Amazing Sunset Cruises in Naples & Marco Island

By Eric Snider

Get on board to experience the awe of a sunset on Florida’s Paradise Coast – from the water.

Most evenings on Florida’s Paradise Coast, the sky is drenched in intense pinks, blues, reds and purples as the sun gradually descends on the Gulf of Mexico horizon. If you’re lucky, you just might glimpse the famous and elusive “green flash.” Several minutes after the sun goes down, the painted sky remains, often becoming even more vivid. It’s breathtaking. 

As good as our sunsets look from the beach, witnessing these natural marvels is out on the water is truly transcendent. Fortunately, the Paradise Coast has an ample selection of sunset boat cruises that sail nightly from both Naples and Marco Island. They’re favorite experience among visitors and locals alike. Here is an overview:

Luxury on the Naples Princess 

A picture of the sun setting behind the Naples Princess on the Gulf of Mexico

A sunset cruise aboard the Naples Princess.

This sleek, three-tiered yacht — 105 feet long — can carry up to 149 passengers on a luxury sunset excursion. There’s not a bad seat in the house, whether it's on the open-air top deck or in the two climate-controlled salons with panoramic views. You’ll glide around Naples Bay, see the opulent homes of Port Royal and, weather permitting (and it usually is), head out into the Gulf. The Naples Princess’s Sunset Dinner Cruise always ranks high on the list of best things to do in Naples. It features a double-entree, buffet-style spread. The “More Than Hors d'oeuvres” Sunset Cruise is a nice alternative. As the name suggests, it offers lighter, more bite-sized fare. The food is prepared fresh daily, right on board. Two cash bars add to the fun and relaxation. The Naples Princess sunset cruises last two hours and leave from Port O Call Marina, which is near downtown and next to the Tin City shopping and dining complex

Miss Naples: Get the wind in your sails

The Miss Naples afloat on turquoise Gulf waters.

Miss Naples, a catamaran offering sunset sails.

If you’re looking for a more open-air, wind-in-your-face, close-to-the water sunset experience, Miss Naples is just the ticket. You’ll cruise through Naples Bay and Port Royal and out onto the Gulf on this 48-foot, custom-built catamaran sailboat. Miss Naples holds up to 48 people for its narrated tours and offers a canopy for anyone who prefers to stay in the shade. More than likely, you’ll see playful dolphins and maybe even manatees, so have your cameras ready. An on-board bar offers beer, wine, soft drinks and snacks. There are two restrooms available. Just so you’re aware, Miss Naples has no air-conditioned areas, so dress weather-appropriately. (Still, you can expect a nice breeze.) The tour sails out of Port O Call Marina.

Sweet Liberty: Sunset Sail from Marco Island

The Sweet Liberty catamaran on the beach

The Sweet Liberty.

Watch the sails go up on your way to see the sun go down. Sweet Liberty is a 53-foot catamaran that’s been cruising Naples Bay and nearby areas since 1991 (when it was built in St. Croix). The cruises max out at 40 people, so there’s plenty of room to stretch out and enjoy. A family affair, Sweet Liberty is operated by Shane and Susan Chaplin, who narrate and do their very best to ensure that everyone has a lovely time. Feel free to bring a small cooler or picnic basket along. Beer and wine are permitted (but not sold onboard). The two-hour adventures sail out of Crayton Cove in Olde Naples.

Pure Florida: Dolphins, Mansions & More

An American flag flies in the breeze during a Pure Florida sunset sail

A Pure Florida sunset sail.

Take a 90-minute, narrated cruise aboard Pure Florida’s M/V Double Sunshine to view a breathtaking sunset. Aboard the double-decker, open-air yacht, you’ll also see wildlife, multi-million-dollar mansions and other sights in Naples Bay, Port Royal and Gordon Pass, where the Bay meets the Gulf and the waterfront homes are marvelous. Grab a beverage — adult or otherwise — and a packaged snack from the onboard bar. The captain stops the boat so you can get a good view — and great photos — as the suns drop below the horizon. The Double Sunshine can carry 128 people and departs from Tin City.

Chill Out with Cool Beans Cruises

A sailboat at full sail on the Gulf at sunset

A Cool Beans cruise at sunset.

Sailing out of the southern tip of Naples, just a mile north of the Marco Island Bridge, the two-and-a-half hour Cool Beans Champagne Sunset Cruise is a can’t-miss. You’ll lounge aboard a sleek, 42-foot catamaran operated and narrated by a friendly and knowledgeable captain. Complimentary beer, wine and soft drinks are part of the fun, and you can join in a celebratory champagne toast as the sun goes down. The Cool Beans has comfortable dinette seating for six, and a unique design that allows for comfortable outdoor and indoor seating. The vessel holds up to 20 passengers.

A Bespoke Sunset Sail with Naples Water Tours

This outfit does things a little differently. Launching out of the Charter Club Resort, the 25-foot pontoon boat takes you through the mangrove forests to see dolphins and other wildlife up close. The 90-minute excursion stops at Keewaydin Island (known for its wonderful sea-shelling), where you get off the boat and take in the sunset from a secluded beach. The brand-new vessel can hold 15 passengers, but Naples Water Tours caps it at six passengers (minimum two). This is standard practice, by the way, not based on social distancing. With such a small tour group, the captain can improvise according to passenger preferences. Want the captain to stop so you can photograph a school of dolphins? Just ask. Grab a drink at the resort tiki bar near the boat launch, or bring your own.

Marco Island Princess: An Iconic Sunset Experience

She’s a beauty. The Marco Island Princess is 90 feet of luxury yacht that is Coast Guard-certified for 149 passengers. The Admiral’s Sunset Dinner Cruise features a bountiful buffet, plus two full-service cash bars. All the food is prepared fresh on board. (You can also take the excursion sans dinner.) Choose between the climate-controlled comfort of the indoor salon or the wind-in-your hair experience of the upper deck — or roam between both. Independently run by Sunshine Tours & Charters, which has been providing tours on Marco Island since 1984, this Princess embarks from Rose Marina, which is five minutes away from anywhere on the island.

Walk the Plank with Black Pearl Pirate Tours

Ahoy, maties — climb aboard the Black Pearl for a pirate-themed, adults-only, 90-minute trek through the waters around Marco Island. Let hearty rum drinks, music (courtesy of an onboard DJ), singing and dancing accompany your sunset-viewing. Pirate-clad crew members keep the party going — or you can find a cozy seat away from the revelry and gaze out over the Gulf. The Black Pearl pirate ship, custom-built in Maryland in 2009, is 60 feet long with a 20-foot beam. It’ll hold 78 buckos looking to have themselves a swashbucklin’ good time. The Black Pearl embarks from a marina on the northern end of Marco Island. 

Ready for more twilight bliss on Florida’s Paradise Coast? Experience sunset on Naples Pier – and keep an eye out for the green flash!