'Tween Waters Island Resort & Spa has anchored Captiva Island's shoreline since 1931, occupying a narrow strip of land between the Gulf of Mexico and Pine Island Sound. Listed on the National Register of Historic Places, the resort's origins trace to F. Bowman and Grace B. Price, who built the original inn and grew it over three decades into one of Southwest Florida's most storied island retreats. Notable guests through the years have included Charles and Anne Morrow Lindbergh and cartoonist Jay "Ding" Darling, who wintered here for seven seasons in the 1930s and '40s.
The resort offers multiple distinct event spaces suited to a range of celebrations and group sizes. The Old Captiva House — originally a one-room schoolhouse built in the early 1900s — anchors the property with restored hardwood floors and floor-to-ceiling French doors that frame Gulf sunsets; it accommodates up to 120 guests for a seated buyout. The Wakefield Room is a second-floor banquet space with beach and sunset views, seating up to 90 guests. For outdoor events, three beachfront ceremony sites face the Gulf directly, and the Serenity Pool area can host up to 130 guests under open sky.
The resort's 137 accommodations — cottages, suites, studios, and guestrooms — sit on the same grounds as the event spaces, making on-property lodging straightforward for traveling guests. In-house catering and a dedicated events team support weddings, rehearsal dinners, corporate gatherings, and private celebrations throughout the year.
