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Go beyond a day trip. Wake up anchored at a deserted island, watch the sunset from the deck, and explore Puerto Rico's most remote coastlines at your own pace.
Puerto Rico's best-kept secrets — Culebra, Vieques, Caja de Muertos, La Cordillera — are too far apart for a single day trip. A multi-day charter lets you visit them all without rushing.
The first day at sea strips away the stress. By the second morning, anchored in crystal-clear water with nowhere to be, you've found a rhythm most vacations never reach.
There's no resort view that compares to watching the sun rise over the Caribbean from your own private deck, coffee in hand, surrounded by nothing but ocean.
Day-trip boats leave by late afternoon. By evening, the most popular beaches and snorkeling spots are completely empty — and they're all yours.
Overnight anchorages at uninhabited cays, bioluminescent bays after dark, fishing for your own dinner — this is the Puerto Rico most visitors never see.
Every multi-day charter is fully customizable. These sample itineraries showcase what's possible — your captain will tailor the route to weather, your interests, and the best conditions of the day.
Perfect for a long weekend getaway
Depart from San Juan or Fajardo in the morning, sailing east toward Culebra Island. Arrive at Flamenco Beach for a late lunch and swimming. Afternoon snorkeling at Carlos Rosario Beach — a protected reef with some of the best underwater visibility in the Caribbean. Anchor for the night in Ensenada Honda and enjoy sunset from the deck with appetizers and cocktails.
Morning snorkeling at the Luis Peña Channel Nature Reserve — a marine sanctuary with sea turtles, rays, and vibrant coral. Cruise past Culebrita's lighthouse (the oldest in the Caribbean still standing) before heading back toward the mainland. Arrive in the late afternoon with a lifetime of memories.
The most popular multi-day option
Depart from San Juan, heading east through La Cordillera natural reserve. Stop at Icacos Island for pristine beach time and snorkeling in shallow turquoise waters. Continue to Palomino Island for paddleboarding and a beach lunch. Anchor near Fajardo for a sunset dinner on board.
Early morning crossing to Culebra — about 17 nautical miles from Fajardo. Full day exploring: Flamenco Beach in the morning, Carlos Rosario for reef snorkeling, and Tamarindo Beach for sea turtles. Dine at a local restaurant in Dewey, Culebra's charming main town, or enjoy a chef-prepared dinner on board.
Sail south to Vieques, stopping at Sun Bay Beach — a wide crescent of golden sand backed by coconut palms. If conditions allow, visit the Bioluminescent Bay at sunset for one of the most magical natural phenomena on Earth. Return to the mainland in the evening, arriving under the stars.
The ultimate Caribbean sailing experience
Depart San Juan and head east. Stop at the uninhabited cays of La Cordillera for your first swim and snorkel. Anchor overnight near Palomino or Icacos Island.
Cross to Culebra in the morning. Afternoon at Flamenco Beach — consistently ranked among the top 10 beaches in the world. Watch the sunset from Punta Melones.
Full day in Culebra: snorkeling at Carlos Rosario reef, kayaking through mangrove channels, and a hike to the WWII tank on Flamenco. Optional trip to Culebrita for the historic lighthouse and tidal pools.
Sail south to Vieques. Explore the wild horses that roam free, visit the former military beaches now part of the Wildlife Refuge, and snorkel at Blue Beach (La Chiva).
Relaxed morning at Sun Bay. Afternoon exploring the eastern coast. At dusk, visit Mosquito Bay — the brightest bioluminescent bay in the world — for an unforgettable night kayak or swim.
Sail along Puerto Rico's southern coast to Caja de Muertos (Coffin Island), an uninhabited nature reserve with pristine reefs, sea turtles, and a 19th-century lighthouse. This is where the Caribbean truly feels untouched.
Final day along the western coast, passing the cliffs of Cabo Rojo and the surfing beaches of Rincón. Return to your home port in the late afternoon with stories that will last a lifetime.
