December 10–20, 2026 · Miami to San Juan · 10 Days · 9 Ports
Sail the Caribbean & Central America in ultra-luxury — butler service in every suite, all-inclusive indulgence, and boutique ports experienced with grace.
December 10–20, 2026
If you're searching for the best luxury Caribbean cruise December 2026, here is why this sailing stands apart:
Butler service in every suite
Small-ship intimacy (approximately 392 guests)
All-inclusive dining, premium beverages & gratuities
Spacious ocean-view suites
Multiple elegant dining venues
Access to quieter, boutique Caribbean and Central America ports
Elevated onboard enrichment and entertainment
This is timeless luxury — understated, polished, and personal.
The Journey
10 Days · 9 Ports · 8 Countries
Day 1 — Dec 10
United States
Embarkation
Day 2–3 — Dec 11–12
Butler service, fine dining, enrichment
Day 4 — Dec 13
U.S. Virgin Islands
5 excursions available
Day 5 — Dec 14
St. Maarten
10 excursions available
Day 6 — Dec 15
Saint Kitts and Nevis
12 excursions available
Day 7 — Dec 16
Guadeloupe
8 excursions available
Day 8 — Dec 17
Martinique
13 excursions available
Day 9 — Dec 18
Montserrat
5 excursions available
Day 10 — Dec 19
British Virgin Islands
4 excursions available
Day 11 — Dec 20
Puerto Rico
Disembarkation
Itinerary based on Silversea voyage SS261210010. Ports and schedule subject to change. December is one of the most desirable times to sail the Caribbean.
100% Recommended
Lilia M. — Delano, MN · Traveled to Hawaii, USA
"Heni did an amazing job making sure all of our wants for this trip to the island of Hawaii were fulfilled. From relaxing at the most wonderful black sand beach to hiking the most breathtaking waterfalls we did it all thanks to her!"
Steph Lynn — Vancouver, WA · Traveled to Europe
"Had a Wonderful time away for our anniversary, Loved the activities planned and all the sites on the itinerary. It was a magical trip. Thank You for all your hard work putting this together it was really special."
Cassandra — Brookings, SD · Traveled to Edinburgh, Scotland
"I would highly recommend working with Heni on any travel arrangements that you may need. She did a great job in helping us with accommodations during Edinburgh's annual Art Festival as well as arranging fun guided tours and exciting places to eat."
Emma — Minneapolis · Traveled to Hawaii, USA
"Heni provided an excellent itinerary with fantastic accommodations! Her knowledge of the best restaurants and hidden gems is exquisite!"
Common Questions
Silver Shadow · Miami to San Juan · December 10–20, 2026
I'll reach out personally within 24 hours with pricing, suite options, and everything you need to decide. No obligation.
Searching For
This 10-day sailing from Miami to San Juan delivers timeless elegance, personalized service, and access to 9 ports across 8 countries. Based in Minnesota, Dream Travels by Heni specializes in ultra-luxury cruise planning for discerning travelers nationwide.