Boating from Fort Myers to Key West: A Travel Guide

If you're dreaming of turquoise waters, laid-back islands, and scenic maritime escapes, boating from Fort Myers to Key West is one of Florida’s most rewarding adventures. This stretch through Southwest Florida offers a perfect blend of island hopping, nature, and vibrant destinations, all accessible by boat.

Why Boating from Fort Myers is the Ultimate Coastal Trip

Boating from Fort Myers isn’t just about reaching Key West—it’s about exploring Florida’s most beautiful coastal gems along the way. The journey spans around 150 nautical miles, filled with hidden coves, charming marinas, and state park stops that are perfect for adventure lovers.

Launching from Fort Myers, you’ll navigate the calm gulf waters, pass through diverse islands, and experience a world of marine life. Whether you’re into relaxing, fishing, or just cruising from park to park, this route has it all.

Ideal Vessels for Boating from Fort Myers

The boat you choose can make or break your trip. When boating from Fort Myers, many opt for cabin cruisers or powerboats. These are fast, comfortable, and can handle long distances with ease. Sailboats are another excellent choice, offering a serene and scenic journey.

Ensure your boat is equipped with essential gear: a VHF radio, navigation systems, fresh water, and updated maps. If you don’t own a boat, several marinas in Fort Myers offer well-equipped rentals. For less experienced travelers, captained charters are also available.

Top Island Stops When Boating from Fort Myers to Key West

Cabbage Key – A Taste of Old Florida

A must-stop when boating from Fort Myers is Cabbage Key. This small, secluded island, accessible only by water, offers classic Florida charm, known for its famous burger and dollar-bill-covered restaurant. It's the perfect stop when spending the day exploring.

Boca Grande – History and Tarpon Fishing

Another highlight on your journey is Boca Grande, a top destination for tarpon fishing. This island features elegant architecture and stunning beaches. Make time for a visit to Gasparilla Island State Park, where you can enjoy kayaking, nature walks, and historical sites.

Pine Island – Culture and Calm

Pine Island offers a more artistic and laid back experience. With quirky art shops, colorful homes, and delicious local seafood, it’s ideal for travelers looking for something different. This is one of the best islands for finding laid back settlements with genuine character.

Explore State Parks While Boating from Fort Myers

One of the best parts of boating from Fort Myers is access to Florida’s beautiful state parks. These preserved natural areas offer pristine beaches, wildlife sightings, and unspoiled nature.

Cayo Costa State Park – A Remote Paradise

Accessible only by boat, Cayo Costa State Park offers nine miles of untouched beach, great for shelling, snorkeling, or hiking. If you're looking for solitude, this is a perfect place to drop anchor and explore. It’s part of what makes boating from Fort Myers so special.

Lovers Key State Park – Romance and Wildlife

Located just south of Fort Myers Beach, Lovers Key State Park is a haven for couples and wildlife lovers. With manatees in the estuaries and miles of walking trails, this state park is a great place for a short, relaxing break during your journey.

Gasparilla Island State Park – Historic and Serene

Located on Boca Grande, this state park offers history with its 1890s lighthouse, scenic beaches, and excellent spots for paddleboarding and swimming. It’s also a perfect photo-op destination.

Planning Your Route While Boating from Fort Myers

Set out from Fort Myers early to maximize daylight. Most boaters take a multi-day route with overnight stops at island inns, marinas, or anchoring spots. Here’s a popular itinerary:

• Day 1: Fort Myers to Cabbage Key
• Day 2: Explore Pine Island and Boca Grande
• Day 3: Head toward Cayo Costa and rest at anchor
• Day 4-5: Cruise through the Lower Keys, landing in Key West

This flexible route offers many ways to enjoy island hopping, with numerous hidden coves and parks waiting to be discovered.

Wildlife & Marine Life on the Route

One of the biggest perks of boating from Fort Myers is the chance to see marine life up close. Dolphins often swim alongside your boat, and manatees can be spotted near mangroves. Birdwatchers will love the pelicans, egrets, and osprey that frequent the islands and state parks.

For snorkelers, the clear gulf waters closer to the Keys reveal coral reefs, sea turtles, and colorful tropical fish. These areas are especially beautiful around Key West and Dry Tortugas.

Dining Along Your Boating Route

There’s no shortage of food stops along the way. Most are only accessible by boat, which makes them feel like hidden treasures.

• Cabbage Key Inn – Iconic and quirky, a must-visit for lunch.
• The Pink Elephant (Boca Grande) – Excellent seafood and an elegant setting.
• Blue Dog Bar & Grill (Matlacha, Pine Island) – Great for local eats and dockside dining.

Eating at these locations lets you sample fresh Florida cuisine in one-of-a-kind surroundings.

Arrival in Key West: What to Expect

Finally, after days of boating from Fort Myers, arriving in Key West is a celebration in itself. Dock at Garrison Bight or one of the other full-service marinas, then explore the town’s lively streets. Duval Street, Mallory Square, and Fort Zachary Taylor State Park are only the beginning.

Take time to enjoy historic landmarks, beautiful locations, and the unmatched energy of Florida’s southernmost city.

Final Tips for Boating from Fort Myers to Key West

• Weather is key. Check marine forecasts daily.
• Stay stocked. Fuel and food aren’t always nearby.
• Respect nature. Many islands are part of protected zones.
• Log your trip. Keeping a captain’s journal makes a great keepsake.

Conclusion: A Journey Like No Other

Boating from Fort Myers to Key West is an experience rich with discovery, from Cabbage Key's charm to the artistic corners of Pine Island, and the historic beauty of Boca Grande. Along the way, you'll encounter diverse islands, peaceful parks, and welcoming ports.

It's not just a trip—it's a moving journey through Florida’s most beautiful locations. Whether you’re navigating a private boat or traveling with a group, this route offers adventure, tranquility, and unforgettable memories.