Sunset Watersports Open Bar Cruise in Key West: Catamaran Sunset Sail with Live Music

Sunset Watersports Key West

Key West Signature Sunset Cruise with Open Bar, Food & Music

★ 4.6 (513) · from $80

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Prices and timetables checked 2026-10-17. Affiliate note: I earn a commission on bookings made through the links on this page.

The Sunset Watersports open bar cruise is a 2-hour evening sail on the Sandie Cat, a 65-foot catamaran that leaves from William Street in Old Town Key West. For $80 you get an unlimited well bar, a platter of finger food and a live musician on the upper deck.

The detail that changes the decision is the food. The listing says "food and drinks", but the operator describes appetizers such as sliders, meatballs and hummus, and GetYourGuide's review summary calls it snacks rather than a meal. Eat dinner after, or book the operator's separate dinner cruise instead.

This page covers the pier, the sunset timing, what the bar pours, and how the cruise compares with the other evening boats on my Key West sunset cruises page. The full list of trips is on my Key West boat tours hub, and other ports are on the Harbour Advisor home page.

What do you get on the Sunset Watersports open bar cruise?

You get a two-hour sunset sail with a bar, food and music, all in one ticket. The ship has three decks and a crew of three, according to a reviewer, with the live music on the upper deck.

• Bar: an unlimited open well bar with draft beer, wine, champagne, margaritas, rum runners, mixed drinks and soft drinks.
• Food: Jamaican jerk chicken sliders on rolls, BBQ meatballs, veggie trays, cheese and crackers, and pita with hummus.
• Music: a live performer, described by the operator as one of Key West's best entertainers.
• Upgrade: $19.95 for a premium liquor package; shots are excluded.

The listing says guests may lend a hand with the sails and ask for a photo at the helm. A reviewer said it felt like no real sailing, so treat this as a motor-and-sail party boat, not a working tall ship.

Where does the Sunset Watersports open bar cruise leave from?

It leaves from the Sunset Watersports base at 201 William Street, near the foot of the street at the Historic Seaport. The operator asks guests to check in 30 minutes before departure with photo ID and a credit or debit card.

Open the departure point before you go. Classic Harbor Line's schooner sails from 202 William Street beside Schooner Wharf Bar, a few doors away, so make sure you walk to the correct booth.

The listing does not include transport to the meeting point. The City of Key West's bus fares page lists $2 for an adult one-way ride on city routes, if you do not want to walk from your hotel.

When does it sail, and does it catch the sunset?

The operator's page says the cruise departs at 6:30 PM with a 5:30 PM check-in and a 2-hour trip, then adds that times change seasonally. The same page also asks guests to arrive 30 minutes before departure, so check the time printed on your ticket.

Sunset moves by 2 hours and 38 minutes across the year, from 5:41 PM in November to 8:19 PM in July. A fixed 6:30 PM departure would suit October but miss sunset entirely from November to February, so the seasonal time change is not a detail.

What is on board and what costs extra?

Included are the open well bar, appetizers and live music. Tips and transport to the pier are not included, and the premium liquor upgrade is $19.95.

• Included: unlimited well drinks, finger food, live music.
• Extra: tips, the $19.95 premium bar, and any transport to the pier.
• Bring: photo ID, a credit or debit card, and a light layer for the wind.
• Weather: the captains judge the day's weather, and an unsafe sailing is postponed or cancelled with a full refund.

How does it compare with other Key West sunset cruises?

This is the party-leaning sunset cruise, with more drinks and noise than the schooner and a lower price than the 2-hour sail that costs $123. The table compares it with the closest evening rivals.

For a quiet, small-scale sunset, Classic Harbor Line's schooner sunset sail costs $43 more and has the highest rating on my list. For a swim plus a sunset, Sunset Watersports' dolphin and snorkel trip is the same price and an hour longer, and the Fury reef trip has a sunset slot at $49.

Is the Sunset Watersports open bar cruise worth it against other Key West sunset boats?

Yes, if you want music, a bar and a crowd, and no if you want a quiet evening. At $40 an hour it costs more than the median, but you are paying for a bar that is unlimited.

1. Best for groups - a boat for up to 149 and a bar that does not run out.
2. Best for drinkers - the premium bar adds top-shelf spirits for $19.95.
3. Trade-off - snack-sized food and standing room on busy nights.

I have not been on board, so this judgement comes from the listing, the operator's page and the reviews in the sample.

5.6 nights was the average length of stay of Florida Keys visitors in 2024.

With under six nights on average, you probably have one evening for a sunset boat. Pick it on the weather forecast from the National Weather Service Key West.

When is the best time to go?

The best months for a sunset sail are March to May, when rain days are lowest and sunset falls between 7:37 and 8:04 PM. Summer sunsets come later, but the rain-day count rises to 15 to 19 a month.

• March to May: 4.3 to 10.8 rain days, sunset at 7:37 to 8:04 PM.
• June to October: 15 to 19 rain days, later sunsets, warm air.
• November to February: cooler evenings, 5:41 to 6:22 PM sunsets, pack a layer.

One reviewer in April called it windy, and another said the evening is about the hour on the water, not the last minute of daylight. Both are fair reminders that the sky is not on a schedule.

What do passengers say?

All 20 reviews I read were 5/5, so the sample is positive-only. The themes are music and crew first, then the sunset and the drinks.

• Music: 11 of 20 praise the live musician.
• Crew: 11 of 20 mention a friendly crew or captain.
• Food: 7 of 20 mention it, with two calling it unremarkable starter food.
• Bar: 7 of 20 praise the drinks or the bartender.
• Space: 3 of 20 mention seating or standing, with opinions split between "just right" and "more seating".

One review in the sample names Fury, a different operator, so some reviewers confuse the Key West sunset boats. Treat the pattern as a guide, not exact proof.

Who should skip the Sunset Watersports open bar cruise?

Skip it if you want a quiet sail, a real dinner, or a boat with fixed seats for everyone. The cruise is built around a bar and a band.

• Quiet seekers: choose the schooner sunset sail.
• Dinner seekers: the operator sells a separate dinner cruise.
• Non-drinkers: soft drinks are included, but the value is in the bar.

The full list of options is on my Key West boat tours page.

How do you book the Sunset Watersports open bar cruise?

Choose the date, then read the departure time against the sunset table above.

Frequently asked questions

Sources: Sunset Watersports Sip & Sail page (boat, bar, menu, address, times, weather policy); GetYourGuide listing 390631 (checked 2026-10-17); National Weather Service Key West; City of Key West bus fares; Monroe County TDC 2024 Visitor Profile Study; Open-Meteo archive API (climate); sunrise-sunset.org (sunset); Nager.Date (US holidays); OSRM on OpenStreetMap (walking time).