Stay Like a Local Blog

St. Augustine, Florida is a stunning coastal city with a rich history and stunning natural beauty. It is a popular tourist destination all year round, but it is especially worth a visit during the winter months. Here are 10 reasons why you should visit Saint Augustine this winter.

1. Warm Winter Weather: While much of the country is experiencing cold and snowy weather, Saint Augustine boasts an average temperature of around 70 degrees Fahrenheit during the winter months. This makes it the perfect place to escape the winter blues and soak up some sun.

2. Rich History: Saint Augustine is the oldest continuously inhabited European settlement in the United States and is steeped in history. The city is home to numerous historical landmarks, such as the Castillo de San Marcos and the St. Augustine Lighthouse & Maritime Museum.

3. Beautiful Beaches: Saint Augustine is situated along the Atlantic coast and boasts some of the most beautiful beaches in the country. Winter is an ideal time to visit the beaches as they are less crowded and the water is still warm enough for swimming.

4. Festive Atmosphere: During the winter months, Saint Augustine comes alive with holiday festivities. The city is adorned with lights, and decorations, and there are numerous events and activities to participate in, such as the St. Augustine Nights of Lights.

5. Wildlife Watching: Winter is an excellent time for wildlife watching in Saint Augustine. Visitors can take a boat tour to see dolphins, manatees, and other marine life, or visit the Alligator Farm Zoological Park to see alligators, reptiles, and exotic birds.

6. Relaxing Getaway: Saint Augustine is a great place to unwind and recharge. The city is known for its laid-back atmosphere and there are plenty of opportunities for relaxation, such as visiting the city’s many spas or taking a leisurely stroll through the historic district.

7. Unique Accommodations: Saint Augustine offers a wide range of unique and charming accommodation options, from bed and breakfasts in historic homes to luxury resorts. Whether you’re looking for a romantic getaway or a family vacation, there’s something for everyone in Saint Augustine.

8. Delicious Dining: Saint Augustine is home to an excellent culinary scene, with a range of dining options to suit every taste and budget. From seafood restaurants to quaint cafes, visitors will not be disappointed with the city’s dining options.

9. Shopping: Saint Augustine is a shopper’s paradise, with a wide range of options from antique shops to boutiques. Visitors can explore the historic district and find unique gifts, or head to one of the city’s malls for more mainstream shopping options.

10. Accessibility: Saint Augustine is easily accessible from many major cities, making it a convenient destination for a winter getaway. The city is just a short drive from Jacksonville and is well-connected to the rest of Florida via major highways.

In conclusion, there are many reasons to visit St. Augustine this winter. With its warm weather, rich history, beautiful beaches, festive atmosphere, wildlife watching, .relaxing getaway, unique accommodations, delicious dining, shopping options, and accessibility, there is something for everyone in this charming coastal city. So pack your bags, grab your sunscreen, and head to Saint Augustine for a winter vacation you won’t soon forget.

St Augustine, Florida is a city steeped in history and culture, and every year it becomes even more magical during the Nights of Lights celebration. This annual event, which takes place from November through January, transforms the city’s historic district into a dazzling display of sparkling lights and holiday cheer.

Tourists visiting St Augustine during the Nights of Lights can expect to see millions of white lights twinkling throughout the city’s streets, squares, and buildings. The lights are strategically placed to highlight the city’s unique architecture and historical landmarks, creating a magical atmosphere that is both enchanting and festive.

One of the most popular spots to see the lights is along St. George Street, the city’s main thoroughfare. This charming street is lined with shops, restaurants, and galleries, and during the Nights of Lights it becomes a wonderland of twinkling lights and holiday decorations. Visitors can stroll along the street, taking in the sights and sounds of the holiday season, and enjoying some of the delicious food and drink that the city has to offer.

Another must-see spot for tourists during the Nights of Lights is the historic Castillo de San Marcos. This 17th-century fort is the oldest masonry fort in the United States, and during the Nights of Lights it is lit up with thousands of white lights, creating a stunning backdrop for holiday photos. Visitors can also take a guided tour of the fort, learning about its history and architecture.

