A Weekend in Sarasota | Ultimate Romantic Itinerary
A weekend in Sarasota offers beautiful beaches, a rich cultural scene, and plenty of restaurants to satisfy any craving. As a mecca full of activities and scenery, it can be tough to decide where to start — especially if you are a couple.
Your search stops here. This 3-day itinerary has everything you need for a romantic weekend getaway in the Sarasota area.
The perfect place for all things romantic, Sarasota offers a gorgeous backdrop of white-sand beaches and crystal blue waters. This cheeky little itinerary is your guide to turning a weekend away into a love story for the ages.
Pack your bags, grab your special someone, and let the swooning begin!
Start your flight search to Sarasota-Bradenton International Airport ✈️
History & Facts
Along Florida’s Gulf Coast, Sarasota is a vibrant city known mainly for its interesting circus history, one-of-a-kind beaches and cultural attractions. Once inhabited by indigenous tribes, the area attracted European settlers in the mid-1800s, drawn by its fertile soil and warm climate. Today, the city is home to a diverse community of artists, retirees, and families.
Here are some of Sarasota’s cool facts & historical highlights:
- Indigenous tribes like the Tocobaga and Calusa called this area home long before European contact.
- The name “Sarasota” first appeared on a 1763 Spanish map as “Zarazote.”
- Scottish settlers came in the 1880s after the Florida Mortgage and Investment Company bought land for development.
- Circus mogul John Ringling was a big part of Sarasota’s growth and even founded the Ringling Museum of Art.
- Ringling used circus elephants to help build the bridge to St. Armand’s Key.
- Post-WWII, Sarasota boomed with new residents and businesses.
- Sarasota is a popular spot for millionaires, with lots of wealthy households in the area.
When to Visit
The ideal time to visit Sarasota is March through May. You’ll enjoy warm (but not scorching) low-80s temps and lighter crowds compared to peak season.
If you prefer a quieter trip with pleasant weather, September to November is another great window, though keep an eye on hurricane forecasts. Just avoid the packed (and pricier) winter months from January to April, when snowbirds flock to the Gulf Coast sunshine.
Hotel recommendation
Roy’s Place
Looking for a private tropical escape? Roy’s Place is one of Sarasota’s most stunning VRBOs. Located minutes from Lido Beach and downtown, this stylish retreat has it all: a saltwater pool, hot tub, and a lush backyard with a privacy fence, making it the perfect oasis after a day of adventure.
Want more options? Don’t miss these 5 Most Romantic Airbnbs in Florida!
How to Get There
By Air
The easiest way to get to Sarasota is by flying into Sarasota Bradenton International Airport (SRQ), just six miles from downtown. This local airport offers direct flights from a bunch of major cities, plus rental cars and ride-shares to get you where you need to go. If you’re looking for more flight options, Tampa (TPA) and Fort Myers (RSW) are also great choices, both about a 60-80-mile drive away.
By Car
If you’re driving, I-75 is your main route into Sarasota. Heading north or south? Just stick to I-75 until you reach your exit. Coming from the east? I-75 is the easiest way, running along the county’s eastern edge and connecting straight to downtown. It’s an easy drive… just don’t forget your sunglasses!
Sarasota 3-Day Romantic Itinerary
The white-sand beaches and dreamy Gulf Coast waters are calling your name! With so many romantic things to do, this 3-day itinerary is perfect for an unforgettable weekend in Sarasota.
Day 1:
Start your morning with breakfast at your hotel, or head to C’est la Vie for a cozy French cafe kinda vibe. The crepes are amazing!
Head to the beach
After breakfast, don’t waste any time and chase that beachside bliss! Siesta Key Beach is the most popular spot, and for good reason. The quartz sand is so soft and the water is calm and crystal clear. There’s also Lido Key Beach, which is another great spot if you’re looking for something quieter and less crowded.
Both spots are perfect for dolphin watching, deep-sea fishing, or just soaking up the sun. If you’re up for it, I recommend making a day of it and visiting both beaches, as traffic can be a nightmare when you’re heading to or from the coast from downtown Sarasota.
Visit Marie Selby Botanical Gardens
If you’re feeling beached out and can’t commit to a full day of sand and sun, I’d check out the Marie Selby Botanical Gardens. The gardens span 15 acres, showcasing rare plants from around the world. The butterfly garden, koi pond, and views of Sarasota Bay are definitely a highlight!
For dinner, head to the downtown area and grab a table at Owen’s Fish Camp. It’s got all the beachy vibes and the seafood is so fresh! Then stroll hand-in-hand along Main Street and raise a glass (or two) at one of the lively bars in the area.
Day 2:
No trip to Sarasota is complete without checking out the Ringling Museum. This beautifully curated museum is dedicated to the famous circus entrepreneur, John Ringling. You can also tour his stunning Venetian-style mansion on the property. Here’s how to make the most of it:
Tour the Ringling Museum
- Head over right when it opens and grab a to-go breakfast from a local spot. Then walk to the back porch of Ca’ d’Zan, the Ringling’s waterfront mansion. Sit back, soak up the view, and channel your inner billionaire. Chances are, you’ll have the place all to yourself!
- After breakfast, buy a couple tickets and tour the opulent Ca’ d’Zan. Then swing by the Circus Museum, where vintage wagons and sparkly costumes bring the golden age of the circus to life.
- Before the midday heat rolls in, wander the Bayfront Gardens. The banyan trees and rose gardens are enchanting to behold, making it the perfect romantic spot.
