Experience boutique cruising aboard Windstar's yachts and get pampered, personalized service. Windstar's ships are large enough to pamper, yet small enough to explore charming villages and remote islands.
Reserve select sailings now and take advantage of this early booking offer:
Choose your sailing below or call our experts at 1 (877) 734-6858 to take advantage of this early booking offer now!
Submit the form below or call us at 1 (877) 734-6858
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
| 8-night Bermuda Bliss Cruise Boston to San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 10/20/26 | From $2,426 |
| 11-night Gems Of The Leeward Islands Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 10/28/26 | From $3,657 |
| 10-night Treasures Of Southern Spain & Morocco Cruise Barcelona to Lisbon | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 10/31/26 | From $4,064 |
| 14-night Star Collector: Lovely Leewards Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 11/8/26 | From $4,093 |
| 7-night Windward Islands Surf & Sunsets Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 11/8/26 | From $2,530 |
| 14-night Ocean Crossings Cruise Lisbon to Bridgetown (Barbados) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 11/10/26 | From $2,525 |
| 14-night Star Collector: Lovely Leewards Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 11/15/26 | From $4,093 |
| 7-night San Juan & The Virgin Islands Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 11/15/26 | From $2,562 |
| 14-night Star Collector: Lovely Leewards Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 11/22/26 | From $4,093 |
| 7-night Windward Islands Surf & Sunsets Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 11/22/26 | From $2,530 |
| 11-night Colombian & Southern Caribbean Coastlines Cruise Bridgetown (Barbados) to Colon (Panama) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 11/24/26 | From $4,030 |
| 14-night Star Collector: Lovely Leewards Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 11/29/26 | From $4,093 |
| 7-night San Juan & The Virgin Islands Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 11/29/26 | From $2,562 |
| 7-night Costa Rica & Panama Canal Cruise Colon (Panama) to Puerto Caldera (Puntarenas) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/5/26 | From $3,869 |
| 10-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package Colon (Panama) to San Jose (C.R.) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/5/26 | From $6,269 |
| 14-night Star Collector: Lovely Leewards Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 12/6/26 | From $4,093 |
| 7-night Costa Rica & Panama Canal Cruise Puerto Caldera (Puntarenas) to Colon (Panama) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/12/26 | From $3,669 |
| 14-night Star Collector: Lovely Leewards Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 12/13/26 | From $4,193 |
| 11-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package San Jose (C.R.) to Colon (Panama) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/8/26 | From $6,069 |
| 7-night Windward Islands Surf & Sunsets Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 12/6/26 | From $2,530 |
| 10-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package Colon (Panama) to San Jose (C.R.) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/19/26 | From $6,069 |
| 7-night Costa Rica & Panama Canal Cruise Colon (Panama) to Puerto Caldera (Puntarenas) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/19/26 | From $3,669 |
| 7-night San Juan & The Virgin Islands Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 12/13/26 | From $2,562 |
| 14-night Star Collector: Lovely Leewards Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 12/20/26 | From $4,493 |
| 7-night Costa Rica & Panama Canal Cruise Puerto Caldera (Puntarenas) to Colon (Panama) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/26/26 | From $3,669 |
| 14-night Star Collector: Lovely Leewards Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 12/27/26 | From $4,393 |
| 7-night San Juan & The Virgin Islands Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 12/27/26 | From $2,862 |
| 7-night Windward Islands Surf & Sunsets Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 12/20/26 | From $2,730 |
| 11-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package San Jose (C.R.) to Colon (Panama) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/22/26 | From $6,069 |
| 7-night Costa Rica & Panama Canal Cruise Colon (Panama) to Puerto Caldera (Puntarenas) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 1/2/27 | From $3,669 |
| 10-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package Colon (Panama) to San Jose (C.R.) | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 1/2/27 | From $6,069 |
| 14-night Star Collector: Lovely Leewards Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 1/3/27 | From $4,193 |
| 7-night Windward Islands Surf & Sunsets Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 1/3/27 | From $2,630 |
| 7-night San Juan & The Virgin Islands Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 1/10/27 | From $2,662 |
Fares/rates are per person, based on double occupancy for select sail and travel dates; are capacity controlled and subject to availability at time booking and may be pulled without notice. We reserve the right to correct errors. Information and pricing is subject to change without notice. While we do our very best to ensure that information and pricing appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. In the event of a pricing error, misrepresentation or omission, we reserve the right to adjust the pricing or make any other corrections.