Sunset Sailing & Champagne Catamaran Cruises in Naples
Naples faces straight west onto the Gulf, so the sun sets right into the water. Do it under sail on a catamaran, glass in hand, and it's the most romantic evening on the Paradise Coast.
Updated June 2026
Naples faces due west onto the Gulf, which means the sun sets straight into the water almost every evening of the year. Do it under sail on a catamaran and you trade a noisy engine for a quiet glide across Naples Bay, the Port Royal estates drifting by on one side and a sky going coral-and-gold on the other. This is the experience that lands on the visitor top-25 lists, and it is worth the booking.
A sailing catamaran is its own thing, calmer and roomier than a speedboat, and it is a different evening than the engine-powered dolphin and sunset cruises we cover separately. Couples love it for an easygoing date, and it is one of the gentlest, most romantic things you can do here. Below are the catamarans we'd actually board, what to expect, and how to choose.
Catamarans we'd sail on
Three long-running sailing catamarans, each with its own dock, size and personality. Confirm times and pricing with the operator when you book, since sunset hour and rates shift through the year.
On board, in short
A few things that hold true across all three.
Pick your catamaran
- Want a champagne toast and the most intimate boat? Lean toward Cool Beans, the smallest of the three.
- Bringing your own food and wine, or a bigger group? Sweet Liberty is the largest and most flexible, right in Old Naples.
- Staying near Port O'Call or want daily public departures? Miss Naples sails year-round from that marina.
- Traveling with small kids or on a budget? Book a daytime shelling or sightseeing sail instead of sunset.
- Whatever you choose, reserve early and reconfirm the night before for weather.
Where to go next
More ways to be on the water and make an evening of it.
Dolphin & Sunset Cruises
The engine-powered alternative, with dolphin-watch trips and classic sunset boat tours.
Romantic Weekend
A two-day plan built for couples, with the sunset sail as the headline evening.
Naples Itineraries
Ready-made plans for a romance, a weekend or a few days, with the sunset sail built in.
Beaches & Outdoors
Every Naples beach, plus shelling, the mangroves and more out on the Paradise Coast.
Book a sunset catamaran sail in Naples
Common questions
What's the difference between a catamaran sail and a regular sunset cruise?
A sailing catamaran is a wide, stable twin-hulled boat that uses sails, so it's quieter and gentler than an engine-powered sightseeing boat. The pace is slower and calmer, which makes it a favorite for couples. We cover the engine-powered dolphin and sunset boat tours on a separate page if you'd rather move faster.
Which catamaran companies sail in Naples?
The main sailing catamarans are Sweet Liberty (a 53-footer from the Naples City Dock in Crayton Cove), Cool Beans Cruises (a smaller 42-foot boat from the Isle of Capri), and Miss Naples (a 48-foot catamaran from Port O'Call Marina). All three were operating as of 2026, but check each operator's site for current schedules before you plan around them.
How much does a sunset catamaran cruise cost in Naples?
Pricing varies by operator and season and changes often, so confirm directly when you book. As a rough guide, recent listings put Cool Beans in the low-to-mid-$70s per person with a champagne toast and drinks included, while Sweet Liberty runs less (recently in the mid-$40s for adults, with lower kids' rates); Miss Naples sits in between. Treat any figure here as a ballpark, not a quote.
Is the champagne and drinks included?
It depends on the boat. Cool Beans typically includes beer, white wine and a champagne toast at sunset. Sweet Liberty lets you bring your own cooler with food and drinks. Miss Naples sells snacks, beer and wine onboard. Ask when you book so you know whether to pack a picnic.
How long is a sunset sail and when does it leave?
Most sunset sails run about two hours and are timed so you're on the water at sundown, which means the departure time shifts earlier or later through the year. Boarding is usually about 30 minutes before departure, so build in time to park at the marina and check in.
Do I need to book ahead?
Yes, especially in the busy December-through-April season. These are small boats and sunset is the most popular slot, so reserve in advance through the operator's website or by phone. Because they're sailboats, also reconfirm the night before, since strong wind or storms can move or cancel a trip.