Key West Sunset Cruise at a glance
- Our pick: Key West Sunset Sail with Open Bar and Live Music, US$ 70 per person (2h, 4.68★ · 3,897).
- Top rated: Key West Sunset Sail Aboard Schooner Appledore, US$ 99 per person (2h, 4.97★ · 370).
- Shortest: Sunset Sail in Key West: Champagne Cruise with Beverages, US$ 79 per person (1h 30m, 4.86★ · 996).
Price per person across the 15 options priced per person: US$ 70–US$ 150 (median US$ 99). With 100+ reviews: 13 of 15.
Of the 15 options: 13 with live guides in English, 15 with free cancellation, 14 with instant confirmation, 13 kid-friendly and 14 bookable last-minute.
How we rank: quality, number of reviews, availability, booking conditions and relevance to the topic. In the comparison table, our top 3 comes first. Price per person. “Top rated” = the highest score among options with at least 100 reviews.
Key West Sunset Cruise
Based on each operator's calendar. Confirmed when you book.
15 options
Key West Sunset Sail with Open Bar and Live Music Sail Key West's harbor on a 70-foot catamaran with an open bar, live local musicians, and chef's hors d'oeuvres as the sun sets over the water. Every day · 16:30, 16:45 and 17:00 · All ages ★ 4.68 (3,897 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 70 per person
Key West Sunset Sail with Wine Tasting: Small-Group Schooner Sail Key West's harbor at sunset aboard a historic schooner with wine tasting, craft beer, and hors d'oeuvres: small groups mean you actually see the sky without crowds. Every day · 16:30 · From age 13 ★ 4.92 (1,493 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 135 per person
Key West Catamaran Sunset Sail: Live band on the water Two-hour sunset sail on Fury's 65-foot catamaran with live band, margaritas, champagne, beer, wine and appetizers. Departs Greene Street daily. Every day · 17:00 · All ages ★ 4.64 (1,063 reviews) Duration: 2h ✓ Free cancellation. from US$ 73 per person
Sunset Sail in Key West: Champagne Cruise with Beverages Sail through Key West Harbor at sunset with champagne, wine and craft beer included: watch the nightly Sunset Celebration from the water and catch. Every day · 17:00 · All ages ★ 4.86 (996 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 79 per person
Key West Sunset Sail: Dolphins, Wine & Tapas Luxury catamaran sunset sail from Key West's Historic Seaport with live dolphin watching, premium wine, and chef's tapas. Small groups, 2.5 hours. Every day · 16:00 · All ages ★ 4.64 (774 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 80 per person
Key West: Schooner Sunset Sail with Drinks & Appetizers Sail aboard America 2.0, Key West's schooner, with complimentary wine, beer and plated hors d'oeuvres. Two-hour cruise past Fort Zachary Taylor and Sunset Pier. Every day · 16:00 and 16:15 · All ages ★ 4.90 (901 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 127 per person
Key West Sunset Sail Aboard Schooner Appledore Sail Key West aboard a 2-masted wooden schooner with premium wine, beer and appetizers included. Every day · 16:00 and 16:30 · All ages ★ 4.97 (370 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 99 per person
Key West Schooner Sunset Sail & Open Bar Two-hour sunset sail on a historic schooner with full open bar, cocktails and premium drinks included. Departs Key West Historic Seaport daily. All ages welcome. Every day · 16:30 ★ 4.90 (286 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 109 per person
Key West Sunset Sail with Open Bar, Live Music & Hors d'oeuvres Catamaran sunset sail in Key West with open bar, live music and appetizers. Two-hour cruise includes well drinks, wine, champagne and food. Every day · 17:00 · All ages ★ 4.50 (423 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 77 per person