Explore our detailed day-trip guides:
Not every boat is built for overnight stays. Multi-day charters require vessels with proper sleeping quarters, galley, and onboard systems for extended time at sea.
Enclosed sleeping quarters with real beds — not just bench cushions. Most charter yachts offer 1-3 cabins with queen or full-size berths.
A proper kitchen for meal preparation with refrigeration, stove, and storage for provisions. Multi-day charters include either a private chef or fully stocked galley.
Enclosed marine head with freshwater shower. Larger vessels have multiple bathrooms so you're never waiting in line.
Onboard generator for air conditioning, lighting, device charging, and water heating. Essential for comfort during overnight stays.
Large freshwater capacity for drinking, cooking, and showering over multiple days without the need to return to port.
Generator-powered A/C keeps cabins comfortable for sleeping, even on the warmest Caribbean nights.
Explore our vessels and contact us to discuss which are best suited for your multi-day adventure.
Browse Our FleetMulti-day charters include everything from a single-day trip — plus overnight essentials. Here's what's covered in your charter fee.
Multi-day charters go beyond single-day trips with dedicated sleeping quarters, full meal service, and overnight amenities. Your crew handles provisioning, navigation, and all logistics — you just enjoy the journey.
Multi-day charter pricing depends on the vessel, duration, season, and provisioning level. Here are typical ranges to help you plan.
$3,000 – $5,000
Ideal for a long weekend. Includes overnight anchorage, all meals, and one or two destination stops.
$5,000 – $8,000
Our most popular multi-day option. Covers three destinations, full provisioning, and two nights aboard.
$10,000 – $20,000+
The ultimate Caribbean experience. A full circumnavigation of Puerto Rico's islands with complete luxury service.
Every multi-day charter is a custom quote. Contact us with your dates, group size, and preferences for a personalized proposal.
Multi-day charters require more advance planning than day trips. Here's when to start for the best availability and preparation.
Book as early as possible for peak season. The best vessels and dates fill up fast, especially during the holiday season and spring break.
Good availability for May–November charters. More flexibility on vessel choice and itinerary customization.
Some availability may remain if you're flexible on dates and vessel. Not recommended for large groups or specific vessel requests.
Confirm dietary requirements, special celebration requests, and any activity preferences. Your crew will handle all provisioning and preparation.
Packing for a yacht charter is different from packing for a hotel stay. Space is limited, and soft-sided bags are essential.
Pro tip: Roll your clothes instead of folding — they'll fit better in the cabin and wrinkle less.
It depends on the vessel. Most of our charter yachts accommodate 2-6 overnight guests in private cabins with real beds. Larger vessels can handle 8+ guests. Contact us with your group size and we'll recommend the ideal vessel.
Yes. Multi-day charters include full meal service — either a private chef who prepares everything on board, or a pre-provisioned gourmet package. We accommodate dietary restrictions and preferences with advance notice.
Your captain monitors weather conditions constantly and adjusts the itinerary for safety and comfort. Puerto Rico offers multiple sheltered anchorages, so there's always a protected alternative. If conditions are truly unsafe, we'll reschedule or modify the route.
Absolutely. Every multi-day itinerary is a starting point, not a fixed schedule. Want to spend an extra day in Culebra? Skip Vieques and head south? Your captain will work with you to create the perfect route based on weather, your interests, and conditions.
Most of our larger vessels offer cellular-based Wi-Fi that works near Puerto Rico's coastline. Coverage can be limited near remote islands like Culebra and Vieques. We recommend treating your charter as a digital detox — but if you need connectivity, let us know and we'll match you with an equipped vessel.
No — if you're a US citizen. Puerto Rico is a US territory, so no passport is required for Americans. You'll need a valid government-issued ID. International visitors need the same documentation required for US entry (passport and visa if applicable), not any additional Puerto Rico-specific documents.
Every multi-day charter is custom-planned to match your group, your dates, and your dream itinerary. Tell us what you're envisioning, and we'll craft a proposal that makes it real.