Insider tip: The Mable Ringling Museum of Art is free on Mondays! If your long weekend stretches into Monday, save this for the end of your trip.
Explore St. Armand’s Circle
For lunch, head to St. Armand’s Circle and settle in at Columbia Restaurant for their legendary Cuban sandwich or saffron-loaded paella. You’ll be in prime location to browse the circle’s boutiques and art galleries.
Take a Trapeze class
Next up: adrenaline time! Book a beginner trapeze class at the Circus Arts Conservatory. Yes, you’ll fly through the air (safely harnessed, of course) with pro coaches guiding you. It’s an absolute blast.
End the day at Indigenous, where the seasonal menu is as creative as it is delicious (they’re wild mushroom bisque is phenomenal!). Make sure you reserve ahead, this spot’s a hot ticket!
Day 3:
Start your final day with breakfast at Millie’s, a charming spot that feels like you’re dining in someone’s cozy French cottage! The food here is excellent, plus there’s solid vegan/vegetarian options.
Snorkel with Manatees
Then, embark on a bucket-list adventure: kayaking with manatees! Drive up 2 hours north to Crystal River. Make sure you’ve booked in advance — early mornings from November to April are the best time to see these gentle giants.
Grab lunch at Seafood Seller & Café, where fresh seafood meets bold Cajun flavors. The owner here is known to perform a few magic tricks for patrons, so maybe you’ll get a show with your meal!
Go on a Sunset Cruise
Head back to Sarasota for some downtime at your hotel. Relax by the pool or enjoy a cocktail before the main event of your evening: a boat cruise from Anna Maria Island. We recommend booking with Party Barge Charters for a more intimate experience. You might even spot some dolphins while you’re out there!
You have to end your weekend in Sarasota with dinner at Mediterraneo. It’s some of the best Italian food I’ve had, with handmade pasta, great wine, the whole deal. Make sure you book ahead and save some room for dessert!
Things You Don’t Want to Miss
- Check out Latin Quarters or Cask Ale for some live music and dancing for a fun night out.
- Rent a kayak or paddleboard and explore the mangrove tunnels at South Lido County Park. You’ll see so much wildlife, and if you’re unsure, the guided tours are awesome!
- While you’re at The Ringling, make sure to swing by the Tibbals Learning Center. It’s a quick walk and so worth it.
- If you’re downtown and need a drink, go to Perspective Rooftop Pool Bar. Don’t forget your swimsuit!
Favorite Places to Eat in Sarasota
Other Fun Things To Do
If you’ve got some extra time or want to swap some activities out, here are a few other romantic things to do in Sarasota:
- Visit the Farmers Market at Lakewood Ranch every Sunday at Waterside Place for fresh produce, baked goods, meals, flowers, and more.
- Check out Myakka River State Park! You can kayak, hop on an airboat tour, hike beautiful trails, and even spot some alligators.
- Tour the Siesta Key Rum Distillery to see how their rum is made and enjoy a behind-the-scenes look.
- Immerse yourself in the tropical charm of Sarasota Jungle Gardens, home to vibrant animals and exotic plants.
- Explore the Mote Marine Laboratory, a working aquarium and research center with manatees, sea turtles, sharks, and more.
Packing Essentials
Clothing
- Lightweight, breathable outfits (shorts, tees, tank tops, linen pants) for warm days
- Swimsuits (1-2) + cover-ups for beach/pool time
- Casual dresses or skirts for evenings
- Light jacket or sweater (for cooler nights)
- Comfortable walking shoes + sandals/flip-flops
- One hot outfit for date night (wink wink)
Gear & Accessories
- Sunscreen, sunglasses, and a wide-brimmed hat
- Insect repellent (Florida bugs are relentless)
- Reusable water bottle to stay hydrated
- Small backpack/cross-body bag for exploring
- Beach bag (for towels, books, snacks)
Feel the Sarasota Spark: Coastal Magic for Two
Sarasota is easily one of the most romantic spots in Florida, offering you and your partner the perfect weekend filled with coastal magic.
Can’t fit everything in? No big deal… that’s just an excuse to come back! Whether it’s your first trip or your fifth, one things for sure: a weekend in Sarasota will leave you sun-kissed and smiling.
Have you been to Sarasota? Fill us in on your vacation must-dos in the comments below! And don’t forget to subscribe to my newsletter for more romantic getaway ideas and tips!
A Weekend in Sarasota – FAQs
Is Sarasota expensive to visit?
Yes, Sarasota can be pricey, especially in spots like Siesta Key, but there are ways to reduce the damage. Be sure to take advantage of free activities like beaches and parks, and look for budget-friendly stays and eats. The time of year you visit is also a major factor here.
Is Sarasota a walkable town?
Totally! Some neighborhoods in Sarasota are super walkable. Downtown is the best, with wide sidewalks, tons of cultural spots, waterfront parks, and great places to eat. If you’re into a more laid-back vibe, check out Laurel Park. It’s historic, has shady streets, and is just a short stroll to downtown.
What is the #1 beach in Sarasota?
Siesta Beach is often ranked the #1 beach in Sarasota, and it’s easy to see why. With soft white sand, clear waters, and amenities like picnic tables, grills, and volleyball courts, it’s a favorite for locals and tourists alike. But Sarasota has many other beautiful beaches to explore, including Lido Beach, Longboat Key Beach, and Venice Beach.
