One of the best parts of boating in Naples? Your weekend options look a whole lot different from the water.

Spend the afternoon tied up off a barrier island. Cruise Naples Bay and dock for lunch. Or pack an overnight bag, fill the tank and turn your boat day into a full Florida getaway.

If you’re looking for the best boating destinations from Naples, Florida, start with these nine. We’ve broken them down into three local tie-up spots, three dock-and-dine favorites and three destinations worth making a trip out of.

Before heading out, make sure your boat is ready for wherever you’re going. The Boat House Naples offers boat sales, service, storage and support right here in Southwest Florida.

TIE UP & STAY AWHILE

1. Keewaydin Island

BEST FOR: The quintessential Naples boat day

There are Naples boating destinations, and then there’s Keewaydin.

Located between Naples and Marco Island, Keewaydin Island is an undeveloped barrier island accessible only by boat. Miles of shoreline and a lack of roads, cars and high-rises make it one of the easiest places to escape without actually going very far.

Cruise down from Naples, find an appropriate spot to anchor or beach, and spend the afternoon swimming, shelling and hanging out on the sand.

There are limited amenities on the island, which is part of the appeal. Bring what you need for the day and take everything back out with you.

If Keewaydin Saturdays are exactly why you’re shopping for a boat, browse new boats for sale in Naples before planning your next one.

2. Ten Thousand Islands

BEST FOR: Exploring the wild side of Southwest Florida

Head south from Naples and the waterfront gradually gives way to something completely different.

The Ten Thousand Islands National Wildlife Refuge protects a sprawling coastal landscape of mangrove islands, bays and winding waterways between Marco Island and the Everglades.

For boaters, it’s an incredible place to explore, fish, watch wildlife or find a quieter place to spend the day away from the busier beaches and sandbars.

This is also an area where navigation matters. Shallow water, tides and unfamiliar routes deserve respect. Know your boat’s draft, plan your route and pay attention to current conditions and protected areas.

Before exploring farther from home, keeping up with routine Naples boat service can help make sure your boat is ready when the weekend is.

3. Cape Romano

BEST FOR: A more adventurous day south

Keep going beyond Marco Island and you’ll reach the Cape Romano area at the edge of the Ten Thousand Islands.

This is less of a traditional sandbar scene and more of a pack the cooler, bring plenty of water and go explore kind of day.

The surrounding waters offer a remote side of Southwest Florida that feels dramatically different from cruising Naples Bay. Find an appropriate place to stop, enjoy the scenery and make the ride itself part of the adventure.

Conditions, tides and access can change, so check current marine information before leaving Naples and give yourself plenty of daylight for the return.

DOCK. DINE. REPEAT.

Sometimes the best destination is the one serving lunch.

4. The Dock at Crayton Cove

BEST FOR: A classic Naples waterfront lunch

You don’t have to leave Naples to make arriving by boat feel like an occasion.

The Dock at Crayton Cove has been part of the Naples waterfront since 1976 and sits beside Naples City Dock on Naples Bay.

Cruise into historic Crayton Cove, tie up nearby and trade the helm for fresh seafood, cocktails and waterfront views.

The adjacent Naples City Dock offers transient slips along with fuel and other boater services, making this area an easy addition to a full day on Naples Bay.

BOATER TIP: Dockage can change with availability, so check current transient-slip information before planning your arrival.

5. The Boathouse on Naples Bay

BEST FOR: An easy boat-to-table afternoon

This one makes dock-and-dine about as simple as it gets.

The Boathouse on Naples Bay sits directly on Naples Bay at Channel Marker 4, with dockage right outside the restaurant.

Pull up for lunch, seafood and drinks, then walk right back out to the boat when you’re ready to keep going.

It’s an easy stop to work into a casual Naples boat day when you don’t necessarily want lunch to become the entire itinerary.

And if you’d rather have your boat ready to go when you are, The Boat House Naples in & out service makes getting from land to water a whole lot easier.

6. Island Gypsy Cafe & Marina Bar

BEST FOR: A laid-back lunch farther south

Make the cruise part of lunch and head toward the Isles of Capri.

