the room itself was rather comfortable, too, with huge windows, a spacious desk complete with a vintage-style rolling chair, and colorful prints by local artists on the walls, as well as a gleaming, marble-tiled bathroom with woodsy C.O. Bigelow amenities.
The next morning, it was time to hop my flight back to Austin and prepare for the next leg of my trip.
A beach break in Puerto Rico
I didn’t have long to pause at home since I’d booked my two trips over back-to-back weekends. Before I knew it, I had to repack my bags … albeit with shorts and bathing suits this time as I jetted off toward my last hope for warm weather and a sandy beach before the winter.
I had been to Puerto Rico about a decade ago on a family trip and have always wanted to return. That trip was actually the first time I really started to get interested in our family DSLR camera, which set me on my path to becoming a professional photographer and photo editor, so it felt like a homecoming of sorts.
This time around, I stayed at the luxurious Fairmont El San Juan hotel, which is about a 10-minute drive from the airport in beachy Isla Verde, and around 30 minutes from Old San Juan.
When I arrived, guests were dancing to a DJ at the pool, which set the tone for what ended up being a very fun trip. Given the beautiful pools and breezy beach, not to mention plenty of the city to explore, I didn’t spend too much time in my room, though it was certainly very comfortable.
The hotel’s restaurants were also excellent, and I got to try some traditional Puerto Rican dishes created by chef Juliana Gonzalez at Caña on my first night. I ordered the hummus de gandules to start, which was a silky-smooth dip made from green pigeon peas with salty, crispy pork skin, which was delicious. I was so hungry after a full day of traveling that I ordered two main courses. The mamposteao de habichuelas blancos y longaniza was a hearty white-bean stew with savory, grilled local sausage. I then dug into the heaping mofongo con carne frita ahumada, an earthy dish of mashed, fried plantains topped with smoked, crispy pork, pickled onions and steaming duck broth. It was substantial and utterly satisfying.
Although I had planned to spend my days adventuring to far-flung beaches, I ended up lounging around the pool and on the hotel’s beach, just soaking in the sun. There were a few pools in the main area and a larger family pool next to the main restaurants. You could order drinks at the swim-up bar, but there were also roaming servers taking orders. While I didn’t book one this time, there were plenty of beach and poolside cabanas that would be perfect to lounge around in all day with a little privacy.
I did, however, make it a point to drive into Old San Juan so I could wander around snapping photos of the historic city’s cobblestone streets and colorful colonial buildings. I also explored the imposing Castillo San Felipe del Morro fort that was constructed in the 16th century at one of the entrances to the harbor to protect it from the British, the Dutch and, yes, even pirates.
Overall, San Juan felt like the ideal getaway — equal parts tropical beach destination and culturally rich historical hot spot, with plenty of excellent places to eat and drink. During my time in town, I grabbed a bite to eat at Barrachina and had another delicious version of mofongo, this time topped with fresh seafood. It hit the spot after a day of meandering down side streets and taking in the Caribbean views between pastel-painted buildings.
Although I’m used to being on the road a lot on assignment for The Points Guy, this was a lot of travel for me over a two-week period … especially after I’d cut back on flights for nearly two years during the pandemic. But the whirlwind of activity felt well worth it as it was one of my first forays back out into the world and allowed me to have two very different but still rewarding experiences.
Seeing some of Maine’s world-renowned fall foliage and enjoying a fresh lobster roll one week and then hitting the beach with a frosty piña colada in hand the next reminded me of just how much joy travel brings me, and how incredible it can be to discover, or rediscover, new and exciting places.
Even better, I actually have some of my 100,000 Southwest points left over and am close to earning the airline’s famed Companion Pass, so I’m looking forward to more travel in 2022, and to bringing someone along.
Featured photo by Wyatt Smith/The Points Guy.
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Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.