All 7 options, side by side
✓ 2026-09-29| Option | Price | Per person | Length | Rating | Cancellation | Extra fee |
|---|---|---|---|---|---|---|
| San Juan: Private Sailing Tour & Old San Juan Forts | US$ 494 per group | US$ 82 (6 share) | 2h–3h | 4.84★ · 163 | free | — |
| San Juan Sunset Pontoon Boat Tour & Rum PunchBest value | US$ 99 p.p. | US$ 99 | 1h 30m | 4.63★ · 1,477 | free | — |
| San Juan Bay: Catamaran Day Sail with Drinks & Harbor Views | US$ 99 p.p. | US$ 99 | 1h 30m | 4.88★ · 570 | free | — |
| San Juan Bay: Small Group Sailing Tour & DrinksOur pick | US$ 99 p.p. | US$ 99 | 1h 30m | 4.58★ · 201 | free | — |
| San Juan Catamaran Sunset Sail & Drinks IncludedTop rated | US$ 119 p.p. | US$ 119 | 2h | 4.93★ · 688 | free | — |
| Day sail to Icacos Island from San Juan with snorkeling | US$ 155 p.p. | US$ 155 | 5h 30m | 4.72★ · 275 | free | — |
| Icacos Island Catamaran Tour: Water Slides & Feast | US$ 195 p.p. | US$ 195 | 6h | 4.83★ · 168 | free | — |
Real price per person across the 7 options: US$ 82–US$ 195 (median US$ 99).
Default order: real price per person — the group price divided by the seats it includes.
San Juan Sunset Pontoon Boat Tour & Rum PunchYou board a pontoon at the San Juan Bay Marina at 6:10 PM and spend ninety minutes floating past Old San Juan's 500-year-old walls, El Morro Fort, Paseo la Princesa, and the Bacardi Distillery as the sun drops. Local beer, rum punch, and snacks come with the ride. You return to the marina before dark, having seen the landmarks from a perspective most visitors miss — the water — without arranging transport or timing it yourself.Is it for me?Book this if you want to see Old San Juan's colonial landmarks from a perspective most visitors skip — the water at sunset — without arranging your own boat or timing the light yourself. The fixed 6:10 PM departure and 1.5-hour duration fit into an evening without eating up your whole day.
San Juan Catamaran Sunset Sail & Drinks IncludedYou board a small catamaran, sail San Juan Bay for two hours as the sun sets, and drink complimentary rum punch or wine while the captain points out La Fortaleza and the San Juan Gate from the water. No shoes, groups of two to six, and you're back on land before full dark.Is it for me?Right for couples or small groups wanting a sunset moment on the water without the noise of a larger cruise. Plan to arrive 20 minutes early and go barefoot — that's the trade for a calm, intimate sail.
San Juan Bay: Catamaran Day Sail with Drinks & Harbor ViewsYou’ll board a catamaran in San Juan Bay for 90 minutes of sailing with complimentary drinks like mimosas or rum punch (not an open bar). Watch city landmarks glide by — including the old San Juan Gate — while your captain shares stories and you relax barefoot on deck. It’s quiet, easygoing, and leaves you with that salty breeze feeling long after you’re back on land.
San Juan Bay: Small Group Sailing Tour & DrinksYou’ll board a real sailboat in San Juan Bay for a small group sailing tour with local drinks included. Expect up-close views of Old San Juan’s forts, stories from your captain, and moments where you forget about everything except the wind and sea spray. If you’re lucky, dolphins might show up too.
San Juan: Private Sailing Tour & Old San Juan FortsYou sail out from a historic fishing dock in San Juan Bay, passing Old San Juan's colonial forts, the Governor's Mansion, and industrial harbor views before heading toward open water. The tour includes a hands-on sailing lesson if you want one, or a bareboat option if you're experienced. All fees, safety gear, coolers, and ice are included; you choose morning, afternoon, or sunset. The boat stays small and the schedule is yours to set.Is it for me?Book this if you want to see Old San Juan's forts and harbor from the water without joining a group tour — the private boat and flexible timing mean you set the pace, and the optional sailing lesson turns it into something you actually learn instead of just watch.
Day sail to Icacos Island from San Juan with snorkelingA day sail from San Juan to Icacos Island aboard the SPREAD EAGLE II, a 51-foot catamaran, includes the 40 to 50-minute sail, snorkeling equipment, a sandwich buffet lunch, and hotel pickup from Condado, Old San Juan or Isla Verde. The reefs hold parrot fish, foureye butterfly fish, sergeant majors and wrasse; crew members carry fish and coral identification charts on board. The tour runs 5.5 hours total, with a live guide in English or Spanish.Is it for me?You're staying in San Juan and want a full day on the water without arranging a boat, a guide or the snorkeling gear yourself—the catamaran, the crew and the lunch all come together, so you show up at your hotel and the rest unfolds on schedule.
Icacos Island Catamaran Tour: Water Slides & FeastThis is a 6-hour all-inclusive catamaran tour from Puerto Rico to Icacos Island and the Cordillera Cays aboard the Getaway Too, a 54-foot luxury sailing vessel. You board with a maximum of 49 guests, explore pristine Caribbean waters with a guided snorkeling clinic, play on water slides and swings, and return to the boat for an authentic Puerto Rican feast with unlimited tropical rum drinks. Arrive 1 hour before departure; the tour operates in English and Spanish with a live guide.Is it for me?At 6 hours, this tour fills most of a free afternoon without consuming your entire day — you can book it, return by evening, and still have time for dinner elsewhere. The small group size and onboard amenities mean you're not managing logistics or hunting for shade; the crew handles the details so you can actually relax.
Frequently asked questions
Can I book with free cancellation?
Yes: 7 of the 7 options offer free cancellation, so you can book now and confirm your plans later.
How long do these experiences last?
Most options last up to 2 hours. There are also shorter and longer formats to fit your itinerary.
Which one is the travelers' favorite?
San Juan Bay: Small Group Sailing Tour & Drinks is the travelers' favorite, rated 4.58 out of 5 across 201 reviews.
More things to do in San Juan
Old San Juan Tours32 optionsSnorkeling San Juan12 optionsSan Juan Food16 optionsZiplining San Juan11 optionsOld San Juan Walking Tour15 optionsOld San Juan Food Tour5 optionsSan Juan Castle Tour5 optionsATV Tours in San Juan5 optionsBoat Tours in San Juan20 optionsIcacos Island Tours20 optionsKayaking San Juan6 optionsSan Juan Airport Taxi14 optionsRainforest Tour from San Juan25 optionsDay Trips from San Juan5 optionsSan Juan Bay5 optionsLuquillo Beach Jet Ski Rental11 optionsWaterfalls near San Juan23 optionsLuquillo Beach Rainforest Tours6 options
