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Cruises to Tobago Cays

23 live cruises call at Tobago Cays — 7 to 21 nights, departing 8 ports, across 2 lines. A NestCruise advisor narrows them to the one that fits.

23 sailings
Emerald AzzurraCaribbean

Emerald Cruises

Grenadines & Windwards yachting

Aboard Emerald Azzurra

Bridgetown → Speightstown → Kingstown → Port Elizabeth, Bequia +3 more

7 nights · 6 departures

Port-rich · 7 ports

Nov 2026 – Nov 2027View details →
Le PonantCaribbean

PONANT EXPLORATIONS

Gliding the Waters of the Windward Islands

Aboard Le Ponant

Pointe-à-Pitre → Grande Anse, Les Anses-d'Arlet → Tobago Cays → Sandy Island +5 more

7 nights · 6 departures

Port-rich · 9 ports

Jan 2027 – Feb 2028View details →
Le ChamplainCaribbean

PONANT EXPLORATIONS

Pearls of the Caribbean

Aboard Le Champlain

Fort-de-France → Port Elizabeth, Bequia → Tobago Cays → Mayreau Island +4 more

7 nights · 4 departures

Port-rich · 8 ports

Dec 2027 – Feb 2028View details →
Emerald SakaraCaribbean

Emerald Cruises

Discover Eastern Caribbean & Grenadines

Aboard Emerald Sakara

Bridgetown → Speightstown → Kingstown → Port Elizabeth, Bequia +10 more

14 nights · 3 departures

Port-rich · 14 ports

Jan 2028 – Feb 2028View details →
Le BougainvilleCaribbean

PONANT EXPLORATIONS

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Aboard Le Bougainville

Vieux Fort → Portsmouth → Îles des Saintes → Port Elizabeth, Bequia +3 more

7 nights · 1 departure

Port-rich · 7 ports

Feb 2027View details →
Emerald KaiaCaribbean

Emerald Cruises

Caribbean Enchantment: roundtrip Antigua

Aboard Emerald Kaia

Saint John's → Îles des Saintes → Soufrière → Bridgetown +6 more

10 nights · 1 departure

Port-rich · 10 ports

Mar 2028View details →
Le LapérouseCaribbean

PONANT EXPLORATIONS

Panama, Colombia & Caribbean Islands

Aboard Le Lapérouse

Colón → San Blas Islands → Cartagena → Santa Marta +7 more

10 nights · 1 departure

Port-rich · 11 ports

Mar 2027View details →
Emerald AzzurraCaribbean

Emerald Cruises

Discover Eastern Caribbean & Grenadines

Aboard Emerald Azzurra

Bridgetown → Speightstown → Kingstown → Port Elizabeth, Bequia +10 more

14 nights · 4 departures

Port-rich · 14 ports

Nov 2026 – Mar 2027View details →
Le PonantCaribbean

PONANT EXPLORATIONS

Gliding the Waters of the Windward Islands

Aboard Le Ponant

Pointe-à-Pitre → Grande Anse, Les Anses-d'Arlet → Tobago Cays → Sandy Island +5 more

7 nights · 1 departure

Port-rich · 9 ports

Mar 2027View details →
Le ChamplainCaribbean

PONANT EXPLORATIONS

Jewels of the Antilles

Aboard Le Champlain

Vieux Fort → Sailing along the Pitons → Port Elizabeth, Bequia → Tobago Cays +4 more

