Guests aboard a private Sand Dollar charter boat under the shade of the bimini on calm water near Naples, Florida

Near Your Stay

Boat Tours Near Hotel Escalante, Naples

Hotel Escalante is the small garden hotel at the quiet west end of 5th Avenue South — and our dock sits at the other end of the same street. Five to ten minutes east, and the boat can be yours alone for the afternoon.

Naples Bay Resort & Marina
1.5–2 hour cruises
Private by default — your group only
USCG Master Captains

Check Availability & Book (239) 301-8913

Nearest dockNaples Bay Resort & Marina

From the propertyabout a 5–10 min drive

Waterprotected Naples Bay & Gordon Pass

You may seedolphins, estates, sunsets — no guarantees

Quiet Water, Small Party

Why we point Escalante guests at a private boat

Hotel Escalante sits at 290 5th Avenue South, a small garden hotel down at the quiet western end of the avenue, close to Third Street South and a short walk from the sand. Our dock is at the other end of the same street: Naples Bay Resort & Marina, 1500 5th Avenue South, tucked on protected Naples Bay. Call it a five-to-ten-minute drive or rideshare, and check your own map app before you go, because season and time of day move that number. We point guests here toward a private charter first rather than a scheduled cruise, because the thing you booked a small hotel for is the thing a private boat hands back to you.

On a private charter the route is a conversation instead of a script. Most guests here start with Port Royal, the hushed neighborhood where the canals meet the Gulf near Gordon Pass — long private docks, coral-stone seawalls, low wide houses built to face the sunset. We idle it slowly and talk about the water, the tides and the ospreys working the seawalls rather than who lives behind which door. From there it’s a short run out the pass toward Keewaydin Island, the wild boat-only barrier island just south of Naples, or back into the flat water of the bay if that suits the mood better. Nobody else is aboard, so nothing’s on a clock but yours.

Push the booking to the back half of the afternoon and the same boat becomes a sunset run: the light goes gold over the Gulf, the bay turns glassy behind you, and there’s no shared rail and no PA system talking over it. Bottlenose dolphins live in these waters year-round and often roll up alongside or surf the wake, so it’s a real chance most evenings — but they’re wild animals on their own schedule, and we never promise them. Bring a light layer, because the ride home cools off quickly once the sun is down. And if it’s wild-island shelling you’re after, we’ll tell you straight: that trip leaves from our Goodland dock down by Marco Island, a longer drive than this one.

Private charter first — the boat is yours alone
Port Royal canals and Gordon Pass at an idle
Quiet sunset runs, no shared rail
About 5–10 minutes east on 5th Avenue South

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A Sand Dollar charter boat with a few guests aboard cruising calm water past waterfront homes near Naples, Florida, at dusk — ⚓ A small party out of Naples Bay, late in the day

Tours That Fit the Stay

The trips that suit an Escalante stay

Private first, scheduled cruise second. Pricing is quoted when you reserve, so tell us the party and the hour you want.

Private ChartersOur default answer for this stay — the whole boat, your group, your route. Port Royal Mansion CruiseIdle the canals near Gordon Pass and read the waterfront estates from the water. Private Port Royal SightseeingThe same canals with nobody else aboard and no fixed script to keep up with. Sunset CruisesGolden hour out toward Keewaydin Island, at an unhurried pace. Special OccasionsAnniversaries, proposals and quiet celebrations, arranged the way you want them. Dolphin ToursWild bottlenose dolphins in the bay and passes — often alongside, never promised.

Getting There

From Hotel Escalante to the dock

One street, west end to east end. Here’s the honest version, step by step.

Start: the west end of 5th Avenue South

Hotel Escalante sits at 290 5th Avenue South, down at the quiet western end of the avenue, close to Third Street South and a short walk from the sand. That corner of Old Naples is the low-key half — shade, side streets and less foot traffic than the restaurant blocks a few hundred yards east. Our boats don’t leave from the beach you can walk to, though. We run out of a sheltered marina on Naples Bay, which is what puts you in flat water on the way to Gordon Pass and the Port Royal canals instead of pounding out through the surf. So the day starts with a short move east, and it’s an easy one.

