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Weekend getaway: Labor Day destinations to round out your summer travels

July 16, 2022
10 min read
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Both summer holiday weekends so far — Memorial Day and Fourth of July — brought with them some of the biggest crowds that airports have seen in years. That trend will likely continue as the unofficial end of summer draws near. Meanwhile, travelers can only hope that the operational challenges seen during those holiday weekends will not be repeated on Labor Day weekend, which is now less than two months away.

Summer travelers wait in line at a TSA checkpoint at Tampa International Airport (TPA). (Photo by Sean Cudahy/The Points Guy)

Here at TPG, we dreamed up some ideas for how you might spend your final summer weekend. And for those concerned about long lines and lost bags at airports, one of our options is to take the train. Remember, prices are likely to go up the closer we get to the holiday, so now is a good time to book if you want to get away Labor Day weekend, which runs from Friday, Sept. 2 through Monday, Sept. 5.

The Berkshires. (Photo by DenisTangneyJr/Getty Images)

New York travelers: Berkshires weekend trip

This is a getaway we noted when Amtrak announced it was launching a direct summer weekend train service to the region and could be something to consider for a nice getaway from the city.

You can catch the Berkshire Flyer out of Manhattan on Friday afternoon, with service to Pittsfield, Mass. You’ll probably need to rent a car in order to explore the region, but the train is certainly a cost-effective option for making your way to the rolling hills of western New England at just $45 each way.

You’ll be in the Berkshires in time for a late dinner on Friday and can catch the train back to New York late Sunday afternoon.

bek
(Screenshot from amtrak.com)

If you've got a haul of points you're ready to use and are looking for a wellness-oriented weekend, check out Hyatt’s Miraval Berkshires.

(Photo by Chris Dong/The Points Guy)

With nightly rates often over $1,000 (and priced at $1,149 per night for Labor Day weekend), it’s not cheap, though a lot of what you’ll need for the weekend is included in the rate. You can stay at the property on Labor Day weekend for 50,000 World of Hyatt points per night, which are worth about $850, according to TPG’s points and miles valuations.

For more affordable options, Marriott and Hilton each operate properties nearby, though not their top-level brands — think Courtyard, Fairfield, and Hampton Inn. Prices at those hotels generally fell in the $300 to $400 per night range for the holiday weekend. You might also see what home-rental sites like Airbnb have for a stay in a more remote location in the region.

Related: 7 must-visit mountain towns in Massachusetts

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Chicago travelers: New Orleans

Check the prices to New Orleans Louis Armstrong International Airport (MSY) from where you live whether that's Chicago or another city. We’ve seen some excellent fares to the Big Easy lately. Your biggest hurdle for this trip might be the heat and humidity — I found the humidity rather stifling when I visited the city on New Year's Day, for that matter. But unlike my visit during the holidays or one you might make during, say, Mardi Gras, you should have a lot less difficulty finding a seat at a prominent French Quarter bar to listen to jazz or getting a restaurant reservation.

french quarter new orleans
The French Quarter in New Orleans. (Photo by Sean Cudahy/The Points Guy)

The airfare I found for the holiday weekend isn't comparable to the sub-$150, round-trip prices we've seen recently for non-holiday weekends. However, you can get a round trip from Chicago's O’Hare International Airport (ORD) to New Orleans for $248 on United nonstop in each direction, a price far below average summer domestic round trip fares which regularly soar over $300.

united booking screenshot
(Screenshot from united.com)

One of the tips we talked about when it comes to both holiday weekend getaways and those trips centered around a major event like the Final Four in New Orleans earlier this year is that you can really save when you shift your trip days just a little bit. That goes for both cash and miles fares.

Check out how many United MileagePlus miles you’ll save if you return from your trip on Wednesday.

united mileage screenshot
(Screenshot from united.com)

For the Saturday departure and Wednesday return, your total comes to 21,900 miles – not an incredible redemption, but pretty comparable to the cash fare.

United booking screenshot
(Screenshot from united.com)

If you’re looking to book a weekend stay using points, try the Le Meridien New Orleans. It has a rooftop pool with poolside cabanas and is within walking distance of the French Quarter, the World War II Museum, the Mississippi riverfront and area casinos.

marriott website screenshot
(Screenshot from marriott.com)

While you’ll pay $368 per night for the four-night stay, consider booking using points. The award stay comes to an average 34,750 points per night, which is worth about $278 according to TPG’s valuations. That's a nice improvement over the cash fare.

marriott bonvoy screenshot
(Screenshot from marriott.com)

Related: 10 TPG-approved hotels in New Orleans

Miami travelers: Puerto Rico

Here’s an option for South Florida travelers who might want to book flights with cash.

