Valentine's Day Ideas - Florida Living

Romantic Valentine’s Day in Winter Park & Surrounding Areas: Best Date Ideas & Thoughtful Gifts

History of Valentine’s Day: If you’re not a fan of the day, your intuition might be telling you this holiday did not start out as the sweet and romantic day we have now grown accustomed to. Yes, it started out a little dark, but thanks to Shakespeare, Chaucer, and Hallmark, the holiday grew sweeter. So, silly or lovely, on February 14th we have love and kissy faces! Happy Valentine’s Day!

Romantic Date Ideas

Winter Park Scenic Boat Tour

Did you know you can book your own private scenic boat tour? Pack a romantic picnic basket to enjoy on your boat tour with your Valentine while you take in the gorgeous Winter Park Chain of Lakes. To make reservations, simply call the Winter Park Scenic Boat Tour.

Private Trail Horseback Ride

Looking for something off the beaten path for the nature lover in your life. How about a private horseback trail ride through the heart of the Lake Jesup Conservation Area where you can see eagle, osprey and hawks? Just you, your guests, and a guide take a private horseback ride with Hidden Palms Ranch and Trail Rides experiencing Florida nature. Contact Hidden Palms Ranch & Trail Rides in Sanford, Florida to make reservations.

Paddle Board Sunset Kayak Tours

Nothing says, romance like a sunset experience by Otter Paddle Board with a guided tour paddle board tour. During your tour you’ll explore the Winter Park Chain of Lakes while winding through the Venetian style canals. Make reservations on-line at Otter Paddle Board. To add to the special date, order take-out or bring a picnic to enjoy in Winter Park’s Central Park located just a couple blocks from the Winter Park Chain of Lakes.

Cooking Classes

Looking for a unique and delicious way to celebrate Valentine’s Day in Orlando? Skip the traditional dinner reservation and spice things up with a hands-on Truffle & Trifle Cooking Class! This interactive experience lets you and your partner create gourmet truffle dishes and decadent trifles while enjoying a fun, romantic atmosphere. Whether you’re a seasoned home chef or just love indulging in sweet and savory flavors, this class is the perfect way to bond over delicious bites. Plus, you’ll take home new culinary skills—and maybe even a few extra treats to share!

Scenic Tourist Drive

Why not take a nice romantic scenic tour on one of Florida’s Scenic Highways?

A1A Scenic Highway weaves through America’s .
Florida Black Bear Scenic Byway just north of Mt. Dora through the Ocala National Forest.
Green Mountain Scenic Byway explores the hills of Florida through Winter Garden, Clermont, Oakland and travel north to Mt. Dora.
Indian River Lagoon explore the Atlantic Coast of Florida.

Wine & Chocolate Tasting

Nothing says, “Happy Valentine’s Day” like chocolate! If you have a chocolate lover, this might be the perfect gift! For a truly indulgent Valentine’s date, visit AJ Chocolate House in Winter Park, Florida. This cozy, elegant spot is a chocolate lover’s dream, offering handcrafted truffles, rich sipping chocolate, and artisanal treats made with the finest ingredients. Whether you’re sharing a fondue platter or savoring a signature hot cocoa, AJ Chocolate House creates the perfect sweet setting for romance.

Westgate River Ranch GLAMPING

Ok… to most camping does not sound very romantic. However, I think Westgate River Ranch might change your mind. Think about GLAMPING with your special someone. They offer a wide variety of accommodations from Luxury Wagons to Teepees, plus everything in between.

Bioluminescent Paddle

A truly magical experience! See the sparkle of bioluminescence comb jellies twinkle and flash in the water as you paddle. This tour starts in Titusville and can be booked with BK Adventures.

Romantic Bike Ride & Lunch

For the active loved ones, explore some of Central Florida’s bike trails. Stop along the way for lunch at one of the local eateries. One of our favorites is the West Orange Trail starting at the Killarney Station.

Original Orlando Tours

The Original Orlando Tours offer a wide variety of experiences from walking tours through historical Central Florida towns to a Royal Pizza Express Train Tour in Mt. Dora. Pick an experience and let Original Orlando Tours do the work.

Shopping Local Gift Ideas

Eyre Home

Surprise your loved one with Eyre Home’s decadent linen sheets, offering the ultimate in comfort and elegance for a truly luxurious night’s sleep. The Eau d’Italie hotel scent reed diffuser, inspired by the iconic Le Sirenuse Hotel in Positano, Italy, evokes romantic summer evenings on the Amalfi Coast with notes of bergamot, incense, and blackcurrant buds, creating a dreamy, inviting ambiance

Maffrey’s

For a meaningful and unique Valentine’s Day gift, visit Maffrey’s in Orlando. This thoughtfully curated boutique offers gifts and accessories for home, pets, bar, and beyond, each with a story that brings good to the world. From eco-friendly finds and handcrafted treasures to Orlando-inspired keepsakes, Maffrey’s is the perfect place to find a gift that’s both stylish and impactful. Whether it’s a beautifully designed piece for the home or a heartfelt token that supports a great cause, you’ll discover something special to make your Valentine smile

Primrose Shop

This is always my go to shop for gifts! They offer jewelry, home gifts, candles, and more. Plus, they will wrap the gift in an adorable bag with their signature green and pink tissue paper and ribbon.

