Sailing in San Juan at a glance
- Our pick: Day sail to Icacos Island from San Juan with snorkeling, US$ 155 per person (5h 30m, 4.71★ · 276).
- Top rated: San Juan: Private Sailing Tour & Old San Juan Forts, US$ 494 per group (2h–3h, 4.84★ · 166).
- Also recommended: Icacos Island Catamaran Tour: Water Slides & Feast, US$ 195 per person (6h, 4.83★ · 169).
Price per person across the 8 options priced per person: US$ 99–US$ 195 (median US$ 119). With 100+ reviews: 8 of 9.
Of the 9 options: 9 with live guides in English, 9 with free cancellation, 5 with instant confirmation, 1 with hotel pickup, 8 kid-friendly, 2 private and 3 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.
Sailing in San Juan
Based on each operator's calendar. Confirmed when you book.
9 options
San Juan Bay Sunset Sailing Tour: Real Sailboat, No Crowds Sail San Juan Bay at sunset aboard a J30 racer-cruiser with complimentary drinks and views of Castillo San Felipe del Morro. Small groups up to six, live English guide. Every day · 17:00 ★ 4.48 (786 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 119 per person
Day sail to Icacos Island from San Juan with snorkeling Sail 40 to 50 minutes aboard a 51-foot catamaran to Icacos Island for snorkeling among parrot fish and butterfly fish. Every day · 09:00 · Hotel pickup · All ages ★ 4.71 (276 reviews) Duration: 5h 30m Live guide: EN · ES ✓ Free cancellation. from US$ 155 per person
San Juan Catamaran Sunset Sail & Drinks Included Sunset catamaran cruise on San Juan Bay aboard a 37ft vessel. Two hours with beer, rum punch and sparkling wine included. Small groups up to 6 with local captain narration. Every day · 17:00 ★ 4.93 (694 reviews) Duration: 2h Live guide: EN · ES ✓ Free cancellation. from US$ 119 per person
Icacos Island Catamaran Tour: Water Slides & Feast Sail to Icacos Island and the Cordillera Cays aboard a 54-foot catamaran with water slides, swings, snorkeling. Every day · 08:45 · All ages ★ 4.83 (169 reviews) Duration: 6h Live guide: EN · ES ✓ Free cancellation. from US$ 195 per person
San Juan Bay: Catamaran Day Sail with Drinks & Harbor Views Sail San Juan Bay on a 37-foot catamaran, sip mimosas or local rum punch, and watch the city drift by. Includes drinks, small group, and captain-led tour. Every day · 10:30 and 14:30 · Up to age 85 ★ 4.88 (581 reviews) Duration: 1h 30m Live guide: EN · ES ✓ Free cancellation. from US$ 99 per person
San Juan: Private Sailing Tour & Old San Juan Forts Sailing excursion around San Juan Bay with views of Old San Juan forts and Governor's Mansion. AM, PM, or sunset departures. Optional hands-on sailing lesson included. Every day · 10:00, 11:00 and 14:00 ★ 4.84 (166 reviews) Duration: 2h–3h Live guide: EN · ES ✓ Free cancellation. from US$ 494 per group
San Juan Bay Sailing Tour: Real Sailboat, Small Groups Sail San Juan Bay on a real J30 racer-cruiser with a live guide, complimentary drinks and views of Old San Juan's colonial fortresses. Every day · 10:30 and 15:00 · All ages ★ 4.58 (201 reviews) Duration: 1h 30m Live guide: EN · ES ✓ Free cancellation. from US$ 99 per person
Old San Juan Sunset Sail: Caribbean views with appetizers Two-hour sail through Old San Juan waters at sunset with appetizers and beverages included. Live guide in English or Spanish. Thu–Sun · 17:00 · From age 4 ★ 4.72 (241 reviews) Duration: 2h Live guide: EN · ES ✓ Free cancellation. from US$ 125 per person
San Juan Bay Private Tour with Sangria and Forts On this private boat tour of San Juan Bay you sail past old forts and the Bacardi rum factory, with local drinks and sangria on board. Every day · No fixed time · All ages ★ 5.00 (55 reviews) Duration: 3h Live guide: EN · ES ✓ Free cancellation. from US$ 166 per person
All 9 options, side by side
✓ 2026-11-14| Option | Price | Duration | Rating | Days and times | Guide languages |
|---|---|---|---|---|---|
| Day sail to Icacos Island from San Juan with snorkelingOur pickPickup offered | US$ 155 per person | 5h 30m | 4.71★ · 276 | Every day · 09:00 | English, Spanish |
| San Juan: Private Sailing Tour & Old San Juan FortsTop ratedPrivate | US$ 494 per group up to 6 people · ≈ US$ 82 per person if 6 go | 2h–3h | 4.84★ · 166 | Every day · 10:00, 11:00 and 14:00 | English, Spanish |
| Icacos Island Catamaran Tour: Water Slides & FeastAlso recommended | US$ 195 per person | 6h | 4.83★ · 169 | Every day · 08:45 | English, Spanish |
| San Juan Bay Sunset Sailing Tour: Real Sailboat, No CrowdsGroup of up to 6 | US$ 119 per person | 2h | 4.48★ · 786 | Every day · 17:00 | English |
| San Juan Catamaran Sunset Sail & Drinks IncludedGroup of up to 6 | US$ 119 per person | 2h | 4.93★ · 694 | Every day · 17:00 | English, Spanish |
| San Juan Bay: Catamaran Day Sail with Drinks & Harbor ViewsGroup of up to 6 | US$ 99 per person | 1h 30m | 4.88★ · 581 | Every day · 10:30 and 14:30 | English, Spanish |
| San Juan Bay Sailing Tour: Real Sailboat, Small GroupsGroup of up to 6 | US$ 99 per person | 1h 30m | 4.58★ · 201 | Every day · 10:30 and 15:00 | English, Spanish |
| Old San Juan Sunset Sail: Caribbean views with appetizers | US$ 125 per person | 2h | 4.72★ · 241 | Thu–Sun · 17:00 | English, Spanish |
| San Juan Bay Private Tour with Sangria and FortsPrivate | US$ 166 per person | 3h | 5.00★ · 55 | Every day · No fixed time | English, Spanish |
By what you need
- Private (2): San Juan: Private Sailing Tour & Old San Juan Forts (US$ 494 per group) · San Juan Bay Private Tour with Sangria and Forts (US$ 166 per person)
- Small groups (up to 15) (4): San Juan Bay Sunset Sailing Tour: Real Sailboat, No Crowds (US$ 119 per person) · San Juan Catamaran Sunset Sail & Drinks Included (US$ 119 per person) · San Juan Bay: Catamaran Day Sail with Drinks & Harbor Views (US$ 99 per person)
- With pickup (1): Day sail to Icacos Island from San Juan with snorkeling (US$ 155 per person)
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