Unusual Date Ideas to Try in Orlando, Florida

2008
2008 | Swan boat on Lake Eola | © Peter Dutton/Flickr
Melissa Sherrard

Whether you’re visiting Orlando as a tourist or you’ve lived in “The City Beautiful” you’re entire life, having a few unusual date ideas up your sleeve is always a good thing. You’ll never have to settle for a boring night out again with these unconventional ideas; bonus points for combining a few to make it a full day of out-of-the-ordinary romance.

https://www.instagram.com/p/BRzOsWnDEHV/?taken-at=234336253

speech icon man in bubble

Destinations Unlocked:

Let our travel expert Stefano help you find your perfect Culture trip

Looking for an expert's perspective?

Uncover my top 3 recommended places from each continent on the map.
speech icon man in bubble
left arrow trip map

CentralAmerica

GORGEOUS GUATEMALA

Gorgeous Guatemala

5 days . Mini
speech icon man in bubble

1. Guatemala

An express adventure for those with limited time off. Prepare yourself incredible experiences. You will hike a volcano, visit mayan temples and witness a ceremony and take in beautiful colonial Antigua.

Next

right arrow next slide
left arrow trip map

CentralAmerica

BEACHY BELIZE

Beachy Belize

5 days . Mini
speech icon man in bubble

2. Belize

A quick trip not too far away for those seeking a relaxing mini break. You will have plenty of free time to relax but also some awesome activities to experience the rainforest and the caribbean sea.
left arrow previous slide

Next

right arrow next slide
left arrow trip map

CentralAmerica

COLONIAL MEXICO

Colonial Mexico

5 days . Mini
speech icon man in bubble

3. Mexico

An exciting mini trip exploring the lesser known colonial towns of central Mexico. This is hte perfect trip for someone with limited time off and still wants to turn on explorer mode and do something different.
left arrow previous slide

Back to Map

left arrow trip map

SouthAmerica

ADVENTUROUS ECUADOR

Adventurous Ecuador

8 days . Epic
speech icon man in bubble

1. Ecuador

A remarkable 8 days adventure through the Andes and the Amazon rainforest. The best choice for adventure seekers wishing to visit the 2 most iconic areas of South America, in only 1 week and no flights.

Next

right arrow next slide
left arrow trip map

SouthAmerica

ANCIENT PERU

Ancient Peru

9 days . Epic
speech icon man in bubble

2. Peru

An alternative itinerary to classic Peru, from Cusco to Arequipa. This itinerary is great combination of highlights Cusco and Machu Picchu with the lesser known Arequipa and Colca Canyon.
left arrow previous slide

Back to Map

left arrow trip map

Europe

SEDUCTIVE SOUTHERN ITALY

Seductive Southern Italy

10 days . Epic
speech icon man in bubble

1. Italy

The ultimate Italian experience from the vibrant streets of Naples to the breathtaking sceneries of the Amalfi Coast followed by Matera and down to Puglia with its golden beaches, intense flavours and fascinating destinations.

Next

right arrow next slide
left arrow trip map

Europe

EDINBURGH AND THE SCOTTISH HIGHLANDS BY TRAIN

Edinburgh And The Scottish Highlands By Train

7 days . Culture
speech icon man in bubble

2. Scotland

Embark on this great adventure starting from London all the way to Scotland with a true Scottish experience made of breathtaking sceneries, whisky tasting and ..lots of fun! Ideal for train lovers and explorers.
left arrow previous slide

Next

right arrow next slide
left arrow trip map

Europe

COMPLETE PORTUGAL BY TRAIN

Complete Portugal By Train

8 days . Culture
speech icon man in bubble

3. Portugal

A wonderful train journey around Portugal, from the romantic city of Porto to the Douro Valley, to the beautiful Aveiro all the way to Lisbon and Sintra. The perfect trip to train, culinary and culture lovers.
left arrow previous slide

Back to Map

left arrow trip map

Asia

SOULFUL SOUTH KOREA

Soulful South Korea

10 days . Epic
speech icon man in bubble

1. South Korea

Discover incredible temples, mountains and modern cities on this 10 day adventure. This trip is perfect for those seeking immersion in the cuisine, culture and natural wonders of South Korea.

