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Caribbean Tours

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Sunset over Philipsburg
from $2,010
EXPLORE

Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Visit Anguilla's white sand coves
  • Tour Tortola to see Soper's Hole
  • Swim South Friars Bay waters
  • Hike Jost Van Dyke trails
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Join an 8-day Caribbean cruise on the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore stunning beaches, historic sites, and vibrant islands like Anguilla, Tortola, Virgin Gorda, and St. Barts.
Cruise Details
0
Visit beautiful Norman Island
from $2,010
EXPLORE

Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Visit Anguilla's white sand coves
  • Tour Tortola to see Soper's Hole
  • Swim South Friars Bay waters
  • Hike Jost Van Dyke trails
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Embark on an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, aboard the Star Flyer, visiting beautiful locations like Anguilla, Tortola, and Virgin Gorda. Enjoy duty-free shopping in St. Barts and explore the colonial history of St. Kitts before returning to St. Maarten.
Cruise Details
0
Beach, harbor and village of Terre-de-Haut
from $2,010
EXPLORE

Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Swim Gustavia beaches
  • Visit Nelson's Dockyard ruins
  • Snorkel Terre-de-Haut waters
  • Hike Dominica trails
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Embark on an 8-day Caribbean cruise from Philipsburg, St. Maarten, aboard the Star Flyer, exploring charming towns, lush rainforests, and beautiful beaches. Enjoy duty-free shopping in Gustavia before returning to St. Maarten.
Cruise Details
0
Stroll along the beaches of Puerto Rico
from $9,295
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Paradise Beaches from the U.S. Virgin Islands to The Bahamas

San Juan - Miami - 10 Day Itinerary aboard Emerald Kaia
  • Tour Grand Turk lighthouse
  • Wander Gordon's Beach
  • Walk Nassau bustling Straw Market
  • Dive San Salvador Island
Starts / Ends
San Juan / Miami
Activities
Snorkeling, Local Market Visits, Archaeological Site Visits
Activity Level
Variable
Set sail on a 10-day Caribbean cruise aboard the Emerald Kaia from San Juan, Puerto Rico, exploring the beautiful Turks and Caicos Islands and vibrant marine life in The Bahamas. Enjoy fresh local seafood and conclude your journey in the lively metropolis of Miami, blending cultural discovery with natural beauty.
Cruise Details
0
Nassau Lighthouse
from $7,590
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Caribbean Escapade

San Juan - Miami - 8 Day Itinerary aboard Emerald Sakara
  • Explore the pristine beaches
  • Snorkel in crystal-clear waters
  • Relax on secluded Gordon’s Beach
  • Explore Grand Turk’s beaches
Starts / Ends
San Juan / Miami
Activities
Kayaking
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites.
Cruise Details
0
Panoramic view from Shirley Heights, Antigua, showing English Harbor and Caribbean landscape
from $6,995
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Pirate Islands With A Yachtie Vibe

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore Gustavia harbor
  • Visit Shirley Heights, Antigua
  • Explore The Baths, Virgin Gorda
  • Sail Sir Francis Drake Channel
  • Experience Virgin Islands fun
Starts / Ends
Philipsburg / Philipsburg
Activities
Small Ship Sailing
Activity Level
Variable
Sail 8 days aboard Sea Cloud Spirit on a Caribbean round-trip from Philipsburg, St. Maarten. Explore Gustavia, St. John’s, Virgin Gorda, Jost van Dyke, and Norman Island with beaches, sailing, and historic sights.
Cruise Details
0
Kayaking in Cuba
from $3,590
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Cuba Kayaking West Tour

8 Day Itinerary
  • See Cuba's great cities
  • Visit the Bay of Pigs
  • Kayak and snorkel in Cuba
  • Enjoy unique architecture & cuisine
Activities
Homestays
Activity Level
Easy Active
Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural wonders. In Havana, meet the artists, musicians, and historians who are preserving tradition. Explore great colonial cities and pristine marine & terrestrial habitats.
Tour Details
0
Enjoy the beautiful blue Caribbean
from $2,880
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Grenada to Grenada

Roundtrip St George - 11 Day Itinerary aboard Star Clipper
  • Explore St. George’s panoramic view
  • Discover Charlotteville coastline
  • Unwind at Englishman’s Bay
  • Visit Martinique ruins
Starts / Ends
St. Georges / St. Georges
Activities
Village Visits
Activity Level
Variable
Set sail on an 11-day cruise from St. George aboard the Star Clipper, featuring Grenada, Tobago, the Grenadines, Martinique, and St. Lucia while exploring picturesque villages and stunning beaches. Enjoy swimming, snorkeling, and local culture, concluding with a visit to Mayreau's serene Saline Bay.
Cruise Details
0
Beautiful beach in Dominica
from $8,370
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Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant
  • Relax on Grande Anse Beach
  • Snorkel Tobago Cays Reefs
  • Visit Port Elizabeth waterfront
  • Discover Portsmouth landscapes
Starts / Ends
Anses d'Arlet / Marie Galante
Activity Level
Variable
Explore Guadeloupe and the Southern Caribbean aboard Le Ponant on an 8-day cruise. Swim in Tobago Cays, snorkel at Sandy Island, discover Grande Anse d’Arlet, visit Portsmouth, sail past The Pitons, and experience Creole culture, beaches, reefs, and island towns across multiple Caribbean destinations.
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, 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
Bicycle on Cuban street
from $4,390
EXPLORE

Cuba Cycling Tour

Quintessential Cuba - 8 Day Itinerary
  • Cycle through western Cuba
  • Visit Hemingway's former home
  • Ride through Cuba's tobacco fields
  • Explore Havana on foot
Activities
Hiking, Biking
Activity Level
Moderate
A cycling tour through western Cuba takes you off the well-traveled tourist track and onto roads where the island's rich history isn't just remembered—it is lived every day. It reveals Cuba’s greatest resource and truest legend: its people.
Tour Details
0
Boats Moored to the Quay at Bridgetown Harbour
from $4,450
EXPLORE

Barbados to Panama

15 Day Itinerary aboard Royal Clipper
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Starts / Ends
Bridgetown / Balboa
Activity Level
Variable
Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to the Panama Canal, visiting Grenada, Bonaire, Curacao, Aruba, and Colombia along the way. Explore the tropical jungles, snorkel in vibrant reefs, immerse yourself in tribal culture, and marvel at the Panama Canal.
Cruise Details
0
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Claudia C.
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