Tween Waters Inn: Captiva’s Historic Waterfront Resort with Classic Island Dining

Nestled between the Gulf of Mexico and Pine Island Sound, Tween Waters Inn on Captiva Island has earned its reputation as one of Southwest Florida’s most iconic island resorts. With more than a century of history, waterfront views on both sides, and a relaxed coastal atmosphere, Tween Waters continues to attract visitors who want an authentic Captiva experience rooted in tradition and natural beauty.

A Legacy That Shaped Captiva Tourism

Tween Waters Inn traces its origins back to the early 1900s, when Captiva was still accessible primarily by boat. What began as a small fishing lodge evolved into a full-service island resort, welcoming generations of families, anglers, honeymooners, and seasonal visitors.

Over the decades, the property expanded thoughtfully while maintaining its old-Florida charm. Today, Tween Waters blends historic character with modern comfort, creating a setting where island history feels alive — from breezy walkways and tropical landscaping to waterfront docks and sunset viewing spots.

A Rare Island Location: Water on Both Sides

Few resorts can match Tween Waters’ unique geography. Located on Captiva’s narrow stretch of land, the property offers access to both:

  • The Gulf of Mexico, known for sugar-sand beaches and legendary sunsets

  • Pine Island Sound, ideal for boating, paddleboarding, kayaking, and wildlife viewing

This dual-waterfront location gives guests flexibility to enjoy beach activities on one side and calmer bay waters on the other — all without leaving the resort grounds.

Dining at Tween Waters Inn

Tween Waters Inn offers three distinct on-site dining venues, each delivering its own atmosphere and island flavor:

Crow’s Nest Restaurant

The Crow’s Nest is the resort’s signature dining room, offering a polished island atmosphere and elevated coastal cuisine. Known for fresh seafood, classic Florida flavors, and sunset-adjacent ambiance, it’s a favorite for romantic dinners, celebrations, and special occasions.

Shipyard Restaurant

Shipyard delivers a relaxed, casual dining experience ideal for breakfast, lunch, and laid-back dinners. Guests appreciate its approachable menu, welcoming vibe, and convenient location near resort amenities. It’s a popular gathering spot for families and groups starting or ending a day on the water.

Island House Restaurant

Island House provides another dining option focused on comfort, convenience, and coastal charm. With an easygoing atmosphere and classic island dishes, it offers guests flexibility and variety during their stay.

Together, these restaurants allow visitors to enjoy everything from casual island fare to refined coastal dining — all without leaving the resort.

More Than a Place to Stay

Beyond accommodations and dining, Tween Waters offers a full island experience:

  • Beach access directly on the Gulf

  • Marina and dock facilities for boaters

  • Resort-style pool areas

  • Fitness, spa, and wellness services

  • Organized island activities and excursions

Whether guests want adventure or relaxation, Tween Waters provides the flexibility to design their perfect Captiva getaway.

Why Tween Waters Remains a Captiva Favorite

What truly sets Tween Waters Inn apart is its ability to preserve tradition while evolving with modern travelers. It’s a place where barefoot walks on the beach meet elegant dinners, where sunrise paddleboarding pairs with sunset cocktails, and where island history blends seamlessly into today’s resort experience.

For visitors seeking an authentic, waterfront Captiva retreat with built-in dining, recreation, and island ambiance, Tween Waters Inn remains one of the island’s most enduring destinations.

FUN FACT: 'Tween Waters dates back to 1931 when is was a small collection of fishing cottages. 19 historic cottages still remain at 'Tween Waters and are named after past guests including: Anne Morrow Lindbergh, J.N. “Ding” Darling and Theodore Roosevelt.