Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Luxury Cultural Road Trip Itinerary: Sarasota, FL - December 2024

Viewed by 75 travelers

Day 1: New Year's Eve in Sarasota

Sarasota, FL

8:00AM

Breakfast at The Breakfast House

Kick off your trip with a hearty breakfast of organic pancakes and artisanal coffee at this local favorite.
Take a 10-minute drive from your hotel to The Breakfast House on Siesta Key.
USD 20, 1.5 hours

10:00AM

Visit The Ringling Museum

Explore the opulent surroundings of one of America's premier art museums featuring collections that reflect the legacy of John Ringling.
A 15-minute drive from breakfast across the John Ringling Causeway.
USD 25, 2 hours

12:30PM

Lunch at The John and Mabel Ringling Museum Cafe

Enjoy a Mediterranean-inspired lunch in a beautiful setting overlooking Sarasota Bay.
Located conveniently within the Ringling Museum.
USD 30, 1.5 hours

2:00PM

Stroll through Marie Selby Botanical Gardens

Experience the stunning tropical gardens and breathtaking views of the bay while learning about flora in their conservation programs.
20-minute drive from the museum.
USD 20, 2 hours

5:00PM

Cocktails at The Haye Loft

Sip on craft cocktails at this rooftop bar with a stunning sunset view over Sarasota's skyline.
A quick 10-minute drive back to downtown Sarasota.
USD 15, 1.5 hours

7:00PM

New Year's Eve Dinner at Michael's On East

Indulge in an exquisite gourmet meal featuring locally sourced ingredients and fine wine options, perfect for welcoming the new year.
A 5-minute drive from the bar.
USD 100, 2.5 hours

10:00PM

New Year’s Eve Celebrations at Ed Smith Stadium

Join the local celebrations with live music, food trucks, and a spectacular fireworks display as you ring in the New Year.
A short 10-minute drive from dinner.
USD 0, 3 hours
Find Hotels in Sarasota

Day 2: Artistic St. Petersburg

St. Petersburg, FL

9:00AM

Breakfast at The Diner

Start your day with a classic American breakfast at this iconic diner known for its friendly service.
30-minute drive to St. Petersburg.
USD 15, 1.5 hours

10:30AM

Visit The Salvador Dali Museum

Delve into the surreal world of Salvador Dali with an impressive collection of his paintings, sculptures, and immersive exhibits.
A short 10-minute drive from breakfast.
USD 25, 2 hours

1:00PM

Lunch at The Hangar Restaurant & Flight Lounge

Savor delicious fare while watching the planes take off and land from this unique restaurant situated next to the airport.
5-minute drive from the museum.
USD 30, 1.5 hours

3:00PM

Explore Fort De Soto Park

Experience the beautiful natural scenery while walking or biking through trails, enjoying beach views, and spotting wildlife.
30-minute drive from lunch.
USD 5, 3 hours

7:00PM

Dinner at Sea Salt

Dine at this chic restaurant featuring a menu of seasonal seafood dishes and a curated wine list in a stylish atmosphere.
30-minute drive from the park.
USD 80, 2 hours

9:00PM

St. Pete Pier Sunset Views

End your day by enjoying stunning sunset views and taking a leisurely walk along the waterfront with beautiful scenery.
10-minute drive from dinner.
USD 0, 1.5 hours
Find Hotels in St. Petersburg

Day 3: Cultural Tampa Adventures

Tampa, FL

9:00AM

Breakfast at Ybor City Saturday Market

Enjoy a vibrant breakfast at this historic marketplace filled with local vendors and diverse food options.
A 30-minute drive from St. Petersburg.
USD 20, 1.5 hours

11:00AM

Explore Ybor City Historic District

Stroll through the charming streets of this historic neighborhood famous for Cuban coffee, cigars, and rich culture.
Walking distance from the market.
USD 0, 1.5 hours

