7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico
1 of 2
Sailing Dec 27, 2027 - Feb 21, 2028
from $2,936 per person* taxes and fees included
Sailing Dec 27, 2027 - Feb 21, 2028
4.9/5 ⭐Google 650+ Reviews | A+ Better Business Bureau
Taxes and fees included in all prices shown
Taxes and fees included in all prices shown
4.3
12 Reviews
Sort by
Jul 18, 2025
5 out of 5 stars
I can't recommend Windstar and this ship enough. The crew are incredibly attentive and the food and itineraries are fantastic. There are fewer evening activities, but we were fine with that since after dinner, we just got a drink in the lounge and then relaxed and recharged for the next day. We met a bunch of people who have done anywhere between 4 and 15 Windstar cruises - they have a very loyal following.
Pros: Great service and only 300 passengers
Cons: Fewer entertainment options
Accommodations
5
Activities
5
Entertainment
4
Food
5
Staff
5
Itinerary
5
Value
0
Overall
5
Recommend
Yes
Jun 10, 2025
5 out of 5 stars
Tom planned us the best trip. The crew were so kind to my mom , sister snd me. Within a day they all knew our names and were so welcoming and friendly. The food is so fresh and tasty. I was impressed by the size and comfort of our cabins. Quite large and wonderfully supplied. The ports are gorgeous and interesting. Scotland has my heart. We loved the ship and hope to book another cruise on Windstar. Ir exceeded our expectations and was just amazing !
Pros: Amazing crew , great food , beautiful ports , huge cabin
Cons: Need to hire a better fitness instructor
Accommodations
5
Activities
4
Entertainment
4
Food
5
Staff
5
Itinerary
5
Value
0
Overall
5
Recommend
Yes
May 14, 2024
5 out of 5 stars
4th cruise on Windstar. Each one has been impressive.
Pros: Great people, great schedule, beautiful scenary, Ephesus was a mountain-top experience
Cons: Corinth canal was inaccessible (not Windstar's fault)
Accommodations
5
Activities
5
Entertainment
5
Food
5
Staff
5
Itinerary
5
Value
0
Overall
5
Recommend
Yes
Aug 10, 2019
5 out of 5 stars
Our cabin was spacious and well appointed. Cabin attendants were always available Ram and Wawan did an outstanding job. The shore trips were varied and all offered the Alaska experience for which we signed up. Guides were knowledgeable. Particularly liked the seaplane trip to Taku lodge, and zodiac tours. Seeing wildlife and hearing about them from enthusiastic guides was a plus. Going ashore in the small villages was enjoyble.
Pros: personal attention
Cons: none
Accommodations
5
Activities
5
Entertainment
4
Food
5
Staff
5
Itinerary
4
Value
0
Overall
5
Recommend
Yes
Jun 5, 2019
5 out of 5 stars
We prefer small ships (the Legend has only 210 passengers) for the more intimate experience this type of sailing provides. Everything on the Legend was perfect - the food, the staff, and the suites - every room is 288 sq ft. with a HUGE picture window.
Pros: The Expedition Team gives you the advantage to zodiac and kayak right off the ship from the watersports platform
Cons: none
Accommodations
5
Activities
5
Entertainment
5
Food
5
Staff
5
Itinerary
5
Value
0
Overall
5
Recommend
Yes
Jun 26, 2019
4 out of 5 stars
Expedition Team is a must for any trip to Alaska. Ship about to be fully renovated, all guests seem happy and very loyal to Windstar
Pros: Itinerary w/ Expedition opportunities, beautiful weather, casual
Cons: Limited on-board technology, in room dining OK, ship to be renovated/stretched
Accommodations
3
Activities
5
Entertainment
3
Food
5
Staff
5
Itinerary
5
Value
0
Overall
4
Recommend
Yes
Taxes and fees included in all prices shown
Taxes and fees included in all prices shown
Published price pp*
taxes & fees included
Published price pp*
taxes & fees included
Published price pp*
taxes & fees included
Monday, December 27, 2027
Departing 7:00 PM
Tuesday, December 28, 2027
Cruising at sea
Wednesday, December 29, 2027
9:00 AM - 10:00 PM
Thursday, December 30, 2027
8:00 AM - 10:00 PM
Friday, December 31, 2027
8:00 AM - 5:00 PM
Saturday, January 1, 2028
10:00 AM - 5:00 PM
Sunday, January 2, 2028
8:00 AM - 3:00 PM
Monday, January 3, 2028
Arriving 7:00 AM
*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.
