Anna Maria Island Romantic Outings & Date Ideas

Anna Maria Island is famous for its inviting Gulf waters and miles of white-sand coastline. Visitors from around the world come to this special slice of the Florida coast to enjoy all the ocean has to offer – fishing, boating, paddle boarding and so much more. But with all the things to do in Anna Maria Island, there’s another reason to visit; romance!

Here, we’ll show you some of the best activities the island has to offer for couples looking to get away the right way – including spas to relax in, galleries to browse, and local restaurants to enjoy. After that, we’re sure that you’ll want to pack your matching suitcases and book your Anna Maria Island rental, today! 

Spoil Yourselves with a Spa Visit

An Anna Maria Island spa is the perfect way to unwind. There’s nothing like a massage to soothe away all your cares and relax. One of the best places to do it is Body & Sol Spa and Wellness. At Body & Sol, they use all-natural products to ensure the best experience. They’ll even come to you ( a travel fee may apply). A 45- or 75-minute massage may be all you need, or you can choose a scalp massage or foot scrub. Romance awaits with a Soul to Sole Package for 2, featuring a private yoga class followed by side-by-side pedicures.

Aluna Wellness is also a popular destination in nearby Bradenton Beach. Inspired by ancient wisdom and cultures, the treatments here are designed to give you the most relaxing experience in an eco-friendly, holistic way. Here, you’ll find private massages in one of five treatment rooms, a meditation room, a yoga studio, and a Zen Garden. Try a Swedish or deep tissue massage or consider a reflexology treatment that targets pressure points on hands and feet to restore balance and harmony. Couples will want to experience Serenity for Two – a relaxing massage for couples that’s a great way to share the spa experience.

If both relaxation and a fabulous hairstyle are on your list, then Acqua Aveda on the Beach is a must. Multi-time winner of People’s Choice Awards, this salon, and spa in historic Downtown Holmes Beach has everything you could want, from acupuncture, facials, nail care, and lash extensions to hair therapy, color, and bridal and wedding packages. When you leave, you’ll look and feel your best, and you’ll be ready for a great evening hitting any of the best Anna Maria Island restaurants.

Explore Local Anna Maria Arts and Culture

Our island is home to sea and surf. It’s the ideal place to sit and relax. But it’s also filled with plenty of art and culture. Anna Maria art galleries are a mainstay, and for couples, it’s the perfect way to take a leisurely stroll to enjoy it all.

To get the best sampling, visit the Artists Guild of Anna Maria Island. This all-volunteer organization promotes and supports local artists – including performers and writers – and has a lot to see. Stop in anytime Tuesday – Saturday from 10 a.m. to 6 p.m. and check out the featured exhibitors. While you’re there, get information on classes and events that you and your partner can enjoy, together.

If you can’t get enough of the local Island art scene, check out Island Gallery West. Open Tuesday through Sunday from 10 a.m. to 5 p.m., this cooperative formed by local Anna Maria Island artists offers a large variety of work including paintings, photos, ceramics, jewelry, mosaics, drawing, and more. Different artists and groups are featured each month, so you never know what you’ll find. Spacious and bright, it really is a unique place to explore.

Photo from Shutterstock

Anna Maria Island Waterfront Restaurants

When you think about a date night for two, what comes to mind? Chances are, you’re thinking of an intimate, moonlit meal somewhere with lots of charm. That’s why no visit would be complete without a dinner overlooking the water at a romantic restaurant, Anna Maria Island style.

Look no further than The Chateau Anna Maria, tucked inside Waterline Villas & Marina in Holmes Beach. This sophisticated dining experience was featured on Food Network and has an extensive menu. Order you and your sweetheart a champagne sangria, sparkling wine, or island margarita. Then, get your culinary journey started the local way with oysters on the half shell, steamed clams, or a shrimp cocktail. Entrees may include grilled chateaubriand, golden tilefish, or black Florida grouper. If you’re snuggled in at your Anna Maria Island rental, and you don’t want to leave, they’ll deliver to you! Happy hour is from 2 p.m. to 5 p.m., with brunch served Saturday and Sunday from 10:30 a.m. to 2 p.m. Dinner is served Tuesday through Sunday from 5 p.m. to 10 p.m. Reservations are welcome.

If you want to be at one of the best Anna Maria Island restaurants that calls itself the “premier waterfront dining experience,” then you have to get to The Waterfront Restaurant – a Reader’s Choice Award winner. The Waterfront prides itself on giving diners a return to a simpler time in laid-back style – “the way it used to be.” Settle in on the patio and take in the waters of Tampa Bay. Lunch, served daily from 11 a.m. to 4:30 p.m., features cold salads and ample main courses such as the fresh catch fish sandwich, signature burger, and gooey truffle-gouda mac & cheese. If you two are in for dinner after 4:30 p.m., start with a hot bowl of lobster bisque or tuna sashimi, then tuck into fresh Frutti di mare with scallops, shrimp, mussels, and clams or a juicy New York strip or grouper cakes. Pair it all with wine, beer, or a delicious cocktail, then a walk on the beach just outside the restaurant and make a memory that will last the two of you a lifetime.

Plan Your Anna Maria Island Vacation

Are you looking for that perfect summer getaway? Contact Mainsail Vacation Rentals to find your perfect Anna Maria Island vacation rental.

Return to Your Anna Maria Island Vacation Rental

After a day of strolling, taking in the local culture, and enjoying an unforgettable meal, we’re sure you’ll want to get back to your Anna Maria Island vacation rental as soon as possible to put your feet up and relax. Imagine you and your sweetheart with a drink, a sunset, and a view you’ll never forget. At Mainsail Vacation Rentals, we’re committed to getting you into the Anna Maria Island vacation rental you want, with the amenities you need to make your getaway for two perfect for you. With fully equipped kitchens, high-speed wireless internet access, TVs, and so much more, you won’t want your stay to end!

At Mainsail, you can book with confidence. The well-being of our guests is our primary concern. That’s why we feature safe cleaning practices and a flexible cancelation policy that ensures you’ll have little stress and maximum fun.

With all the Anna Maria Island rentals to choose from, you want the one that will get you closest to all the things you want to see and do. Whether it’s an intimate two-bedroom condo with endless ocean views or a three-bedroom townhome with room for everyone, Mainsail Vacation Rentals has it. So, go get your partner, ask them if they’re ready to make great memories, and book with us today!