1:00PM

Lunch at the Columbia Restaurant

Savor authentic Spanish-Cuban cuisine in Florida’s oldest restaurant, a feast for both your stomach and your eyes.
5-minute walk from Ybor City.
USD 40, 2 hours

3:30PM

Visit Florida Aquarium

Immerse yourself in marine life through interactive exhibits, including an impressive collection of sharks and stingrays.
A 10-minute drive from the restaurant.
USD 30, 2 hours

6:00PM

Cocktails at Bar Arcadia

Unwind with craft cocktails in this sophisticated bar, perfect for relaxing after a busy day of exploration.
15-minute drive from the aquarium.
USD 25, 1.5 hours

8:00PM

Dinner at Bern's Steak House

Indulge in an extravagant dinner experience at one of the finest steakhouses in Tampa with its award-winning wine list.
A 10-minute drive from the bar.
USD 150, 3 hours
Find Hotels in Tampa

Day 4: Relax & Explore Bradenton

Bradenton, FL

9:00AM

Breakfast at The Starfish Company

Start your day with fresh seafood-inspired breakfast options while taking in the waterfront views at this local gem.
30-minute drive from Tampa.
USD 25, 1.5 hours

11:00AM

Visit the Village of the Arts

Explore this eclectic community of artists and enjoy local galleries and studios showcasing colorful and unique artwork.
15-minute drive from breakfast.
USD 0, 2 hours

1:00PM

Lunch at O’Bricks Irish Pub and Martini Bar

Savor a selection of Irish dishes and martinis in a relaxed setting that feels just like home.
5-minute drive from the Village.
USD 30, 1.5 hours

3:00PM

Walk Along the Riverwalk

Enjoy a leisurely stroll along the scenic Riverwalk, taking in the art installations and beautiful views of the Manatee River.
10-minute drive from the pub.
USD 0, 2 hours

5:30PM

Cocktails at The Brige Street Bistro

Sip on a delightful cocktail while enjoying views of the beach in this charming bistro.
20-minute drive from the Riverwalk.
USD 20, 1.5 hours

7:30PM

Dinner at The Waterfront Restaurant

Indulge in a delicious dining experience overlooking the waterfront, with seasonal dishes and a variety of flavors.
A short drive from the bistro.
USD 60, 2 hours
Find Hotels in Bradenton

Day 5: Return & Relax in Sarasota

Sarasota, FL

9:00AM

Brunch at Shore Diner

Feast on brunch staples with a coastal twist and refreshing drinks while enjoying the relaxing atmosphere.
30-minute drive from Bradenton.
USD 35, 1.5 hours

11:00AM

Visit Siesta Key Beach

Spend the morning lounging on one of the most beautiful beaches in the US, where soft white sands await.
15-minute drive from brunch.
USD 0, 3 hours

2:30PM

Lunch at Captain Curt's Crab & Oyster Bar

Experience local seafood awash in exciting flavors at this informal waterside restaurant in Siesta Key.
A short drive from the beach.
USD 25, 1.5 hours

4:00PM

Spa Treatment at The Ritz-Carlton Spa

Unwind with a luxurious spa treatment, ensuring you feel rejuvenated and relaxed before the end of your trip.
A 15-minute drive from lunch.
USD 150, 2 hours

7:00PM

Farewell Dinner at Selva Grill

Indulge in a culinary journey of Latin-inspired dishes and craft cocktails in a vibrant atmosphere for your final meal.
20-minute drive from the spa.
USD 80, 2 hours

9:30PM

Evening Walk at Lido Key Beach

End your adventure with a breathtaking sunset on Lido Key Beach, a perfect way to reflect on your incredible journey.
A 10-minute drive from dinner.
USD 0, 1.5 hours
Find Hotels in Sarasota
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version

More About Sarasota, FL

4-Day Trip to Sarasota
Packing List
Trip Packing List: Sarasota, Florida (April)
Packing List
Itinerary created by AI-assisted, human-reviewed

Plan Your Sarasota, FL Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go