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Umbrellas and sunbeds lined up along the White Bay Beach of Jost Van Dyke, British Virgin Islands
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 Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Visit Anguilla's beaches, explore the British Virgin Islands, hike Jost Van Dyke, and enjoy shopping in St. Barts while uncovering historical sites and natural beauty.
Cruise Details
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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
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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
Activities
Snorkeling
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
Areal view of Old city of Santo Domingo
from $3,013
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Best of Dominican Republic

8 Day Itinerary
  • Visit UNESCO site in Santo Domingo
  • Taste the culture and local food
  • Visit coffee factory in Jarabacoa
  • Learn about tobacco production
  • Visit cocoa & chocolate plantation
  • See the beaches of Las Terrenas
Starts / Ends
Punta Cana / Punta Cana
Activities
Hacienda Visits, Volunteering
Activity Level
Relaxed
Visit Dominican Republic and uncover hidden gems, from Jarabacoa coffee farms and cigar factories to coastal escapes in Punta Cana. Our tours include top-rated attractions, immersive cultural visits, and unforgettable nature experiences. Discover the best things to do in the Dominican Republic, from the capital to the coast.
Tour Details
0
Nassau Lighthouse
from $7,590
Save $150
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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
EXPLORE

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
Sunset view by the cliff houses
from $4,438
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Dominican Republic: North Coast Expedition

8 Day Itinerary
  • Enjoy canyoning in Puerto Plata
  • See the landscape using 4x4 buggy
  • Visit the Los Pepines murals.
  • Learn about tobacco production
  • See the lovely bay of Rio San Juan
  • Zip line over the Laguna Dudu
Starts / Ends
Puerto Plata / Puerto Plata
Activities
Rainforest Exploration, Ziplining, Hiking
Activity Level
Easy Active
Spend your week on the vibrant North Coast of the Dominican Republic. During this 8-day Dominican Republic trip, experience stunning landscapes, beautiful pristine beaches, and rich cultural traditions, and discover the beauty of this magical stretch of coast.
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
Local Market 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
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
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
Relax on the shores of the Caribbean
from $12,295
Save $150
EXPLORE

Grenadines, Colombia & Panama Canal Transit

Bridgetown - Panama City - 12 Day Itinerary aboard Emerald Azzurra
  • Explore Bequia Caribbean lifestyle
  • Admire Cartagena Old Town
  • See San Blas Islands nature
  • Navigate the Panama Canal
Starts / Ends
Bridgetown / Panama City
Activities
Village Visits, Archaeological Site Visits, Urban Exploration
Activity Level
Variable
Set sail on a 12-day Caribbean cruise from Bridgetown aboard the Emerald Azzurra, exploring islands like Bequia and Mayreau. Conclude your journey in Panama City after traversing the historic Panama Canal and enjoying vibrant local cultures and stunning coastal views.
Cruise Details
0
37-48 of 61 Results

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Jess H.
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