Orlando’s Most Romantic Experiences

Most Romantic Experiences in Orlando

A local guide to the most romantic experiences in Orlando for couples

From leisurely boat tours to beautiful gardens and intimate dining, the City Beautiful is full of romantic escapades for couples. Need a little help planning an enchanting date? Here’s our guide to the most romantic experiences in Orlando.

ACTIVITIES

Winter Park Sunset Kayaking

Watching a sunset is already quite romantic, but why not take it up a notch by pairing this amorous activity with a leisurely kayak tour in a clear kayak. After launching at Dinky Dock, a Get Up and Go Kayaking tour guide will lead you through the scenic canals linking Lake Virginia, Lake Osceola, and Lake Maitland, all part of the Winter Park Chain of Lakes. This local company sets themselves apart with their fleet of clear tandem kayaks and small tour group sizes that keep the experience low key. The 2-hour sunset kayak tour costs $45/person. We also recommend the Rock Springs Run tour.

Private Trail Ride for Two

It’s worth braving I-4 to head north to Sanford, especially when you include horseback riding at Hidden Palms Ranch in your day trip itinerary. Located amidst the Lake Jesup Conservation Area, a prime example of Orlando North’s natural beauty, owner Beki Herrbach’s ranch provides couples with private trail rides in the area. Saddle up and let Beki guide you through her favorite places, including peaceful tree-canopied trails and waterfront expanses. Trail rides are $75/person. Here’s a review and video of our experience

Most romantic experiences in Orlando - Trail ride at Hidden Palms Ranch
Hidden Palms Ranch

All Jazzed Up

Music-loving couples have no shortage of options for a musical night out, especially when it comes to live jazz. The V Lounge at Eddie V’s Prime Seafood has a lineup of nightly jazz entertainment. Catch weekly jazz jams at Pilar’s Martini in Winter Garden (Sunday evenings) and Austin’s Coffee (Thursdays at 9:30) in Winter Park.

Morning Balloon Flight

One of my favorite and most memorable dates of all time was the sunrise hot air balloon flight my boyfriend John and I embarked on with Bob’s Balloons. We’re so lucky to have access to this amazing adventure right here in Central Florida and it’s worth the higher price tag. Most local companies, including Bob’s Balloons, will invite you to help set up the balloon before take off. Our flight lasted about an hour and was a serene cruise over Central Florida’s diverse landscape. Landing is all part of the adventure, as the wind direction will determine your route. Private flights are available if you’d like to soak up the trip by yourselves.

10 Over the Top Experiences to Save for a Special Occasion in Orlando

Leisurely Boat Tour

While we can’t claim the Winter Park Scenic Boat Tour is a hidden gem (most locals already know of this awesome tour), embarking on the pontoon boat tour will make you feel as though you’ve stumbled upon something special. For locals and out-of-towners alike, this is one of those must-have Orlando experiences. Whether you just want to chill out on the pontoon boat while gazing longingly at each other and the stunning Venetian-style canals, learn some history, or check out the waterfront mansions, this tour is always $14 very well spent.

Romantic Gardens

Need to change things up from a night out in the city? Spend a day wandering a local garden. We’re blessed to have Leu Gardens (and their awesome monthly BYOB-friendly outdoor movie night) right here in our backyard. Another option that’s totally worth the drive is Bok Tower Gardens in Lake Wales. Occasional carillon bell concerts originating from the Singing Tower provide the soundtrack for your romantic afternoon meanderings.

Bok Tower Gardens

Dinner + a Movie Revisited

Another must-have Orlando experience: dinner and a movie at our resident independent theater, Enzian Theater and Eden Bar. This much-loved theater has big plans to expand their current space, no doubt to accommodate the horde of passionate supporters who attend screenings of the latest indie favorites and 35mm cult classic films. Make it a complete date with drinks and dinner at Eden Bar before the show. The stunning oak trees dressed in twinkling lights make this one of Orlando’s best outdoor patio spaces.

