Monticello, Florida – Tallahassee travel blog

If you live in North Florida or are planning a trip through the area, consider Monticello. Although the town itself can be thoroughly explored in a day, there is plenty more to do in the surrounding areas (Tallahassee is only a short 30 minute drive). I decided to take Alex for a surprise overnight trip up to Monticello for Valentine’s Day and we had a wonderful, relaxing North Florida weekend.

First on the agenda was a stop for lunch at Tupelo’s Bakery & Cafe. This charming cafe makes you feel like you went over to a friend’s house for lunch and coffee. The food is organic and locally sourced, as noticed by a list on the wall of the local farms from which Tupelo’s gets all of its ingredients. The highlight for me was definitely the bakery-buying a treat (or two!) is definitely a must. The cafe has free wi-fi, a take a book/leave a book library, and sells several items including honey, handmade candles and soaps, artwork, and beautiful handmade wood cutting boards. What to eat: Roast Beast sandwich, homemade Oreo cookies. Protip: Arrive early for lunch. When we ate at Tupelo’s, they had run out of several menu items, including bread!


Next up was a walk around historic downtown Monticello, self-guided by the many well-placed historical markers. We saw the old court house, opera house, and numerous beautiful homes. We also wandered in and out of the many antique shops in Monticello. Our favorite was Huckleberry’s Creations, which features both antique pieces and custom-built furniture. It had such beautiful items and I definitely plan to purchase a custom piece or two in the future!

Monticello Court House
Monticello Court House
Monticello Opera House
Monticello Opera House
Old Jefferson County High School
Old Jefferson County High School

We next attempted to stop at the Jefferson Arts Gallery to see the monthly exhibit, but it was closed on the day we visited. If you are interested, call 850-997-3311 or email for an appointment.

Next, it was time to check into our adorable bed and breakfast, the 1872 John Denham House. We stayed in Jefferson’s Blue Room and were greeted by Pat, the innkeeper, with homemade baked goods and fresh camellias. A very warm Southern welcome!

1872 John Denham House
1872 John Denham House
Sitting room, looking into the dining room
Sitting room, looking into the dining room
Jefferson's Blue Room
Jefferson’s Blue Room



Since happy hour at the B&B wasn’t due to start for another hour, we drove over to Monticello Vineyards and Winery for a “tour” and tasting. Cynthia Connolly and her adorable dogs immediately greeted us and we were treated to a brief history of the winery. Cynthia and her friends and family have a hand in the winery and farm operations from start to finish, even handpicking every single grape. Cynthia grows over 18 different varieties of Muscadine grapes (unique to the Southern United States) and then bottles various batches and varietals. Unfortunately, the winery was running low on stock, but we were still able to taste three different wines, a dry Florida red, a semi-sweet red, and the Magnolia, a sweet white wine. Cynthia is a fascinating woman and was patient and thorough in answering our questions. We left with a bottle of semi-sweet Florida red and can’t wait to enjoy it!

Monticello Vineyards & Winery
Monticello Vineyards & Winery
Alex and I enjoying our wine tasting on a beautiful Florida Valentine's day!
Alex and I enjoying our wine tasting on a beautiful Florida Valentine’s day!

We then returned to the B&B to freshen up for dinner and had more wine at the happy hour provided by Pat. While we sipped wine, we read excerpts from Haunted Monticello, Florida by Betty Davis and the Big Bend Ghost Trackers. It was fun to read about the supposed ghost sightings at some of the places we had visited earlier in the day, and even in our B&B! If you are really into haunted stories, you can even take a Historic Monticello Ghost Tour.

For dinner, we drove out to Honey Lake Plantation. If you haven’t heard of it, Honey Lake Plantation is an incredibly beautiful resort on nearly 5000 sprawling acres, including an 80 acre lake and ample trees and wildlife. It is a very popular place to get married or take a hunting retreat in North Florida and includes meeting facilities and its own church. If you decide to book a visit, take the time to read this article about the owner of Honey Lake Plantation, Bob Williamson, and his enthralling life. We took some time to walk around the beautiful grounds and enjoy the sunset before our dinner reservation. As beautiful as the grounds were, the dinner was not very impressive and the restaurant is more of a sports bar or golf club cafe. It was an overpriced set menu with very bland choices and my chicken was totally undercooked (and worse, nothing was done about it). I still recommend going to the plantation; just don’t expect a 5 star meal if you visit the restaurant. IMG_3833

