10 NIGHTSEastern CaribbeanWindstar Cruises
Star Pride
Roundtrip from Boston, MA
Cruise ports Hamilton • St. George’s, GD • Gustavia • Virgin Gorda/prickly Pear • San Juan, PR
▼ 49% 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
10 NIGHTSEastern Caribbean
7 NIGHTSNorthern Europe
7 NIGHTSNorthern Europe
17 NIGHTSEastern Caribbean
7 NIGHTSCentral America
4 NIGHTSCruise
10 NIGHTSCentral America
11 NIGHTSCentral America
10 NIGHTSNorthern Europe
7 NIGHTSEastern Caribbean
14 NIGHTSEastern Caribbean
7 NIGHTSEastern Caribbean
7 NIGHTSEastern Caribbean
11 NIGHTSSouth Pacific
4 NIGHTSNorthern Europe
11 NIGHTSEastern Caribbean
7 NIGHTSNorthern Europe
8 NIGHTSEastern Caribbean
4 NIGHTSNorthern Europe
8 NIGHTSNorthern Europe
11 NIGHTSCanada/New England
14 NIGHTSEastern Caribbean
14 NIGHTSEastern Caribbean
11 NIGHTSNorthern Europe
14 NIGHTSEastern Caribbean
3 NIGHTSNorthern Europe
7 NIGHTSCentral America
8 NIGHTSNorthern Europe
7 NIGHTSNorthern Europe
7 NIGHTSCruise
14 NIGHTSEastern Caribbean
7 NIGHTSEastern Caribbean
7 NIGHTSEastern Caribbean
11 NIGHTSNorthern Europe
14 NIGHTSEastern Caribbean
5 NIGHTSNorthern Europe
7 NIGHTSNorthern Europe
7 NIGHTSNorthern Europe
7 NIGHTSSouthern Caribbean
5 NIGHTSNorthern Europe
16 NIGHTSEastern Caribbean
16 NIGHTSEastern Caribbean
3 NIGHTSNorthern Europe
11 NIGHTSNorthern Europe
23 NIGHTSEastern Caribbean
11 NIGHTSSouth Pacific
14 NIGHTSNorthern EuropePer person per night (PPPN)
| Cabin Type | Low | Median | High | Data Points |
|---|---|---|---|---|
| Inside | $188 | $480 | $645 | 43 |
View full price history for each sailing
| Departs | Nights | From | Region | Best Price | Score | |
|---|---|---|---|---|---|---|
| Oct 9, 2026 | 11 | Montreal | Canada/New England | $4,334 | 68 | Price history → |
| Oct 9, 2026 | 19 | Montreal | Canada/New England | $6,194 | — | Price history → |
| Oct 20, 2026 | 8 | Boston, MA | Canada/New England | $3,648 | 57 | Price history → |
| Oct 28, 2026 | 11 | San Juan, PR | Caribbean | $4,785 | 63 | Price history → |
| Nov 8, 2026 | 14 | San Juan, PR | Caribbean | $5,600 | 7 | Price history → |
| Nov 8, 2026 | 7 | San Juan, PR | Caribbean | $3,472 | 1 | Price history → |
| Nov 15, 2026 | 7 | San Juan, PR | Caribbean | $2,723 | 53 | Price history → |
| Nov 15, 2026 | 14 | San Juan, PR | Caribbean | $4,970 | 50 | Price history → |