5-Day Sanibel Island Itinerary 

When you’re lucky enough to have five days to spare in the name of vacation fun, there’s no better place to set your travel sights than Sanibel Island. The following 5-day Sanibel Island itinerary is a great place to start when you can’t wait to make the most of every single moment.

Day 1: Focus on Sanibel Island Fun

The first day of your stay will focus on Sanibel Island adventures. This pristine destination along Florida’s southwest coast is open and inviting and refreshingly lacks overdeveloped tourist areas so you can really appreciate the beauty of nature while you’re here. Begin by heading over to Billy’s Bike Shop and renting wheels to get you around. Once you’ve settled on your bike rental, take some time to explore the historic Sanibel Lighthouse that dates back to 1884. Since this sits on the eastern end of the island, you’ll be in the right place to follow it up with stops at local restaurants and shops. Afterward, make your way to Blind Pass Beach and spend some quality time shelling with your traveling crew. You also have options to cast a line if angling is your passion. Nature lovers can end the day in a kayak booked through Tarpon Bay Explorers or hiking their way to fun at the sprawling J.N. “Ding” Darling National Wildlife Refuge which is home to a stunning mangrove ecosystem and more than 245 species of birds.

Day 2: Check Out Captiva

The bridge over Blind Pass connects Sanibel and Captiva Islands so it won’t take you long to access fun under the sun on day two of your stay. This is another great place to enjoy shelling fun with the entire family which is what you’ll want to do at the start of the day. When you’ve filled your bucket, take time to head over to Turner Beach where you can fish from the shoreline at your own preferred pace. Spend some time sunbathing before booking a wildlife-watching tour out on the waves combined with some quality time snorkeling or diving. When cravings come calling, stops like the Sunset Grill, Key Lime Bistro and RC Otters are all great places to enjoy award-winning eats and beautiful views.

Day 3: Spend Time on Pine Island

The third day of your Sanibel Island 5-day stay has you heading over to Pine Island in the name of even more fun. This barrier island is brimming over with small-town charm and the Old Florida fishing village vibe so many travelers are after. Pine Island is a place for respite and a locale where you can slow down and really relish your time away from the crowds. It’s also a hub for outdoor recreation and you won’t want to miss out on taking time to rent a boat and explore the waters of Pine Island Sound. The coastline is home to mangroves which are great to explore in a kayak or on a paddleboard. When you’re looking to learn more about the area, a trip to the Museum of the Islands is a must followed by a trek on the Calusa Heritage Trail. End your day with sunset views from the sand over at Cayo Costa.

Day 4: Elevate the Adventure with Local Tours

The fourth day of your stay is a chance to get out and explore the area further alongside local guides. Start with Adventures in Paradise-Outfitters located at 2019 Periwinkle Way in Sanibel. This family-owned and operated company has been serving Sanibel Island since 1986 and provides custom outings with a focus on spotting dolphins, manatees and sea otters that are sure to thrill. They also build shelling experiences into their excursions upon request and if you want to take your fun from sea to land, be sure to book the tour that also includes a tour of Sanibel Island onboard the historic trolley.

Over on Captiva Island, you’ll want to partner up with Captiva Cruises at 11401 Andy Ross Lane. They’ve also been crafting customized adventures since 1986 and operate a fleet of vessels that are ideal for exciting tours. Book a private charter or group outing depending on preference and plan on enjoying an educational and engaging experience on the water.

Day 5: Relax in Style

On the last day of your stay, you’re going to want to spend time on the sand and pair it with well-deserved relaxation in your luxury rental booked through Dream Vacation Rentals. Savor the sights from your private balcony or enjoy a delicious meal in when you book a stay with a full kitchen included. For an even more restorative experience, consider adding a stop at the Sanibel Day Spa located at 2075 Periwinkle Way. Here, you can enjoy a session focused on massage, exfoliating, nail services, aromatherapy, hot stone treatments, and more!

Book Your Getaway Today

When a Sanibel Island adventure is calling your name, make sure you partner with Dream Vacation Rentals so you can enjoy accommodations that showcase the luxury, comfort, and style standards you deserve! Reach out today to learn more about our many exciting options and to start planning your next trip.