5 Haunted Cities To Wander On Vacation

As temperatures drop and everything starts to smell (and taste!) like pumpkin spice, the wind begins to whisper haunted tales and legends of ghosts. Don’t forget to make plans to explore the spooky streets of your next destination vacation. Throw on your most comfortable fall fashion and head to one of these five resorts, perfect for the thrill-seekers, adventurers, and history buffs in your crew. Be sure to bring a camera — you never know what mysterious oddity you’ll be able to capture.

1. Old San Juan, Puerto Rico

If you’re looking for a fright-filled fiesta, Margaritaville Vacation Club by Wyndham - Rio Mar will give you all the fun you’re looking for. Just a quick 45-minute trek to Old San Juan will give you an out-of-this-world experience. Not only do the ghosts of Betancourt, Marîa Dolores, and Doña Ana de Lansos y Menendez de Valdez (a few of Puerto Rico’s most famously tragic stories) still linger in their old haunts, but you’ll also get the opportunity to watch a show at the historic Teatro Tapia — don’t be too spooked, but you may just sit next to a disgruntled spirit.

2. St. Thomas, U.S. Virgin Islands

Spooky seekers, look no further than the end of your paddle on this enchanted and haunted moonlit kayak tour through Mangrove Lagoon. While staying at Margaritaville Vacation Club - St. Thomas you can take an exhilarating evening paddle where you’ll learn about the ecosystem of St. Thomas’s native mangroves. Settle in as you hear tales about the ghosts that linger above and the pirates that lurk below the shallow waters.

3. St. Augustine, Florida

If you’ve come to Florida for some sun and fun, Club Wyndham Ocean Walk will surely fit your needs. As the evenings start to cool down, and you’re looking for adventure, head straight up the coast to the nation’s oldest city, historic St. Augustine. You’ll be able to peer into the windows of the Old Jail, visit Cromwell’s Parlour of Paranormal Curiosities, and hear hair-raising tales of the Castillo de San Marcos. Take a walking tour, or hop on a trolley to explore the supernatural world of vampires and ghosts.

4. The Bay Area, Florida

While Florida’s Bay Area is known for its amusement parks and cultural attractions, there’s also a dark underbelly of haunted mansions, wandering spirits, and supernatural phenomena. Schedule a candlelight tour through Tampa or a frightful stroll through the streets of St. Pete. Heading back to the safe haven of Club Wyndham Clearwater Beach will surely be a welcome end to your chilling night.

5. Oahu, Hawaii

Pack your walking shoes next to those flip flops as you’re prepping for your Hawaiian vacation. While you’re staying at Club Wyndham Waikiki Beach Walk or Club Wyndham Royal Garden at Waikiki, you will have the unique experience of walking in the very same steps as ancient Hawaiian warriors called the Night Marchers. Said to roam at night with raised torches, drum beats, and chants, hear stories of Hawaii’s traditions and spirits on a Night Marchers Ghost Tour.