Jost Van Dyke Small Ship Cruises

from $8,390

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Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Azzurra

• Discover Culebra Island’s shores
• Explore Vieques Island waterfront
• Tour St. John’s Annaberg ruins
• Relax on Jost Van Dyke’s White Bay

Starts / Ends

San Juan / St. John's

Activity Level

Variable

Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.

Cruise Details

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from $11,070

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Cruising the Leeward Islands

Marigot Roundtrip - 8 Day Itinerary aboard Emerald Sakara

• Explore Virgin Gorda’s iconic Baths
• Swim Norman Island coves
• Unwind Jost van Dyke beach
• Stroll Anegada’s quiet beaches

Starts / Ends

Marigot / Marigot

Activity Level

Variable

Set sail on an 8-day cruise from Marigot, Saint Martin, aboard the Emerald Sakara, visiting stunning destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, exploring grottoes, and embracing the relaxed island lifestyle amidst breathtaking coastal views.

Cruise Details

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from $9,990

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Cruising the Leeward Islands

Roundtrip Marigot - 8 Day Itinerary aboard Emerald Azzurra

• Explore Anguilla’s coral coastlines
• Visit Virgin Gorda granite boulders
• Discover Norman Island's coves
• Relax on Anegada’s remote sands

Starts / Ends

Marigot / Marigot

Activities

Hiking

Activity Level

Variable

Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.

Cruise Details

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from $2,010

Air Credit

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Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper

• Explore St. John's dockyards
• Sail Sir Francis Drake Channel
• Swim Virgin Gorda Baths
• Hike Jost van Dyke trails

Starts / Ends

St. John's / St. John's

Activity Level

Variable

Set sail on an 8-day round-trip cruise from St. John’s, Antigua, aboard the Star Clipper, exploring St. Barts, the British Virgin Islands, and Anguilla. Highlights include duty-free shopping, scenic hikes, and beautiful beaches before concluding in Antigua.

Cruise Details

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from $2,010

Air Credit

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Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper

• Hike St. Kitts rainforests
• Tour Basseterre colonial history
• Shop Philipsburg Dutch bargains
• Explore Tortola to see Soper's Hole

Starts / Ends

St. John's / St. John's

Activity Level

Variable

Experience an 8-day round-trip cruise from St. John's, Antigua, aboard the Star Clipper, visiting destinations like St. Barts, the British Virgin Islands, and St. Maarten. Enjoy duty-free shopping, stunning beaches, and historic sites before concluding your journey in Antigua.

Cruise Details

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from $2,010

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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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from $2,010

Air Credit

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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

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from $2,010

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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

Activities

Snorkeling, Small Ship Sailing

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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from $6,955

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Sailing On The Trade Winds

Philipsburg Roundtrip - 11 Day Itinerary aboard Sea Cloud II

• Explore Philipsburg harbor
• Walk Terre-de-Haut
• See Piton peaks
• Sail Drake Channel

Starts / Ends

Philipsburg / Philipsburg

Activities

Local Market Visits, Village Visits

Activity Level

Variable

Experience an 11-day Caribbean sailing itinerary from and to Philipsburg, St. Maarten aboard Sea Cloud II. Visit St. Lucia, Martinique, Îles des Saintes, St. Barths, and the British Virgin Islands, with time at sea focused on hands-on sailing and relaxed days ashore.

Cruise Details

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from $1,970

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Antigua to Antigua

Roundtrip St John - 8 Day Itinerary aboard Star Clipper

• Explore St. John's dockyards
• Sail Sir Francis Drake Channel
• Stroll Norman Island's beach
• Tour Basseterre's old plantations

Starts / Ends

St. John's / St. John's

Activity Level

Variable

Embark on an 8-day cruise in the Caribbean aboard the Star Clipper, starting and ending in Antigua. Discover the beaches and boutiques of St. Barts, explore Norman Island, and enjoy the charm of Jost van Dyke, while swimming at Virgin Gorda and experiencing St. Kitts’ history and nature.

Cruise Details

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from $21,980

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Discover the Yachting Islands of the Caribbean

Roundtrip Saint John’s - 15 Day Itinerary aboard Emerald Azzurra

• Explore Barbuda’s iconic pink sands
• Visit Les Saintes’ quaint towns
• Discover Deshaies’ lush hills
• Swim off Norman Island’s shores

Starts / Ends

St. John's / St. John's

Activity Level

Variable

Embark on a 15-day cruise with Emerald Azzurra, exploring the Caribbean from St. John’s, Antigua, with stops at stunning destinations like Barbuda, Guadeloupe, and the British Virgin Islands. Enjoy snorkeling in Culebra and the relaxed vibe of Esperanza on Vieques, all amidst beautiful beaches and vibrant island culture.

Cruise Details

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from $15,980

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Discover the Pearls of the Caribbean

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra

• Explore Soufriere’s volcanic peaks
• Tour Falmouth’s colonial forts
• Snorkel Anguilla’s coral reefs
• Wander Marigot’s French markets

Starts / Ends

Marigot / Bridgetown

Activities

Wildlife Viewing, Archaeological Site Visits

Activity Level

Variable

Embark on a 15-day Caribbean cruise aboard Emerald Azzurra, exploring stunning coral reefs, granite pools, and picturesque landscapes across destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, hiking, and vibrant local culture while visiting Saint Barthelemy and the British Virgin Islands.

Cruise Details

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from $21,780

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Discover the Pearls of the Caribbean

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Azzurra

• Explore Soufriere’s volcanic peaks
• Tour Falmouth’s colonial forts
• Snorkel Anguilla’s coral reefs
• Wander Marigot’s French markets

Starts / Ends

Bridgetown / Marigot

Activities

Kayaking

Activity Level

Variable

Embark on a 15-day cruise aboard Emerald Azzurra from Barbados to Marigot, visiting highlights like Nelson’s Dockyard and the beaches of Iles des Saintes. Discover serene islands, snorkel vibrant reefs, and enjoy cultural experiences across the enchanting Caribbean.

Cruise Details

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from $2,210

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Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Visit Gustavia French boutiques
• Hike Jost Van Dyke scenic trails
• Tour Tortola to see Soper's Hole
• Explore Basseterre landmarks

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore scenic spots like St. Barts, Jost Van Dyke, Virgin Gorda, and Anguilla, blending natural beauty and rich history.

Cruise Details

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