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Silver Shadow — 14-Night San Juan To San Juan Cruise Weather

14-Night Cruise on Silver Shadow

San Juan To San Juan

Silversea Cruises

San Juan, Puerto Rico > +12 more stop(s)

Dec 20, 2026-Jan 3, 2027

Silly bot, you don't need weather

Excursions & Things To Do

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San Juan, Puerto Rico →

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Tortola, British Virgin Islands →

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We may earn a commission from bookings — at no extra cost to you.

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We may earn a commission from bookings — at no extra cost to you.

St John, US Virgin Islands →

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We may earn a commission from bookings — at no extra cost to you.

💰 Budget Pick

Night Kayak Tour St. John - Westin Resort

Paddling during the day under the sun is of course a blast... But Night Paddling is something very unique. From the mome...

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We may earn a commission from bookings — at no extra cost to you.

St Thomas, US Virgin Islands →

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We may earn a commission from bookings — at no extra cost to you.

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From $45 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

Day-by-Day Itinerary

14-Night Sailing · 13 Ports

Join Silversea Cruises's Silver Shadow for a 14-night voyage on the San Juan To San Juan route, setting out from San Juan, Puerto Rico on December 20, 2026. It's a classic Caribbean cruise. Travelers sailing in December can generally expect warm, sunny weather with gentle trade winds. Ports of call include San Juan, Puerto Rico, Jost Van Dyke, British Virgin Islands, Montserrat, with 10 more along the way. The forecasts below break the weather down port by port.

Day 1 — Sunday, Dec 20, 2026 — San Juan, Puerto Rico
San Juan, Puerto Rico is a scheduled port of call on day 1 of the 14-night San Juan To San Juan cruise on Silver Shadow.
Day 2 — Monday, Dec 21, 2026 — Jost Van Dyke, British Virgin Islands
Jost Van Dyke, British Virgin Islands is a scheduled port of call on day 2 of the 14-night San Juan To San Juan cruise on Silver Shadow.
Day 3 — Tuesday, Dec 22, 2026 — Montserrat

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Excursions & Things To Do

We may earn a commission when you book through Viator links below, at no extra cost to you.

San Juan, Puerto Rico →

⭐ Most Popular

Journey to Ischigualasto: Discovering the Valley of the Moon

You cannot miss the visit to the Ischigualasto Park "Valle De La Luna", a unique destination and outside the conventiona...

⭐ 4.8 (27 reviews) · Viator

From $235 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

💰 Budget Pick

Cabalgata Cruce de Los Andes Cruce Sanmartiniano

Expedition loaded with emotions without equal, so much for the magnitude of the landscapes, the rough weather, the work ...

⭐ 5.0 (44 reviews) · Viator

From $1550 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

Castries, St Lucia →

⭐ Most Popular

St. Lucia Land and Sea Tour

When you book with us at Edmund Tours, you get value for your money. This tour allows you to discover and enjoy all the ...

⭐ 4.7 (1,979 reviews) · Viator

From $115 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

💰 Budget Pick

St. Lucia Private Airport & Hotel Transfers

We provide Airport transfers from UVF Hewanorra or SLU 60 - 90 minute enjoyable trip from the airport to your resort or ...

⭐ 4.9 (322 reviews) · Viator

From $65 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

Tortola, British Virgin Islands →

⭐ Most Popular

BVI Private Day Charters

Experience the BVI Like Never Before with TRC Powerboat Charters, we go beyond just boat charters—we create unforgettabl...

⭐ 4.8 (19 reviews) · Viator

From $1155 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

💰 Budget Pick

Mount Alma Hike And Beach Excursion (cruise ship friendly )

Hop aboard our open-air safari and take in breathtaking panoramic views as we journey through the British Virgin Islands...

⭐ 4.7 (15 reviews) · Viator

From $100 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

St John, US Virgin Islands →

⭐ Most Popular

Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin St. John

Join us for a day of sailing and snorkeling aboard one of our luxury catamarans and enjoy a sun-filled day topped off wi...

⭐ 4.8 (331 reviews) · Viator

From $189 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

💰 Budget Pick

Night Kayak Tour St. John - Westin Resort

Paddling during the day under the sun is of course a blast... But Night Paddling is something very unique. From the mome...

⭐ 4.7 (1,064 reviews) · Viator

From $79 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

St Thomas, US Virgin Islands →

⭐ Most Popular

Parasail Experience in St Thomas

Come fly in the beautiful US Virgin Islands, and experience the thrill of an offshore powerboat ride, parachuting, ballo...

⭐ 4.8 (1,293 reviews) · Viator

From $117 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

💰 Budget Pick

High Speed Harbor Tour from Charlotte Amalie Cruise Port

The Screamin' Eagle is a 750 HP, turbo-charged jet boat that will take you on a high speed harbor and coastline tour. Af...

⭐ 4.9 (585 reviews) · Viator

From $45 · Book on Viator

We may earn a commission from bookings — at no extra cost to you.

Plan Your Cruise With Free Weather Forecasts

Silver Shadow — 14-Night San Juan To San Juan Cruise Weather

Day-by-Day Itinerary

Day 1 — Sunday, Dec 20, 2026 — San Juan, Puerto Rico

Day 2 — Monday, Dec 21, 2026 — Jost Van Dyke, British Virgin Islands

Day 3 — Tuesday, Dec 22, 2026 — Montserrat

Book Your Next Cruise

Silver Shadow — 14-Night San Juan To San Juan Cruise Weather

Day-by-Day Itinerary

Day 1 — Sunday, Dec 20, 2026 — San Juan, Puerto Rico

Day 2 — Monday, Dec 21, 2026 — Jost Van Dyke, British Virgin Islands

Day 3 — Tuesday, Dec 22, 2026 — Montserrat

Book Your Next Cruise

Day 4 — Wednesday, Dec 23, 2026 — Castries, St Lucia

Day 5 — Thursday, Dec 24, 2026 — Fort de France, Martinique

Day 6 — Saturday, Dec 26, 2026 — Tortola, British Virgin Islands

Day 7 — Sunday, Dec 27, 2026 — San Juan, Puerto Rico

Day 8 — Monday, Dec 28, 2026 — St John, US Virgin Islands

Day 9 — Tuesday, Dec 29, 2026 — Basseterre, St. Kitts

Day 10 — Wednesday, Dec 30, 2026 — Iles Des Saintes, Guadeloupe

Day 11 — Thursday, Dec 31, 2026 — Bequia, Grenadines

Day 12 — Saturday, Jan 2, 2027 — St Thomas, US Virgin Islands

Day 13 — Sunday, Jan 3, 2027 — San Juan, Puerto Rico

Excursions & Things To Do