High rollers will find their happy place on the sister islands of Sanibel and Captiva off Florida’s southwest coast, near Fort Myers. From a luxurious resort to dinner on a private yacht, here’s how to splash out on these islands.

South Seas Island Resort on Captiva Island provides the perfect backdrop for a luxe getaway. Complete with its own marina, this family-friendly resort is packed with amenities and offers a variety of accommodation options, from spacious guest rooms to sprawling private homes. Parents will love the beaches, spa and oceanside golf course, while the waterslides, pools and ice cream parlour will keep the kids happy. 

If you feel like spending some time on the water, book a day trip with Captiva Cruises, which offers a variety of tours that set sail from the resort’s marina. Go dolphin-watching, explore the surrounding islands or charter a private vessel and choose your own adventure. 

For high-end keepsakes, head to Periwinkle Place on Sanibel Island—the immaculately landscaped grounds of this shopping area lead to galleries full of contemporary arts and crafts, as well as home decor and clothing shops and restaurants. 

Book a sunset cruise aboard the sleek Sanibel Harbour Princess, a 100-foot luxury yacht. Enjoy a lavish dinner buffet, then pick a glass from the extensive wine selection and head upstairs to the observation deck to watch the twinkling lights of nearby Fort Myers slip silently by under starry skies. 

Getting There: WestJet flies to Fort Myers 13 times a week from Toronto and Ottawa.