Bioluminescent Paddling

While bioluminescence doesn’t occur in any Orlando waterways, it’s only a short drive to the space coast to see this wondrous occurrence on a guided nighttime kayak tour. In the summer months, tiny bioluminescent organisms called dinoflagellates set the waters of the Merritt Island National Wildlife Refuge aglow with a greenish/blue hue. The organisms do not glow constantly, but rather light up the water as they are disturbed by the wake of passing boats and kayaks. On a good night, you can dip your hand into the water and remove it to observe the organisms aglow on your hand. Some nights are much better than others and your best bet is to go as close to a new moon as possible. While paddling, don’t forget to look up, as you can easily spot the Milky Way and shooting stars on a clear night.

Local companies, A Day Away Kayak Tours and Get Up and Go Kayaking, offer excellent tours and have moon phase calendars on their websites to help you select a date. Inquire about the state and intensity of the bioluminescence when booking your trip, as it can vastly vary from day to day due to water quality and other factors.

Swan Boat Adventure

While most couples would argue that Lake Eola’s swan boats are more workout than leisure, this activity still tops our list of romantic endeavors. Pair a swan boat rental with a progressive meal at the Orlando Farmer’s Market for a local date that won’t break the bank and still has a romantic, spontaneous feel. Or, grab an early dinner in Thornton Park followed by a paddle around the lake at sunset. Swan boat rentals are available 10am-7pm Sunday-Tuesday and 10am-10pm Wednesday-Saturday for $15/half hour.

Orlando Buzz

Broadway Show

A list of the most romantic experiences in Orlando just isn’t complete without a mention of the Dr. Phillips Center for the Performing Arts. Housing local events such as PechaKucha Night Orlando, concerts from big names like Jason Mraz, musical performances from the Orlando Philharmonic Orchestra and Broadway shows like Rent, our local hub for the arts delivers on all fronts. Arrive early to relax with a glass of wine before the show. Nearby dinner options include Kres Chophouse, The Rusty Spoon, and The Boheme, just to name a few.

Private Orlando Eye Champagne Flight

Taking flight on the Coca-Cola Orlando Eye in a private capsule, complete with two glasses of champagne, has romantic proposal written all over it (guys, take note). This slightly over-the-top excursion sends you 400 feet in the air to marvel at Orlando. Try timing your flight with the sunset or the theme park fireworks. Private capsules are available for $350 with champagne. You also have the option to include champagne with a non-private flight for $34/person. Regular tickets sans champagne begin at $25/person, but there’s almost always a Florida Resident promotion available.

Image credit: Orlando Eye

Boardwalk Bliss

One of our resident Disney experts and contributors, Hannah Green, considers Disney’s BoardWalk one of the more romantic, outside-the-parks experiences to be had. Some of her recommended date night experiences include an upscale dinner at Flying Fish, renting a 2-person surrey bike, sharing a boozy dessert at Ample Hills Creamery, and ending the evening by wandering the grounds of Disney’s BoardWalk Resort. You can also catch the nightly fireworks from the boardwalk!

SPAS

The Spa – Four Seasons Resort Orlando

If you’re going to splurge on a spa day, you might as well treat yourselves to The Spa at Four Seasons Resort. Book an 80-minute treatment at this high-end resort spa and then stay and play all day at the resort’s adults-only pool, lazy river, and water slides. For a completely new spa experience, try the recently introduced “Healing Honey” treatment, in which local honey from Winter Garden Honey Co. acts as the primary massage medium. Keep it classic with a couples massage, where you’ll have your pick of techniques from deep tissue, Swedish, Reflexology, and pressure point therapy. Enjoy your treatment in one of four couples’ suites, or in a private spa bungalow. 

