7-night Windward Ways & Tobago Cays Cruise
+1 more deal
1 of 2
Sailing Jan 25, 2026
from $3,624 per person* taxes and fees included
Sailing Jan 25, 2026
4.9/5 ⭐Google 600+ Reviews | A+ Better Business Bureau
Taxes and fees included in all prices shown
Taxes and fees included in all prices shown
4.7
18 Reviews
Sort by
May 20, 2025
5 out of 5 stars
Complete joy to travel on the Wind Surf. The low number of passengers makes this one a totally comfortable environment. The layout of the boat makes for easy access to any part of the trip with great views from anywhere. The staff were beyond friendly and courteous.
Pros: size of boat and number of possible passengers
Cons: nothing
Accommodations
5
Activities
5
Entertainment
5
Food
5
Staff
5
Itinerary
5
Value
0
Overall
5
Recommend
Yes
Sep 9, 2024
5 out of 5 stars
The itinerary was of great interest to us. We found the destinations and tours most interesting. The cuisine was outstanding and the presence of the James Beard Foundation chefs added glamour and inventiveness. The ship itself was comfortable and the atmosphere most relaxed and enjoyable. The Sports Deck provided an opportunity to swim in the Mediterranean Sea. We can't wait to sail with Windstar again!
Pros: Excellent ship; itinerary; cuisine; fun atmosphere; activities;
Cons: Wish there were a few more days when the sports deck would be open for use; would enjoy an evening of entertainment off the ship
Accommodations
5
Activities
5
Entertainment
4
Food
5
Staff
5
Itinerary
5
Value
0
Overall
5
Recommend
Yes
Jun 18, 2023
5 out of 5 stars
From the crew and their sincere politeness and kindness to the ease of the embarkation, excursions and disembarkation, I have absolutely no complaints. One reason you should consider the smaller boutique experience of WindStar is we were in port in Montenegro and so was NCL & Princess and the lines for them to board the tenders to return were so very long. For us on Windstar, no lines, no waiting, just walked right past and onto the ship immediately. So very very nice
Pros: No lines, no waiting, just perfect
Cons: The sails did not work
Accommodations
5
Activities
4
Entertainment
5
Food
5
Staff
5
Itinerary
5
Value
0
Overall
5
Recommend
Yes
Jun 14, 2023
5 out of 5 stars
Looking forward to another cruise
Pros: Perfect cruising conditions
Cons: None
Accommodations
5
Activities
5
Entertainment
5
Food
5
Staff
5
Itinerary
5
Value
0
Overall
5
Recommend
Yes
Jun 2, 2023
5 out of 5 stars
The staff on this ship was outstanding. They are very attentive and helpful.
Pros:
Cons:
Accommodations
4
Activities
4
Entertainment
5
Food
5
Staff
5
Itinerary
5
Value
0
Overall
5
Recommend
Yes
Feb 5, 2020
5 out of 5 stars
Everything on this cruise was great. However if you are looking for Las Vegas shows and entertainment this is not for you. There is a good 4 piece band and a duo for entertainment. For us that was perfect after the "monster" as they call them, cruise ships with 3000 - 4500 people on board. The staff called us by name after two days, you could go to the bridge almost any time to talk to the captain and other ship officers. Never more than a 5 minute wait to get off the ship by tender. The food in the regular dining room was perhaps the best in the 15 other cruises I've taken on other lines.
Pros: Small, Clean, Super Friendly staff, never crowded, great food, small port of calls
Cons: None
Accommodations
5
Activities
5
Entertainment
5
Food
5
Staff
5
Itinerary
5
Value
0
Overall
5
Recommend
Yes
Taxes and fees included in all prices shown
Taxes and fees included in all prices shown
*Amenities may not be combinable with all fares shown. Additional restrictions apply.
Sunday, January 25, 2026
Departing 6:00 PM
Monday, January 26, 2026
8:00 AM - 5:00 PM
Tuesday, January 27, 2026
8:00 AM - 6:00 PM
Wednesday, January 28, 2026
8:00 AM - 4:00 PM
Thursday, January 29, 2026
Cruising at sea
Friday, January 30, 2026
1:00 PM - 10:00 PM
Saturday, January 31, 2026
8:00 AM - 6:00 PM
Sunday, February 1, 2026
Arriving 6:00 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.
