A Weekend Getaway to DeLand, Florida

de la Vega restaurant

DeLand, Florida, is a short distance from Orlando and is filled with history, outdoor adventure, shopping, and delicious food. With so much to do, a weekend getaway to DeLand has something for the whole family.

Once known as Persimmon Hollow because of the abundance of wild persimmons, DeLand began to grow in popularity following the end of the Civil War. In 1876 Henry DeLand visited the area and purchased what was known as the “Hampton Homestead” with 159 acres of land. From this land purchase, the town of DeLand, Florida was formed.

In 1883 Henry DeLand founded DeLand Academy, which became Stetson University in 1889 to honor John Stetson. When DeLand, on the brink of financial ruin could no longer support the school, Stetson stepped in as the major benefactor and supporter.

Today DeLand features a thriving downtown filled with boutique shops, captivating restaurants and bars, and coffee shops housed in historic buildings dating back to the 1920s.

Deland Downtown florida

Where to Eat and Drink in DeLand

DeLand boasts more than 40 restaurants and bars, most of them locally owned. From casual, on-the-go fare to Southern BBQ, Sushi, and more, DeLand is a foodie lovers paradise.

Great Tasting Tours

This guided tasting tour explores DeLand’s historic downtown and is a unique way to discover DeLand, Florida. You’ll stop into an eclectic collection of excellent restaurants, curious shops, and end your tour at a wine bar or brewery.

downtown deland florida with great tasting tour

Great Tasting Tours offers three tour options, a Sip & Shop, Brews & Browse, and Sweet & Savory. All of the tours include a selection of restaurants, bars, and shops.

Abbey Bar & Odd Elixir Meadworks

Abbey Bar is a craft beer bar that offers wine by the glass and by the bottle, as well as wine flights. They also offer over 100 bottled beers, and ten beers on draft. Love bar food? The 

Abbey Bar offers a selection of upscale bar food that is freshly prepared, and a delicious accompaniment to wine, beer, or mead.

Odd Elixir Meadworks is a small batch meadery located inside of the Abbey Bar. Mead goes back to Medieval times and is the epitome of farm-to-table. Mead uses honey, water, and yeast, and can be flavored with fruits, spices, grains or hops. Our hands-down favorite mead from Odd Elixir is the Mango flavored mead.

Persimmon Hollow Brewery

Since 2014 Andy Sistrunk and Robbie Carelli have been brewing some fantastic beer in Deland. The taproom is family-friendly with arcade games and plenty of seating, and pet-friendly. Though their draft list may change, their offerings include:

  • Funky Freddy Fitz-a stout that gives you the all sweet, malty flavors of a traditional stout without weighing your palate down
  • Gypsy Hiker-a New England Style IPA brewed with Mosaic, Lumberjack, and Cascade hops
  • Blood Orange Wheat- an American Pale Wheat, created with Vacation Wheat brewed with Blood Oranges
  • Daytona Dirty Blonde- an easy-drinking but flavorful blonde ale (full disclosure here, I am not a beer drinker, but I love this beer)
persimmon hollow brewery beer

Airport Restaurant & Gin Mill

This is one of DeLand’s coolest restaurants! Where else can you eat an incredible burger and watch skydivers coming in for landings? This fun family-friendly restaurant has a wonderful outdoor deck and dining area where the kids will be glued to the planes and skydivers.

airport restaurant and gin mill

Bake Chop

Scratch kitchens are popping up all over the place, and basically, a scratch kitchen means that their food is made from scratch. Bake Chop elevates the scratch kitchen by coming full circle – their focus is on creating food with a lot of love, sourcing local, and using meats that are pasture-raised, cage-free, and hormone and antibiotic-free. Creating a sense of community, Bake Chop is where family and friends gather for good food and good times.

Located in DeLand’s Artisan Alley, they offer a selection of sandwiches (“handhelds”), salads, small plates, and a selection of gluten-free items.

De La Vega Restaurante y Galeria

This is one of our top favorites in DeLand! De La Vega is modern Latin fusion with rich flavors and textures using traditional foods like chiles and corn. With innovative and creative dishes like their Hibiscus Tacos, De La Vega will quickly become one of your favorite places to dine in Deland!

de la Vega restaurant

The Elusive Grape Wine Bar

“Where Good Friends and Good Wine Meet” is the motto of the Elusive Grape, and we would have to agree.  With a selection of over 40 wines by the glass, there truly is a new wine for everyone to fall in love with. On our recent visit, we stopped into the Elusive Grape for their Happy Hour (2:00-6:00 PM Monday – Friday). It was jam-packed, but we found a seat and had an opportunity to chat with several locals. That is community, and the Elusive Grape fosters networking and community.

elusive grape wine bar florida

Where to Play in DeLand

DeLand Historic Mural Walk

Strolling the DeLand Historic Mural Walk you see the history of DeLand, Florida unfold. There are over a dozen murals portraying scenes of the area’s early settlement, celebrating the town’s history and its beloved citizens. Each mural has hidden elements the artists have placed in them for you to find.

