Where To Travel This Labor Day—For Free With Miles And Points – Forbes Advisor


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With an extra day off of work for many Americans, Labor Day weekend is an easy excuse to plan a trip. Though three days isn’t much time, it’s long enough to get a sense of place somewhere and enjoy a change of scenery. If you can extend it longer, even better.

Last-minute travel can often be expensive, especially over holidays, but don’t lose hope yet if you haven’t booked a trip for Labor Day. Anyone with a stash of miles and points has an opportunity to take advantage of award redemptions that can highly subsidize the cost of travel, or in some cases, cover it completely.

Here’s where to go over Labor Day weekend using points and miles.

San Francisco, California

If you’ve already been to San Francisco, you know that it’s ever-innovative nature means there’s always something new to see. With only a long weekend, you’ll never be able to see it all, so make this the trip you commit to exploring a neighborhood in depth. Check out the new Presidio Tunnel Tops if you’re looking for an outdoor experience within city limits or chow down at the Off the Grid food truck market in Fort Mason every Friday.

United Airlines is the leading carrier into San Francisco, which should make it easy for you to find flights from home using your choice of MileagePlus miles or other Star Alliance rewards, such as Air Canada Aeroplan or Singapore Airlines Krisflyer miles. Though prices vary based on your home airport and exact dates of travel, aim for one-way flights in economy for 12,500 miles or less.

In such a large city, you’ll be spoiled with hotel redemption choices. You’ll find options with all programs, in every corner of the city and at all price points. If you’re overwhelmed with where to start, consider the Hyatt Regency San Francisco Downtown SOMA. It recently underwent a $70 million dollar renovation and you’ll be able to walk to the arts district, Union Square, the Theater District, Nob Hill and more—starting at 17,000 World of Hyatt points per night.

Cumberland, Maryland

Maryland’s mountainside feels a world away from the eastern seaboard, despite being less than two and a half hours away from Washington, D.C. Once there, the athletically inclined can rent a bike and pedal the Great Allegheny Passage, which runs all 150 miles to Pittsburgh past spectacular scenery. Not that motivated? Turn around at Frostburg, about 16 miles away, for a taste of the adventure. Or, skip the cycle altogether and enjoy the views from the Western Maryland Scenic Railroad.

Downtown Cumberland is accessible by foot, meaning you can leave the car at home and redeem Amtrak Guest Rewards to arrive. The Capitol Limited stops in Cumberland on its run from Chicago to Washington. For lengthier journeys, expect to travel overnight but even roomettes and family bedrooms are bookable with points at reasonable rates. Book early for the best deals.

If you’re limited to hotels within walking (or biking) distance, you’ll find points redemptions at the Fairfield Inn & Suites by Marriott Cumberland. The Ramada by Wyndham Cumberland Downtown also has a stellar location for 15,000 Marriott Bonvoy points per night. You can transfer Capital One Rewards or Citi Thank You Points into Wyndham Rewards if needed.

Taos, New Mexico

For a small city, Taos packs a varied punch. Taos Pueblo is a UNESCO World Heritage Site with incredible history and culture, Taos Ski Valley offers great hiking in the summer and downtown Taos has several museums and art galleries. Bonus: while much of the southwest is still sweltering over Labor Day, the altitude in Taos keeps things pleasant so that you can enjoy your visit.

Santa Fe (SAF) airport is an easy drive away and is served by American Airlines and United. If you don’t have miles with those airlines, remember to check for pricing through partner airlines. For example, you can use Alaska Airlines Mileage Plan miles to fly on American or Avianca LifeMiles (a common credit card transfer partner) to book on United. If you still can’t find award flights, you can also fly into Albuquerque (ABQ) to take advantage of additional airlines.

Hilton Honors will be your best bet when redeeming hotel points. The Hampton Inn Taos has everything you need, including free breakfast and an indoor pool. For a more upscale stay, consider the Hotel Don Fernando de Taos, Tapestry Collection. You’ll find southwest decor around the hotel to add to your experience.


Beach vacations make excellent long weekend getaways, but Labor Day is in the middle of hurricane season. Luckily, Aruba’s southern location means it escapes the storms and its relatively small size means you can see a lot in only a few nights—if you can peel yourself away from the soft sands and turquoise waters. On second thought, settle in with a bucket of Balashi beer during the day and join a sunset catamaran at night.

From the U.S., you’ll find nonstop flights from most major east coast airports, such as New York, Atlanta and Fort Lauderdale, plus a handful out west. Cash fares can be surprisingly affordable this time of year, so don’t be afraid to pull out points that are normally correlated with purchased fares. JetBlue’s pricing, for example, might work out to your favor.

