Fall & Winter Travel on a Budget: Big Fun, Strategic Spending

Fall and winter are some of my favorite seasons to travel—not just because of the cooler weather, but because it’s the perfect time to mix points, short trips, and selective splurges. From pool parties in Palm Springs to concerts in Houston, here’s how I made the most of several trips without blowing up my budget.

September: Palm Springs for Dinah — Round 2! (Girlfriend Edition)

Five days in Palm Springs for Dinah Shore Weekend sounds like a budget nightmare… unless you plan it right. This trip was all about prioritizing experiences while keeping transportation and lodging costs reasonable.

How I saved:

• Flights were booked using American Airlines miles, costing 32,000 miles + $22.40 roundtrip from Albuquerque.

• I split lodging between an Airbnb (2 nights for $377.32) and the host resort (3 nights for $709.15) to balance convenience and cost. The Airbnb was close to the offsite events and the resort was perfect for the pool parties. Our room was right next to the entrance so it was easy to go back to the room for bathroom breaks and beverage refills!

Where I splurged (on purpose):

• Two Dinah Festival Passes: $607.88

• Entertainment: $725.36, which included 2 tables at La Reforma for 12 people, buying drinks from two cast members of The L Word, and nonstop pool and club parties.

Other costs:

• Lyft: $21.27

• Groceries: $178.30

This trip proves that festivals don’t have to wreck your finances—use points for flights, split accommodations, and save your cash for the memories that actually matter. And buying groceries kept meal costs wayyyy down. 

October Travel Marathon: Vegas, Phoenix, and Houston

October was all about short, strategic trips that packed in a lot of fun without taking time off work.

Las Vegas Getaway

Four nights in Vegas meeting up with an old friend, enjoying specialty dining, pool time, and some light gambling.

Budget wins:

• Flight to Vegas: 5,000 points + $5.60

• Return flight: 19,000 miles + $11.20 (for two)

• Two comped nights at New York-New York, paying only $102.04 in resort fees and taxes.

Other costs:

• Two nights at Harrah’s: $368.70

• Groceries: $119.86 (split across multiple stops)

• Lyft: $31.16

• Parking: $24.75

• Souvenirs/Misc: $103.67

Vegas is where points really shine—comped rooms and cheap award flights kept this trip very wallet-friendly.

Phoenix Bestie Trip

A quick weekend getaway with a best friend, complete with Pride festivities, bar hopping, and a stop at the Museum of Illusions.

Costs:

• RT Southwest flights for two: $419.20

• Condo: $498.78

• Lyfts: $71.30

• Groceries: $102.62

• Restaurants: $66.96

• Entertainment: $77.38

• Souvenirs: $37.23

Splitting accommodations and groceries made this trip comfortable without being excessive, and keeping it short helped cap spending.

Houston for the Doechii Concert

An overnight trip to Houston for a concert might sound wild, but it was surprisingly budget-friendly when split among friends. Plus it was a once in a lifetime experience to see this amazing artist at a small venue!

Group savings:

• RT United flights for five people: $779.85

• Moxy Hotel: $249.86

• Concert tickets for five: $910.22

Other expenses:

• Meals: $51.87

• Transportation: $73.80

• Parking: $28

• Souvenirs: $97.42

When costs are divided across a group, even a quick concert trip can make financial sense—and still feel special.

Final Thoughts: Budget Travel Is About Choices

These trips weren’t about being cheap—they were about being intentional. I used miles where I could, kept trips short, split costs with friends, and spent money where it counted most: experiences, concerts, and quality time.

If fall and winter travel feels out of reach, start small. A points flight, a comped hotel night, or even a one-night trip can go a long way when planned thoughtfully.

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