Have questions? We're here.
Scuba diving in the reefs

Top Tobago Cays Trips & Vacation Packages

Travel made your way ™
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
Filter (18 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Tobago Cays
The vivid colors of the San Blas Islands
from $4,330
SS 25%
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
Activities
Small Ship Sailing, Local Market Visits
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
Save $150
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
Save $150
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
Activities
Village Visits
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
Save $150
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
Wildlife Viewing, Snorkeling, Archaeological Site Visits
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
13-18 of 18 Results
  • 1
  • 2

Relax. We've got this.

Talk with an expert trip planner 1.800.344.6118

Plan My Trip
Claudia Corona Adventure Life employee profile
Claudia C.
About to go kayaking with my son
Caribbean

Chat Tobago Cays with a specialist

Our team is waiting and ready to talk with you about your next adventure. So go ahead and book an appointment with one of our specialized trip planners.

Let's Chat
1.800.344.6118

Where is your next adventure?

Contact Chat Call

Why Travel With Us?

Rewards That Go Further

Secure your 5% Past Traveler Rewards across a wide range of ships and destinations - not a single brand and not just cruises.

Seamless Trip Planning

We guide you through every detail beyond the cruise—from flights to pre- and post-trip stays—so your journey feels effortless.

Unbiased Cruise Expertise

We're not tied to any one cruise line, so you receive honest guidance on the best ship and itinerary for you—not a sales pitch.

As Featured In

USA Today
Los Angeles Times
Travel Weekly
Outside
National Geographic Traveler
The New York Times
Travel + Leisure
Condé Nast Traveler
National Geographic

How it Works

Connect

No cost, no commitment. Talk with our experts about your dream trip.

Plan

Share your travel style—we match you with the right itinerary or create one just for you.

Book

Lock in knowing every detail is handled and you’re fully supported.

Travel

Enjoy a seamless journey—and unlock 5% off your next adventure.

Claudia Corona Adventure Life employee profile
Claudia C
Plan My Trip
We love travel, talk with an expert 1.800.344.6118