Sunset over the Caribbean

Mary & Michael Sperry –Yacht Club Members Profile

We’re kicking off the launch of our newly enhanced loyalty program by celebrating our past guests during Yacht Club Member Appreciation Week. Each day we’ll be profiling a Yacht Club Member to showcase the member’s Windstar experiences and memories.

Number of Windstar Cruises: 35 weeks of cruising
Our first Windstar Cruise was the Istanbul to Athens Cruise, on Wind Spirit in 1998. The most memorable destination was Kusadasi, followed closely by Santorini. This was our first cruise of any kind, and we knew our lives had changed forever.
A photo of Mary and Michael Sperry
Mary and Michael Sperry
Here are some of our favorite places we’ve visited over the years:
Mediterranean Highlights: Kusadasi (ruins of Ephesus), Santorini (unbelievably beautiful), Malta (amazing history), Rome (the city itself, St. Marks, the Vatican Museums, the Roman Ruins), Granada (The Alhambra!), Florence (The Duomo, Statue of David), Venice (The Doge, Bridge of Sighs, etc.), Dubrovnik (The old city). Some great not-to-miss sites: Pompeii, Aix-en-Provence, Eze, Statue of Columbus in Barcelona harbor, the Greek Ruins in Athens.
In the Caribbean: Brimstone Hill Fortress in St Kitts, The Pitons in St. Lucia, Fort Napoleon in Les Saintes, The Baths in Virgin Gorda, Soper’s Hole in Tortola, Birthplace of Alexander Hamilton in Nevis.
The sun setting with a view of the Wind Surf orange ring on the deck
The Caribbean sunset taken from Wind Surf.
Most memorable Windstar moment?
It is hard to pick just one. But my first choice has to be from our very first cruise, the Sail Away from Santorini. We were there on a Thursday and were anchored in the harbor for the onboard barbecue. After the meal, as the ship was starting to sail, the ship entertainers began their performance. I could not believe it! I went up to their leader and said: “Excuse me, but we must have the sailing music during the Sail Away.” She was not happy, but she readily acquiesced. When the Sail Away music began, the passengers began to applaud and lifted their glasses in salute to us. There are some things you just don’t mess with!
A significant—but somewhat underappreciated—advantage of Windstar Cruises is the camaraderie that naturally develops among passengers. I am always amazed at the way total strangers seem to naturally bond once they come aboard. It starts immediately at check-in. I find myself saying,over and over again, as it proves to be the case: “You can never tell who you’ll meet on a Windstar cruise!” We have long-time close friends we have never seen or met except on a Windstar cruise. Reconnecting with them is part of what keeps us coming back to the same ship at the same times.
What else keeps us coming back?
More than anything else, it is the ship itself. Close second is the crew, those wonderful people who transform a cruise from a vacation trip into a memory. Early on we were excited about the destinations. But after traversing all of the Med, from Venice to Lisbon, at least three times, and after sailing most of the Caribbean several times, we finally realized that the destination was less important than the sailing and the camaraderie we enjoy with new friends we meet and old friends from previous cruises. So, when people ask us where we like to go, we say: “wherever Wind Surf goes.”
Cruises on Windstar’s sailing ships are unique. The sails are what make them so. People actually fall in love with these ladies of the sea, especially after they experience what it’s like to sail without the engines.
View of the sail and the moon at night
Take in the view of the sails as you dine under the moonlight at Candles.
We are booked for our favorite Caribbean cruise in February. We love the 14-day cruises that combine Classic Caribbean and Yachtsman’s Caribbean itineraries. We are looking forward to seeing Soper’s Hole again which was badly destroyed by the last hurricane and was only added back to the Surf’s itinerary in 2020. We are hoping our favorite store “Latitude 18” has been restored as well.
We have six tips for new to Windstar cruisers:
  1. Do not over pack. The laundry service is excellent and eliminates the need to bring more than enough clothing for 3 or 4 days.

  2. Honor the dinner dress code. Country club casual (maybe a jacket, but no ties) is the standard. PLEASE: no blue jeans, tennis shoes, or flip-flops!

  3. Bring lots of cash. You will be pampered more than you expect, and you will want to give lots of tips to lots of crew members. And go big: my rule of thumb is that tips be paid with nothing smaller than a Grant or a Franklin. Plan ahead and go big!

  4. Never miss a Sail Away. This event has effects which cannot be reduced to words. It will transform you, drawing you back to the mystical powers of the sea for the rest of your life.

  5. Make sure to sign up for Candles. Dining under billowing sails and stars not dimmed by shore lights is something not available on a typical cruise ship.

  6. Be extra nice to your cabin steward. He/she will be helpful if you need anything for your room, from the laundry, or pretty much anything else. Do not forget to leave them a nice tip

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