Next

right arrow next slide
left arrow trip map

Asia

THAILAND, CAMBODIA & VIETNAM

Thailand, Cambodia & Vietnam

11 days . Epic
speech icon man in bubble

2. Thailand

From Bankgok to Angkor Wat to Ho Chi Minh City and everything in between - adventure through the heart of South-East Asia. Taste the delights, see history brought to life and unwind on a Mekong River cruise.
left arrow previous slide

Next

right arrow next slide
left arrow trip map

Asia

SECRETS OF SRI LANKA BY TRAIN

Secrets Of Sri Lanka By Train

10 days . Culture
speech icon man in bubble

3. Sri Lanka

A fantastic adventure that showcases Sri Lanka's fantastic landscapes, wildlife and flavours. With 3 epic rail journeys, 3 UNESCO heritage sites and time to relax, this trip has loads to offer at a great price
left arrow previous slide

Back to Map

left arrow trip map

Africa

EPIC MOROCCO

Epic Morocco

11 days . Epic
speech icon man in bubble

1. Morocco

An epic journey across Morocco: from Casablanca to Marrakech, through the blue city of Chefchaouen to the wonders of the desert and deep to the High Atlas Mountains - this trip has it all! Ideal for true explorers!

Next

right arrow next slide
left arrow trip map

Africa

ULTIMATE EGYPT

Ultimate Egypt

9 days . Epic
speech icon man in bubble

2. Egypt

From Cairo to Aswan, this trip brings the land of the pharaohs to life. You'll visit the Pyramids, Valley of the Kings and Luxor Temple and cruise down the Nile in style. This is the perfect way to explore Egypt.
left arrow previous slide

Next

right arrow next slide
left arrow trip map

Africa

IMMERSIVE KENYA

Immersive Kenya

8 days . Epic
speech icon man in bubble

3. Kenya

An immersive blend of culture and wildlife for first time travelers to Africa. Learn about Nairobi, sample local coffee in the Aberdares and finish up with a fantastic safari stay in the Masai Mara.
left arrow previous slide

Back to Map

Pick your own strawberries

For an unusual daytime date, harvest some natural sweets with your sweetie at one of Orlando’s several “u-pick” farms, such as Brook Hollow Farms, Southern Hill Farms and Pappy’s Patch. Each farm offers something a little different, so consider stopping at a couple to make sure you two go home with delicious strawberries, blueberries, peaches and more.

https://www.instagram.com/p/BKKK1ttgjX3/?taken-at=8941289

Try tapas and tango

Certain areas of Orlando, Florida, exhibit a distinctly Spanish flair, so take that inspiration to heart and make a night of it by taking in some tapas and tango lessons with your favorite partner. You can reserve spots at the next Tapas & Tango night at Arthur Murray Dance Studio with some friends to make it a group date.

https://www.instagram.com/p/BeLxA0xFRzP/?taken-at=3239751

Go ice-skating

Beat the Florida heat by taking your date ice-skating at the RDV Sportsplex Ice Den, an Olympic-size ice-skating rink kept chilly enough to serve hot chocolate all year long. A DJ plays music on Friday and Saturday evenings, making for a fun night unlike anywhere else in Orlando.
https://www.instagram.com/p/x2sILHPEMF/?taken-at=246841309

Attend DIY wine tasting

If you love wine tastings but are looking for something a little different, check out The Wine Room at Winter Park. With more than 150 types of wine available to sample at the touch of a button, The Wine Room lets you and your date peruse the intimate eaterie and its wines at your leisure.

https://www.instagram.com/p/BeQ281znSXO/?taken-at=465509

Go to an alternative cinema

If going to a movie is one of your go-to date ideas, consider attending the small, alternative cinema called the Enzian Theater. It shows classic, independent and foreign films in an eclectic space that serves food and drinks, and you can end the night enjoying cocktails at Enzian’s Eden Bar.

https://www.instagram.com/p/BUVcRBeDwT_/?taken-by=sakcomedylab

Attent a comedy show

For a date night filled with laughs, go to a comedy show at one of Orlando’s many improv and comedy clubs, such as Bonkerz Comedy Club and SAK Comedy Lab.

