Key West Sailing 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).
- Best value: Key West Sunset Catamaran Cruise: Champagne & Views, US$ 43 per person (1h 30m, 4.65★ · 598).
Price per person across the 23 options priced per person: US$ 43–US$ 159 (median US$ 98). With 100+ reviews: 20 of 25.
Of the 25 options: 24 with live guides in English, 23 with free cancellation, 24 with instant confirmation, 20 kid-friendly, 2 private and 23 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. Prices are per person, except options priced per group: that price is for the whole group, and the per-person figure assumes the group is full. “Top rated” = the highest score among options with at least 100 reviews.
Key West Sailing
Based on each operator's calendar. Confirmed when you book.
25 options
The 15 best
Ranked by quality, reviews, availability and booking conditions.
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
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 Snorkeling: 3rd Largest Reef with Breakfast & Mimosas Sail Key West's fastest catamaran for breakfast and mimosas, then snorkel the 3rd largest living coral reef with expert guides who provide all gear. Every day · 09:00 · All ages ★ 4.47 (745 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 54 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 Champagne Cruise: Adults Only, Small Group Sail Key West's shallow waters at sunset with 14 adults on a catamaran, sipping bottomless Moët & Chandon Brut and tasting four international cheeses. Every day · 16:15 and 16:30 · From age 21 ★ 4.89 (1,016 reviews) Duration: 2h Live guide: EN ✓ Instant confirmation. from US$ 109 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 Sunset Catamaran Cruise: Champagne & Views Sail into the Key West sunset on a 60-foot catamaran with wine, beer, champagne and sangria included: 1.5 hours on the water as the sun drops and the sky changes color. Every day · 17:00 · All ages ★ 4.65 (598 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 43 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 Snorkeling, Kayaking & Sailing: Historic Schooner Sail a historic schooner into Key West National Wildlife Refuge, snorkel in clear water, kayak around mangroves, and stop at a shallow sandbar. Every day · 09:30 · All ages ★ 4.90 (852 reviews) Duration: 6h 30m Live guide: EN ✓ Free cancellation. from US$ 159 per person
Snorkeling in Key West: 54' Sailing Yacht, Small Groups Snorkel North America's only living coral reef from a 54-foot sailing yacht with small groups, instruction and drinks included. Every day · 09:00 and 13:00 · All ages ★ 4.73 (250 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 79 per person
Key West Morning Snorkel Sail & Gourmet Breakfast Morning catamaran snorkel tour from Key West with gourmet breakfast, unlimited mimosas & reef exploration. Small group, 4-5 hours, snorkel gear included. Every day · 09:00 · All ages ★ 4.70 (216 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 50 per person
Key West Snorkeling & Dolphin Watching Small Group Tour Snorkel shallow reefs and wrecks on a Key West sailing catamaran with 14 passengers max, spotting wild dolphins while hunting and playing in their natural habitat. Every day · 11:30 and 13:30 · From age 5 ★ 4.63 (476 reviews) Duration: 4h Live guide: EN ✓ Instant confirmation. from US$ 109 per person
Also popular with travelers
The ones most travelers have taken, by number of reviews.
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: Afternoon Dolphin Sail on 60' Catamaran Sail from Key West's Historic Seaport on a 60-foot catamaran to watch wild Atlantic bottlenose dolphins. Small groups, beer and wine included, relaxed afternoon pace. Every day · 10:00 and 13:00 · All ages ★ 4.54 (224 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 50 per person
Key West: Schooner America 2.0 Sailing Tour & 2 Drinks 1.5-hour sail aboard the 1851 America's Cup replica schooner. Includes 2 drinks, views of Fort Zachary Taylor and Sunset Pier. Kids sail free on afternoon departures. Every day · 13:30 · All ages ★ 4.91 (215 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 82 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 Schooner Sail & Full Bar: 2-Hour Tall Ship Sail a historic 2-masted schooner in Key West for 2 hours with full open bar, crew guidance, and a turn at the wheel. Departs from the seaport daily. Every day · 13:30 · All ages ★ 4.91 (113 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 54 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
Compare 4 more options for Key West Sailing
From US$ 98 per person · 2 h to 5 h
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
Private 90-Minute Harbor Sailing Charter in Key West Private sailboat charter for up to six in Key West: 90 minutes under sail with captain and mate, soft drinks included, your choice of morning, midday or afternoon departure. Every day · 10:00, 12:00 and 14:00 ★ 4.90 (20 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 425 per group
Key West Christmas Cruise: Schooner America 2.0 with Live Band Sail the Key West harbor aboard the 105-foot Schooner America 2.0 decorated in holiday lights, enjoying live Christmas music and hot cocoa under the stars. Mon–Thu · 12:30 and 19:00 · All ages ★ 5.00 (6 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 98 per person
Private Sunset Boat Charter Key West: Music, Drinks & Snorkeling Private 38-foot boat charter in Key West for up to 13 guests with captain, music, drinks and snorkeling gear included. Choose 2, 3 or 4 hours on the water. Every day · 16:00, 16:30, 17:00, 17:30 and 18:00 ★ 5.00 (2 reviews) Duration: 2h–4h Live guide: EN · ES ✓ Free cancellation. from US$ 899 per group
The top 12 of 25 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 |
| Key West Sunset Catamaran Cruise: Champagne & ViewsBest value | US$ 43 per person | 1h 30m | 4.65★ · 598 | 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 |
| Sunset Sail in Key West: Champagne Cruise with Beverages | US$ 79 per person | 1h 30m | 4.86★ · 996 | Every day · 17:00 | English |
| Key West Sunset Sail: Dolphins, Wine & Tapas | US$ 80 per person | 2h 30m | 4.64★ · 774 | Every day · 16:00 | English |
| Key West Snorkeling: 3rd Largest Reef with Breakfast & Mimosas | US$ 54 per person | 3h | 4.47★ · 745 | Every day · 09:00 | 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 Sunset Champagne Cruise: Adults Only, Small GroupGroup of up to 14 | US$ 109 per person | 2h | 4.89★ · 1,016 | Every day · 16:15 and 16:30 | 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 Snorkeling, Kayaking & Sailing: Historic Schooner | US$ 159 per person | 6h 30m | 4.90★ · 852 | Every day · 09:30 | English |
By what you need
- Private (2): Private 90-Minute Harbor Sailing Charter in Key West (US$ 425 per group) · Private Sunset Boat Charter Key West: Music, Drinks & Snorkeling (US$ 899 per group)
- Small groups (up to 15) (2): Key West Sunset Champagne Cruise: Adults Only, Small Group (US$ 109 per person) · Key West Snorkeling & Dolphin Watching Small Group Tour (US$ 109 per person)
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