Itineraries

• 2025 - 8 Day Grenadines & Windwards Yachting: Bridgetown to Bridgetown aboard Emerald Sakara (Cruise) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  12/13/25, 3/7/26

  Ports of Call

  Starting in Bridgetown with stops in Port St. Charles, Bequia Island, Mayreau Island, Union Island, Tobago Cays

  Duration

  8

• 2025 - 15 Day Discover Eastern Caribbean & Grenadines: Bridgetown to Marigot aboard Emerald Sakara (Cruise) from $15,180.00 (USD)

  Destination

  Caribbean

  Departures

  12/13/25, 3/7/26

  Ports of Call

  Starting in Bridgetown with stops in Port St. Charles, Bequia Island, Mayreau Island, Union Island, Tobago Cays, Soufriere, Iles des Saintes, Falmouth Harbour, Cades Bay, Gustavia, Marigot

  Duration

  15

• 2025 - 8 Day Eastern Caribbean with St. Barths: Bridgetown to Marigot aboard Emerald Sakara (Cruise) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  11/22/25, 12/20/25, 1/17/26, 2/14/26, 3/14/26, 3/28/26

  Ports of Call

  Starting in Bridgetown with stops in Soufriere, Iles des Saintes, Falmouth Harbour, Charlestown-Cades Bay, Gustavia, Marigot

  Duration

  8

• 2025 - 8 Day Cruising the Leeward Islands: Marigot to Marigot aboard Emerald Sakara (Cruise) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  12/27/25, 2/21/26

  Ports of Call

  Starting in Marigot with stops in Anguilla, Norman Island, Jost van Dyke, Anegada, Gustavia

  Duration

  8

• 2025 - 8 Day Eastern Caribbean with St. Barths: Marigot to Bridgetown aboard Emerald Sakara (Cruise) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  12/6/25, 1/3/26, 1/31/26, 2/28/26

  Ports of Call

  Starting in Marigot with stops in Gustavia, Charlestown, Falmouth Harbour, Iles des Saintes, Soufriere, Bridgetown

  Duration

  8

• 2025 - 15 Day Discover Eastern Caribbean & Grenadines: Marigot to Bridgetown aboard Emerald Sakara (Cruise) from $15,180.00 (USD)

  Destination

  Caribbean

  Departures

  12/6/25, 2/28/26

  Ports of Call

  Starting in Marigot with stops in Gustavia, Charlestown, Falmouth Harbour, Iles des Saintes, Soufriere, Bridgetown, Port St. Charles, Bequia Island, Mayreau Island, Union Island, Tobago Cays

  Duration

  15

• 2025 - 8 Day Caribbean Yachting Hideaways: San Juan to St. John's aboard Emerald Azzurra (Cruise) from $7,990.00 (USD)

  Destination

  Caribbean

  Departures

  12/20/25, 1/3/26, 1/17/26, 1/31/26, 2/14/26, 2/28/26

  Ports of Call

  Starting in San Juan with stops in Culebra Island & Vieques Island, Jost van Dyke, Gustavia, Little Bay, St. John's

  Duration

  8

• 2025 - 15 Day Discover the Yachting Islands of the Caribbean: San Juan to San Juan aboard Emerald Azzurra (Cruise) from $15,980.00 (USD)

  Destination

  Caribbean

  Departures

  1/3/26, 1/17/26, 1/31/26

  Ports of Call

  Starting in San Juan with stops in Culebra Island & Vieques Island, Jost van Dyke, Gustavia, Little Bay, St. John's, Barbuda, Iles des Saintes, Deshaies, Virgin Gorda, Norman Island

  Duration

  15

• 2025 - 8 Day Caribbean Yachting Discovery: St. John's to San Juan aboard Emerald Azzurra (Cruise) from $7,990.00 (USD)

  Destination

  Caribbean

  Departures

  12/13/25, 1/10/26, 1/24/26, 2/7/26

  Ports of Call

  Starting in St. John's with stops in Barbuda, Iles des Saintes, Deshaies, Gustavia, Virgin Gorda, Norman Island, San Juan

  Duration

  8

• 2025 - 15 Day Discover the Yachting Islands of the Caribbean: St. John's to St. John's aboard Emerald Azzurra (Cruise) from $15,980.00 (USD)