The Nights of Lights also includes a variety of other activities and events for visitors to enjoy. For example, there are several boat tours available that take visitors on a tour of the city’s waterways, allowing them to see the lights from a different perspective. Additionally, there are several musical performances and other live entertainment events taking place throughout the celebration.

For those looking to combine the beauty of the Nights of Lights with some holiday shopping, the city’s Christmas on the Bayfront event is a great option. This event features a variety of local artisans and vendors selling unique gifts and crafts. Visitors can also enjoy live music, food and drinks, and a visit from Santa Claus.

In addition to all the lights and activities, St Augustine’s Nights of Lights is also a great opportunity to enjoy some of the city’s other attractions. Visitors can take a ghost tour of the city’s historic district, visiting some of the most haunted places in St Augustine. They can also visit the St Augustine Lighthouse and Museum, which offers tours of the lighthouse, as well as exhibits on the history of the lighthouse and the city.

All in all, the Nights of Lights in St Augustine is a must-see event for tourists visiting the area during the holiday season. With millions of sparkling lights, festive activities, and a charming atmosphere, it is the perfect way to experience the magic of the holidays in one of the most beautiful and historic cities in the United States. Whether you’re looking for a romantic getaway, a family vacation, or a fun trip with friends, St Augustine’s Nights of Lights is sure to leave you with lasting memories.

And the closing of Hypolita 

At the beginning of 2020, the pandemic happened and by March 2020 TeamBonding, our live event business lost all of its future bookings. Nobody knew how long it was going to last and for a couple of months in St. Augustine, people stopped coming.  We approached our landlord and decided that we weren’t going to be able to continue with our original guest house on Hypolita Street downtown. We were saddened by it but we didn’t know what the future was going to bring and we needed to make sure that we were able to pay the mortgage on the new house. He was kind enough to allow us to end the lease early.   

As our event business was able to pivot to virtual events, we were able to spend the winter in St. Augustine and work remotely from January to April 2021.  After a few months, people did start coming back and we adapted to the Covid policies and rented our one guest house in the second half of 2020 and again after we left in April. Right before were scheduled to return to Boston, a house went for sale, just a few blocks away and right near the Fountain of Youth. It was a very cool house, a Southern dogtrot house with a warehouse right behind it.  We took a leap of faith and bought it. In August 2021 we introduced Sanchez Suites.   

Wendy was really good at decorating and designing by this point and she really outdid herself with the artwork and the furniture, the adding of color and the renovation of the bathroom in the studio. Guests that stay at this house love it as much if not more than they did the other houses. As of this writing, we have 254 reviews and 98% of them are 5*reviews we have been awarded as an Airbnb Superhost seven different times as well as a preferred partner for VRBO.   

In January 2022 Wendy and I stayed at Sanchez Suites while we went through the permitting process to turn the warehouse into an industrial-style vacation rental.  We hired an architect and a builder and are currently creating a three-bedroom, two-bath vacation rental behind Sanchez Suites.   

You may be wondering what we know about renovating a house from the ground up. In 2019 we renovated our house in Sharon, Massachusetts which is now our primary residence and our empty nesting house. It is across from the lake and the design and the artwork are fun and colorful, and it overlooks the lake where I grew up.  

This project, this industrial vacation rental is going to be the best one yet.  One-of-a-kind won’t really describe it.  You’ll be able to stay at it with your friends and family and we hope to have both properties connected so you can stay with a larger group/family.   

Then there were Two St. Augustine Guest Houses 

Wendy and I were in love. Not only with each other but with St. Augustine and we loved being vacation rental hosts. As we were heading out of town, we decided to extend another day and look at a house that was about a 10-minute walk from downtown. We went into this really cute neighborhood with hidden streets and saw a house that had a circular driveway and a Spanish influence and we toured it. Across the street was another house, and leaning against the house was a for sale sign, we were curious. 

