Panoramic view of a warm, sunny Culebra beach in Puerto Rico, a winter escape destination
Winter Charters

Winter Vacation Private Yacht Charters in Puerto Rico

Trade the cold for turquoise water — private charters to Icacos, Palomino & the US Virgin Islands, warm all winter long.

☀️ Warm Year-Round🏝️ Icacos & Palomino🌎 USVI Trips Available💬 Custom Quote
21
Boats Available
15-20
Minutes to Icacos & Palomino
240
5-Star Reviews
100%
Private & Custom
Fajardo · Icacos, Palomino & USVI

Escape the Cold on a Private Puerto Rico Charter

Puerto Rico's tropical climate makes it a go-to winter escape for travelers from colder parts of the US and Canada. Instead of a crowded resort pool, a private boat charter puts your group directly on the warm, turquoise water — Icacos and Palomino are both roughly 15–20 minutes from Marina Puerto del Rey in Fajardo.

For a longer winter getaway, a full-day charter to Culebra, Vieques, or the US Virgin Islands is also available for travelers who want to island-hop further out. Winter is high season in Puerto Rico, so we recommend messaging us with your travel dates as early as possible.

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Private boats anchored in turquoise water near Culebra Puerto Rico, a warm winter escape
Where To Go

Winter Escape Destinations in Puerto Rico

Why Puerto Rico for Winter

Unlike a lot of winter destinations, Puerto Rico's water and weather stay warm year-round — no wetsuits, no seasonal closures. It's a straightforward flight from much of the US East Coast, which makes it an easy winter escape without the long-haul travel of other tropical destinations.

Book Early — Winter Is High Season

Winter is one of our busiest seasons as travelers flee the cold. Popular boats and dates book up, so message us with your travel window as early as possible to lock in your charter.

Booking Request

Request Your Winter Charter

Tell us your group size, dates and which destination interests you — we'll send boat options and a custom quote.

We reply within minutes by WhatsApp or email · no payment required to submit a request.

Every Boating Puerto Rico Charter

All-Inclusive, By Default

Every private charter includes the same standard inclusions — no hidden fees.

USCG-Licensed CaptainEvery charter, every boat
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First MateOn 6h+ and larger-boat charters
Fuel IncludedNo surprise fuel surcharges
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Water, Sodas & IceStocked and ready on board
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BeerIncluded for guests 21+
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Fresh Fruit & SnacksLight bites throughout the trip
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Sandwiches or WrapsOn 6-hour and 8-hour charters
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Bluetooth Music & Floating MatYour playlist, your afternoon on the water

Flying in from out of town? Roundtrip transportation from your San Juan hotel is $40 per person, so you can skip the rental car.

Gallery

Real Winter Charters — Puerto Rico

Explore Our Fleet

Explore Our Boat Charters

FAQ

Winter Vacation Puerto Rico Yacht Charter — FAQ

Yes — Puerto Rico has a tropical climate year-round, which is exactly why it's a popular winter escape for travelers from colder parts of the US and Canada.
A 6-hour or 8-hour private charter to Icacos or Palomino covers a full island day, while a full-day trip to Culebra, Vieques, or the US Virgin Islands works well for a longer winter getaway.
Yes — winter is high season in Puerto Rico as travelers escape the cold, so we recommend booking your dates as early as possible.
A USCG-licensed captain, fuel, water, sodas, ice and beer, fresh fruit and snacks, sandwiches or wraps on longer charters, a floating mat, and Bluetooth music — all standard, no hidden fees.
Yes — we offer full-day charters from Fajardo to the US Virgin Islands for travelers who want to island-hop during their winter trip.
Message us on WhatsApp with your travel dates and group size and we'll send boat options and a custom quote before you even land.

Plan Your Winter Escape Charter

Send us your group size, dates, and which destination interests you — we'll send options and an exact quote.

💬 WhatsApp — Ask Now 📞 (787) 717-3779

Custom quote by request · No payment required to inquire · Instant reply

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