Island Gypsy Cafe & Marina Bar sits right on the marina with the kind of relaxed Old Florida atmosphere that just makes more sense when you arrive by boat.

It’s especially easy to work into a day that already includes Keewaydin, Marco Island or exploring farther south.

Grab seafood and a waterfront table, take a break from the sun and then get right back to boating.

Dock availability isn’t guaranteed, so contact the restaurant or Isles of Capri Marina ahead of time for current dockage information.

WORTH THE TRIP

Now we’re packing a bag.

These are the boating destinations from Naples that turn a day on the water into an actual getaway.

7. Captiva Island + ‘Tween Waters Island Resort & Spa

BEST FOR: Dock the boat, stay the night

If you’re making the run north from Naples, don’t automatically turn around at sunset. Make Captiva the getaway.

‘Tween Waters Island Resort & Spa sits between the Gulf of Mexico and Pine Island Sound, with ‘Tween Waters Marina giving boaters the opportunity to arrive by water, dock and stay right on Captiva.

And there’s something especially meaningful about making this trip today.

Hurricane Ian left a lasting mark on Captiva and communities throughout Southwest Florida. In the years since, local businesses, residents and visitors have played a huge role in bringing these islands back. Resorts reopened, docks welcomed boats again and the places that have made this coastline special for generations began their next chapter.

A trip to Captiva isn’t just a great boating getaway. It’s another opportunity to support the restaurants, resorts, marinas and people behind Southwest Florida’s incredible comeback.

Dock at ‘Tween Waters, hit the beach, grab dinner, stay the night and wake up on Captiva. Then make the cruise back to Naples part of day two.

For trips that put more miles between you and your home dock, make sure maintenance isn’t an afterthought. Schedule boat service in Naples before your next longer run.

8. Boca Grande

BEST FOR: A full-day Southwest Florida adventure

Want to keep going north? Set your sights on Boca Grande.

Located on Gasparilla Island, Boca Grande is one of Southwest Florida’s most recognizable boating and fishing destinations, especially around Boca Grande Pass.

From Naples, this is no quick lunch run. It’s the kind of trip where the ride is half the reason you’re going.

Plan your route, check your fuel range and identify where you’ll stop before leaving the dock. Give yourself enough time to explore without racing daylight home, and always let Gulf conditions determine whether it’s the right day to make the run.

If longer coastal adventures are high on your boating wish list, browse all boats for sale in Naples to compare models built for the way you want to use the water.

9. Key West

BEST FOR: The ultimate Naples boating getaway

Okay. Now we’re really going somewhere.

For experienced captains with a properly equipped boat, a Naples-to-Key West trip turns your boat into transportation for an actual Florida vacation.

And if you’re going to make the crossing, don’t just arrive and wonder where you’re putting the boat.

The Perry Hotel & Marina Key West on Stock Island combines waterfront hotel accommodations with The Perry Marina, a 288-slip deep-water marina that welcomes transient boaters.

That means the itinerary can be ridiculously simple:

Leave Naples. Cross to the Keys. Dock the boat. Check into the hotel. Go to dinner. Wake up in Key West.

The marina offers fuel and other boater amenities, while the resort gives you access to pools, waterfront dining and a complimentary shuttle into Old Town Key West.

Stay one night or turn it into a long weekend before heading back across the Gulf.

This is a serious open-water trip, though. Weather, sea conditions, fuel capacity, vessel range, safety equipment and captain experience all matter. Plan your route carefully and never attempt an offshore passage that exceeds your experience or your boat’s capabilities.

NINE DESTINATIONS. ONE VERY GOOD REASON TO OWN A BOAT IN NAPLES.

That’s the beauty of boating in Southwest Florida.

Saturday can mean Keewaydin. Lunch can be a cruise across Naples Bay. And your next vacation can start at the helm instead of on the highway.

The right boat doesn’t just get you on the water. It changes where you can go.

Ready to find yours? Browse new boats for sale in Naples or explore all Naples boat inventory at The Boat House.

Already have the boat? Keep it ready for the next destination with boat storage in Naples, Naples in & out service and marine service in Naples.

WHERE ARE YOU HEADING NEXT?