DeLand Naval Air Station Museum

This small museum is housed in a historic hanger and features exhibits of World War II-era archives and memorabilia, military vehicles, and aircraft.

Deland naval air station plane

In 1941, the small municipal airport built in the 1920s was donated to the US military and turned into DeLand Naval Air Station. Its mission was a training base for teams flying the PBO Ventura and PB4Y-2 Privateer patrol bombers and the SBD Dauntless dive bombers.

Deland Naval air station retiree

The Stetson Mansion

The Stetson Mansion was built in 1886 by John B. Stetson, the hat baron, as his winter snowbird estate. Henry Flagler even built a private railway spur to the estate so that building materials could be delivered directly to the estate. In 1886, the mansion was cutting edge, with electricity installed by Thomas Edison.

It is still a private estate but is open for tours between February and September (reservations are required for all tours). Restored and updated with 16 original floor patterns, 11 new bathrooms, and over 10,000 panes of glass, the Stetson Mansion is listed by Tripadvisor as one of the “Top Places to Visit in Florida.”

The Springs

Blue Spring is the largest spring on the St. Johns River and is a designated Manatee Refuge and the winter home of West Indian Manatees. Blue Spring State Park means fun for the whole family, with seasonal activities that include swimming, canoe, and kayak rentals, narrated river cruises, Segway tours, miles of walking trails, and camping (note that Blue Spring is closed to all water activities mid-November through March for Manatees).

One of the most fun activities is to rent a tube and float the spring. With the water in the spring a constant 72 degrees, it is refreshing, particularly on those hot, steamy, Florida days.

DeLeon Springs State Park

DeLeon Spring was called “healing waters” by the Timucuan Indians who inhabited the area, and now you can cool off in the spring, roam the trails that have massive bald cypress that are hundreds of years old, and experience history.

A perfect activity for a hot summer day is to take a dip in the pool at DeLeon Springs. Like Blue Spring, the water is a constant 72 degrees.

Highlights of DeLeon Springs State Park include the Old Spanish Sugar Mill Restaurant. Located in the park in a 100-year old replica of the original 1830s sugar mill, you can cook your own pancake creations right at the table. A visit to the Old Spanish Sugar Mill Restaurant is a perfect way to cap off a morning of exploring or swimming.

Skydive DeLand

Skydive DeLand is world-renowned as the place for skydive instruction. Whether you are a beginner, wanting to learn to skydive, or a champion skydiver, Skydive DeLand is where you want to be! Both the Tandem and Accelerated Free Fall training programs were developed in Deland, so you’ll be in great hands as you discover this adrenaline-filled sport.

Deland Skydive

When you book an experience with Skydive DeLand, you must be between 18 years old, weigh less than 220 lbs., and have a valid photo ID.

Where to Stay in DeLand

For a little taste of Old Florida, with a side of kitsch, try Hontoon Landing Resort and Marina. The rooms are simple, clean, and bright. We chose a room with a river view. It opened up to a shared balcony overlooking the St. John’s River. The mist coming off of the water in the morning gave it an ethereal appearance.

Hontoon Landing

For those who want to be right in the heart of downtown, the Artisan Downtown is just a short walk from shopping and restaurants. The Artisan Downtown is a true boutique hotel with only 14 rooms.

Opened in the 1920s as the DeLand Hotel, it was an integral part of the community. Still an integral part of the community, the hotel has evolved into a historically-rooted modern hotel with Southern roots.

The DeLand Hotel dating back to 1925, is the town’s oldest operating hotel. Each room is filled with a selection of period furniture and comfortable beds that seem to snuggle you as you drift off to sleep after a fun-filled day of exploring DeLand.

historic deland florida hotel

Though there are more choices for places to stay when visiting DeLand, these are our top choices.

Deland is a great way to cap off a visit to Disney World. But once you visit DeLand you’ll discover a small town packed with lots of fun for the entire family. You may even be planning your return trip before you head back home.

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itinerary for deland Florida
weekend getaway to deland florida


Article written by Betsi Hill of Betsi’s World. Betsi was hosted on this trip by Visit West Volusia, but all opinions and reviews are 100% unbiased and her own.

Read more about Florida: 

A 42-Restaurant Guide to Vero Beach

Day Trip to New Smyrna Beach

Visiting Silver Springs State Park, Ocala

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