Silversea Caribbean cruises from San Juan

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

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11-night Caribbean from San Juan

Silversea · Silver Dawn

9 ports
Round trip
Sails Jan 4, 2028
From $5,950 pp
Luxury

Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

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7-night Caribbean from San Juan

Silversea · Silver Shadow

5 ports
Round trip
Sails Dec 20, 2026
From $5,950 pp
Luxury

Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
Castries Cosol Tours: All-Island Private Safari with 7 Stops

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7-night Caribbean from San Juan

Silversea · Silver Shadow

6 ports
Round trip
Sails Dec 27, 2026
From $7,050 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Iles des Saintes Sunrise Hike to Le Chameau's Summit Fort

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7-night Caribbean from San Juan

Silversea · Silver Dawn

6 ports
Round trip
Sails Dec 21, 2027
From $5,150 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night San Juan to Bridgetown

Silversea · Silver Shadow

10 ports
One way
Sails Feb 6, 2027
From $4,250 pp
Luxury

Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

10-night San Juan to Bridgetown

Silversea · Silver Shadow

10 ports
One way
Sails Jan 10, 2027
From $4,650 pp
Luxury

Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Codrington Barbuda's Pink Sand Beach at Dawn, Private & Empty

See the whole trip →

10-night Caribbean from San Juan

Silversea · Silver Dawn

10 ports
Round trip
Sails Dec 11, 2027
From $6,050 pp
Luxury

Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts

See the whole trip →

10-night Caribbean from San Juan

Silversea · Silver Dawn

10 ports
Round trip
Sails Jan 15, 2028
From $5,750 pp
Luxury

Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

9-night Caribbean from San Juan

Silversea · Silver Dawn

8 ports
Round trip
Sails Feb 10, 2028
From $5,050 pp
Luxury

Anguilla Sandy Island by Private Boat: Barefoot Sandbar Escape
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

7-night Caribbean from San Juan

Silversea · Silver Shadow

7 ports
Round trip
Sails Jan 3, 2027
From $6,650 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Codrington Barbuda's Pink Sand Beach at Dawn, Private & Empty

See the whole trip →

7-night Caribbean from San Juan

Silversea · Silver Shadow

7 ports
Round trip
Sails Jan 30, 2027
From $6,150 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
Codrington Barbuda's Pink Sand Beach at Dawn, Private & Empty

See the whole trip →

7-night Caribbean from San Juan

Silversea · Silver Shadow

7 ports
Round trip
Sails Feb 26, 2027
From $5,450 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

11-night Caribbean from San Juan

Silversea · Silver Dawn

9 ports
Round trip
Sails Jan 25, 2028
From $6,050 pp
Luxury

Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

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