Key West has exactly two sunset cruises built around a meal, and they take different routes to the same sky. The sushi cruise from Barefoot Billy's boards at the Casa Marina Resort and pours drinks as part of the ticket. The Sunset Watersports trip serves dinner alongside an open bar and live music, with free cancellation if your plans move. Both spend two hours on the water. Here they are side by side, most reviewed first.
Sushi with complementary drinks on one deck, dinner with an open bar and live music on the other. Both sailings last two hours, and the open-bar trip allows free cancellation.
Short answer
The format shapes the whole evening. Barefoot Billy's sushi cruise leaves from the Casa Marina Resort and keeps the mood contained: rolls served on deck, drinks already covered, two hours of quiet water. The Sunset Watersports dinner cruise leans the other way, putting an open bar and a live band behind the meal, which makes it the louder and more social boat. Each sails at golden hour and each heads back for the harbor once the sun is down. Both list a from-price that moves with your date and demand, so treat the live listing as the final word for the evening you want.
Logistics are simple on both trips. Each boards from Key West itself, within a short walk or a quick ride of most Old Town guesthouses, so there is no ferry connection or harbor choice to plan around. Arrive near golden hour, eat on the water, and you are back on Duval Street shortly after dark. That compactness is a real part of what a dinner cruise in this town sells you.
The second fork is what dinner means on your ticket. On one boat it is sushi, plated with drinks already in the fare, a format that suits couples and anyone who prefers a calmer deck. On the other it is a broader dinner spread backed by an open bar and live music, which draws a party crowd and keeps the deck loud after the plates are cleared. The sunset is identical from either rail, and from the water it is a good one.
No fixed fare appears on either listing, so the live booking page settles what your evening costs.
Top-reviewed boat in this category
A two-hour dinner cruise from Sunset Watersports Key West, pairing a sunset sail with an open bar, live music, and a served meal. Free cancellation applies, and the rating runs 4.5 across 283 reviews. Check the live listing for current pricing and departure details.
Barefoot Billy's runs this two-hour dinner cruise out of the Casa Marina Resort, and the menu is the draw: fresh sushi served aboard while the sun drops over the Gulf. Complementary drinks come with the fare, so there is no bar tab to settle at the end. Guests have rated it a full 5 stars across 212 reviews, which puts it among the best-reviewed trips on this site. It is one of only two sunset dinner cruises in the roster, and the only one where sushi replaces the usual buffet spread.
Start with the meal and boarding columns. What separates these sailings is the food that reaches your table and where you step aboard, not the sunset, which looks the same from both decks.
| Boat | Departure | Meal | From |
|---|---|---|---|
| Sushi Sunset Cruise (Barefoot Billy's) | Casa Marina Resort (719 Palm Ave) | Sushi served on deck, complementary drinks | $151 |
| Sunset Dinner Cruise with Open Bar & Live Music (Sunset Watersports) | 201 William St | Buffet dinner, open bar, live music | $93 |
| Boarding time | Boats board roughly 30 to 45 minutes before departure, and departure tracks the sun: Key West sunset ranges from about 5:38pm in November to about 8:20pm in June. |
|---|---|
| Drinks | Florida's drinking age is 21 and crews check ID before serving. Both cruises fold drinks into the fare: complementary drinks with the sushi, an open bar with the Sunset Watersports dinner, so there's no separate bar tab on either boat. |
| Dress | Nothing here enforces a dress code. Resort casual covers every boat, and flat shoes beat heels on any deck that moves. |
Both cruises list a starting price that moves with your date and the season. The sushi sailing leaves from Casa Marina Resort and serves drinks with the meal; the Sunset Watersports outing pours from an open bar while a band plays. Both are two hours on the water. The live booking page gives the exact price for the evening you have in mind, and the open-bar cruise can be cancelled free if the weather or your plans turn.
The sushi cruise wins on score: five stars from 212 reviews (checked September 2026), against 4.5 from 283 for the open-bar dinner trip. A perfect mark on that many bookings is rare, and it puts Barefoot Billy's evening near the top of everything listed on this site. The tall ships keep it company, though, with three schooners also carrying five stars.
Two boats in Key West put a real plate of food on the table at sunset. One is the sushi cruise from Barefoot Billy's, sailing out of the Casa Marina Resort. The other is the dinner sail from Sunset Watersports Key West, which adds an open bar and live music to the meal. The catamaran fleet sticks to hors d'oeuvres and drinks, and those options are laid out on the catamaran sunset sails page.
Yes, both of them. Barefoot Billy's runs a two-hour sushi sunset cruise with drinks included, rated 5 across 212 reviews (checked September 2026). Sunset Watersports Key West runs a two-hour dinner cruise with an open bar and live music, rated 4.5 across 283 reviews (see Is a sunset cruise in Key West worth it?). Neither treats the food as garnish for the sail. The meal is the reason the boat goes out, and two hours is enough to eat well and still catch the sky turning.
Captains call off sailings for safety, not for gray skies, and a bit of cloud over Key West often makes the more dramatic evening. If the operator cancels, you get rescheduled or refunded. The Sunset Watersports dinner cruise lists free cancellation, so an ugly forecast on your end costs nothing either.
Let the menu decide. The Barefoot Billy's sushi cruise leans lighter and quieter, with drinks folded into the fare. The Sunset Watersports sail brings a full dinner plus an open bar and a live band, so it reads as the rowdier night out. Both spend two hours on the water, so the clock is a wash.
The same sky with drinks and hors d'oeuvres instead of a plate: four catamaran sails cover that ground.
Three tall ships chase the same sunset under real sail, among them a 105-foot replica of the 1851 schooner America.
A BYOB tiki boat and a booze cruise with unlimited draft beer and wine, built for a group that wants the whole boat.