The short ride east

Plan on about a five-to-ten-minute drive or rideshare, traffic and season depending. The dock sits on the same avenue you’re staying on, just at the far end — roughly a mile and a bit east, past the shops and out toward the bay. That’s further than most people want to walk in the middle of a Naples afternoon, especially carrying a bag and a cooler, so we’d honestly rather you ride it. A rideshare also means nobody has to think about the car after a sunset run, and downtown Naples is a quick pickup. Drop your own address into your map app before you leave; our range is a range, not a promise.

The dock: Naples Bay Resort & Marina

We meet you at Naples Bay Resort & Marina, 1500 5th Avenue South, on protected Naples Bay a few blocks past the east end of the restaurant district. It’s a calm, walkable marina rather than a busy Gulf-front ramp, which makes finding your captain simple and stepping aboard simpler still. Once you’ve booked, we send the exact slip and a short where-to-meet note so nobody ends up wandering the docks reading transom names. Restrooms are right there before you board. If you turn up early, Crayton Cove and Tin City are a couple of minutes away and worth the stroll while you wait. The bay itself is the reason we start here: it stays protected all the way down to Gordon Pass, which means the first twenty minutes of your trip are glass instead of chop, and you can hear your captain without shouting.

Parking and arrival

There’s parking at and around the marina and through the 5th Avenue South district if you drive yourself, though a rideshare skips the question entirely and is our usual suggestion for an evening cruise. Aim to be at the dock about ten minutes before your booked time — enough to sort shoes, sunglasses and whatever you’ve brought aboard without anybody hurrying. If a car runs late or plans shift, call us at (239) 301-8913 and a real person answers; we’d far rather move something around than have you arrive flustered. We don’t pick up at the hotel, so the ride over is the one piece of the day that’s on you.

What to bring

Keep it light: soft-soled shoes, sunglasses, a hat and reef-safe sunscreen. Late-day and sunset trips run cooler on the water than they feel on the avenue, so carry a layer for the ride back in. A camera or a clean phone lens earns its keep on the Port Royal cruise and at golden hour, when the light is doing most of the work anyway. We handle water and the shaded seating; whatever you’d like to sip or snack on is yours to bring, and we’re glad to help you plan that when you book. Leave anything you’d hate to drop over the side back in the room.

Then: the water is yours

Once you’re aboard, the logistics end. Your captain points the bow wherever the trip calls for — up the Port Royal canals, out Gordon Pass toward Keewaydin, or a slow loop of Naples Bay to look for dolphins — and narrates as much or as little as you like. On a private charter that route stays a conversation, so linger somewhere pretty or turn for home early and nobody minds. An hour and a half to a couple of hours later you’re back at the same slip, five to ten minutes from your door. That’s the whole shape of it: a short ride over, then quiet water and no schedule but yours.

Who It Suits

A good fit if you’re…

Escalante guests tend to want the small, unhurried version. Here’s who books us.

Travelling as a couple

Two of you, one captain and a quiet stretch of bay. No shared bench, no seating chart, and nobody talking over the sunset you came out for.

Marking an occasion

An anniversary, a proposal or a milestone that deserves its own boat — set up the way you want it, at the hour you want it, without an audience.

Out as a small party

A handful of family or friends, stable shaded seating and a pace nobody has to keep up with. Kids and grandparents are welcome aboard.

Wanting the quiet version

You chose a small hotel over a big resort on purpose, and the water day can follow the same logic. A private charter is that same choice, made once more out on the bay.

On the Water

What the afternoon looks like

The boat, the canals you’ll idle, and the light at the end of it.

A clean, shaded Sand Dollar charter boat with cushioned seating tied up on calm water near Naples, Florida — The whole boat, and nobody else on it

Waterfront estates and private boat docks along the Port Royal canals in Naples, Florida — Port Royal, read from the water

A couple sitting on the bow of a Sand Dollar boat as the sun sets over the Gulf near Naples, Florida — Golden hour, out toward the Gulf

Keep Planning

More ways to plan your Naples days

A sibling stay, the private side of our fleet, and every property we serve.