Couples Suite at The Spa at Four Seasons Resort Orlando
Couples Suite at The Spa at Four Seasons Resort Orlando. Image credit: Four Seasons Resort Orlando

The Ritz-Carlton Spa – The Ritz-Carlton Orlando, Grande Lakes

Our founder and editor, Kristen Manieri, has hailed a spa day at The Ritz-Carlton Spa as one of her go-to date day indulgences with her husband. Start with a couples massage to relax, ease tension, and set the tone for a special day together. You can even upgrade your experience with the couples bath, an add-on treatment in the private hydrotherapy tub followed by champagne and chocolate-covered strawberries enjoyed in a private section of the spa. Booking a spa appointment grants you access to the stunning outdoor spa pool for lazing the day away. Wash up before ending your day at one of the hotel’s restaurants (We love Highball & Harvest!)

Ritz Carlton Orlando Spa - Over the Top Experiences for a Special Occasion

Mandara Spa – Walt Disney World Swan and Dolphin

Located inside the Walt Disney World Swan & Dolphin, this palatial 10,500-square foot spa is a dream retreat for the day. Featuring worldly décor and multiple spa gardens, including a Tea Garden and Meditation Garden, relaxation is inevitable at Mandara Spa. Relish the seclusion of private couples retreats (complete with bathing boudoir) for a signature couples massage.

Mandara Spa at Walt Disney World Swan and Dolphin
Image credit: Mandara Spa

Blue Harmony Spa – Wyndham Grand Orlando Resort Bonnet Creek

Come to Blue Harmony Spa for the amazing couple’s suite complete with soak tubs, and stay for the stunning outdoor spa garden and hot tub area. Plush outdoor furniture provides cozy seating for two in the secluded outdoor nook housing the bubbling hot tub. You can even reserve the space to have it all to yourselves! Consider cooking the Couples Package ($385/couple) which includes a massage and aqua immersion bath soak, plus champagne and strawberries.

Waldorf Astoria Spa, Waldorf Astoria Orlando

Tupelo honey is the star of the show at the Waldorf Astoria Spa, incorporated into a variety of treatments designed to soothe. Ladies can indulge in the Queen Bee Tupelo Honey pedicure, while the guys will enjoy the Gentlemen’s Refinery pedicure. For massage, consider the peaceful Honey Butter massage, or indulge together with a classic couples massage. After your treatments, chill out in the tea lounge and continue to unwind.

DINING

Fireworks Show

You don’t need to step foot in the theme parks to catch a glimpse of the nightly fireworks displays. And one of our favorite ways to watch fireworks outside of the parks is while dining at a restaurant with stellar vantage points. Located on the 15th floor of Disney’s Contemporary Resort, California Grill is an obvious choice. Cinderella’s Castle sits in plain view and you can watch the fireworks tableside or step outside on the spacious deck to catch the show. Other stellar options include Narcoossee’s at Disney’s Grand Floridian and Eleven, the latter of which is located on the rooftop level of Reunion Resort.

California Grill
California Grill. Image credit: Kent Phillips/Walt Disney World Resort

Hidden Courtyards & Patios

Dining al fresco is a possibility in Orlando nearly every month of the year. As such, you’ll find patio space at most local dining establishments. Looking for a cozier, more intimate outdoor space? Head to K Restaurant in College Park, where a secluded courtyard out back provides seating for a handful of couples. For a casual date, sit outside at Yellow Dog Eats in Gotha where multi-colored lights set the outdoor space aglow as you dig into the creative fare. Alternatively, share a Wine Lover’s Board while dining al fresco at Maxine’s on Shine.

Chef’s Tables

Interactive Fun: Highball & Harvest (The Ritz-Carlton Orlando)
Don’t let the higher price point ($185/person) deter you from treating your date to the stellar Highball & Harvest chef’s table. The dining experience includes a five-course meal, custom tailored to the couple based on dietary and flavor preferences. And that customization extends to the cocktails, too! In addition to the Chef’s Table Experience, you can imbibe in style by booking the Cocktail Table Experience. Sip on custom cocktails while noshing on expertly paired small plates.

Over the Top: Victoria & Albert’s
Often hailed as one of the most romantic restaurants in Orlando, Victoria & Albert’s is a restaurant worthy of inclusion on your date night bucket list. As reported by Lauren Delgado in the Orlando Sentinel, the restaurant recently received the 2018 Forbes Travel Guide Five-Star Award along with the AAA Five Diamond award, the latter of which has been awarded to the restaurant for 18 consecutive years. Pricing begins at $250/person (wine pairings are an additional $150/person), but everyone we know who has been states that the price is worth it for the incredible service, food, and experience.

