Anna Maria Island offers a coastal setting that invites couples to slow down, reconnect, and experience the charm of Florida’s Gulf Coast. Known for its pristine beaches, turquoise waters, and local character, the island delivers an ideal atmosphere for romance. Whether you’re planning a surprise outing or building a special memory together, this Anna Maria Island itinerary reflects a full day of meaningful experiences.
At Duncan Real Estate, we provide carefully selected Anna Maria Island vacation rentals to complement every part of your stay, offering comfort and direct access to the island’s most scenic spots.
Watch the Sunrise at Bean Point Beach
Begin your romantic day with sunrise at Bean Point Beach, located at the northernmost tip of the island. This stretch of shoreline is known for its open views and quiet ambiance, where the soft light of dawn reflects across both the Gulf and Tampa Bay. Without the interruption of nearby development, the beach offers an unobstructed place for reflection, ideal for couples looking to start their day together in calm and silence. The horizon becomes a canvas of color as the sun lifts, and the sound of gentle surf replaces any need for conversation. Bean Point remains a favorite for early risers who prefer a more private beach experience. Here, the landscape’s simplicity allows the moment to speak for itself.
Breakfast at Ginny’s & Jane E’s Cafe
Following the sunrise, Ginny’s & Jane E’s Cafe offers a relaxed breakfast in a setting full of character. Housed in a former general store, the cafe features quirky décor, vintage accents, and locally made items throughout the space. The atmosphere reflects the island’s independent spirit, and the menu offers generous portions of scratch-made pastries, breakfast sandwiches, and coffee. It’s a venue that encourages lingering. Couples can enjoy a slow meal before exploring the attached marketplace, which carries handmade crafts, art, and beach-themed goods. This stop on the Anna Maria Island itinerary captures the area’s creative pulse while offering a nourishing start to the day.
Kayaking or Paddleboarding at Bimini Bay
Mid-morning provides the perfect window for kayaking or paddleboarding in Bimini Bay. Located on the island’s eastern side, this calm body of water is ideal for paddlers of all experience levels. Its clear, shallow waters offer the chance to observe marine life, such as manatees and dolphins, as well as the lush mangroves that define the shoreline. Rental equipment is readily available in the area, and self-guided routes enable couples to move at their own pace. Whether weaving through mangrove tunnels or floating side by side in open water, the experience brings a sense of peaceful adventure. It’s a way to connect with the natural surroundings while sharing quiet moments away from the busier beach scenes.
Visit the Anna Maria Island City Pier
Next, head toward the historic Anna Maria Island City Pier. Originally constructed in 1911, the pier extends into Tampa Bay, offering broad views of the horizon, including the distant Sunshine Skyway Bridge. Its wooden planks and relaxed pace create a setting ideal for hand-in-hand walks and shared pauses over the water. A small gift shop and eatery offer refreshments, but it’s the surrounding water and sky that define the visit. The pier adds a touch of history and timelessness to the day, making it a thoughtful stop along the romantic path.
Lunch at The Waterfront
For lunch, The Waterfront Restaurant delivers an elevated coastal dining experience just steps from the City Pier. Set in a restored cottage surrounded by mature oaks and tropical plants, the restaurant offers views of the bay and a menu focused on local seafood, crisp produce, and seasonal flavors. The garden patio provides a shaded, intimate space for couples to dine in a relaxed atmosphere. Service is attentive without being intrusive, and the quality of the dishes enhances the midday break. The Waterfront’s balance of refinement and approachability makes it a perfect fit for a romantic lunch offering substance, style, and a sense of place.
Coquina Beach
Spend the afternoon at Coquina Beach, located at the southern end of Anna Maria Island. Known for its wide, powdery shoreline and swaying pine trees, the beach offers natural shade and quiet pockets to unwind. Ample parking and public amenities make the beach easy to access, and its length allows for privacy even during peak season. Whether relaxing under the trees or strolling barefoot along the tide line, Coquina provides a welcome change of pace. The surrounding Coquina Baywalk and Leffis Key Preserve offer trails for those interested in light walking while remaining immersed in nature. It’s a restful, beautiful location that adds balance to the day’s more active moments.
Sunset Cruise
As late afternoon arrives, embark on a sunset cruise from one of the local charter operators. These cruises sail along the Gulf of Mexico and provide stunning views as the sun sets into the water. Dolphins frequently accompany the boat, and the changing colors of the sky create a perfect frame for the close of day. Most charters offer drinks on board, and the relaxed pace gives couples a chance to reflect on the day while enjoying the view. The boat’s gentle motion and the rhythmic sound of waves complete the setting. A sunset cruise remains one of the most memorable experiences available on Anna Maria Island, offering a unique perspective of the shoreline and the sea beyond.
Plan Your Visit
Your romantic getaway on Anna Maria Island starts with the perfect place to stay! Browse our full inventory of AMI vacation rentals to find your ideal accommodations.
Dinner at The Sandbar
End your romantic day with dinner at The Sandbar Restaurant. Known for its direct beach access and open-air dining, The Sandbar sets its tables right in the sand, allowing diners to feel the ocean breeze and hear the surf just feet away. The restaurant is especially popular for post-sunset dining, as tiki torches light the tables and the sky fades into deep blue. The menu highlights fresh seafood, seasonal vegetables, and handcrafted cocktails. The setting, combined with thoughtful service, makes dinner here a quiet celebration of the day. It’s more than just a meal—it’s an experience that captures everything the island represents: simplicity, beauty, and the ability to slow down and enjoy the moment.
Book Your Anna Maria Island Vacation Rental with Duncan Real Estate
To make the most of a romantic getaway, choosing the right accommodations is essential. Duncan Real Estate offers a portfolio of Anna Maria Island vacation rentals that deliver both privacy and convenience. From coastal cottages to spacious beachfront vacation rentals on Anna Maria Island, our properties offer the perfect base for couples looking to explore the island at their own pace. Our team specializes in pairing guests with the right home based on lifestyle, location, and preferences. Whether you plan to follow this Anna Maria Island itinerary or chart your own course, a quality vacation rental provides the freedom and comfort that elevate each experience. Duncan Real Estate ensures that every stay is backed by local insight and reliable service, helping you create memories that last long after you’ve left the beach behind.