  Destination

  Caribbean

  Departures

  12/13/25, 1/10/26, 1/24/26, 2/7/26

  Ports of Call

  Starting in St. John's with stops in Barbuda, Iles des Saintes, Deshaies, Gustavia, Virgin Gorda, Norman Island, San Juan, Culebra Island & Vieques Island, Jost van Dyke, Little Bay

  Duration

  15

• 2026 - 15 Day Discover the Yachting Islands of the Caribbean: San Juan to St. Thomas aboard Emerald Azzurra (Cruise) from $16,780.00 (USD)

  Destination

  Caribbean

  Departures

  2/28/26

  Ports of Call

  Starting in San Juan with stops in Culebra Island & Vieques Island, Jost van Dyke, Gustavia, Little Bay, St. John's, Barbuda, Iles des Saintes, Deshaies, Virgin Gorda, Norman Island, St. Thomas

  Duration

  15

• 2026 - 8 Day Caribbean Yachting Discovery: St. John's to St. Thomas aboard Emerald Azzurra (Cruise) from $8,390.00 (USD)

  Destination

  Caribbean

  Departures

  3/7/26

  Ports of Call

  Starting in St. John's with stops in Barbuda, Iles des Saintes, Deshaies, Gustavia, Virgin Gorda, Norman Island, St. Thomas

  Duration

  8

• 2026 - 8 Day Caribbean Escapade: San Juan to Miami aboard Emerald Sakara (Combo) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  11/21/26

  Ports of Call

  Starting in San Juan with stops in Grand Turk, Gordon's Beach, San Salvador Island, Emerald Bay, Nassau, Miami

  Duration

  8

• 2026 - 8 Day Grenadines & Windwards Yachting: Bridgetown to Bridgetown aboard Emerald Azzurra (Cruise) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  11/29/26, 12/27/26, 1/23/27, 2/20/27, 3/20/27

  Ports of Call

  Starting in Bridgetown with stops in Port St. Charles, Bequia Island, Mayreau Island, Union Island, Tobago Cays

  Duration

  8

• 2026 - 8 Day Caribbean Escapade: Miami to San Juan aboard Emerald Sakara (Combo) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  11/30/26

  Ports of Call

  Starting in Miami with stops in Nassau, Emerald Bay, San Salvador Island, Gordon's Beach, Grand Turk, San Juan

  Duration

  8

• 2026 - 14 Day Discover the Vibes of the Caribbean: Miami to St. Thomas aboard Emerald Sakara (Combo) from $14,580.00 (USD)

  Destination

  Caribbean

  Departures

  11/30/26

  Ports of Call

  Starting in Miami with stops in Nassau, Emerald Bay, San Salvador Island, Gordon's Beach, Grand Turk, San Juan, Cruz Bay, Nevis, Falmouth Harbour, Gustavia, Prickly Pear Cays, Saint Thomas

  Duration

  14

• 2026 - 8 Day Eastern Caribbean with St. Barths: Bridgetown to Marigot aboard Emerald Azzurra (Cruise) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  12/6/26, 1/30/27, 2/27/27, 3/27/27

  Ports of Call

  Starting in Bridgetown with stops in Soufriere, Iles des Saintes, Falmouth Harbour, Cades Bay, Gustavia, Marigot

  Duration

  8

• 2026 - 15 Day Discover the Pearls of the Caribbean: Bridgetown to Marigot aboard Emerald Azzurra (Cruise) from $15,180.00 (USD)

  Destination

  Caribbean

  Departures

  12/6/26

  Ports of Call

  Starting in Bridgetown with stops in Soufriere, Iles des Saintes, Falmouth Harbour, Cades Bay, Gustavia, Marigot, Anguilla, Norman Island, Jost van Dyke, Anegada

  Duration

  15

• 2026 - 7 Day Splendours of the Caribbean: San Juan to St. Thomas aboard Emerald Sakara (Combo) from $6,990.00 (USD)

  Destination

  Caribbean

  Departures

  12/7/26

  Ports of Call

  Starting in San Juan with stops in Cruz Bay, Nevis, Falmouth Harbour, Gustavia, Prickly Pear Cays, Saint Thomas

  Duration

  7

• 2026 - 8 Day Vibes of the Virgin Islands: St. Thomas to St. Thomas aboard Emerald Sakara (Combo) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  12/13/26, 12/20/26, 12/27/26, 1/16/27, 1/30/27, 2/20/27, 2/27/27, 3/6/27, 3/27/27

