Why Florida’s St. Augustine is the Sweetest Escape

6 minute read | October 19, 2019

Read the original article on CouplesBest.com.

Located on Florida’s northeastern coast, Saint Augustine is the oldest city in the United States. For almost 500 years, historic Saint Augustine has seen its neighboring land expand into our country today. Playing an instrumental part in America’s early history, this bewitching little city has been there, watching America’s growth as its establishing flag first waved on September of 1565. Both history enthusiasts and vacationers equally experience a cozy retreat as Saint Augustine seeps with history and sweet nostalgia. This historic city welcomes guests to its miles of beautiful beaches, historical landmarks, top-rated restaurants, museum explorations, boutique and antique shopping, and state parks; something for everyone looking for a serene escape.

Romantic St. Augustine

We checked in at the colorful and contemporary Tryp by Wyndham Sebastian St. Augustine hotel, a refreshing contrast to the quaint city surrounding us. This coastal-chic retreat features comforting amenities like a heated outdoor pool, a glorious hot tub, free parking for car, bus and RV is available, Tesla charging stations, laundry services and same day dry-cleaning service, gift shop and shuttle service was also a wonderful convenience during our stay. Our room was sleek, but cozy; and we were grateful for the lovely view of the river from our balcony. Their staff was hospitable and prompt, securing us extra amenities like a microwave and extra coffee. Greeted with a warm welcome, we began our stay in Saint Augustine in a comforting, modern space in this romantic centenarian city.

Our exploration of Saint Augustine began aboard the St. Augustine Scenic Cruise at sunset. We arrived to check-in 20 minutes before departure at The Saint Augustine Municipal Marina, then walked around to tour the beautiful boats docked nearby. After we set sail, we toured Florida’s historic coast cruising by unique views and landmarks, like the Saint Augustine Lighthouse and the Castillo de San Marcos, the oldest standing fortress in the continental US completed in 1695. Deeply breathing in the breeze, we wore a light jacket in October and celebrated Florida’s winter warmth against a beautiful sunset backdrop. It was a picturesque start to an enchanting vacation.

After dusk, we strolled hand-in-hand by the San Sebastian River and caught gorgeous sights and a skyline framed by beautiful colonial Spanish architecture. Regal horse-drawn carriages carried romantic couples and sweet families onboard, and they excitedly waved as they strutted on through the Old City District on St. George Street, or what is known as the “main drag.”

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Just across the street at Harry’s Seafood Bar and Grille, we found their charming courtyard patio and a table for two. Every local we asked confirmed Harry’s as their first recommendation of great dining in the area, so we knew this restaurant was to be part of our itinerary. Their Cajun-inspired menu was a happy feast to our taste buds as they focus on traditional New Orleans flavors, like Etouffee and Jambalaya. The attentive service was impressive and personal; our server offered her menu selections tailored to our liking. She got to know us and our preferred flavor-profiles to ensure an excellent experience. Besides the delicious dining, what made this stop so special was the ambiance. A lively instrumentalist covered acoustic fan-favorites adding to the cozy, quaint feel of our surroundings.

We finished the late evening with Ghost Tours of St. Augustine, a fun walking tour featuring animated storytelling and lore. We meandered through old, narrow brick streets in the dark to find notoriously haunted hubs. Beside another couple, we listened to tales based on the history of the city, detailing the personalities that developed today’s St. Augustine, told by an eccentric actor named Gail who played her kooky character flawlessly throughout. We’re not big believers in the occult, and we don’t often enjoy guided tours (we’re travel loners); but we were surprised to have so much fun following along with Gail! We still reference her quirky mannerisms with a laugh–every time she’d finish a spooky story, she’d look over her shoulder, raise an eyebrow and in a deep southern dialect, she’d lure, “but that’s just what they say…” We got a kick out of that, and still reference her signature line jokingly. We loved the theatrics and thrills, and it was a fun way to explore hidden alleys, passageways and even score a peek at a cemetery with gravestones dated centuries ago. This evening adventure set an exciting tone for a delightful time during the rest of our stay.

Bright and early, we awoke in our comfy abode the following morning at The Tryp by Wyndham ready for another excursion! After a quick, warm breakfast at their café, we rolled into the world’s first-ever oceanarium, Marineland Dolphin Adventure, to check off another item on our bucket list. We spent the afternoon in the water with friendly dolphins and their trainers, interacting and communicating with them, and learning how to support their preservation and protection of marine life.  Presentations at Marine Studios evolve from simple dolphin feedings.

into complex demonstrations of animal behavior and training.
The Town of Marineland is founded in 1940.
1 9 4 7 : Spray is the first dolphin successfully born in human care

I am not a confident swimmer: I can doggy paddle for a bit to get to the edge of the pool and I can mermaid underwater, but the dolphin trainers made me feel safe for my well-being and that of the animals, too. The whole experience was unforgettable, especially when we gave our new dolphin-friend a sweet kiss, shared a flipper shake and hitched a quick ride on its dorsal fin. They also feature meet-and-greets with their red-footed tortoises and even dockside interactions with them.

To be completely honest, I have heavy feelings about swimming with dolphins. Although there was a lot of education on protecting these highly intelligent mammals, I felt guilty knowing they’re trapped in their underwater cages; but they also can’t survive in the wildlife anymore after a lifetime of captivity. I had a lovely afternoon, but I left with a weight in my heart.

In search of a location where the locals hang, we came across Cafe Eleven, a lowkey cafe and bar with a pet-friendly patio & a killer live music lineup. Located just across the street from the beach, their popular brunch and happy hour features an adventurous selection of craft beers on tap. We grubbed on lunch and sipped on a cold, refreshing brew in this casual environment offering free Wi-Fi and a welcome to stay and relax. One usually sticks to a strict schedule when vacationing, but it was so nice to chill at a cool spot without being rushed. We reference this place all the time, “I wish we had a Cafe Eleven at home!”

St. Augustine is surrounded by beautiful water views. From our lakeside hotel balcony to the sunset cruise on the San Sebastian River to our fun aquatic excursion with dolphins – a major theme of our stay was water. We knew we wanted to end our trip with another beautiful, coastal view. For our final dinner feast, we found Cap’s on the Water. Voted as the “best outdoor dining” in the area, this waterside oyster bar and restaurant offers local seafood on their wooden, outdoor deck and garden canopy. A fresh catch paired with scenic views gave us the perfect dining experience to end our amazing vacation. Looking into the horizon, we sipped on cocktails and paired them with briny St. Augustine oysters. Their space was surprisingly large and busy, but their attentive service team offered a laid-back experience framed by their gorgeous riverscape.

We celebrated the beauty and easy pace of this city, a relaxing paradise perfect for lovers.

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For more feedback, check out what everyone else is saying on their TripAdvisor!

For more on St. Augustine, visit www.visitstaugustine.com.

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