Behind the white fence were two dogs, and I bravely opened the gate (they were small dogs), befriended the dogs, and rang the bell. When the woman answered the door, I asked her if her house had just been sold. She said no, it was about to be listed the next day. We asked for a tour of the house and she walked us through and it was amazing. I wasn’t expecting the giant parrot as we opened the door to the backyard when I screamed and we all laughed.  Wendy and I had a plane to catch.  Could we buy this house?  Should we buy this house? We were new to the vacation rental business, but we couldn’t resist the opportunity and we got home and bought the house the next day after seeing it for about 10 minutes. 

This house was amazing and fairly new as it was built 10 years ago in a historic neighborhood.  The concrete block home had been freshly updated with the finest appointments–travertine floors, new carpet, granite, and quartz countertops, LED lighting, a fireplace, custom closets, and so much more. We decided to rent it as a long-term rental for a year while we got our feet wet in the vacation business, learned more about St. Augustine, and got to know the house.  We rented it to a nice family for a year as we continued our St Augustine vacation rental adventures and became a 5* Airbnb Superhost and VRBO Preferred Partner with our downtown guest house. 

It’s been a few years now and people love this house and we love this house. Our family loves this house. Our friends love this house and our guests love this house as it’s so close to the historic district, so close to Francis field where all the festivals are and so close to the Village Inn where they have Free pie on Wednesdays. 

How we found and started the St. Augustine Guesthouse 

Truth be told we had never heard of St. Augustine before coming here in 2015. Wendy and I were at a Florida marketing conference on Amelia Island and we had a free night. We were looking for a place to go for dinner, and we stopped by the table that was promoting St. Augustine as America’s oldest city.  The man at the table suggested we drive an hour down the road and we’d come to St. Augustine, so we did.  Our first stop was Caps on the Water which has the most breathtaking sunsets. After dinner, we went into the historic city for dessert at Cousteau’s Waffle and Milkshake Bar on Hypolita Street during the Nights of Lights Festival.  This wasn’t just any festival. This was the 450th anniversary of St. Augustine and it was spectacular. Where were we? 

After driving around and seeing the thousands and thousands of white lights on the historic buildings, talking to the horse and buggy drivers, seeing and hearing the Holly Jolly Trolley, and seeing people everywhere enjoying the festivities, we had to learn more. Although we had to get back to Amelia Island, our curiosity was piqued. We had just been to one of the most beautiful places we had ever been to, and it was in Florida.   

Shortly after we got back to Boston, we scheduled a trip to St. Augustine and stayed at Casa Monica. We toured the city, went to the beach and we took advantage of their package with the Serenata Beach Club which we now offer to our guests. We walked all around enjoying the music and the food and we decided we needed to find a way to live here, at least part-time.  We decided that we were going to buy a house and start a short-term rental and promote it on Airbnb and VRBO. We visited a few more times with friends and family and stayed at a few vacation rentals in Lincolnville, and one by the Bayfront. We looked and we looked and we couldn’t find a house to buy but we fell in love with the city a little more each time.  We decided to walk back to where it all began on Hypolita Street, in the heart of the historic district. 

As we were walking down the street, we saw an apartment for rent and it was in the most amazing location and the two floors and spiral staircase to the master made it perfect for a guest house. It was above a wine store and across the street from a spice and tea shop and a great location. Could we possibly rent this apartment and turn it into a vacation rental?  We could and we did. We opened the first St Augustine Guest House in March 2018 and after shopping, decorating, marketing, designing, and planning, we loved every minute of it, except one. 

Wendy went down the night before I did and stayed in the future guest house. At about 1:00 AM, I got a phone call and Wendy was a little panicked as the bar next-door had speakers pointed out the windows, and the whole building was shaking.  What had we done? As we had never visited the apartment at night, we didn’t know that the bar was loud and that there were no other neighbors as we were in the commercial district. Did we make a mistake?   

After a few conversations with the neighbors and the landlord, it was agreed that we would buy them an air conditioner, and they would shut their windows and bring the speakers in. We made plans to prepare the house for soundproofing and let the guests know that there was a bar next door.  The vacation rental was a hit from day one and people loved the location being in the middle of it all, and they loved what we did with the place as far as decorating it with fun colors and lots of local art, and we loved being hosts.   

As luck would have it, shortly after we signed the lease, we found a house to buy.