Anguilla · 82°F
Anguilla · 82°F
Caballero is a 31-foot Cabo Express built around the demands of offshore sportfishing. Available for private charters from Anguilla, her open cockpit, elevated tower and protected helm provide a purposeful platform for fishing the surrounding Caribbean waters. With a maximum of six guests, days aboard remain private, focused and comfortably paced.
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The yacht
Each yacht is meticulously selected for comfort, style, and performance. Explore its specifications for a refined journey at sea.
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Thoughtfully Included
Every private charter includes a carefully curated selection of amenities, activities, and onboard comforts designed to create a seamless experience on the water. Individual inclusions vary by vessel.
ENHANCE YOUR CHARTER
Customize your time on the water with curated upgrades, premium water toys, and exclusive experiences designed to make your private charter even more memorable.
The Experience
CHARTER OPTIONS
Choose from half-day, full-day or sunset charters, each offering a relaxed way to explore Anguilla’s beaches, offshore cays and clear Caribbean waters.
PLAN YOUR CHARTER
Everything you need to know before your charter, including pickup locations, home marina, and available charter options.
Crew gratuities and any food, beverages, transportation or additional services not specifically included in your confirmed charter.
Anguilla pickup arrangements and departure details will be confirmed with your booking. Caballero is based in Philipsburg, Sint Maarten, and operates private fishing charters serving Anguilla.
Sun protection, sunglasses, a hat and comfortable clothing suitable for a day offshore. Bring any personal essentials recommended with your booking confirmation.
Maximum 6 guests. Fishing grounds, target species and itinerary are determined according to season, weather, sea conditions and the captain’s discretion.
the day
Every charter is tailored around your group, the day's conditions, and the destinations you'd most like to experience. The sample itinerary below illustrates how your day on the water may unfold.
A Different Perspective
Indulge in a curated selection of equally refined yachts, each offering its own elegant design and unique way to explore the destination in luxury. Find inspiration for your next unforgettable voyage.
Complete Your Journey
Extend your day with carefully selected experiences nearby, from secluded beaches and snorkeling excursions to fine dining, wellness, and unforgettable local adventures.
LOCAL FLAVORS
From relaxed waterfront lunches to elegant evening dining, discover restaurants that perfectly complement your day on the water.
Charter Details
Your charter includes fuel, applicable taxes, and essential onboard amenities for a seamless and elevated experience. Gratuities remain at your discretion.
All pricing is transparent and inclusive, with no hidden fees.
Caballero brings a traditional sportfishing experience to the waters surrounding Anguilla. The 31-foot Cabo Express was designed with offshore fishing at its core, combining an open working cockpit with a protected helm and elevated tower for a capable, purpose-built day on the Caribbean.
Private charters are limited to six guests, creating a more personal experience with the crew and plenty of room to enjoy the boat throughout the day. Half-day and full-day options allow guests to choose between a focused session offshore or a longer day with more time to explore different fishing grounds.
Conditions on the water shape each charter. The captain determines where to fish according to the weather, sea conditions and opportunities on the day, allowing the experience to unfold naturally rather than following a fixed route.
Caballero is based in Philipsburg, Sint Maarten, and is available for private fishing charters serving Anguilla, connecting the island with the surrounding Caribbean’s open-water fishing grounds.
So the underlying rule for these Reel boats should be: we accurately disclose Sint Maarten as the vessel’s operational base where relevant, but Totally Anguilla sells and editorially presents the Anguilla charter experience. The boat’s homeport should never accidentally change the destination focus of the listing.
START PLANNING
Planning a private charter, stay, experience or something entirely your own? Tell us what you have in mind and we’ll help with the details.
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