You can get a round trip to San Juan, Puerto Rico, aboard low-cost carrier Spirit Airlines for a $185 base fare. You’ll have to watch out for those added fees, but if you can go without seat selection for the relatively short flight, your biggest fee would be baggage.

On this itinerary, it looks like it’s cheaper to actually check a bag for $77 round trip instead of bringing a full-sized carry-on, making your round trip total $262.

spirit booking screenshot
(Screenshot from spirit.com)

Once in Puerto Rico, one lodging option for enjoying its beaches is the Hyatt Regency Grand Reserve. This sprawling property boasts beautiful pools and easy ocean access.

(Photo by Chris Dong/The Points Guy)

TPG reviewed the resort in 2021 and found it's an ideal property for a weekend stay. You can get a room for $280 per night or if you’ve got World of Hyatt member with points accrued (or transferrable points) you can book for 15,000 points per night.

hyatt booking screenshot
(Screenshot from hyatt.com)

It’s worth noting, that the 15,000 points per night rate is only 3,000 points above the off-peak rate (a points difference worth about $51 per TPG’s valuations) so you’re really not shelling out too many additional points for the benefit of booking on a U.S. holiday weekend.

hyatt award calendar
(Screenshot from hyatt.com)

Related: A beginner’s guide to visiting Puerto Rico

Los Angeles travelers: Seattle

Temperatures in Southern California won't cool off too much by winter, and they sure won't be cooler by Labor Day weekend. That could make it a great time to visit the Pacific Northwest. In Seattle, the average September high temperatures hover around 70 degrees.

Pikes Place Market, Seattle. (Photo by Lonnie Kishiyama/Getty Images)

I wasn't a fan of either coffee or seafood when I last visited Seattle as a teenager, but that's changed — which is why the Pike Place Market and coffee scene are just two of the reasons Seattle is on my short list of U.S. cities I hope to soon visit if a great redemption opportunity comes on my radar.

For Labor Day weekend, you could get a round-trip flight from Los Angeles International Airport (LAX) to Seattle/Tacoma International Airport (SEA) for $230 aboard Seattle's hometown carrier, Alaska Airlines. Again, that's a price well below the average summer domestic fare.

alaska booking screenshot
(Screenshot from google.com/travel/flights)

Related: A Hyatt hop through Seattle

Try staying at the Kimpton Hotel Monaco in downtown Seattle. You can get the stay for 58,000 IHG One Rewards points per night, worth about $290 according to TPG’s valuations — in contrast to the $340 nightly cash rate.

ihg booking screenshot
(Screenshot from ihg.com)

The hotel is within walking distance of the Public Market and original Starbucks location. If you get tired and want to eat on-site one night, you could enjoy locally-sourced cocktails and what I'd describe as elevated bar food at the Outlier Restaurant. There's also plenty of outdoor seating to enjoy the (hopefully mild and clear) Pacific Northwest weather.

(Photo by Diana Robinson Photography/Getty Images)

Bottom line

While it remains to be seen if airlines will make it through Labor Day weekend without major hitches, there’s excitement in having more flexibility to plan travel in 2022 after a couple of years when it was more risky and unpredictable. While some of the inconveniences and uncertainties surrounding this year's summer travel months aren't likely to disappear completely on the season's final holiday weekend, they will hopefully get better as the airlines and airports address operational issues and ramp up staffing.

If you're apprehensive about traveling on the last big weekend of summer though, we still have some good news. Prices usually go down around Labor Day and stay lower through the autumn months. And crowds will be thinner as children head back to school. So if you don't book a getaway in early September, watch for an opportunity later that month or in October and November before the Thanksgiving holiday season is here.

Featured image by SEAN CUDAHY/THE POINTS GUY
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)

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  • Packed with credits foodies will enjoy
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Cons

  • Not as useful for those living outside the U.S.
  • Some may have trouble using Uber and other dining credits
  • You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
  • Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
  • Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
  • Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
  • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
  • $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
  • $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
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  • Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
  • No Foreign Transaction Fees.
  • Annual Fee is $325.
  • Terms Apply.
Apply for American Express® Gold Card
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Best for dining at restaurants
TPG Editor‘s Rating
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Rewards Rate

4XEarn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
4XEarn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
3XEarn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
2XEarn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
1XEarn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
  • Intro Offer

    As High As 100,000 points. Find Out Your Offer.
  • Annual Fee

    $325
  • Recommended Credit

    Excellent to Good

Why We Chose It

There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)

Pros

  • 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
  • 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
  • Packed with credits foodies will enjoy
  • Solid welcome bonus

Cons

  • Not as useful for those living outside the U.S.
  • Some may have trouble using Uber and other dining credits
  • You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
  • Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
  • Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
  • Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
  • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
  • $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
  • $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
  • $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
  • Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
  • No Foreign Transaction Fees.
  • Annual Fee is $325.
  • Terms Apply.