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Memorial Day Getaways: Parades, Music, Sunshine and More

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Sun, sand, services for our fallen heroes, history lessons, parades, picnics … Can you have it all this Memorial Day? TPG Contributor Adam Erace lays out six great destinations (with good points-redeeming opportunities) for the holiday weekend, from urban centers to evergreen islands.

The Longwood Fountains in Philadelphia, PA
The Longwood Fountains outside Philadelphia, Pennsylvania.

Philadelphia, Pennsylvania

Arrive: Philadelphia International Airport (PHL)

Do: Philly is a city steeped in history. Get your fix at the National Constitution Center, which has special Memorial Day weekend programming ranging from flag ceremonies to a thank-a-vet letter-writing station, then make the drive out to Chester County’s dazzling Longwood Gardens, kicking off its summer-long Fireworks and Fountains show on Saturday, May 24.

Stay: The newest Starwood property in town is the artsy Le Meridien (SPG Category 5), which makes up for its slightly awkward location north of City Hall with Georgian Revival architecture and crisp black-and-white rooms. Rates for the weekend start at $245 or 16,000 Starpoints per night. On the other side of City Hall, the posh Ritz-Carlton (Marriott Tier 3) is going for $299 or 50,000 points per night.

The Marriott Key West
The Marriott Key West.

Key West, Florida

Arrive: Key West International Airport (EYW)

Do: For those of us in the Northeast US, Memorial Day weekend is the real beginning of summer, but in Key West, it’s been 78 and sunny all year. Take advantage of this weather with local events such as the Yamaha Dolphin Masters Invitational, a race to catch the largest mahi-mahi for up to $13,000 in prizes (with a kick-off party and weigh-in at Conch Republic Seafood Company). Nearby at Schooner Wharf Bar, the hilarious 24th annual Schooner Wharf Minimal Regatta has teams building (and racing) mini boats from materials including plywood and duct tape. For more ideas, check out Destination of the Week: Key West.

Stay: Key West has some of the country’s highest average room rates, making the little island a prime place for redeeming points. Take the Category 9 Marriott Beachside Hotel, where the island-chic rooms (think seashell-print pillows and mahogany headboards) are running $314 or 45,000 points per night. Even better: The beachy condo-style rooms at the Category 6 Hyatt Windward Pointe are $569 or only 25,000 points per night.

The San Diego Jazz Fest
The San Diego Jazz Fest. Photo courtesy of

San Diego, California

Arrive: San Diego International Airport (SAN)

Do: From La Jolla to Coronado, San Diego’s sun-splashed beaches make a strong case for doing nothing but sunbathing over Memorial Day weekend, but the annual San Diego Jazz Festival also coincides with the holiday, featuring artists such as Toni Braxton, Maxwell and Erykah Badu. For more suggestions, be sure to check out Destination of the Week: San Diego.

Stay: Rock-wall showers, complimentary minibars and windows that actually open are a few of the plusses at the Hyatt Category 5 Andaz San Diego, which is going for $279 or 20,000 points per night. The Category 6 Hilton La Jolla Torrey Pines will get you closer to the ocean but at a weaker redemption rate; rooms start at $219 or 40,000 points per night.

U.S. Army Soldiers march during the National Memorial Day Parade in Washington, D.C., May 27, 2013. (U.S. Army photo by Staff Sgt. Teddy Wade/ Released)
US. Army Soldiers march during the National Memorial Day Parade in Washington, DC, May 27, 2013. (U.S. Army photo by Staff Sgt. Teddy Wade/ Released)

Washington, DC

Arrive: Reagan National Airport (DCA) or Dulles International Airport (IAD)

Do: Our nation’s capital hosts the country’s biggest Memorial Day parade, with more than a quarter-million marchers organized by the American Veterans Center promenading down Constitution Avenue. At dusk, the west lawn of the US Capitol becomes an al fresco performance space for the free National Memorial Day Concert featuring the National Symphony Orchestra and hosts Joe Mantegna and Gary Sinise. For more ideas, see Destination of the Week: Washington, DC.

Stay: Would you ever guess that the most expensive Hyatt available Memorial Day weekend is a Hyatt Place? With rates of $427 a night, the category 3 Hyatt Place Downtown, which debuts in May on K Street, is almost double the Park Hyatt. Steep for a Hyatt Place (even a brand-new one), but a great redemption value at only 12,000 points per night. For other hotel ideas, check out The Points Guy’s reviews of the W Washington DC and the Grand Hyatt Washington.

The WW2 Museum
The WWII Museum in New Orleans.

New Orleans, Louisiana

Arrive: Louis Armstrong New Orleans International Airport (MSY)

Do: New Orleans has a fantastic WWII Museum where you can learn about the Second World War through multimedia exhibits that range from troop diaries to fighter jet replicas to immersive galleries that recreate the Allied Powers’ campaign from Tunisia to Berlin. Decompress at the weekend-long Greek Festival with Hellenic dancers, live music, cooking demos and toga contests at the Holy Trinity Greek Orthodox Cathedral. For more suggestions, see Feasting in New Orleans and Destination of the Week: New Orleans.

Stay: Rooms at the IHG Category 5 Hotel Indigo Garden District, which resides in one of New Orleans’ prettiest neighborhoods, start at $157 or 30,000 points per night on Memorial Day weekend. Also see The Points Guy’s review of The Ritz-Carlton, New Orleans.

The Virgin Hotel in Chicago, IL
The Virgin Hotel in Chicago, Illinois.

Chicago, Illinois

Arrive: Chicago O’Hare (ORD) or Chicago Midway (MDW)

Do: You want to get to the Green City Market, Chicago’s biggest farmers’ market, in Lincoln Park early—both to get first dibs on great souvenirs such as Indiana pecans and buttermilk-fed pork brats and to get back to Daley Plaza in time for the wreath-laying ceremony at 11 am on Saturday, May 23. The city’s massive Memorial Day parade follows at noon. Also check out Destination of the Week: Chicago and 8 Chicago Restaurant Hot Spots for Every Occasion.

Stay: Sir Richard Branson has expanded his stylish travel brand into the hospitality industry with the first Virgin Hotel, which opened last winter in downtown Chicago. Think XL rooms with Bow & Truss coffee, street-price minibars and a companion app that lets you check in and adjust the temperature from your smartphone. Memorial Day weekend rates start at $299 per night, and while there are no point-redeeming options (yet) you can earn points for stays toward your Virgin Elevate account. Silver and Gold status flyers get perks like free upgrades. Also see these reviews of the Hyatt Regency Chicago, the Radisson Blu Aqua Chicago (where the fitness center goes the extra mile) and The Langham Chicago.

Hungry for more culture and food in these destinations? Be sure to check out:

7 Ways to Save Money on Museum Admissions
12 Best Irish Pubs in America
10 Divine Restaurants for a Holiday Brunch

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