7 nights · 3 departures

Port-rich · 8 ports

Mar 2028View details →
Emerald SakaraCaribbean

Emerald Cruises

Grenadines & Windwards yachting

Aboard Emerald Sakara

Bridgetown → Speightstown → Kingstown → Port Elizabeth, Bequia +3 more

7 nights · 2 departures

Port-rich · 7 ports

Jan 2028 – Feb 2028View details →
Le BougainvilleCaribbean

PONANT EXPLORATIONS

Renaud Capuçon’s Caribbean Celebration: 50 Years in Paradise

Aboard Le Bougainville

Fort-de-France → Union Island → Tobago Cays → Mayreau Island +4 more

7 nights · 1 departure

Port-rich · 8 ports

Dec 2026View details →
Emerald AzzurraCaribbean

Emerald Cruises

Tropical Retreat: Roundtrip Bridgetown

Aboard Emerald Azzurra

Bridgetown → Speightstown → Soufrière → Saint Pierre +5 more

9 nights · 2 departures

Port-rich · 9 ports

Dec 2027View details →
Le ChamplainCaribbean

PONANT EXPLORATIONS

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Aboard Le Champlain

Vieux Fort → Portsmouth → Îles des Saintes → Port Elizabeth, Bequia +3 more

7 nights · 1 departure

Port-rich · 7 ports

Feb 2028View details →
Emerald SakaraCaribbean

Emerald Cruises

Epic Voyage: Barbados to Sint Maarten

Aboard Emerald Sakara

Bridgetown → Speightstown → Kingstown → Port Elizabeth, Bequia +12 more

21 nights · 2 departures

Port-rich · 16 ports

Jan 2028 – Feb 2028View details →
Emerald AzzurraCaribbean

Emerald Cruises

Discover Barbados, Panama & Costa Rica

Aboard Emerald Azzurra

Bridgetown → Speightstown → Kingstown → Port Elizabeth, Bequia +11 more

18 nights · 2 departures

Port-rich · 15 ports

Jan 2028 – Jan 2029View details →
Emerald SakaraCaribbean

Emerald Cruises

Caribbean Island Hopping: Sint Maarten to Barbados

Aboard Emerald Sakara

Philipsburg → Norman Island → Virgin Gorda → Gustavia +7 more

10 nights · 1 departure

Port-rich · 11 ports

Jan 2028View details →
Emerald AzzurraCaribbean

Emerald Cruises

Beaches of the Grenadines

Aboard Emerald Azzurra

Bridgetown → Speightstown → Soufrière → Kingstown +4 more

8 nights · 1 departure

Port-rich · 8 ports

Dec 2027View details →
Emerald SakaraCaribbean

Emerald Cruises

Epic Voyage: Sint Maarten to Barbados

Aboard Emerald Sakara

Philipsburg → Basseterre, Saint Kitts → Anguilla → Virgin Gorda +12 more

21 nights · 1 departure

Port-rich · 16 ports

Feb 2028View details →
Emerald AzzurraCaribbean

Emerald Cruises

Classic Caribbean

Aboard Emerald Azzurra

Marigot → Gustavia → Basseterre, Saint Kitts → Falmouth +6 more

9 nights · 1 departure

Port-rich · 10 ports

Nov 2026View details →
Emerald AzzurraCaribbean

Emerald Cruises

Discover the Grenadines & Windwards islands

Aboard Emerald Azzurra

Bridgetown → Speightstown → Kingstown → Port Elizabeth, Bequia +9 more

13 nights · 1 departure

Port-rich · 13 ports

Dec 2026View details →
Emerald AzzurraCaribbean

Emerald Cruises

Discover the Best of the Caribbean

Aboard Emerald Azzurra

Marigot → Gustavia → Basseterre, Saint Kitts → Falmouth +10 more

16 nights · 1 departure

Port-rich · 14 ports

Nov 2026View details →
Emerald AzzurraCaribbean

Emerald Cruises

Epic Caribbean Escape: Barbados to Costa Rica

Aboard Emerald Azzurra

Bridgetown → Speightstown → Kingstown → Port Elizabeth, Bequia +19 more

25 nights · 1 departure

Port-rich · 23 ports

Jan 2028View details →

Frequently asked

How many cruises to Tobago Cays does NestCruise have?
23 live sailings, 7 to 21 nights. A NestCruise advisor narrows them to the one that fits.
Which cruise lines visit Tobago Cays?
Emerald Cruises and PONANT EXPLORATIONS, among others.
How long are cruises to Tobago Cays?
Most run 7 to 21 nights.
How much do cruises to Tobago Cays cost?
NestCruise doesn't publish fares — it's a quote-only concierge. Share your dates and party size and an advisor prices your exact sailing at no cost.