On the Water · Sailing
Charters, day sails and schools
Fajardo's Puerto del Rey is the hub: most boats leave from there, and the trip most sold is a catamaran day to Cayo Icacos. Bareboat supply is small. Before you book, ask for the Tourism Company's nautical-tourism certification and the captain's Coast Guard license.
Day sails
| Operator | Base | Trips | Published prices |
|---|---|---|---|
| East Island Excursions | Puerto del Rey, Fajardo | Catamaran day trips to Icacos, Vieques and Culebra; sunset sails. "Since 1994"; a Blue Flag operator (its site)Sailing catamarans Zatara and Bellaventuras; power catamarans Ocean Ray and Eco Isleño | Icacos half day: $110 a personIcacos: $135 a personVieques: $150 a personCulebra: $160 a personPrivate charter: $2,427 to $2,510 |
| Caribe Bliss | Puerto del Rey, Fajardo787-439-1672 | Icacos snorkel tour (5 h, ages 3 and up) and private trips to Icacos, Palomino, Culebra and Vieques; a Blue Flag operator (its site)Tortuga (up to 40 passengers); a Grady-White for private charters (up to 10) | Icacos snorkel tour: from $99Private, 4 to 6 h: from $1,150 |
| Puerto Rico Sailing Trips (catamaran Janise) | Puerto del Rey, Fajardo | Small-group day sails, at most 6 guests "to follow its USCG boat permits" | Day charter: $285 an adult (reseller listing)unconfirmed |
| Spread Eagle II | Renaissance Villa Marina, Fajardo | Icacos day sail on a 51-ft sailing catamaran, about 5.5 hours from 9:00 | Icacos day sail: $130 to $155 (listings disagree) |
| Sail PRunconfirmed | San Juan Bay Marina | Two-hour sunset sails in San Juan Bay on a 37-ft catamaran, at most 6 guests | Sunset sail: $119 an adult (reseller)unconfirmed |
Prices as published on Oct 18, 2026; they change by season.
Sources (7)
- East Island Excursions (operator) (opens in a new tab)
- Caribe Bliss (operator) (opens in a new tab)
- Discover Puerto Rico, Janise sailing charters (opens in a new tab)
- AAA TripCanvas listing (opens in a new tab)
- Discover Puerto Rico, Spread Eagle II (opens in a new tab)
- Happy to Visit listing (opens in a new tab)
- Travelocity listing (opens in a new tab)
Bareboat and skippered charters
Sail Caribe
- Contact
- 787-889-1978; toll-free 888-234-2050; website
- Offers
- Bareboat and skippered charters, day sails, ASA courses (101, 103, 104, 114), "Long Weekend in Culebra"
- Fleet
- Six boats listed on Oct 16, 2026: Lagoon 42 (two), Lagoon 46, a 42-ft and a 46-ft catamaran, and a 44-ft monohull (Sun Odyssey 440)
- Sun Odyssey 440, a week
- $5,470 to $8,000 by season
- Lagoon 42, a week
- $7,500 to $10,500 by season
- Lagoon 46, a week
- $11,150 to $15,000 by season
- ASA instructor-skipper, a day
- $350 to $495
- Good to know
- Peak season Dec 20 to Jan 9 and Feb 12 to Apr 4; lowest Jun 7 to Oct 31 and Dec 7 to 19. $500 cash deposit; boarding 10:00 with a 2 to 3 hour briefing. No pets, no smoking, no scuba from the boats. ASA liveaboard courses need five nights.
Sailing schools
| School | Base | Courses |
|---|---|---|
| Puerto Rico Sailing School | Isleta Marina, Fajardo(787) 370-0909 | ASA 101, 103, 104 |
| Sail Caribe | Puerto del Rey, Fajardo | ASA 101, 103, 104, 114 (catamaran)Liveaboard courses on charter, five nights minimum |
| Academia de Vela, Club Náutico de San Juan | Club Náutico de San Juan | Federation-sanctioned youth and racing program; US Sailing status unconfirmedunconfirmedRuns IC24, dinghy and youth regattas; a summer camp ending with the Summer Cup |
| Marlin Sailing School | Former Roosevelt Roads base, Ceiba | Not US Sailing per the sources found (unconfirmed)unconfirmedYouth from age 7; 787-409-2001 (2021 article) |
The national sailing authority since 1963 and a member of the Caribbean Sailing Association; info@sailingpur.com, +1 787-300-1600 (CSA listing). No US Sailing accredited school in Puerto Rico was confirmed.
Sources (6)
- ASA school listing, Puerto Rico Sailing School (opens in a new tab)
- Sail Caribe ASA courses (operator) (opens in a new tab)
- Federación de Vela de Puerto Rico (opens in a new tab)
- El Nuevo Día, sailing at the former Roosevelt Roads base (2021) (opens in a new tab)
- Primera Hora, sailing in Ceiba (opens in a new tab)
- Caribbean Sailing Association members (opens in a new tab)
Not listed, and why
- The Moorings (Puerto del Rey base) Announced for 2017; its Puerto Rico pages now return 404 and the base's status is unconfirmed.
- Capitana Sailing School A directory listing only.