The teal-canopied Sand Dollar Avalon pontoon on calm water at sunset near Naples, Florida, with palms and a low shoreline behind

Near Your Stay

Boat Tours Near Lovers Key Resort, Fort Myers Beach

You’re at the far south end of Estero Island, and our Naples slip is the better part of an hour down the coast. That’s a real drive — so let’s build you a day that comes back worth every mile of it.

Naples Bay Resort & Marina
45–60 min south of Estero Island
1.5–2 hour cruises
USCG Master Captains

Check Availability & Book (239) 301-8913

Nearest dockNaples Bay Resort & Marina

From Lovers Key Resort45–60 min drive south

WaterNaples Bay, Gordon Pass & the Gulf

You may seedolphins, shell beaches, sunsets — no guarantees

Own the Drive

Plan it like an expedition, not an errand

Lovers Key Resort sits at 8771 Estero Boulevard, at the south end of Estero Island where the road runs down toward Lovers Key State Park. From that address to our slip at Naples Bay Resort & Marina is about a 45 to 60 minute drive, and that range moves with the season and with traffic on Estero Boulevard and US 41. There it is, up front, before you read another word. The short way out is south — over the pass, past the state park, down to Bonita Beach Road, then east and south into Naples. The road on the day always knows more than a web page does, so run the route through your own map app before you leave.

What the drive buys is the water on the far side of Gordon Pass. Our Naples boats leave a protected bay, slide past Crayton Cove and the mangrove edges of Dollar Bay, and come out into the Gulf between the seawalls of Port Royal and the north end of Keewaydin Island — miles of barrier-island beach with no bridge, no road and no parking lot, so every footprint on it arrived by boat. Keep going south and the coast stays quiet through Rookery Bay Reserve and on into the Ten Thousand Islands. That is a genuinely different coastline from the one at the end of Estero Boulevard, and it is the whole argument for the mileage.

So give the day a shape instead of leaving it to chance. Pull out of Lovers Key Resort in the morning with the bag already packed, take an earlier departure rather than the last one on the schedule, and you tie up back at the marina with your whole afternoon intact — lunch on the water in Naples, a wander through Tin City or Crayton Cove, then the drive home in daylight. Guests who have come this far tend to book the private charter, and we think they are right: one boat, your own route, your own clock, nobody else’s schedule to make. Drive it once, do it properly, and the odometer stops mattering by the time you clear the pass.

About 45–60 minutes to our Naples dock — say it plainly, then plan it
Take an earlier slot and keep your afternoon
Private charters make the most sense once you’ve driven
Keewaydin, Gordon Pass and Rookery Bay — coast with no road on it

Check Availability

The Sand Dollar Island Hopper landing boat beached bow-first on an empty shell beach with the open Gulf behind it — ⚓ Boat-only sand — the reason the drive pays

Worth the Miles

The trips that repay a drive from Lovers Key Resort

Every one of these leaves our slip at Naples Bay Resort & Marina, 1500 5th Avenue South — one address, one arrival, one properly good day.

Private ChartersThe whole boat, your own route and your own clock — the honest best value once you’ve driven an hour. Beach & Island TripsStep off onto barrier-island sand out past Gordon Pass, the kind no road reaches. Sunset CruisesGolden hour off the Gulf, then dinner in Naples before you point the car north. Dolphin ToursWild bottlenose in the bay and the pass — often right alongside, never promised. Shelling ToursFrom $125 adult, $90 child. The full wild-island version runs from our Goodland dock, further south still.

The Route

Lovers Key Resort to our Naples slip, step by step

Six honest stages, from the night-before packing to the ride home.

Start: the south end of Estero Island

Lovers Key Resort is at 8771 Estero Boulevard, about as far south as you can get on Estero Island before the road hands you over to Lovers Key State Park. That position is the reason this page exists. You are at one end of a barrier island, our slip is on a bay an hour down the coast, and there is no ferry and no shortcut between the two — only the road. Once you accept that, the planning gets easy. This is not an outing you decide on at eleven in the morning; it is a day you put on the calendar the night before, the way you would a state park hike or a ballgame two towns over. Treat it that way and it works beautifully. Treat it as a whim and the traffic will make the decision for you.