Affordable Luxury: Luma on Park
At $75/person, Luma on Park’s chef’s table is more affordable without skimping on quality. Expect to be served up to nine courses, prepared expertly after your personal chef for the evening learns your preferences and restrictions. Each menu is unique, so no two experiences are the same. Make sure to ask for the kitchen-side table when making your reservation by phone.

Luma on Park Orlando Chef's Table
Luma on Park. c/o Park Lights Hospitality

Here’s our full guide to the best chef’s table experiences in Orlando

Sunset Views

There’s a reason Hillstone Restaurant in Winter Park is popular for proposals and special occasions. Besides fantastic food, the outdoor ambiance and coveted seating over the water provide stunning sunset views. Few Orlando restaurants rival this gem when it comes to soaking up the sunset while dining. Another favorite, Enzo’s on the Lake serves Italian cuisine in a waterfront setting, with gardens to explore before or after your meal. Canvas Restaurant & Market in Lake Nona is also situated waterfront, with a menu just as delightful as watching the sun dip below the horizon as you dine.

Hillstone Winter Park
Hillstone restaurant in Winter Park by Kristen Manieri

Private Dining

Why wait for a special occasion? Make your usual date night extraordinary just because. Many local restaurants are equipped with private dining spaces to help you set the stage for an intimate night out. A few of our favorites include Bull & Bear (Suite Life Experience available in-room) and Christner’s. Check out the full list here in our guide to private dining

Around the Attractions

Don’t rule out the tourist and attraction areas when planning a romantic dinner; Disney Springs and Magic Kingdom have a good deal to offer theme park-going couples. Cheers to the sunset or feast on late-night bites at Paddlefish’s stunning rooftop deck (there’s often live music), wander through the tunnel leading to Enzo’s Hideaway, a new (and hotly-anticipated) speakeasy-style restaurant and bar space serving Roman cuisine and craft cocktails, or dine waterside at The Boathouse, a Disney Springs go-to. Inside the parks, Be Our Guest Restaurant is the ideal place to live out your Disney fairytale dreams, if only for the night.

DRINKS & SWEETS

Sultry Desserts

Sinfully sweet dessert is the only thing on the menu at Better Than Sex, a romantic restaurant in Ivanhoe Village. From the racy art on the red walls to the playful names and presentation of each dessert on the menu, this restaurant has date night written all over it. This may be your last stop of the night, but we’re willing to bet a visit here is just the beginning of a memorable evening.

The Fever from Better Than Sex

Classy Cocktails

Enter Mathers Social Gathering and you’re transported into the past (after you’ve found the secret entrance, that is). Vintage photographs and books line the walls, Frank Sinatra croons in the background, and craft cocktails flow freely. Cozy up together on the swinging armchair or snuggle up next to one another on the large, inviting leather sofas and stay awhile. For a low key date night, visit on a weekday evening before or after happy hour. FYI, Mathers is closed Sunday-Tuesday.

Date Night Dessert Booth

One of the most coveted seats in the house, the date night booth at The Glass Knife in Winter Park is the perfect space to sit while you indulge in desserts. (We’re partial to the doughnuts.) As of now, reservations aren’t accepted for the date night booth, but we hope that changes soon!

Dessert booth at The Glass Knife. Photo credit: @_dwayneanthony on Instagram; photo taken by @sallenphot

Coffee in the Courtyard

For a casual date without skimping on romance, head to Park Avenue in Winter Park where quiet courtyards await around practically every corner. Greeneda Court offers plenty of seating and a picturesque fountain and serves as a dreamy location for a breakfast, coffee, or lunch date at Barnie’s Coffee Kitchen. Step across the street afterward for a stroll through the Central Park Rose Garden.

