Westgate Resorts 2019 Military Weekend – After Action Report

As Part of Military Appreciation Month Westgate Resorts, for the 8th year in a row, invited thousands of military families to enjoy a free vacation weekend.

Each year on Veteran’s Day Westgate Resorts offers the chance to be one of these lucky families by being one of the first to register. Over the years Westgate has offered between 1,000 and 2,500 free 2-night vacations to our community each year.

This year over 5,500 families were able to participate!

The event is absolutely fantastic, offering a full schedule of events to participate in, or you could just chill out by the pool.

The Weekend was capped off by a free concert for participants!

Check out the full weekend schedule below.

This year’s event was held at Westgate’s Town Center Resort, just a mile and a half by car from Walt Disney World property.

Event History

In 2011 Westgate Resorts began offering free weekend stays to military families to thank them for their service.

David Siegel Westgate CEO, a veteran himself is proud to do this for military families each year.

As a veteran, I understand the dedication and sacrifice required of our troops,” said Siegel.  “I am incredibly proud of these national heroes, and it is our pleasure to thank them the best way we know how at Westgate Resorts – with an unforgettable vacation experience.”

Our U.S. military and their families make a constant sacrifice. We hope to give those who have served in combat a chance to spend some quality time with their loved ones. Nothing can ever replace the family time that’s lost, but by creating these weekends for them, we’re trying to help make new memories and give these men and women the recognition they deserve.”

During the first few years of offering these vacations, those who registered in time could select their vacation dates and location from a list of Westgate Resorts.

But starting in 2017 Westgate stepped it up and offered a Big Special Weekend that all would attend together. Doing this allowed them engage with partners to offer many special events and other offers.

I’ve now attended both the pick your date and resort, and the consolidated military weekend, and the latter is by far the best way to do it.

The first time I participated in this offer I picked my dates and picked the Westgate Town Center Resort as my location due to it’s proximity to Walt Disney World. There were no special events or other military families there that time, I just went to WDW. You can see that trip report here

This time around there was so much to do with our community right there, though I did find time for lunch at Disney Springs.

As you may know, Westgate Resorts are timeshare resorts, but this event is a totally separate experience. There are absolutely no strings attached and no sales presentations whatsoever. Just an offer to say thanks for serving.

Westgate’s Town Center Resort

As I mentioned this year’s event was held at Westgate’s Town Center Resort, a huge resort located a very short distance to the south of Walt Disney World property.

For accommodations, Town Center and the other Westgate resorts offer Studio, 1 Bedroom, and 2 Bedroom suites.

Amenities include:

• A huge on-site Water Park
• 14 Heated pools
• Playground
• Movie Theatre
• Mini golf
• Paddle boat rentals
• Bike rentals
• Outdoor activates like: Basketball, volleyball, tennis, shuffleboard, and horseshoes
• Grocery & sundry store
• Many dining options: Sports bar, bistro, deli shop, ice cream shop, and poolside bars

All this just a 15 minute drive from Disney World.

Westgate’s Orlando Florida Disney Resorts

Saturday Night Concert

The stars of this year’s concert was the Lt Dan Band, with special guest Lee Greenwood.

On Saturday night the concert was held on a huge grassy area on resort property. Military families chilled out on their blankets or in chairs and had a fantastic time.

Hamburgs, hot dogs, chips soda, and water were provided for free. Beers were a dollar with all proceeds going to military charities.

The concert opened with Florida Governor Ron DeSantis (a Naval Reservist) thanking the troops and families for their service. David Siegel then gave his thanks to the military community and event sponsors, then turned the stage over to Lee Greenwood, who sang his famous “God Bless the USA.”

After Mr. Greenwood, the Lt Dan Band took the stage.

The Lt. Dan Band is the creation of actor Gary Senise, who famously portrayed Lt. Dan Taylor in Forest Gump.

The band usually plays covers of popular songs to entertain the troops worldwide and in the US as part of special events and USO tours.

The band is just one of the many programs of the Gary Sinise Foundation, you can learn more about the Lt. Dan Band on the official site

A Grateful American

Besides performing at the concert Gary Senise took the time to have a moderated chat about his new book, A Grateful American, a memoir that tells the story of how he found his true calling to ensure that those who protect our great nation and its freedoms are never forgotten.

Close to All that Central Florida Has to Offer

Orlando and Central Florida have a lot to offer military families as a vacation destination. And Westgate offers year-round military discounts at their Orlando locations as well as nationwide.

Westgate’s Town Center has convenient shuttle buses to Disney World, Universal, and SeaWorld.

In Central Florida Military Discounts are available for:

• Walt Disney World
• Universal Studios Orlando
• SeaWorld Orlando
• Legoland Florida
• Busch Gardens Tampa
• Kennedy Space Center
• Gatorland
• The Orlando Magic
• Orlando’s International Drive Attractions

See our Military Discounted Tickets Page for more details.

Tickets can be purchased at your Base Ticket Office, Shades of Green’s Ticket Office, and the Orlando ITT.

Watch for Next Year’s Announcement

Interested in being able to participate next year?

Then watch for an announcement on MDT most likely in October 2019!

This year one lucky MDT reader received a guaranteed slot at the 2019 Military Weekend. Hopefully next year we’ll be able to offer more slots.

You can see this year’s announcement here.

In Closing

Military Disney Tips thanks David Siegel and Westgate Resorts for providing this awesome display of thanks and appreciation for the military community year after year!

The planning, effort, and cost that go into it are truly impressive.

Over to you, did you participate in this year’s event (or a previous one)? Tell us all about it in the comments section below!

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Planning a Disney Trip? Want to get the best military discounts that are available? Feeling a little confused? See Our Great Disney Discount and Planning Info:

• Disney Veteran & Military Discount Eligibility Guide
• The Military Family’s Walt Disney World Comprehensive Vacation Planning and Preparation Guide 
• Military Disney Tips Disney Packing Checklist 
• Disney Military Tickets – Your Start to Finish Guide

Learn about the Disney Armed Forces Salute the best military discount that there is for Disney. See our Topic Overview Pages:

• Resorts/Hotel Overview Page
• Dining Overview Page
• Transportation Overview Page
• Technology Overview Page
• Shades of Green, WDW’s Military Only Resort