Enquire
← Modify search

Caribbean voyages

1027 voyages found

Cruise Line
Destination
Dates
Duration

1027 voyages match your search

Not sure where to start? Tell us what matters most and we will shortlist the right voyages for you — no commitment required.

Speak to an advisor
Grenadines & Windwards yachting
Emerald Azzurra
Grenadines & Windwards yachting
7 nights 7 Ports of Call  ·  Departs 27 Dec 2026
From
$8,263
per person
Embarkation Bridgetown
Barbados
27 Dec 2026
Disembarkation Bridgetown
Barbados
3 Jan 2027
Journey type Fly - Cruise
✓ Alcohol included ✓ Daytime activities ✓ Flights included ✓ Gratuities included ✓ Meals included ✓ Shore excursions included ✓ WiFi included
Request a Proposal View details
A Journey of Sparkling Skies & Bright Beginnings
Explora I
A Journey of Sparkling Skies & Bright Beginnings
8 nights 8 Ports of Call  ·  Departs 27 Dec 2026
From
$7,590
per person
Embarkation Miami
United States
27 Dec 2026
Disembarkation San Juan
Puerto Rico
4 Jan 2027
Journey type Cruise only (please call for flight options)
✓ Alcohol included ✓ Daytime activities ✓ Gratuities included ✓ Meals included ✓ WiFi included
Request a Proposal View details
Classic Caribbean
Wind Surf
Classic Caribbean
7 nights 6 Ports of Call  ·  Departs 26 Dec 2026
From
$2,822
per person
Embarkation Philipsburg
Sint Maarten
26 Dec 2026
Disembarkation Philipsburg
Sint Maarten
2 Jan 2027
Journey type Cruise only (please call for flight options)
✓ Alcohol included ✓ Daytime activities ✓ Meals included ✓ Soft drinks, tea and coffee included
Request a Proposal View details
Star Collector: Caribbean Explorations
Wind Surf
Star Collector: Caribbean Explorations
14 nights 10 Ports of Call  ·  Departs 26 Dec 2026
From
$5,822
per person
Embarkation Philipsburg
Sint Maarten
26 Dec 2026
Disembarkation Philipsburg
Sint Maarten
9 Jan 2027
Journey type Cruise only (please call for flight options)
✓ Alcohol included ✓ Daytime activities ✓ Meals included ✓ Soft drinks, tea and coffee included
Request a Proposal View details
Renaud Capuçon’s Caribbean Celebration: 50 Years in Paradise
Le Bougainville
Renaud Capuçon’s Caribbean Celebration: 50 Years in Paradise
7 nights 8 Ports of Call  ·  Departs 23 Dec 2026
From
$8,172
per person
Embarkation Fort-de-France
Martinique
23 Dec 2026
Disembarkation Fort-de-France
Martinique
30 Dec 2026
Journey type Cruise only (please call for flight options)
✓ Alcohol included ✓ Daytime activities ✓ Meals included ✓ Shore excursions included ✓ WiFi included
Request a Proposal View details
Caribbean Celebration
Marina
Caribbean Celebration
14 nights 9 Ports of Call  ·  Departs 22 Dec 2026
From
$4,328
per person
Embarkation Miami
United States
22 Dec 2026
Disembarkation Miami
United States
5 Jan 2027
Journey type Cruise only (please call for flight options)
✓ Daytime activities ✓ Gratuities included ✓ Meals included ✓ Soft drinks, tea and coffee included ✓ WiFi included
Request a Proposal View details
Bridgetown to Santo Domingo
Sea Cloud II
Bridgetown to Santo Domingo
13 nights 11 Ports of Call  ·  Departs 22 Dec 2026
From
$9,525
per person
Embarkation Bridgetown
Barbados
22 Dec 2026
Disembarkation Santo Domingo
Dominican Republic
4 Jan 2027
Journey type Cruise only (please call for flight options)
✓ Alcohol included ✓ Daytime activities ✓ Gratuities included ✓ Meals included ✓ Soft drinks, tea and coffee included
Request a Proposal View details
Miami to Miami
Silver Ray
Miami to Miami
14 nights 8 Ports of Call  ·  Departs 22 Dec 2026
From
$9,065
per person
Embarkation Miami
United States
22 Dec 2026
Disembarkation Miami
United States
5 Jan 2027
Journey type Cruise only (please call for flight options)
✓ Alcohol included ✓ Daytime activities ✓ Gratuities included ✓ Meals included ✓ Shore excursions included ✓ WiFi included
Request a Proposal View details
Philipsburg to Philipsburg
Sea Cloud Spirit
Philipsburg to Philipsburg
14 nights 9 Ports of Call  ·  Departs 21 Dec 2026
From
$11,652
per person
Embarkation Philipsburg
Sint Maarten
21 Dec 2026
Disembarkation Philipsburg
Sint Maarten
4 Jan 2027
Journey type Cruise only (please call for flight options)
✓ Alcohol included ✓ Daytime activities ✓ Gratuities included ✓ Meals included ✓ Soft drinks, tea and coffee included
Request a Proposal View details
Bridgetown to San Juan
Silver Nova
Bridgetown to San Juan
8 nights 8 Ports of Call  ·  Departs 21 Dec 2026
From
$3,788
per person
Embarkation Bridgetown
Barbados
21 Dec 2026
Disembarkation San Juan
Puerto Rico
29 Dec 2026
Journey type Cruise only (please call for flight options)
✓ Alcohol included ✓ Daytime activities ✓ Gratuities included ✓ Meals included ✓ Shore excursions included ✓ WiFi included
Request a Proposal View details
San Juan (Puerto Rico) Roundtrip
Ilma
San Juan (Puerto Rico) Roundtrip
7 nights 6 Ports of Call  ·  Departs 21 Dec 2026
From
$9,877
per person
Embarkation San Juan
Puerto Rico
21 Dec 2026
Disembarkation San Juan
Puerto Rico
28 Dec 2026
Journey type Cruise only (please call for flight options)
✓ Daytime activities ✓ Gratuities included ✓ Meals included ✓ WiFi included
Request a Proposal View details
Balmy Island Holiday
Vista
Balmy Island Holiday
7 nights 4 Ports of Call  ·  Departs 21 Dec 2026
From
$2,793
per person
Embarkation Miami
United States
21 Dec 2026
Disembarkation Miami
United States
28 Dec 2026
Journey type Cruise only (please call for flight options)
✓ Daytime activities ✓ Gratuities included ✓ Meals included ✓ Soft drinks, tea and coffee included ✓ WiFi included
Request a Proposal View details
Comparing
Select a voyage ×
Select a second voyage ×