Which wind star cruise is right for me?

I am a long time mega-ship cruiser, excited to transition to the smaller port-focused Wind Star ships and itineraries. I am hopelessly torn between two itineraries...

1. San Juan & Virgin Islands on Star Legend out of San Juan

http://www.windstarcruises.com/cruise/itinerary-ports/caribbean/san-juan-and-the-virgin-islands/?id=100&sid=20762

2. Jewels of the Windward Islands on Wind Star out of Barbados

http://www.windstarcruises.com/cruise/itinerary-ports/caribbean/jewels-of-the-windward-islands/?id=41&sid=20730

Our goal is for a relaxing vacation with beautiful beaches in the more remote, exotic Caribbean islands. Diving options are a plus, but not a necessity. I am curious about the differing opinions of Star Legend vs. Wind Star, but the ports are the priority.

I am leaning towards the first option, since it boasts zero sea days and an extra port...but I'd love to hear all opinions on these itineraries. I have been to St. Maarten, Virgin Gorda (favorite of the three), and St. Lucia and enjoyed them all...so I am most interested in opinions on the other stops.

Thanks for any advice!!

Welcome, sarg04. Prior military, I would guess, so hooah. You've posed a really good question. There are several regular posters that have been on countless Windstar cruises, so they are probably best to answer the questions about specific ports.

Both of these itineraries sound really wonderful and I think you'd love them, but for different reasons. We'll probably get around to doing each one eventually. I think I'd choose the Wind Star "Jewels of the Windward Islands" out of Barbados for my first one. The romance of the sails is something I really want to experience really soon. Plus, I have been to Puerto Rico, and the port of San Juan has more negatives than positives, IMHO. (Old San Juan is nice, but the city proper is pretty dirty, crowded with traffic, tourists are everywhere, and there's lots of urban blight, especially for a Caribbean island). I would have to guess, but Barbados might be a better starting point for the relaxing, low-key experience you're craving.

Having said that, the Star Legend will give you a suite for the same money. And if you have time for a few days to unwind before sailing, the remote areas in Puerto Rico are lush and scenic. Find a nice B&B or resort and take the time to explore the rainforests.

For us, we decided our first Windstar cruise will be on the Star Breeze, because it has a perfect 9-night itinerary and the price couldn't be beat. But we will definitely go for something on the Wind Surf or Wind Star next time.

Whatever you decide, please post a thorough review so that we get your first timer impression. Like you, we have decided to leave the big boats behind, and we can't wait to do our first cruse on Windstar (102 days out, but who's counting?)

Oh by the way, sarj04, please check out the video posted on another thread, "Tell Me About the Sailing Ship Wind Star". It shows highlights from the "Jewels of the Windward islands". I found it to be very interesting, and now I know what to expect from that particular itinerary. :cool:

Have not done the Star Legend itinerary yet, so I can't really help you on that one.

However, have done the Jewels of the Windward Islands twice - so you could say that we thoroughly enjoyed it and would be happy to do it again. Here is my review: http://boards.cruisecritic.com/showthread.php?t=1989753.

The Wind Star (and Spirit) are the smallest ships in the fleet. Since you are jumping from large cruise ships to a very small one, do your homework on what to expect and you won't be disappointed. Does the small ship have all the multiple amenities of a mega-ship - no. Does it provide everything necessary for a relaxing and enjoyable trip - yes.

Good luck with your decision-making!

I have done the Windwards and also just booked the Legend out of San Juan. For your first cruise go with the Windwards cruise. Based on what you described, the ports on the Windwards cruise will be nicer for you. Mayreau and the Tobaco Cays are beautiful as is Grenada. The water colour is Aqua and not the same as the eastern Caribbean. The sailing ship is special. Enjoy

I would vote for the Wind Star as well. That is a great itinerary, we did a similar one a couple of years ago on the Wind Surf. On the other hand, we're trying the Star Legend from Iceland through Norway to Ireland this summer, so I could probably give a more informed opinion then.

We did Jewels of the Windward Islands on Wind Star out of Barbados and we loved it. Loved every stop and we wish to do it again in the future.

Direct flight from Toronto for us and Barbados got great scenery too.

dandee2

Can only speak to the Windward Islands itinerary - we did it December 15, and are repeating Feb 17 - loved it that much. Had only been on the Windsurf prior, and instantly fell in love with the Windstar. My husband does not want to go back to the Windsurf now. Loved the feel and crew on the Windstar. Bon Voyage - hard to go wrong with either choice:)

Sails are beautiful. There is something magical about sailing. When the motor is off and the sails are up, there is a serene feeling that you cannot get on the motor yachts.

Sarj04, good morning.

We did the San Juan & Virgin Islands itin on the Legend last December. First time on Windstar and absolutely LOVED it. We had previously visited most of the islands but this schedule provided access to 2 new ones for us - Culebra and Montserrat. Loved both those islands. I wrote a rather detailed review back in Dec and my wife (Mrs Tiki) posted a review on the CC Review board.

We thought the Legend was ideal for what we wanted. Rooms are so spacious. The only issue with the trip was the Tender situation but I am guessing they have that solved by now. The layout of the ship was easy, service was of course outstanding, and the itinerary was ideal. Diving might have been a bit tough (not offered through Windstar) but there were private operators that could have accommodated at most stops (I choose not to dive).

We have not tried the Jewels itin yet but are intrigued with Bequia and some of those islands. I will say that sailing to and from San Juan made things very easy and LOTS of options in regards to flights, that is why we choose the San Juan itinerary for our first try.

Cheers

Tiki

We have not done the "Jewels" with Windstar (have visited those islands at other times) but have done Yachtsman's Caribbean twice on the Surf and the BVI's on the Legend out of San Juan last year. It was an easy and inexpensive plane ride from Florida which was a real plus. We also wanted to revisit Montserrat as we were there in the 80's before the volcano and were very much interested in returning. We are so glad that we did as there is nothing else like it on the planet. We toured with Sun's Montserrat Island Tours (there are others) and had one of the most astounding days we ever experienced in the Caribbean. I would go on that itinerary again just to revisit Montserrat which is so different than any other island. They are also desperately trying to resurrect a tourism industry and Windstar is really doing the right thing by having regular weekly stops there. As for the rest, all of the islands on both cruises are lovely. We love Jost Van Dyke and have been there the past three years. Our only disappointment with the Legend trip is that WS guests are no longer able to visit the Bitter End Yacht Club which we dearly love. If you go on the San Juan trip see if you can arrange a tour to Necker Island with Gumption. It might be a little tricky now as two years ago he was able to pick us up at the BEYC. If you're interested you might see if he could pick you up at the Prickly Pear dock. His website is seaitcleartours. He is the only person who can do tours of Sir Richard's island and it's quite a marvelous place. If you go wear sturdy shoes, sunscreen and mosquito repellent. It's a few hours of walking but so worth it. Whichever itinerary you choose, have fun! You can't go wrong on the islands with WS!