Near The Capri InnThe other small Old Naples hotel we serve, a few blocks over. Private Charters in NaplesHow a private Naples-side run works, dock to dock on the bay. Boat Tours in Olde NaplesEverything we run from the downtown side of the water. All Stays We ServeEvery hotel and marina we run boat tours near.

Good to Know

Boat tours near Hotel Escalante, Naples

The honest answers to what guests at the Escalante ask us most.

How far is the dock from Hotel Escalante?

Plan on about a five-to-ten-minute drive or rideshare from 290 5th Avenue South to Naples Bay Resort & Marina at 1500 5th Avenue South. It’s the same street, west end to east end, roughly a mile and a bit, so it’s a short hop rather than a cross-town trip. That’s a range and not a promise — season and time of day move it, and your own map app will always beat our estimate. Most guests rideshare so nobody has to park or drive home after a sunset run, and downtown Naples is a quick pickup either way.

Do you pick up at the hotel?

No — we depart from the marina, not the property, so there’s no lobby or beach pickup. You meet your captain at Naples Bay Resort & Marina, and once you’ve booked we send the exact slip along with a short where-to-meet note so nobody ends up reading transom names. We’re also not affiliated with Hotel Escalante in any way, and there’s no package or partnership between us; we’re a local, captain-led company that’s simply glad to look after guests staying there. If getting to the dock is the sticking point, call (239) 301-8913 and we’ll talk it through.

Why do you recommend a private charter instead of a scheduled cruise?

Because it matches the stay. Guests who choose a small hotel in Old Naples usually aren’t looking to share a rail with a boatload of strangers for ninety minutes. On a private charter you get the boat, the captain and the route — the Port Royal canals, a run out Gordon Pass, a slow loop of Naples Bay, or all three if the light cooperates — and you pick the hour instead of fitting into a posted departure. Our scheduled dolphin and sunset cruises are genuinely good, and plenty of people take them; here they’re simply the second thing we suggest rather than the first. The other practical reason is timing. A private boat can leave when the light is right for you rather than when a departure board says so, which matters a lot in the hour before sunset.

Can you keep the group small?

Yes — on a private charter the only people aboard are the ones you bring. Tell us your party size when you book and we’ll match the right boat and the right captain to it, whether that’s the two of you on a sunset run or eight of you out for an afternoon. We don’t fill leftover seats with other bookings, and there’s no crowd we have to reach before a trip will go. If your numbers change between booking and the day, call (239) 301-8913 and we’ll adjust it rather than leave you guessing at the dock. A small party is often the better trip anyway: fewer people means a slower idle through the Port Royal canals and more room to move around the boat when something turns up alongside.

Will we see dolphins or manatees?

Often, but never on demand. Wild bottlenose dolphins live in Naples Bay and the passes year-round and frequently surf the wake or roll up alongside the boat, so most trips find them — we just won’t promise an animal that keeps its own schedule. Manatees gather in the calmer backwaters when the water drops below about 68 degrees, roughly November through March, and around Naples they’re scattered rather than bunched up the way they are in the spring-fed rivers further north. The birdlife is the sure thing: herons, ospreys and pelicans working the seawalls all year long.

How do we book, and what does it cost?

Tap any ‘Check availability’ button on this page to reach our booking calendar, or call (239) 301-8913 and a local person will help you pick the run. Private charter pricing depends on the boat, the length of the trip and the size of your party, so we quote it when you reserve rather than posting a number that wouldn’t fit your day. Sunset slots go early in season, so if a particular evening matters, lock it in before you fly. Mention that you’re staying at the Escalante and we’ll help you time it around dinner on the avenue.

Reserve Your Seats

Ready for a quiet hour on the water?

Check availability and book a boat tour — five to ten minutes east of the Escalante, and the boat is yours.

Or call (239) 301-8913

Your Old Naples Stay, On the Water

Book your boat from Hotel Escalante

Private charters, the Port Royal canals and a quiet sunset out Gordon Pass — all from our Naples Bay dock at the east end of your street. Tell Sand Dollar Shelling & Boat Tours your dates and your party size and we’ll shape the hour around you.

Book a Boat Tour (239) 301-8913

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