The drive south: the short way out

From the south end of the island the natural line is south, not north: over the pass, along the edge of Lovers Key, down Hickory Boulevard into Bonita Springs, then east to US 41 — the Tamiami Trail — and south through North Naples into downtown. Figure 45 to 60 minutes door to slip. In February and March, with beach traffic loading onto Estero Boulevard and season traffic on the Trail, take the higher end of that and add a little. In September you will probably beat it. I-75 is the alternative when the coast road is crawling: a longer distance, often a shorter clock. We are not going to pretend to know which one is faster on your particular Tuesday, so let your navigation app pick it live. Whichever way you come, the last few minutes are the same — 5th Avenue South, all the way east, until the street runs out of shops and starts showing you water.

Book the earlier slot, and leave before you think you need to

Here is the single most useful thing on this page: when you have an hour of road each way, book earlier in the day rather than later. An earlier departure gives the drive a buffer, keeps a bridge opening or a fender-bender on the Trail from turning into a missed boat, and leaves the back half of your day free instead of spent. It also means you are out while the bay is at its calmest, which most mornings it is. Aim to be pulling into the marina 20 to 30 minutes before your scheduled departure — that is not us being fussy, that is the cushion that lets you park, find the slip, use the restroom and step aboard without your heart rate up. If something goes sideways on the road, call (239) 301-8913 and talk to us rather than guessing.

The dock: Naples Bay Resort & Marina

We meet you at Naples Bay Resort & Marina, 1500 5th Avenue South, at the water end of downtown Naples. It is a working marina on protected Naples Bay, which is exactly why our Naples fleet lives here: you board in flat water with the bay, Gordon Pass and the Port Royal canals all within a few minutes of the slip, instead of launching into whatever the Gulf is doing that morning. Once you have booked, we send you the exact slip and a note on where to meet, so the final ten minutes of a long morning are not spent wandering docks reading transom names. Restrooms are right there before you board. And to be clear about something guests sometimes assume: we do not offer hotel pickup anywhere, and no Sand Dollar boat leaves from Estero Island. Your car is the connection between the island and the water.

Parking, and what goes in the bag

You drove, so you will park. There are spaces around the marina and spilling back through the Bayfront blocks, and in season you should leave a few extra minutes to find one. For the boat: soft-soled shoes or bare feet, sunglasses, a hat that will survive twenty knots of apparent wind, reef-safe sunscreen, and a light layer for the ride back, because the bay cools off faster than a parking lot does. Bring more water than you think and a real snack — you started this day an hour up the coast and lunch may land later than you planned. We provide water and shaded seating; whatever else you want to sip or eat aboard, you bring. If you are shelling, a mesh bag beats a plastic one. And leave anything in the car that you would hate to watch go over the side.

The cruise, then the road home

From the moment you step aboard, the driving is somebody else’s problem for an hour and a half to two hours. Your captain runs the route the trip calls for — down the bay toward Gordon Pass, out along Keewaydin’s beach, up into the Port Royal canals, or wherever the tide and the day point — and tells you what you are looking at as you go. Then you are back at the same slip. If you booked the morning, Naples is still in front of you: a table on the water, Tin City, the pier, a beach. If you booked the sunset, eat downtown afterward and let the Trail thin out before you head north. Either way you get back to Lovers Key Resort having actually done something, which is the only real test of a day trip.

Who It Suits

A great fit if you’re…

This page is written for people who don’t mind a drive when there’s something real at the end of it.

Ready to make it a day trip

You would rather drive an hour for water that has no road to it than settle for whatever floats nearest the parking lot. That trade makes sense to you.

Booking one boat for everybody

A private charter turns a long drive into a single clean arrival: one plan, one departure, your whole group on one deck and nobody left coordinating cars.

Chasing boat-only sand

Keewaydin and the islands off Gordon Pass have no road running to them — that is precisely what you drove for. You cannot walk to this beach.

A planner by nature

Bag packed the night before, departure slot already booked, a cushion built into the drive. This is a trip that rewards the person who thinks ahead.

On the Water

What you drove down for

Boat-only sand, wild dolphins in the wake, and a deck with nobody on it but your people.

A wild, unraked barrier-island beach with shells scattered along the tideline near Naples, Florida — Sand you can only reach by boat

A bottlenose dolphin leaping clear of the whitewater in a boat wake with a second dolphin surfacing behind it — Wild dolphins, on their own schedule

A Sand Dollar private charter cruising protected Naples Bay near downtown Naples, Florida — Your own boat, your own clock

Keep Planning

More ways to fit our water into a Fort Myers Beach week

The Fort Myers and Estero pages, the private-charter details, and every stay we run from.

