5th Avenue South
Olde Naples’ main restaurant & shopping strip, a few easy blocks from the dock — perfect for lunch before or dinner after your trip.
Departing Southwest Florida
Boat Tours from Olde Naples & Downtown
Olde Naples — the historic grid of 5th Avenue South, 3rd Street South and the Naples Pier — sits right on the water, and that’s no accident. Walk a few blocks from the shops and restaurants and you’re stepping onto a boat bound for Naples Bay, the Port Royal mansions, Gordon Pass and a Gulf sunset. It’s the most walkable way to get from brunch to the bow of a boat in Southwest Florida.
Walk to the dockA few blocks from 5th Ave S to Naples Bay Resort & Marina
Departs fromNaples Bay Resort & Marina, 1500 5th Ave S
You’ll passPort Royal mansions & Gordon Pass
Best forSunset cruises & Naples Bay sightseeing
Why Olde Naples
The most walkable launch to the water in Naples
Olde Naples is the historic heart of the city — the leafy grid of 5th Avenue South and 3rd Street South, the boutiques and restaurants, and the iconic Naples Pier reaching into the Gulf. It grew up on the water for a reason: Naples Bay borders the district on the east, and the beach is a short walk west. That means you can browse the shops, grab lunch on 5th Ave, and be standing on a boat dock within a few blocks — no bridge, no long drive, no second parking lot.
Our Naples departure, Naples Bay Resort & Marina at 1500 5th Avenue South, sits right at the edge of Olde Naples — an easy walk from the district’s restaurants and shops. From the dock your captain eases down Naples Bay, past the yachts of Crayton Cove and the mansions of Port Royal’s Millionaire’s Row, then out through Gordon Pass where the bay meets the Gulf. Wild bottlenose dolphins work that current often, whether you’re headed to a sunset cruise or a longer trip toward Keewaydin Island.
Because it’s so close, an Olde Naples boat trip folds easily into a bigger day downtown — a bay cruise before dinner on 5th Ave, or a sunset run timed to end with the sky still glowing as you walk back to your table. Want more time on the water? The same dock is the launch point for our shelling, dolphin and private-charter trips out to the wilder barrier islands south of town.
- An easy walk from 5th Avenue South & 3rd Street South
- Depart Naples Bay Resort & Marina, steps from downtown
- Cruise past Port Royal mansions & Gordon Pass dolphins
- Pair a bay or sunset cruise with dinner downtown
Pick Your Adventure
Boat tours you can walk to from Olde Naples
All of these depart Naples Bay Resort & Marina, an easy walk from 5th Avenue South. Tap a tour for full details and live booking.
Naples & Port Royal ToursCruise the mansions of Millionaire’s Row & Gordon Pass.
Sunset CruisesGolden-hour Gulf cruising as the sky lights up over the water.
Dolphin & WildlifeWild bottlenose dolphins, manatees, ospreys & roseate spoonbills.
Naples Water ShuttleHop between Naples’ waterfront restaurants & docks by boat.
Private ChartersThe whole boat is yours — a captain and a route built around you.
Your Downtown Playground
What’s within reach of the Olde Naples dock
A single trip can touch the shopping district, a millionaire’s back yard and a dolphin-filled inlet — all a short walk or cruise from downtown.
3rd Street South
The district’s other boutique-and-dining row, equally walkable from Naples Bay Resort & Marina.
Naples Pier
The iconic fishing pier at the Gulf end of downtown — a Naples landmark you’ll spot from Gulf-side cruises.
Naples Bay
Calm, protected water lined with yachts and waterfront homes — the gentle start to every trip from Olde Naples.
Port Royal & Millionaire’s Row
Naples’ most exclusive address, just south of downtown — jaw-dropping mansions and mega-yachts from the water.
Gordon Pass
Where Naples Bay spills into the Gulf — current and bait stack up here, so it’s prime dolphin territory.
🚶 Everything above is within an easy walk or a short cruise of the Olde Naples dock — no second parking lot required.
Find Your Trip
Perfect for every kind of downtown visitor
Staying, dining or shopping in Olde Naples? Here’s the trip that fits.
Downtown visitors
Staying in an Olde Naples hotel or rental? Walk to the dock and skip a second drive to the water.
Couples
Dinner on 5th Ave and a private sunset cruise make an easy, unforgettable Naples date night.
Families
A calm Naples Bay sightseeing trip pairs naturally with an afternoon at the Naples Pier or the shops.
Sightseers
Port Royal mansions and Gordon Pass dolphins in one relaxed loop, minutes from your table.
On the Water Downtown
A few moments from our Olde Naples trips
Real guests, real downtown water. Tap any photo to look closer.
Keep Exploring
More ways to reach the water
Staying elsewhere around Naples? Here’s the closest route to a Sand Dollar dock.
Boat Tours in North Naples, FloridaDeparting near Vanderbilt Beach & the north side of town.
Boat Tours from East Naples, FloridaThe closer-to-Marco side of town, a short drive from downtown.
Boat Tours from Golden Gate EstatesInland Naples’ fastest route to our downtown or Goodland dock.
Boat Tours from Ave Maria, FloridaDriving in from Ave Maria? Here’s the route to the water.
Good to Know
Olde Naples boat tour questions
Planning a trip from downtown? Here’s what guests ask most.
Where do boat tours leave from near Olde Naples?
Our Naples trips depart Naples Bay Resort & Marina at 1500 5th Avenue South, right at the edge of the Olde Naples district. Your exact dock, directions and parking details come with your booking confirmation; plan to arrive about 15 minutes early.
Can I walk to the dock from 5th Avenue South?
Yes — Naples Bay Resort & Marina sits at the end of 5th Avenue South, an easy walk of a few blocks from the district’s restaurants and shops. It’s the most walkable boat departure in Naples.
Do your boat tours pass the Naples Pier?
Most Olde Naples trips explore Naples Bay, the Port Royal mansions and Gordon Pass rather than running right up to the Gulf-side pier itself. Some Gulf-facing sunset and sightseeing routes can bring the Naples Pier and coastline into view depending on conditions — ask your captain about routing if seeing the pier is a priority.
What will we see on a trip from Olde Naples?
Most trips cruise Naples Bay and the Port Royal waterfront estates, then out through Gordon Pass, where wild dolphins are common. Depending on your tour you’ll also catch a Gulf sunset or run further to a shelling beach like Keewaydin Island.
Is there parking if I don’t want to walk?
Yes, there is parking at and around Naples Bay Resort & Marina, and the downtown location makes rideshare easy too. We’ll send specific parking guidance with your booking confirmation.
Can we book a private charter from the Olde Naples dock?
Absolutely. Any of our Naples departures can be booked as a private charter — just your group, your captain and a custom route through the bay, Port Royal and Gordon Pass, or further out to the barrier islands.
Reserve Your Seats
Book your Olde Naples boat tour
Live availability and instant confirmation — pick your date and trip and check out securely through FareHarbor, or call and a local captain will help you plan the walk from 5th Ave to the water.
Just steps from 5th Ave
Trade the sidewalk for the bow of a boat
Naples Bay, Port Royal mansions, Gordon Pass dolphins and a Gulf sunset — all an easy walk from Olde Naples. Book your boat tour today.