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Step aboard Tradition for a six-hour day sail to Anguilla’s Prickly Pear Cays—snorkel the reef, enjoy a lobster beach barbecue, and experience authentic Caribbean sailing aboard a historic sloop. Limited to 12 guests, the trip blends hands-on seamanship with relaxed beach time.
Step aboard Tradition for a six-hour day sail to Anguilla’s Prickly Pear Cays—snorkel the reef, enjoy a lobster beach barbecue, and experience authentic Caribbean sailing aboard a historic sloop. Limited to 12 guests, the trip blends hands-on seamanship with relaxed beach time.
The deck rocks gently as Tradition slips out of Sandy Ground, sails filling with trade wind breath. Morning mimosas circulate; the crew runs lines with practiced economy while the island of Anguilla recedes into a strip of green and limestone. By mid-morning the Prickly Pear Cays appear: low, white beaches framing shallow reefs that glint aquamarine in the sun.
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Operated by Tradition Sailing Charters · Sandy Ground, Anguilla
The deck rocks gently as Tradition slips out of Sandy Ground, sails filling with trade wind breath. Morning mimosas circulate; the crew runs lines with practiced economy while the island of Anguilla recedes into a strip of green and limestone. By mid-morning the Prickly Pear Cays appear: low, white beaches framing shallow reefs that glint aquamarine in the sun.
The trip traces centuries of Caribbean seamanship. Tradition itself began life in 1978 as a working sloop, part of a coastal trading culture that moved goods between islands. The cays sit on limestone platforms formed by coral growth and uplift, with sandy spits that attract nesting seabirds and the occasional leatherback during migration.
On shore, a Caribbean barbecue—often lobster—replaces the day’s work with hospitality: rum punch, fresh watermelon and a tiki-bar vibe that feels purposeful rather than staged. Snorkeling here is reef-focused; expect branching corals, parrotfish, and a steady current that invites drift-through viewing. The return sail is brighter and brisker: an upwind beat toward Road Bay that rewards those who watch the horizon and learn the rhythm of sheets and telltales.
Practical notes: the excursion runs about six hours, suitable for most fitness levels, and is limited to 12 guests. Bring reef-safe sunscreen, a light wind jacket for the return, and shoes that handle sand and boat decks. If you want to help raise sail, wear non-marking soles and be ready for short bursts of activity. Timing your visit in the dry season improves visibility for snorkeling and keeps the sails fuller on return legs.
Yes—use of snorkel equipment and swim aids is included; feel free to bring a preferred mask if you have one.
The vessel hosts a maximum of 12 guests, keeping the experience personal and allowing quick shore landings.
Lunch (typically Caribbean lobster or a beach barbecue) and unlimited drinks from an open bar are included in the excursion.
Trips may be canceled for safety or insufficient numbers; refunds or alternatives are offered if canceled at least 24 hours before departure.
Tradition Sailing Charters operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
The deck rocks gently as Tradition slips out of Sandy Ground, sails filling with trade wind breath. Morning mimosas circulate; the crew runs lines with practiced economy while the island of Anguilla recedes into a strip of green and limestone. By mid-morning the Prickly Pear Cays appear: low, white beaches framing shallow reefs that glint aquamarine in the sun.
The deck rocks gently as Tradition slips out of Sandy Ground, sails filling with trade wind breath. Morning mimosas circulate; the crew runs lines with practiced economy while the island of Anguilla recedes into a strip of green and limestone. By mid-morning the Prickly Pear Cays appear: low, white beaches framing shallow reefs that glint aquamarine in the sun.
The trip traces centuries of Caribbean seamanship. Tradition itself began life in 1978 as a working sloop, part of a coastal trading culture that moved goods between islands. The cays sit on limestone platforms formed by coral growth and uplift, with sandy spits that attract nesting seabirds and the occasional leatherback during migration.
On shore, a Caribbean barbecue—often lobster—replaces the day’s work with hospitality: rum punch, fresh watermelon and a tiki-bar vibe that feels purposeful rather than staged. Snorkeling here is reef-focused; expect branching corals, parrotfish, and a steady current that invites drift-through viewing. The return sail is brighter and brisker: an upwind beat toward Road Bay that rewards those who watch the horizon and learn the rhythm of sheets and telltales.
Practical notes: the excursion runs about six hours, suitable for most fitness levels, and is limited to 12 guests. Bring reef-safe sunscreen, a light wind jacket for the return, and shoes that handle sand and boat decks. If you want to help raise sail, wear non-marking soles and be ready for short bursts of activity. Timing your visit in the dry season improves visibility for snorkeling and keeps the sails fuller on return legs.