Roosevelt Relaxed Here


One of the original ‘Tween Waters Inn cottages in the early 1900s.
Though it feels like an undiscovered corner of paradise, Captiva Island has been delighting visitors for nearly 100 years. Nestled beneath the pines between the Gulf of Mexico and Pine Island Sound, the 13 lush acres that make up today’s ‘Tween Waters Inn were a natural choice for the fishermen who built their cottages here in the 1920s. The first overnight guests rented these cottages in 1931, and ‘Tween Waters Inn was born. You will find 19 of these unique historic cottages throughout the property. Each is named after and decorated in the spirit of some of our most famous guests, combined with cozy historic charm of today’s comforts.

We’ve welcomed a number of well-known visitors over the decades. Avid outdoorsman and U.S. President Teddy Roosevelt frequently visited Captiva Island on deep-sea fishing excursions. A contemporary of Roosevelt in the early conservation movement of the 1930s, celebrated cartoonist J.N. “Ding” Darling was also a ‘Tween Waters Inn devotee, and is the namesake of the nearby National Wildlife Refuge.


“One is forced against one’s mind, against all tidy resolutions, back into the primeval rhythms of the seashore. Rollers on the beach, wind in the pines, the slow flapping of herons across sand dunes, drown out the hectic rhythm of city and suburb, time tables and schedules.”

From “Gift from the Sea” by Anne Morrow Lindbergh.
Pioneer aviator Charles Lindbergh was also an early fan of the resort. Inspired by the beach, shells and wildlife of Captiva, his wife Anne wrote her classic “Gift from the Sea” while on the island in 1955. The book shares her reflections on youth and age; love and marriage; and peace, solitude and contentment in the lives of mid-20th-century American women.

During your visit, be sure to tour our lobby and the walls of the historic Old Captiva House restaurant, where many Ding Darling cartoons depicting a Captiva vacation from the 1930s and 1940s, as well as early photos of the resort, highlight our décor.




The early days of the Old Captiva House restaurant, originally a schoolhouse cottage in 1914.

The bayside marina has been welcoming boaters for more than half a century.