Postcard perfect
Postcard perfect
Happy Valentine's Day!
Happy Valentine’s Day!
Honey Lake church
Honey Lake church
Oak obsessed
Oak obsessed
North Florida sunset
North Florida sunset


Relaxing back at the B&B
Relaxing post-dinner back at the B&B

The next morning, we had a full breakfast at the B&B, including poached pears, egg souffle, homemade biscuits and jam, and coffee. I had initially planned on having brunch at one of the other two breakfast/lunch spots in Monticello, Electric City Wheels and Grinds or Brick House Eatery, but since we enjoyed our breakfast so much, we opted for another long walk around town to see more of the beautiful, historic homes. We will have to return for lunch and an afternoon of antiquing one day soon!

In front of the John Denham house
We will have to visit Electric City Wheels and Grinds on our next day trip to Monticello!
One of the other local bed and breakfasts, The Daffodale House
Beautiful Japanese magnolias

On our way out of town, we made a couple of pit stops and I just have to share the pictures! The first picture was taken at Lake Miccosukee and just completely captures North Florida’s beauty. It is so beautiful and different from the southern portion of our state. The next two pictures were taken at the Letchworth-Love Mounds, which features the tallest Native American ceremonial mound, built between 1100 and 1800 years ago. The park has a wonderful interpretive trail and several informative displays. We had the whole park to ourselves and enjoyed learning a bit about Native American history in this area.

Lake Miccosukee
Lake Miccosukee – this kind of natural beauty is why I love North Florida so much!
Lechtworth-Love Mounds
Letchworth-Love Mounds
Native American ceremonial mound
Native American ceremonial mound

And with that, I’d love to hear if you have traveled to the north Florida region. If so, what are your favorite destinations? Thanks for reading and see you next time!

Tupelo’s Bakery and Cafe, 220 W Washington St, Monticello, FL 32344

Monticello Vineyards and Winery, 1211 Waukeenah Hwy, Monticello, FL 32344

Huckleberry’s Creations, 210 W Washington St, Monticello, FL 32344
Honey Lake Plantation, 1290 Honey Lake Rd, Greenville, FL 32331
Letchworth-Love Mounds Archaeological State Park, 4500 Sunray Road, Tallahassee, FL 32309

1872 John Denham House, 555 W. Palmer Mill Road, Monticello, FL 32344



  1. What an amazing photos you have! All these places reminded me of series and movies I saw about American history. I have never traveled to USA because I need visa to go there (I am Croatian) so it is a bit daunting for me as I don’t plan ahead my trips. I read also the post about restaurant in Atlanta and I would def love to eat there. Looking forward to your new adventures!
    Have a nice weekend.

    • Thank you so much, Katinha! I hope you are able to visit the USA soon and that my blog can offer some suggestions and inspiration when you do! I’ve been to Croatia (Split and Zagreb) and it is a beautiful country with very kind people. Thank you for reading my blog. I hope you have a wonderful weekend as well!

  2. Oh really? I am from Split, but lived in Zagreb last 10 years, just before I moved to Spain. It makes me really happy when someone likes my small country! Thank you for visiting my blog too and looking forward to your adventures in Abu Dhabi and Johannesburg! 🙂

    • You will like my favorite memory from Croatia then: my friends and I stayed in a home and our hosts would bring us an afternoon treat of strawberries and cream. Even though we didn’t speak the same language, it was such a nice way to connect with our hosts over a small meal.

      I look forward to following your adventures as well!

  3. Awesome post about a very under-visited Florida town! I studied in Tallahassee and happened to just end up in Monticello once and I was really surprised by how pleasant and quaint it was, but I didn’t see as much of it as you did. Looks like it’s worth a visit on my next pass through the Panhandle!

    • Thank you, Jakob! I agree that it is an under-visited town. I think it would be a great addition to any North Florida itinerary. And of course, it is an easy day trip from Tallahassee. Thank you for reading!

  4. Hong Kong Travel Guide
    Hello, I think your blog might be having browser compatibility
    issues. When I look at your blog in Chrome, it looks
    fine but when opening in Internet Explorer, it has some overlapping.
    I just wanted to give you a quick heads up! Other then that, wonderful blog!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s