Barnie’s CoffeeKitchen
Photo credit: HypeOrlando

Wine for Two

Sip vino while engaging in connective conservation at one of our local wine bars. The Parkview is an underrated Winter Park restaurant that doubles as a wine bar with boutique offerings. The Wine Room on Park Avenue and Imperial Wine Bar are additional recommendations.

If you’d prefer to sip locally made wine, Quantum Leap Winery creates sustainable wines crafted with high-quality grapes sourced around the globe. Pull up a seat in the tasting room and settle in to sip and sample one of Central Florida’s best wineries.

NEARBY OVERNIGHTS

Streamsong Resort

You’ll hardly know you’re in Florida once you arrive at Streamsong Resort for a secluded stay. Located about an hour and a half from Orlando, the stunning property is a haven for golfers and any couples looking to get away from it all for a few days. Golf enthusiasts can play three 18-hole courses, boasting scenic views amidst sweeping sand dunes and designed specifically to be walked. While you’re here, plan on doing little else besides enjoying the great outdoors (the resort has award-winning golf courses), lazing by the pool, relaxing in the grotto-style spa, and dining at the resort’s four signature restaurants.

Whether you’re avid golfers, in need of a spa retreat, or want to try something new like sporting clays or bass fishing, the hotel offers a multitude of packages to suit your interests. The “Streamsong Experience” package includes a two-night stay, late checkout, plus your choice of experience starting at $111/person per night.

Streamsong Resort

The Alfond Inn

Tucked away just off Park Avenue in Winter Park, The Alfond Inn is a boutique hotel where couples can relax and relish the local art scene during a culture-focused weekend staycation. Feast your eyes on delectable cuisine at Hamilton’s Kitchen, book your stay around the hotel’s recurring “Get Your Jazz On” music and dining event, and explore the contemporary art collection. Free in-house tours of the hotel’s art collection are offered every Sunday at 1pm, or you can join in the monthly happy hour tour on the first Wednesday of the month at 5:30pm.

The “A Night at the Museum” package includes a two-night stay, two art-inspired cocktails in the lounge, museum passes to three local Winter Park museums (including the Charles Hosmer Morse Museum of American Art), and a self-guided tour of the hotel’s current art installation. Rates begin at $239/night. Spa packages, pet-friendly packages, and a Florida Resident special are also available.

Westgate River Ranch

If your idea of camping includes a luxurious tent complete with a plush king-size bed, air conditioning, a private bathroom and your own personal concierge, glamping at Westgate River Ranch is your ideal getaway. This working Central Florida dude ranch offers some of the area’s most unique staycation digs and activities for couples. When you’re not sleeping or lounging in your luxe outdoor accommodations, explore the ranch’s daily happenings. Choose from the weekly Saturday night Rodeo, horseback riding, archery, airboat rides, fishing, boat rentals and more.

Florida and Georgia residents can save 10% off nightly rates through April 8, 2018, or 15-20% off nightly rates between April 8 and December 31, 2018. Get the details here.

Westgate River Ranch glamping in Central Florida
Image credit: Westgate River Ranch

Grand Bohemian Hotel Orlando

For a stay in one of Downtown Orlando’s swankiest hotels, book a room at the Grand Bohemian Hotel. Laze by the rooftop pool, book a treatment at the Poseidon Spa, peruse the art gallery, or take a seat at the sophisticated lobby bar, Bösendorfer Lounge, for cocktails, jazz (the lounge has a Grand Bösendorfer Piano), and charcuterie. The hotel is within walking distance of the Dr. Phillips Center for the Performing Arts, as well as a handful of Church Street District eateries. Before you go, stop into The Boheme, the hotel’s restaurant, for the popular Sunday jazz brunch.

The “Exactly Like Nothing Else” package includes a 50-minute couple’s massage, two tickets for Orlando Food Tours, two tickets to the Orlando Museum of Art, a $100 hotel gift card, breakfast for two daily, a private Art & Treasure Tour at the hotel, plus valet parking.

More options we love:

Looking for a more intimate experience? Check out these unique Airbnb rentals around town. 

Feature image credit: Get Up and Go Kayaking