Key West: Sunset Sail Cruise on Schooner Jolly II Rover Feel the sea breeze on a classic Key West sunset sail cruise, help raise the red sails, and watch cannons fire: includes snacks, water, and a local crew. Every day · 16:15 and 16:30 · All ages ★ 4.94 (297 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 102 per person
Key West Sunset Cruise: BYOB Tiki Bar Boat for Up to 6 Board a custom tiki bar boat in Key West and toast the sunset with your own drinks while a USCG captain navigates past Mallory Square. Every day · 16:30 · From age 4 ★ 4.76 (177 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 81 per person
Key West Historic Schooner Sunset Cruise: Champagne Toast Two-hour sail aboard the When And If, commissioned by General George Patton in 1939, with champagne toast at sunset and the chance to take the wheel yourself. Every day · 16:15 · All ages ★ 4.85 (145 reviews) Duration: 2h ✓ Free cancellation. from US$ 117 per person
Key West: Reef Snorkel & Sunset Cruise with Beer & Wine 3-hour snorkel tour at two Key West reefs with equipment, then sunset cruise with unlimited beer and wine. Small catamaran, all fitness levels. Next departure: 7 Mar 2027 · All ages ★ 4.71 (210 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 75 per person
Key West Dolphin Watch and Sunset Sail on Catamaran Three hours aboard a 42-foot catamaran searching for Atlantic Bottlenose Dolphins, then anchored for the Key West sunset. Every day · 15:15 and 16:00 ★ 4.72 (43 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 124 per person
Key West snorkeling: Reef, sandbar & sunset sail Snorkel Florida Keys coral reefs on a 42-foot catamaran with an in-water guide, then return at sunset with fresh fruit and gear provided for groups up to 24. Next departure: 1 May 2027 ★ 4.98 (56 reviews) Duration: 4h 30m Live guide: EN ✓ Free cancellation. from US$ 150 per person
The top 12 of 15 options, side by side
✓ 2026-11-14| Option | Price | Duration | Rating | Days and times | Guide languages |
|---|---|---|---|---|---|
| Key West Sunset Sail with Open Bar and Live MusicOur pick | US$ 70 per person | 2h | 4.68★ · 3,897 | Every day · 16:30, 16:45 and 17:00 | English |
| Key West Sunset Sail Aboard Schooner AppledoreTop rated | US$ 99 per person | 2h | 4.97★ · 370 | Every day · 16:00 and 16:30 | English |
| Sunset Sail in Key West: Champagne Cruise with BeveragesShortest | US$ 79 per person | 1h 30m | 4.86★ · 996 | Every day · 17:00 | English |
| Key West Sunset Sail with Wine Tasting: Small-Group Schooner | US$ 135 per person | 2h | 4.92★ · 1,493 | Every day · 16:30 | English |
| Key West Catamaran Sunset Sail: Live band on the water | US$ 73 per person | 2h | 4.64★ · 1,063 | Every day · 17:00 | — |
| Key West Sunset Sail: Dolphins, Wine & Tapas | US$ 80 per person | 2h 30m | 4.64★ · 774 | Every day · 16:00 | English |
| Key West: Schooner Sunset Sail with Drinks & Appetizers | US$ 127 per person | 2h | 4.90★ · 901 | Every day · 16:00 and 16:15 | English |
| Key West Schooner Sunset Sail & Open Bar | US$ 109 per person | 2h | 4.90★ · 286 | Every day · 16:30 | English |
| Key West Sunset Sail with Open Bar, Live Music & Hors d'oeuvres | US$ 77 per person | 2h | 4.50★ · 423 | Every day · 17:00 | English |
| Key West: Sunset Sail Cruise on Schooner Jolly II Rover | US$ 102 per person | 2h | 4.94★ · 297 | Every day · 16:15 and 16:30 | English |
| Key West Sunset Cruise: BYOB Tiki Bar Boat for Up to 6Group of up to 6 | US$ 81 per person | 2h | 4.76★ · 177 | Every day · 16:30 | English |
| Key West Historic Schooner Sunset Cruise: Champagne Toast | US$ 117 per person | 2h | 4.85★ · 145 | Every day · 16:15 | — |
By what you need
- Small groups (up to 15) (1): Key West Sunset Cruise: BYOB Tiki Bar Boat for Up to 6 (US$ 81 per person)
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