Anna Maria Island, with the most beautiful beaches, breathtaking sunsets, and laid-back atmosphere, offers the perfect backdrop for a romantic Valentine’s Day getaway. Whether you’re strolling hand-in-hand along the pristine shores or enjoying a candlelit dinner at one of the island’s cozy, waterfront restaurants, this small slice of paradise promises a great time. From intimate beach picnics to boutique shopping, couples spa packages, and stunning views, Anna Maria Island has everything you need for a dreamy, love-filled celebration. With plenty of Anna Maria Island vacation rental options you can be sure to find the perfect romantic home away from home. Let’s dive into why this hidden gem should be your destination of choice for this Valentine’s Day…
What to Do for Valentine’s Day on Anna Maria Island
Beyond its world-renowned beaches, Anna Maria Island offers plenty of activities that are perfect for a special occasion like Valentine’s Day. Whether you’re seeking relaxation or adventure, there’s something for everyone. Here are a few of our favorite ways to enjoy a romantic getaway on the island:
Brunch at Local Favorites: Kickstart your day with a delicious brunch at the island’s best spots like Anna Maria Island Beach Café, Paradise Bagels & Café, and La Creperie — all offering tasty dishes and cozy vibes.

Explore the Island by Bike: With perfect February weather (averaging around 75°F), hop on a bike and take a leisurely ride around the island. There’s no better way to enjoy the natural beauty of Anna Maria than cruising along its charming streets. Check out these convenient bike rentals.

Sightseeing on the Free Island Trolley: Hop aboard the free island trolley and take a sightseeing tour. Stop to browse the unique shops or grab a bite to eat. It’s a great way to explore the island without worrying about parking!

Stroll Through Pine Ave & Historic Bridge Street: Explore the island’s quaint boutiques, such as Two Sides of Nature, Pineapple Marketplace, and Bridge Street Bazaar. Find the perfect souvenir to remember your special day.
Couples Spa Treatment: Treat yourselves to a relaxing couples’ massage or spa treatment at Body & Sol Spa or Aluna Wellness. After all, nothing says romance like a little pampering together.
Beach Day with a Twist: Pack a picnic, grab your favorite snacks, and spend a laid-back day on the beach. For a bit of extra flair, why not book with Sandy Toes Luxury Beach Picnics or Luxury Gulf Picnics ? They’ll take care of all the details so you can just show up and enjoy.

Boat or Fishing Charter: If you’re looking for something a little more adventurous, why not take a boat charter or a fishing trip? Soak in the sun, feel the sea breeze, and enjoy the stunning views of marine life all while cruising the beautiful waters around Anna Maria Island.
Browse Local Art Galleries: Anna Maria Island has a thriving art scene. Visit galleries like Artist Haven AMI or the Artists Guild to discover unique, handmade works of art by local creators. It’s the perfect place to find a meaningful keepsake.
Capture the Moment: Hire a local photographer for a personalized session and let the beautiful scenery of Anna Maria Island serve as the backdrop for your romantic memories.
Where to Eat on Valentine’s Day

Anna Maria Island boasts some of the best dining in the area, with an impressive selection of restaurants offering delicious dishes and stunning views. For a truly special Valentine’s Day dinner, here are some top recommendations with special menus for the occasion:
Mademoiselle Paris: Enjoy an unforgettable four-course meal with live music at this charming French bistro. Valentine’s Day Dinner at their Anna Maria location is available from 5:00 PM to 10:00 PM on February 14th, 2025. RSVP now for an evening of romance! Location: 9906 Gulf Dr, Anna Maria, FL 34216
Floridays Woodfire Grill & Bar: Indulge in a romantic dinner by the water with Floridays Four-Course Prix Fixe Menu. Available February 14-16.
Location: 12332 Manatee Ave. West, Bradenton, FL 34209
Phone: (941) 741-8700
Pier 22: Though off-island, Pier 22 in Bradenton is a local favorite for holidays and special occasions. They are offering a chef crafted menu starting at 3 PM on February 14th, 2025.
Location: 1200 1st Ave W., Bradenton, FL 34205
Phone: (941) 748-8087
While they may not offer specialty menus, some other notable spots to consider include: The Beach House, The Waterfront Restaurant, The Sandbar, Mar Vista on Longboat Key, and Salt Bar & Table.
Where to Stay: Your Romantic Retreat

Anna Maria Island is a sought-after romantic destination, especially around Valentine’s Day, so it’s essential to book your accommodation early. Whether you’re dreaming of a beachfront property, a cozy canal-front home, or a condo with sweeping views of the horizon, Island Real Estate Vacations has something to suit your needs. With over 50 years of industry experience, we pride ourselves on helping you find the perfect vacation rental for your getaway. Let us make your Valentine’s Day stay truly unforgettable.
Ready to plan your dream Valentine’s Day on Anna Maria Island? Contact us today to book your perfect vacation rental, and make this year’s celebration one for the books!
Speak with one of our Vacation Rental Specialist today and secure your stay!
(941) 778-6066 X 1
www.IslandReal.com