On Aruba, you’ll find points hotels with every major chain, running the gamut from basic to luxury. The vast majority are on Palm Beach, putting you in walking distance from restaurants, shopping, nightlife and watersports. At the Holiday Inn Resort Aruba-Beach Resort & Casino, IHG® Rewards Premier Credit Card* holders who redeem points for their stay can get the fourth night free.

Read More: 6 Caribbean Vacations Where Hurricane Season Doesn’t Matter

Kansas City, Missouri

Kansas City is built for the Labor Day long weekend, with something fun to do each day. Start your holiday weekend in the Crossroads Art District—galleries are open late the first Friday of the month. Come Saturday to hop between jazz club performances. Sunday, shop at City Market’s combined farmer’s market and specialty grocers before catching a Royals game on Monday. In-between, you’ll still have time for museums, barbecue, parks, shopping and craft brews.

Kansas City (MCI) gets a sizable amount of direct air traffic, with Southwest Airlines in particular serving the airport. Pull out your Companion Pass and bring a friend for no extra points, making it an even more spectacular redemption.

You’ll be spoiled for choice with hotel options in Kansas City, with some particularly posh options around Country Club Plaza. The Raphael Hotel, part of Marriott’s Autograph Collection, has a classy European feel and hosts live music several nights a week.

The Vegas, Nevada

You either love or hate Las Vegas, but assuming you fall into the first camp, an extra day off from work means more time for going out and for recovering when you get home, depending on how you want to do it. Hit up the classic Las Vegas activities—casinos, dining, spas, shows, nightlife, shopping and pools—but don’t forget to head off The Strip, too. The Fremont Street Experience, Valley of Fire State Park and Mob Museum are equally enticing ideas.

Finding flights to Las Vegas (LAS) is usually the easy part, with nearly all U.S.-based airlines serving the airport—that means you can look for the best deal. If comparing prices across multiple airlines sounds too tedious, you can get a real-time look at aggregated options through the subscription-based Point.me award flight service.

There’s no lack of hotel award redemptions in Vegas but this might be the time to pull out your Best Western Rewards. At The STRAT Hotel, Casino & Skypod, BW Premier Collection, you can redeem points traditionally for a free night or you can Pay With Points to apply rewards toward a cash discount—in which case, you’ll have the option of booking suites for extra space.

Tortuguero, Costa Rica

For an international adventure without the jetlag, head south to Costa Rica. In September, there’s a good chance the Pacific Coast is being hammered by rain but Tortuguero, on the Atlantic side, has more reasonable weather. Once you’re there, you’ll be delighted by the chance to see nesting sea turtles at night. By day, head out on a boat to search for monkeys, turtles, caiman and other wildlife.

The closest international airport to Tortuguero is San Jose (SJO), which is served by nearly all U.S.-based airlines (pro tip: search specifically for SJO, to avoid inadvertently flying to San Jose, California). From there, you’ll need to connect on a short flight to Tortuguero, purchased separately and a great way to use up included travel credits from cards like the Chase Sapphire Reserve®.

While you’ll need flexible points or cash to book a hotel in Tortuguero itself, most major hotel programs have properties in San Jose for award nights on your way to or from the coast. Marriott Bonvoy points in particular are lucrative here—choose the Courtyard San Jose Airport Alajuela for the shortest airport shuttle ride possible or spring for the gorgeous Costa Rica Marriott Hotel Hacienda Belen, 15 minutes away. Both are frequently available under 35,000 Bonvoy points, meaning you can redeem a free night certificate from your Marriott Bonvoy Boundless® Credit Card.

Ponta Delgada, Portugal

Yes, you can head to Europe for a long weekend and in the Azores you’ll even escape the brunt of the crowds. Ponta Delgada, on São Miguel Island, blends fabulous cuisine with lush, green scenery and chances to observe marine life. Factor in everything else you love about Europe, such as history and architecture, and you’ll find plenty to enjoy in Ponta Delgada.

The Azores Islands might sound far away, but they’re closer to Boston than Los Angeles is with a flying time under five hours. Better yet, United runs a daily flight from Newark (EWR) to Ponta Delgada (PDL) and low-priced economy awards are frequently available. Book with United miles, a Chase Ultimate Rewards® partner, or look for tickets with one of United’s many airline partners.

There aren’t a ton of chain hotels in the Azores, which adds to the archipelago’s charm. However, there’s a number of independent properties bookable via the Chase, Citi or Capital One travel portals. Or consider staying at an Airbnb and use your Chase Sapphire Reserve® to Pay Yourself Back.

Bottom Line

Labor Day is coming up quickly but it’s not too late to book your travel dreams. With miles and points, you can find options for all types of travel styles to design your own perfect long weekend getaway.


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