  Ports of Call

  Starting in Saint Thomas with stops in Saint John, Norman Island, Philipsburg, Gustavia

  Duration

  8

• 2026 - 8 Day Cruising the Leeward Islands: Marigot to Marigot aboard Emerald Azzurra (Cruise) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  12/13/26, 1/9/27, 2/6/27, 3/6/27, 4/3/27

  Ports of Call

  Starting in Marigot with stops in Anguilla, Norman Island, Jost van Dyke, Anegada, Gustavia

  Duration

  8

• 2026 - 8 Day Eastern Caribbean with St. Barths: Marigot to Bridgetown aboard Emerald Azzurra (Cruise) from $7,590.00 (USD)

  Destination

  Caribbean

  Departures

  12/20/26, 1/16/27, 2/13/27, 3/13/27

  Ports of Call

  Starting in Marigot with stops in Gustavia, Cades Bay, Falmouth Harbour, Iles des Saintes, Soufriere, Bridgetown

  Duration

  8

• 2026 - 14 Day Discover the Grenadines & Windwards Islands: Bridgetown to Marigot aboard Emerald Azzurra (Combo) from $14,780.00 (USD)

  Destination

  Caribbean

  Departures

  12/27/26

  Ports of Call

  Starting in Bridgetown with stops in Port St. Charles, Bequia Island, Mayreau Island, Union Island, Tobago Cays, Soufriere, Iles des Saintes, Falmouth Harbour, Cades Bay, Gustavia, Marigot

  Duration

  14

• 2027 - 7 Day Splendours of the Caribbean: St. Thomas to San Juan aboard Emerald Sakara (Combo) from $7,190.00 (USD)

  Destination

  Caribbean

  Departures

  1/3/27

  Ports of Call

  Starting in Saint Thomas with stops in Cruz Bay, Nevis, Falmouth Harbour, Gustavia, Prickly Pear Cays, San Juan

  Duration

  7

• 2027 - 7 Day Caribbean Sojourn: Bridgetown to Marigot aboard Emerald Azzurra (Combo) from $7,190.00 (USD)

  Destination

  Caribbean

  Departures

  1/3/27

  Ports of Call

  Starting in Bridgetown with stops in Soufriere, Iles des Saintes, Falmouth Harbour, Cades Bay, Gustavia, Marigot

  Duration

  7

• 2027 - 14 Day Discover the Hidden Wonders of the Caribbean: Bridgetown to Marigot aboard Emerald Azzurra (Combo) from $15,180.00 (USD)

  Destination

  Caribbean

  Departures

  1/3/27

  Ports of Call

  Starting in Bridgetown with stops in Soufriere, Iles des Saintes, Falmouth Harbour, Cades Bay, Gustavia, Marigot, Anguilla, Norman Island, Jost van Dyke, Anegada

  Duration

  14

• 2027 - 8 Day Quintessential Caribbean: San Juan to St. Thomas aboard Emerald Sakara (Combo) from $7,990.00 (USD)

  Destination

  Caribbean

  Departures

  1/9/27, 2/13/27, 3/20/27

  Ports of Call

  Starting in San Juan with stops in Cruz Bay, Nevis, Deshaies, Falmouth Harbour, Gustavia, Prickly Pear Cays, Saint Thomas

  Duration

  8

• 2027 - 15 Day Discover the Pearls of the Caribbean: Marigot to Bridgetown aboard Emerald Azzurra (Cruise) from $15,980.00 (USD)

  Destination

  Caribbean

  Departures

  1/9/27, 2/6/27, 3/6/27

  Ports of Call

  Starting in Marigot with stops in Anguilla, Norman Island, Jost van Dyke, Anegada, Gustavia, Cades Bay, Falmouth Harbour, Iles des Saintes, Soufriere, Bridgetown

  Duration

  15

• 2027 - 8 Day Quintessential Caribbean: St. Thomas to San Juan aboard Emerald Sakara (Combo) from $7,990.00 (USD)

  Destination

  Caribbean

  Departures

  2/6/27, 3/13/27, 4/3/27

  Ports of Call

  Starting in Saint Thomas with stops in Cruz Bay, Nevis, Deshaies, Falmouth Harbour, Gustavia, Prickly Pear Cays, San Juan

  Duration

  8