Simply Cheese

An artisan and specialty cheese shop offering hand-selected and globally-sourced products for the cheese lovers, mongers and everyone in between. Owned and operated by a Midwest-raised cheese enthusiast, the shop is located in sunny Winter Park, Florida serving up both cheese and cheese-friendly products like meats, sweets, jams and spreads making it your one stop cheese shop

The Salty Don ut

Really freakin’ good donut, baked goods and a perfectly crafted coffee.

Gideon’s Bakehouse

This bakehouse had one goal: to create an extraordinary Chocolate Chip Cookie. Mission accomplished! Voted best Cookies in Orlando, Florida, the United States, and the Planet Earth!

Peterbrooke Chocolatier

The place where chocolate covered popcorn became a thing. This place offers a huge variety of chocolate treats! Great for those chocolate lovers in your life.

The Tiny Orchid

There is probably no other gift more beautiful than an orchid. I don’t think you can ever go wrong with this gift. Did you know the orchid is one of the oldest family of flowering plants? You can even include some of these fun orchid facts with your gift.

The Ancient Olive

So many flavors to choose from will be your biggest dilemma with this gift. This is a great gift if your special someone loves to cook. They offer olive oil and vinegar in array of flavors the combinations are endless.

Best Homemade Gift Ideas

Looking to impress your significant other? I can’t think of a better way to show someone you love them than to make a homemade gift.

Conversation Cups

Make your own Conversation Cups. You can make these or purchase them from Uncommon Goods. Create or buy your conversation cups, fill with your favorite beverage and let the beverage line will be the conversation starter.

Supplies: Clear Plastic/Glass, Sharpie

Using a sharpie and a clear plastic or glass cup draw a line at the half way mark.
Then draw a line half-way between those lines above and below so you have eight lines.
Next, at the top of one of the cups write, “talk about your…”
Finish the first cup by writing, “best, worst, favorite, most embarrassing, last, next, quickest, ideal”.
On the second cup, divide the cup in half and draw a line like you did the first cup.
Then write, “concert, teacher, birthday, costume, job, apartment, car, vacation, date.

Bucket List Date Jar

Make a list of bucket list date ideas to share with your loved one. Remember to write the date on the back to create a memory jar when you’re done!

Supplies: Mason jar or can, popsicle sticks or slips of paper

Write 10-20 date ideas on each popsicle stick or slip of paper.
Place the sticks or paper in the mason jar or can.
Set a day once a week or month to pick something out of the bucket list to do on your special day.
Here are a few ideas to get you started:

Pick up Take-out and have a picnic at a local park. (Kraft Azalea, Mead Gardens, Lake Ivanhoe)
Visit a local brewery
Pack a picnic and watch the sunset (Lake Killarney behind Trader Joes has amazing sunset views)
Take a bike ride and stop along the way for breakfast or lunch.
Karaoke Night at Home. (Play your favorite tunes and find the lyrics on-line to sing along- no equipment necessary.)
Pick a local small town to explore for the day. (Deland, Sanford, Winter Garden are just a few great ones)
Pick an off the beaten path tourist location to visit. (Black Hammock, Gatorland, Wild Safari, Scenic Winter Park Boat Tour, Paddle Boat Lake Eola, )
Visit a local museum you’ve never been to before. (The Albin Polasek Museum & Sculpture Gardens, Chocolate Kingdom Orlando, Charles Hosmer Morse Museum, Cornell Fine Arts Museum Orlando, Winter Park History Museum)
Take an adventure date and visit a local zip line park, paddle boarding, kayaking, water adventure park. (Orlando Tree Trek, Wekiva Island, Get Up and Go Kayaking)
Visit a local landmark. (Mary McLeod Bethune Home, Bok Tower Gardens, Dade Battlefield, Ponce de Leon Inlet Light Station)

What I Love About You, book

Grab a composition book from your local store and start writing about all the things you love about your true love! Don’t worry if you have blank pages it leaves room to add to the book each year. Here are a few sentence starters to help you overcome writer’s block:

I never get tired of …
I love that you …
One of my fondest memories is when…
It never gets old when you…
It really makes me laugh when you…
You have the best taste in …
I’m a little obsessed with your…
The first thing that caught my eye about you is …
You really know about…
I love how passionate you are about …