2008

Tour a graveyard at night

For a really different date night, take a Moonlight Walking Tour at the historic Greenwood Cemetery in downtown Orlando. A sexton will guide you on a four-mile stroll through the 100-acre graveyard to visit nearly 100 burial sites of notable residents and point out beautiful sights on the grounds. The tours are free, but make a reservation quickly as spots on these small night-time tours fill up quick.

https://www.instagram.com/p/BO8kFrQj32q/?taken-by=seminoleplanet

Visit a planetarium

For a unique visual experience, take that special someone to the Emil Buehler Perpetual Trust Planetarium at Seminole State College, which shows interactive shows on the domed overhead screen on a weekly basis. When it’s not showing how stars are born and beautiful images of the universe, the screen lights up with fabulous laser shows set to music.

2011

A day and night at Leu Gardens

On the first Friday of most months, visit the the beautiful, 50-acre Harry P. Leu Gardens during the day and stay for a free outdoor movie showing that night. Where else can you snuggle under the stars amid lovely gardens and watch a great movie?

2006

Make your own pancakes at a restaurant

The Old Spanish Sugar Mill Grill puts a twist on the classic “going out to breakfast” date. Since 1961, guests have been making their own pancakes just how they like them on griddles that grace the center of every table. Servers provide home-made pancake batter and toppings as well as other breakfast items from the kitchen, but you and your date will flip flap-jacks yourself. Afterwards you can enjoy the clear waters of De Leon Springs, which the restaurant overlooks.

Ride a swan on Lake Eola

Treat that special someone to a view of Orlando from the waters of Lake Eola by taking him or her out an iconic “swan” paddleboat ride. It’s a relaxing way to get close to the lake’s real resident swans and enjoy some fresh air.

2014

Ride the SunRail for a day

Take a day to explore Orlando together riding the SunRail. You’ll be able to see everything from Winter Park to Church Street Station together.

2013

Hike your hearts out

Spend the day exploring some of the award-winning hiking trails, such as the Seminole-Wekiva Trail or the Bear Creek Nature Trail, that Orlando has to offer. Pack a picnic to make it even more romantic.

https://www.instagram.com/p/xuM8G-kzuT/?taken-at=255579461

Check out an oddities shop

If you’re looking for a really unusual date idea to try in Orlando, Florida, stop by local oddities shops such as Carmine’s Oddities Boutique and Ripley’s Believe it or Not! You’re bound to find interesting things to talk about for the rest of the day.

https://www.instagram.com/p/l0aBcqHoXC/?taken-by=seeartorlando

“See Art” around the city

You and a loved one can take the See Art Orlando self-guided walking tour to see eight large, permanent contemporary art sculptures inspired by “The City Beautiful.” It’s a fun, intimate way to see a part of the city that’s often overlooked.

culture trip left arrow
 culture trip brand logo

Volcanic Iceland Epic Trip

meet our Local Insider

Hanna

women sitting on iceberg

HOW LONG HAVE YOU BEEN A GUIDE?

2 years.

WHAT DO YOU LOVE ABOUT YOUR JOB?

It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.

WHAT DESTINATION IS ON YOUR TRAVEL BUCKET-LIST?

I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!

culture trip logo letter c
group posing for picture on iceberg
group posing for picture on iceberg

Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.

map of volcanic iceland trip destination points
culture trip brand logo
culture trip right arrow
landscape with balloons floating in the air

KEEN TO EXPLORE THE WORLD?

Connect with like-minded people on our premium trips curated by local insiders and with care for the world

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.

X

Holiday Sale Offers on Our Trips

Incredible Savings

Edit article