24 reviews | Dec 02, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 5 Nights | Gustavia | Jost Van Dyke, Great Harbour | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $1,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Nov 03, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 6 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | Virgin Gorda | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 07, 2025 | Windstar | Star Pride | Caribbean | San Juan | Colon | 6 Nights | Cartagena | Colón | San Blas | San Juan | Santo Domingo | $2,899 Up To $300 Onboard Credit | | Suite! |
2 reviews | Apr 25, 2024 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 7 Nights | Bora Bora | Huahine | Moorea | Motu Mahaea (Tahaa) | Papeete | Raiatea | $2,699 Up To $300 Onboard Credit | | Suite! |
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10 reviews | Apr 27, 2024 | Windstar | Wind Star | Greek Isles | Civitavecchia | Athens (Piraeus) | 7 Nights | Athens, Greece | Gythion | Messina (Taormina) | Monemvasia | Ponza | Rome | Sorrento | $1,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Apr 28, 2024 | Windstar | Wind Spirit | Mediterranean | Barcelona | Civitavecchia | 7 Nights | Barcelona | Bastia | Calvi | Mahon | Palma de Mallorca | Portoferraio | Rome | $2,819 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | May 04, 2024 | Windstar | Wind Star | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $5,899 Up To $750 Onboard Credit | | |
11 reviews | May 05, 2024 | Windstar | Wind Spirit | Greek Isles | Civitavecchia | Athens (Piraeus) | 7 Nights | Athens, Greece | Gythion | Messina (Taormina) | Monemvasia | Ponza | Rome | Sorrento | $2,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | May 11, 2024 | Windstar | Wind Star | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $4,199 Up To $500 Onboard Credit | | |
11 reviews | May 12, 2024 | Windstar | Wind Spirit | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $4,499 Up To $500 Onboard Credit | | |
10 reviews | May 18, 2024 | Windstar | Wind Star | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $3,799 Up To $500 Onboard Credit | | |
11 reviews | May 19, 2024 | Windstar | Wind Spirit | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | May 25, 2024 | Windstar | Wind Star | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $3,799 Up To $500 Onboard Credit | | Onboard Credit! |
11 reviews | May 26, 2024 | Windstar | Wind Spirit | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $3,899 Up To $500 Onboard Credit | | |
10 reviews | Jun 01, 2024 | Windstar | Wind Star | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $4,099 Up To $500 Onboard Credit | | |
11 reviews | Jun 02, 2024 | Windstar | Wind Spirit | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $3,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
2 reviews | Jun 06, 2024 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 7 Nights | Bora Bora | Huahine | Moorea | Motu Mahaea (Tahaa) | Papeete | Raiatea | $4,219 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Jun 08, 2024 | Windstar | Wind Star | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $3,899 Up To $500 Onboard Credit | | |
11 reviews | Jun 09, 2024 | Windstar | Wind Spirit | Greek Isles | Athens (Piraeus) | Athens (Piraeus) | 7 Nights | Athens, Greece | Kusadasi | Monemvasia | Mykonos | Nafplio | Patmos | Santorini | $3,899 Up To $500 Onboard Credit | | Onboard Credit! |
2 reviews | Jun 13, 2024 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 7 Nights | Bora Bora | Huahine | Moorea | Motu Mahaea (Tahaa) | Papeete | Raiatea | $4,079 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |