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Top Tobago Cays Trips & Vacation Packages

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    • Tobago Cays
Stroll along the beautiful beaches of the Caribbean
from $3,860
EXPLORE

Grenadine Islands Christmas Cruise

Roundtrip Bridgetown - 11 Day Itinerary aboard Royal Clipper
  • Relax on beaches in Martinique
  • Snorkel reefs in Terre de Haut
  • Swim in South Friar's Bay
  • Explore the Tobago Cays
Starts / Ends
Bridgetown / Bridgetown
Activities
Hiking
Activity Level
Variable
Set sail on an 11-day New Year's Caribbean cruise aboard the Royal Clipper, visiting beautiful spots like Grenada, St. Lucia, and Dominica. Enjoy snorkeling in Tobago Cays, relaxing at Diamond Falls, and exploring historic sites in Antigua and St. Kitts before concluding your adventure in Bridgetown.
Cruise Details
0
St. George's, Grenada's charming capital city known for having the most beautiful harbor in the Caribbean.
from $3,150
EXPLORE

Grenada Roundtrip

Roundtrip St George - 12 Day Itinerary aboard Star Clipper
  • Tour St. George's Sendall Tunnel
  • Taste Castara Bay Tobago's Creole
  • Stroll Admiralty Bay waterfront
  • View Saint Pierre colonial ruins
Starts / Ends
St. Georges / St. Georges
Activities
Local Market Visits
Activity Level
Variable
Embark on a 12-day cruise through the Southern Caribbean aboard the Star Clipper, starting in St. George’s, Grenada. Experience stunning beaches, vibrant local culture, and historical sites across Tobago, the Grenadines, Martinique, and Barbados.
Cruise Details
0
The vivid colors of the San Blas Islands
from $4,330
EXPLORE

Barbados to Panama

Bridgetown - Balboa - 15 Day Itinerary aboard Star Clipper
  • Explore Bridgetown’s heritage
  • Discover St. George’s coastal views
  • Admire Kralendijk’s marine life
  • Wander Willemstad’s streets
Starts / Ends
Bridgetown / Balboa
Activity Level
Variable
Set sail on a 15-day cruise with Star Clipper from Bridgetown, Barbados, exploring the Caribbean’s rich culture and history, ending in Balboa, Panama. Visit stunning destinations like Tobago Cays, Grenada, and the San Blas Islands, and experience the Panama Canal.
Cruise Details
0
Dock going out into the crystal blue ocean
from $2,080
EXPLORE

Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper
  • Explore Antigua’s vibrant dockyards
  • Discover Les Saintes’ beaches
  • Relax on Martinique’s white sands
  • Stroll Grenada’s aromatic markets
Starts / Ends
St. John's / Bridgetown
Activity Level
Variable
Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush rainforests, Grenada’s spice markets, and Barbados’ rich heritage.
Cruise Details
0
Experience laid-back Marigot
from $15,980
EXPLORE

Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Anguilla, serene landscapes
  • Savor Barbados’s cultural delights
  • Visit Antigua’s historic dockyard
  • Stroll Nevis’s serene beaches
Starts / Ends
Marigot / Bridgetown
Activity Level
Variable
Set sail on a 15-day Caribbean journey, where pristine beaches, vibrant coral reefs, and island-hopping adventures immerse you in diverse cultures. Experience the genuine warmth of local hospitality as you explore tropical paradises aboard the Emerald Azzurra.
Cruise Details
0
Relax on the pristine beaches of the Virgin Islands
from $13,390
EXPLORE

Discover Eastern Caribbean & Grenadines

Bridgetown - Philipsburg - 15 Day Itinerary aboard Emerald Sakara
  • Visit Bequia Island sandy beaches
  • See Mayreau Island ocean views
  • Admire Soufriere hot sulfur springs
  • Tour Iles des Saintes Fort Napoleon
Starts / Ends
Bridgetown / Philipsburg
Activity Level
Variable
Join a 15-day Caribbean cruise from Bridgetown on the Emerald Sakara, exploring the Eastern Caribbean and Grenadines. Experience local culture in Speightstown, enjoy water sports in Kingstown, and relax in natural hot springs in Soufriere before returning to Barbados.
Cruise Details
0
Lush green forests and clear blue waters of the Caribbean
from $13,340
EXPLORE

Discover Eastern Caribbean & Grenadines

Philipsburg - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
  • Discover Virgin Gorda The Baths
  • Wander Gustavia wooden houses
  • Visit St. John's Nelson's Dockyard
  • See Soufriere volcanic domes
Starts / Ends
Philipsburg / Bridgetown
Activity Level
Variable
Set sail on a 15-day Caribbean cruise from Philipsburg on the Emerald Sakara, exploring the Eastern Caribbean and Grenadines. Visit charming islands like Virgin Gorda, Saint Barthelemy, and Bequia for stunning beaches, local cuisine, and water activities amidst breathtaking views.
Cruise Details
0
Enjoy the beautiful blue Caribbean
from $5,590
EXPLORE

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Roundtrip Vieux Fort - 8 Day Itinerary aboard Le Champlain
  • Visit scenic Les Saintes
  • Swim at Pompierre Beach
  • Relax on Mayreau Island
  • Explore historic Bridgetown sites
Starts / Ends
Les Saintes / Bridgetown
Activities
Scuba Diving
Activity Level
Variable
Embark on an 8-day cruise aboard Le Champlain and explore Saint Lucia, Dominica, Les Saintes, Bequia, Mayreau Island, Tobago Cays, and Barbados. Snorkel coral reefs, swim in turquoise lagoons, discover historic towns, visit beaches, and encounter marine life across the Caribbean.
Cruise Details
0
Tropical waterfall and turquoise pool in lush forest of Dominica
from $7,995
OBC $200
EXPLORE

Caribbean Flair Away from the Everyday

St. Maarten Roundtrip - 9 Day Itinerary aboard Sea Cloud Spirit
  • Visit historic Saint-Pierre ruins
  • Watch the crew hoist the sails
  • Snorkel the clear Tobago Cays
  • Explore St. Lucia's twin Pitons
  • Wander through Charlestown, Nevis
Starts / Ends
Philipsburg / Philipsburg
Activities
Village Visits
Activity Level
Variable
Embark on a 9-day Caribbean cruise aboard the Sea Cloud Spirit. You depart from St. Maarten and visit Martinique, the Tobago Cays, St. Lucia, Dominica, and Nevis, then explore historic ruins, volcanoes, and reefs.
Cruise Details
0
St. George's harbor in Grenada, where historic cannons overlook scenic ocean views and colorful hillside estates
from $7,995
OBC $200
EXPLORE

More Time for Island Dreams

St. Maarten Roundtrip - 9 Day Itinerary aboard Sea Cloud Spirit
  • Discover Terre-de-Haut
  • Snorkel Tobago Cays
  • Discover Grenada’s spices
  • Spot flamingos in Bonaire
  • Explore historic Willemstad
Starts / Ends
Philipsburg / Willemstad
Activities
Wildlife Viewing, Snorkeling, Small Ship Sailing, Archaeological Site Visits
Activity Level
Variable
Experience a 9-day Caribbean cruise aboard the Sea Cloud Spirit. Depart from St. Maarten and sail to stunning destinations including Îles des Saintes, St. Lucia, the Tobago Cays, Grenada, and Bonaire before disembarking in Curaçao. Enjoy historic ports, coral reefs, and volcanic landscapes along the journey.
Cruise Details
0
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Jess is funtastic! She listens and fines the adventure I want to share with my granddaughter
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Angie was great! Always kept us informed of our trip. Great personality and easy to work with! Jean Hershey
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