Boat Tours from Fort MyersThe whole Fort Myers side of the map, and how it connects to our water. Boat Tours from EsteroThe Estero side of the map, and how the run south works from there. Private Charters in NaplesThe whole boat, your own route — what most drive-down guests end up booking. All Stays We ServeEvery hotel, resort and neighborhood we run boat tours near.

Good to Know

Boat tours near Lovers Key Resort

The questions Fort Myers Beach guests actually ask before they commit to the drive.

How far is Lovers Key Resort from your Naples dock?

About a 45 to 60 minute drive, and we would rather say that plainly than dress it up. From 8771 Estero Boulevard the quickest line is usually south over the pass, down through Bonita Beach and east to US 41, then south into downtown Naples and east on 5th Avenue South to Naples Bay Resort & Marina at 1500. Season and Estero Boulevard traffic are the two variables that move that number, and I-75 sometimes beats the coast road. Check your own map app the morning you go rather than trusting any single figure.

Do you pick up at the resort or run a shuttle from Fort Myers Beach?

No on both counts. We are a boat company, not a transport service, and every trip on this page leaves from our slip at Naples Bay Resort & Marina. We should also say plainly that we have no affiliation, partnership or arrangement with Lovers Key Resort; we are a locally owned, captain-led outfit that happens to serve a lot of guests who drive down from Fort Myers Beach. Getting yourself to 1500 5th Avenue South is the one piece of the day that falls to you.

Which departure should we book if we’re driving down?

Take an earlier slot. With a real drive on both ends, a mid-morning or early-afternoon departure protects you against a slow Estero Boulevard and still leaves the rest of the day usable. Sunset cruises are wonderful and plenty of Lovers Key guests book them — just plan on dinner in Naples afterward and a later drive north rather than racing back. Whichever you choose, aim to reach the marina 20 to 30 minutes early. If you want help matching a departure to your drive, call (239) 301-8913 and we will talk it through with you.

Is it really worth driving an hour when there are boats closer to us?

Honestly, that depends on what you want. If you mainly want an hour on the water with a cold drink, no — take something local and enjoy it. What you cannot get up there is the coast south of Gordon Pass: Keewaydin Island, the mouths of Rookery Bay and the beginning of the Ten Thousand Islands, where the shoreline stops having roads on it. That is a different ecosystem and it looks and feels different from the deck. People drive down for that, for our captains’ knowledge of it, and for a boat they do not have to share. If none of that matters to you, save the miles.

Can we go shelling, and what are the rules?

Yes, and here is the honest layout. From the Naples dock our beach and island trips and private charters put you on barrier-island sand off Gordon Pass, which is real shelling and asks nothing more of you than the drive you were already making. The full wild-island shelling day — deep into the Ten Thousand Islands — runs from our other dock at San Marco Marina in Goodland, which is further south still, so give it its own date. Shelling starts at $125 per adult and $90 per child. Collier and Lee counties are empty shells only: no live shells, sand dollars or starfish. Florida’s state shell is the horse conch.

Will we see dolphins, and does this work with kids?

Wild bottlenose are in this water all twelve months, and they regularly come up beside the hull or drop into the wake behind it — a good chance on most trips, never a promise, because they are animals keeping their own calendar. Be wary of anyone who guarantees it. Birdlife is close to a given. Manatees move into the quieter backwaters once the water falls below about 68 degrees, roughly November through March, so there is a chance of one then. Kids do well aboard: cruises run about an hour and a half to two hours, seating is shaded, and our family-first tiki boat carries 39.5-inch child rails.

Reserve Your Seats

Ready to point the car south?

Check availability and book a boat tour from our Naples slip — then build the morning around it.

Or call (239) 301-8913

One Drive, One Very Good Day

Book your boat before you leave Fort Myers Beach

Private charters, beach and island runs, dolphin trips and sunset cruises — all from Naples Bay Resort & Marina, about an hour south of Estero Boulevard. Tell us your dates and we’ll help you pick the slot that makes the drive worth it, or call (239) 301-8913 and we’ll sort it out on the phone.

Book a Boat Tour (239) 301-8913

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