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Crystal Serenity Crystal Cruises
9 nights · Caribbean · 10 ports
30 December – 8 January 2027
San Diego · Day at sea · Day at sea · Manzanillo · Puerto Vallarta … +5
Suite15 276 $
from 15 276 $ 1 697 $ per night
Details
EXPLORA III Explora Journeys
14 nights · Caribbean · 11 ports
6 – 20 December 2026
Miami · Cruz Bay · St. John`s · Terre-de-Haut · Gustavia … +6
Suite15 322 $
from 15 322 $ 1 094 $ per night
Details
EXPLORA III Explora Journeys
8 nights · Caribbean · 7 ports
28 December – 5 January 2027
San Juan · St. John`s · Pointe a Pitre · Tortola Island · Самана … +2
Suite15 504 $
from 15 504 $ 1 938 $ per night
Details
LE BOUGAINVILLE Ponant Cruises
7 nights · Caribbean · 9 ports
23 – 30 December 2026
Fort-de-France · Union Island · Tobago Cays · Mayreau Island · Port Elizabeth … +4
Suite15 641 $
from 15 641 $ 2 234 $ per night
Details
ILMA Ritz-Carlton Yacht Collection
7 nights · Caribbean · 8 ports
14 – 21 December 2026
San Juan · Sailing Time · St. George`s · Canouan · Soufriere … +3
Suite15 600 $
from 15 600 $ 2 229 $ per night
Details
LE LAPÉROUSE Ponant Cruises
12 nights · Caribbean · 12 ports
7 – 19 December 2026
Fort-de-France · Marie-Galante · Pigeon Island Beach · Soufrière · Union Island … +7
Suite16 598 $
from 16 598 $ 1 383 $ per night
Details
EXPLORA I Explora Journeys
14 nights · Caribbean · 12 ports
13 – 27 December 2026
Miami · Cruz Bay · St. John`s · Terre-de-Haut · Philipsburg … +7
Suite16 758 $
from 16 758 $ 1 197 $ per night
Details
ILMA Ritz-Carlton Yacht Collection
7 nights · Caribbean · 8 ports
21 – 28 December 2026
San Juan · Marigot · Terre-De-Haut (Marina Day) · Portsmouth · Sailing Time … +3
Suite18 200 $
from 18 200 $ 2 600 $ per night
Details
LE BELLOT Ponant Cruises
10 nights · Caribbean · 12 ports
8 – 18 December 2026
Puntarenas · Curú Wildlife Refuge · Drake Bay · Rio Esquinas · Coiba Island … +7
Suite18 468 $
from 18 468 $ 1 847 $ per night
Details
ILMA Ritz-Carlton Yacht Collection
7 nights · Caribbean · 8 ports
28 December – 4 January 2027
San Juan · Sailing Time · Bequia · Canouan · Soufriere … +3
Suite18 800 $
from 18 800 $ 2 686 $ per night
Details
Silver Ray SilverSea Cruises
11 nights · Caribbean · 8 ports
11 – 22 December 2026
Miami · San Juan · St. John`s · Basseterre · Gustavia … +3
Suite19 000 $
from 19 000 $ 1 727 $ per night
Details
LE BELLOT Ponant Cruises
10 nights · Caribbean · 12 ports
18 – 28 December 2026
Colón · Fort San Lorenzo (Colón) · San Blas Islands · Crossing the Panama Canal · Pearls Islands … +7
Suite19 654 $
from 19 654 $ 1 965 $ per night
Details
EXPLORA I Explora Journeys
15 nights · Caribbean · 13 ports
27 December – 11 January 2027
Miami · Puerto Plata · Catalina Island · Cruz Bay · Jost van Dyke … +8
Suite20 030 $
from 20 030 $ 1 335 $ per night
Details
LE LAPÉROUSE Ponant Cruises
10 nights · Caribbean · 12 ports
19 – 29 December 2026
Colón · Fort San Lorenzo (Colón) · San Blas Islands · Crossing the Panama Canal · Pearls Islands … +7
Suite20 634 $
from 20 634 $ 2 063 $ per night
Details
EXPLORA III Explora Journeys
15 nights · Caribbean · 12 ports
13 – 28 December 2026
San Juan · Perth · St. John`s · Basseterre · Grand Turk … +7
Suite20 862 $
from 20 862 $ 1 391 $ per night
Details
Viking Sea Viking Cruises
21 nights · Caribbean · 21 ports
15 December – 5 January 2027
San Juan · San Juan · Caribbean Sea (cruise) · Bridgetown · Caribbean Sea (cruise) … +16
With a balcony20 998 $
Suite35 998 $
from 20 998 $ 1 000 $ per night
Details
Seabourn Ovation Seabourn Cruises
14 nights · Caribbean · 13 ports
19 December – 2 January 2027
Bridgetown · Castries · Little Bay · St. John`s · CARAMBOLA BEACH … +8
Suite21 430 $
from 21 430 $ 1 531 $ per night
Details
LE PONANT Ponant Cruises
7 nights · Caribbean · 11 ports
19 – 26 December 2026
Marigot · Sandy Island · At sea aboard Le Ponant · Virgin Gorda · Cooper Island … +6
Suite21 614 $
from 21 614 $ 3 088 $ per night
Details
Seabourn Quest Seabourn Cruises
16 nights · Caribbean · 13 ports
20 December – 5 January 2027
Miami · San Juan · Perth · CARAMBOLA BEACH · Marigot … +8
Suite22 114 $
from 22 114 $ 1 382 $ per night
Details
EXPLORA I Explora Journeys
15 nights · Caribbean · 14 ports
20 December – 4 January 2027
San Juan · Basseterre · Tortola Island · Gustavia · Gustavia … +9
Suite23 347 $
from 23 347 $ 1 556 $ per night
Details
Four Seasons I Four Seasons Yachts
7 nights · Caribbean · 2 ports
20 – 27 December 2026
Miami; Florida · Philipsburg
Suite24 000 $
from 24 000 $ 3 429 $ per night
Details
Four Seasons I Four Seasons Yachts
7 nights · Caribbean · 2 ports
27 December – 3 January 2027
Philipsburg · Miami; Florida
Suite25 000 $
from 25 000 $ 3 571 $ per night
Details
EXPLORA III Explora Journeys
16 nights · Caribbean · 13 ports
28 December – 13 January 2027
San Juan · St. John`s · Pointe a Pitre · Tortola Island · Самана … +8
Suite25 354 $
from 25 354 $ 1 585 $ per night
Details
EXPLORA III Explora Journeys
16 nights · Caribbean · 13 ports
20 December – 5 January 2027
Miami · Ocho Rios · Catalina Island · Jost van Dyke · Philipsburg … +8
Suite27 611 $
from 27 611 $ 1 726 $ per night
Details