14 NIGHTSEastern CaribbeanWindstar Cruises
Star Legend
Roundtrip from San Juan, PR
Cruise ports Funchal • Casablanca • Lisbon, PT
▼ 10% below 90-day avgAt all-time low

Score 75+
Distinct routes
Balcony • PPPN
Every route this ship sails — best price and deal score across all departure dates
14 NIGHTSEastern Caribbean
7 NIGHTSEastern Caribbean
10 NIGHTSMediterranean
7 NIGHTSMediterranean
15 NIGHTSSouthern Caribbean
8 NIGHTSMediterranean
8 NIGHTSMediterranean
8 NIGHTSCruise
8 NIGHTSMediterranean
8 NIGHTSMediterranean
8 NIGHTSMediterranean
7 NIGHTSCentral America
10 NIGHTSMediterranean
15 NIGHTSSouthern Caribbean
8 NIGHTSCentral America
11 NIGHTSMediterranean
8 NIGHTSSouthern Caribbean
6 NIGHTSMediterranean
12 NIGHTSMediterranean
7 NIGHTSEastern Caribbean
7 NIGHTSMediterranean
7 NIGHTSMediterranean
8 NIGHTSMediterranean
8 NIGHTSMediterranean
4 NIGHTSMediterranean
9 NIGHTSMediterranean
3 NIGHTSMediterranean
7 NIGHTSCentral America
6 NIGHTSMediterranean
8 NIGHTSSouthern Caribbean
7 NIGHTSMediterranean
4 NIGHTSMediterranean
7 NIGHTSMediterranean
6 NIGHTSSouthern Caribbean
7 NIGHTSSouthern Caribbean
21 NIGHTSEastern Caribbean
14 NIGHTSEastern Caribbean
8 NIGHTSMediterranean
6 NIGHTSMediterraneanPer person per night (PPPN)
| Cabin Type | Low | Median | High | Data Points |
|---|---|---|---|---|
| Inside | $277 | $522 | $1016 | 63 |
View full price history for each sailing
| Departs | Nights | From | Region | Best Price | Score | |
|---|---|---|---|---|---|---|
| Oct 11, 2026 | 8 | Athens (Piraeus), GR | Mediterranean | $4,328 | 48 | Price history → |
| Oct 19, 2026 | 8 | Istanbul | Mediterranean | $4,328 | 58 | Price history → |
| Oct 27, 2026 | 8 | Athens (Piraeus), GR | Mediterranean | $4,024 | 50 | Price history → |
| Nov 4, 2026 | 8 | Barcelona, ES | Mediterranean | $2,928 | 63 | Price history → |
| Nov 4, 2026 | 23 | Barcelona, ES | Mediterranean | $4,163 | — | Price history → |
| Nov 12, 2026 | 15 | Malaga | Mediterranean | $3,510 | 74 | Price history → |
| Nov 12, 2026 | 22 | Malaga | Caribbean | $6,688 | — | Price history → |
| Nov 27, 2026 | 7 | Barbados, BB | Caribbean | $2,702 | 8 | Price history → |