All 53 sailings visiting Tobago Cays
Ordered soonest first. Prices per person, including taxes and fees. Want to filter by price, date, or ship?
Open these cruises in search →| View | Sailing | Departs | Nights | Ship | From |
|---|---|---|---|---|---|
| Classic Caribbean | Nov 20, 2026 | 9 | Emerald Azzurra |
from $18,915 $2,101 / night |
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| Discover the Best of the Caribbean | Nov 20, 2026 | 16 | Emerald Azzurra |
from $35,550 $2,221 / night |
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| Classic Yachtsman's | Nov 28, 2026 | 7 | Royal Clipper |
Call for price |
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| Grenadines & Windwards Yachting | Nov 29, 2026 | 7 | Emerald Azzurra |
from $5,253 $750 / night |
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| Renaud Capuçon’s Caribbean Celebration: 50 Years in Paradise | Dec 23, 2026 | 7 | Le Bougainville |
Call for price |
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| Grenadines & Windwards Yachting | Dec 27, 2026 | 7 | Emerald Azzurra |
from $5,322 $760 / night |
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| Discover the Grenadines & Windwards Islands | Dec 27, 2026 | 13 | Emerald Azzurra |
Call for price |
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| Pearls of the Caribbean | Dec 30, 2026 | 7 | Le Bougainville |
Call for price |
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| Gliding the Waters of the Windward Islands | Jan 2, 2027 | 7 | Le Ponant |
Call for price |
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| Grenadines & Windwards Yachting | Jan 23, 2027 | 7 | Emerald Azzurra |
Call for price |
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| Cruising the Caribbean's Windward Islands – with Smithsonian Journeys | Feb 17, 2027 | 7 | Le Bougainville |
Call for price |
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| Grenadines & Windwards Yachting | Feb 20, 2027 | 7 | Emerald Azzurra |
Call for price |
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| Vieux Fort to Vieux Fort | Mar 3, 2027 | 7 | Le Bougainville |
Call for price |
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| Colón to Fort-de-France | Mar 12, 2027 | 10 | Le Laperouse |
Call for price |
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| Grenadines & Windwards Yachting | Mar 20, 2027 | 7 | Emerald Azzurra |
from $6,221 $888 / night |
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| Ultimate South America to the Caribbean through the Panama Canal | Mar 21, 2027 | 24 | Scenic Eclipse II |
from $20,576 $857 / night |
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| Fort-de-France to Fort-de-France | Mar 22, 2027 | 12 | Le Laperouse |
Call for price |
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| Pristine islands of the Caribbean & the Panama Canal | Apr 3, 2027 | 11 | Scenic Eclipse II |
from $10,089 $917 / night |
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| Splendours of the Caribbean | Oct 15, 2027 | 8 | Scenic Eclipse II |
from $6,463 $807 / night |
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| Pristine Islands of the Caribbean & the Panama Canal | Oct 20, 2027 | 11 | Scenic Eclipse |
from $9,863 $896 / night |
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| Grenadines & Windwards Yachting | Nov 27, 2027 | 7 | Emerald Azzurra |
from $4,715 $673 / night |
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| Grenadine Islands | Nov 27, 2027 | 7 | Royal Clipper |
Call for price |
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| Grenadines & Windwards Yachting | Dec 4, 2027 | 7 | Emerald Azzurra |
from $4,715 $673 / night |
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| Beaches of the Grenadines | Dec 11, 2027 | 8 | Emerald Azzurra |
from $5,532 $691 / night |
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| Tropical Retreat: Roundtrip Bridgetown | Dec 19, 2027 | 9 | Emerald Azzurra |
from $5,974 $663 / night |
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| Tropical Retreat: Roundtrip Bridgetown | Dec 28, 2027 | 9 | Emerald Azzurra |
from $6,399 $711 / night |
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| Discover Barbados, Panama & Costa Rica Bridgetown to Panama City | Jan 6, 2028 | 18 | Emerald Azzurra |
from $15,824 $879 / night |
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| Epic Caribbean Escape: Barbados to Costa Rica | Jan 6, 2028 | 25 | Emerald Azzurra |
from $22,284 $891 / night |
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| Grenadines & Windwards Yachting | Jan 6, 2028 | 7 | Emerald Azzurra |
from $5,028 $718 / night |
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| Caribbean Island Hopping: Sint Maarten to Barbados | Jan 12, 2028 | 10 | Emerald Sakara |
from $8,012 $801 / night |
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| Discover the hidden treasures of the Caribbean from Bridgetown | Jan 22, 2028 | 21 | Emerald Sakara |
from $16,827 $801 / night |
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| Grenadines & Windwards Yachting | Jan 22, 2028 | 7 | Emerald Sakara |
from $5,075 $725 / night |
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| Discover the hidden treasures of the Caribbean from Marigot | Feb 5, 2028 | 21 | Emerald Sakara |
from $16,779 $799 / night |
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| Discover the hidden treasures of the Caribbean from Bridgetown | Feb 19, 2028 | 21 | Emerald Sakara |
from $16,827 $801 / night |
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| Grenadines & Windwards Yachting | Feb 19, 2028 | 7 | Emerald Sakara |
from $5,075 $725 / night |
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| Epic Caribbean Escape: Costa Rica to Barbados | Feb 22, 2028 | 25 | Emerald Azzurra |
Call for price |
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| Caribbean Enchantment: Roundtrip Antigua | Mar 1, 2028 | 10 | Emerald Kaia |
from $8,131 $813 / night |
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| Grenadines & Windwards Yachting | Mar 11, 2028 | 7 | Emerald Azzurra |
Call for price |
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| Grenadines & Windwards Yachting | Mar 18, 2028 | 7 | Emerald Azzurra |
from $5,028 $718 / night |
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| Grenadines & Windwards Yachting | Mar 25, 2028 | 7 | Emerald Azzurra |
from $5,028 $718 / night |
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| Grenadines & Windwards Yachting | Apr 1, 2028 | 7 | Emerald Azzurra |
from $4,848 $692 / night |
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| Classic Caribbean | Dec 7, 2028 | 9 | Emerald Sakara |
from $5,870 $652 / night |
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| Grenadines & Windwards Yachting | Dec 9, 2028 | 7 | Emerald Azzurra |
from $4,949 $707 / night |
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| Grenadines & Windwards Yachting | Dec 16, 2028 | 7 | Emerald Azzurra |
from $4,949 $707 / night |
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| Grenadines & Windwards Yachting | Dec 23, 2028 | 7 | Emerald Azzurra |
from $4,949 $707 / night |
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| Grenadines & Windwards Yachting | Dec 30, 2028 | 7 | Emerald Azzurra |
from $4,949 $707 / night |
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| Grenadines & Windwards Yachting | Jan 6, 2029 | 7 | Emerald Azzurra |
from $5,309 $758 / night |
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| Discover Barbados, Panama & Costa Rica Bridgetown to Panama City | Jan 6, 2029 | 18 | Emerald Azzurra |
from $16,456 $914 / night |
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| Grenadines & Windwards Yachting | Mar 12, 2029 | 7 | Emerald Azzurra |
from $5,309 $758 / night |
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| Grenadines & Windwards Yachting | Mar 19, 2029 | 7 | Emerald Azzurra |
from $5,309 $758 / night |
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| Grenadines & Windwards Yachting | Mar 26, 2029 | 7 | Emerald Azzurra |
from $5,309 $758 / night |
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| Grenadines & Windwards Yachting | Apr 2, 2029 | 7 | Emerald Azzurra |
from $5,129 $732 / night |
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| Grenadines & Windwards Yachting | Apr 9, 2029 | 7 | Emerald Azzurra |
from $5,129 $732 / night |
The Captain's Log
Exceptional cruises. Intelligent prices.
The Captain's Log
