FAWQ: Frequently Asked Windjammer Questions

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Got Questions?
You’re about to embark on one of the best vacations of your life! We want to make sure that you feel comfortable every step of the way. Following are some of the most commonly asked questions about Island Windjammers and our Caribbean tall ship sailing cruises. If there is anything else you’d like to know, please give us a call, 727.776.5213 or email us. We’re standing by to lend a hand.
Life on Board
Q. What is there to do on board?
A. From bowsprit to stern, this is your home for the week, so make yourself comfortable. Take a dip from the ship and laze around on a “floatie mat,” or cruise on one of the ship’s kayaks to a secret cove. You can help raise the sails, take the helm, or simply relax and watch the action. The ship’s saloon features a DVD player, board games and playing cards.

Let us know what you came to enjoy, and we’ll do our best to ensure that you’re a happy sailor.

Q. How’s the food?
A. Delicious and plentiful! Breakfast, lunch, and dinner are served on board, as well as afternoon and evening snacks. We make every effort to buy provisions locally. This helps the local economy and brings you the freshest fruits, meats, fish and vegetables available. We will do our best to accommodate guests with special dietary needs.

Q. Is there a full bar on board?
A. Due to space constraints, we carry only a basic selection of alcohol. Guests are welcome to bring their own spirits on board to mix their favorite drinks.

Q. Do you provide mixers?
A. Depending upon availability, we provide Coke, Diet Coke, Sprite, Ginger Ale and Tonic Water.

Q. What’s included in the price of my sailing cruise?
A. Your six night tall ship sailing cruise price includes accommodations for the week, all meals aboard the ship, complimentary soft drinks, locally brewed beer and wine and use of ship’s snorkel gear. Your cruise fare also includes port taxes and government fees.

Q. How far ahead should I reserve my cabin?
A. We suggest reserving your preferred cabin at least six months in advance. With our limited capacity, dates fill up fast.

Q. Do we tip the crew and our host, and if so, how much?
A. Tipping is solely at your discretion. If you feel that our windjammer crew has done an outstanding job, a tip of $150 per person, per week is suggested. You may charge your gratuity at the end of your cruise on a credit card. An appropriate tip for the O&A host is $25 – $30

What to Bring
Q. What style and type of clothes will I need to pack?
A. Bring T-shirts, shorts, a hat, a couple of bathing suits and a sweatshirt or light jacket for cooler evenings on deck. Bare feet are best on wet decks, but do pack a comfortable pair of shoes or sandals for beach days and excursions. Don’t forget sunscreen and a beach towel! Keep all prescription medications with you in your carry on. Cabins on tall sailing ships, while comfortable, are very compact. Extra space is at a premium. Pack light!!

Q. Do you have space to store my luggage?
A. Due to our limited space, you are encouraged to pack lightly and bring soft-sided luggage or a duffel bag. We do not have extra storage space for large hard-sided luggage.

Q. Should I bring snorkel gear? Are there opportunities for scuba diving?
A. We offer complimentary use of snorkel gear for your sailing week. If you have your own mask and snorkel, we encourage you to bring them, as they will probably be the best fit for you. We have plenty of fins, if you’d like to leave yours at home. For those interested in scuba diving, you can make arrangements with local dive shops.

Flotsam and Jetsam
Q. Will I get seasick?
A. Sensitivity to motion is not always based on weather conditions. If you have experienced motion sickness in the past, or you’re not sure how you will adjust, we recommend that you pack your preferred remedy. If you are prone to seasickness, you should take your medication approximately four hours prior to setting sail. If you wait until you start to feel sick, the medication may not be effective.

Q. I have physical limitations. Can I still enjoy this trip?
A. To access your cabin, you will need to be able to climb down a fairly steep stairway. There are overhead rails to grab at the bottom landings. While we are at anchor, you will need to be able to climb down a stairway and board the dinghy if you wish to go ashore.

Outings & Adventures has exclusively chartered Island Windjammers’ ALL new ship Vela, our largest tall ship with capacity for 30 guests. The ship is all ours!

What makes our departure different from the other 51 weeks of the year?
First, Outings & Adventures’ alliance with Island Windjammers is very unique. There is something to be said about the company one keeps and for that reason Outings & Adventures only teams up with top tour operators and hospitality industry leaders. Island Windjammers has a pristine reputation for an unparalleled commitment to safety and seamanship. Check out their reviews.

Next, after having chosen the ideal cruising partner, Outings & Adventures then added its own touches to our exclusive departure. Some of the touches are still surprises, however there are many we are eager to share with you.
• Traveling with the camaraderie of likeminded gay men
• Customizing the itinerary
• Themed socials and ‘mixer’ type activities
• Nightly Happy Hour

Outings & Adventures founder, Robert Geller, your host during the inaugural voyage has researched nearly every detail of the itinerary, experienced every hike and as many of the excursions as possible so that our trip could be customized just for us!
So weather you choose to relax on a lounge chair with the Caribbean breeze blowing over you or take in a vigorous hike, at the end of the day we come together under stars for a wonderful meal and the sharing of our experiences!

We’re available to answer any questions you may have, call us at: 727.776.5213

 The SMART Ride 11





  1. John Livingston says:

    I have never sailed like this, but I am adventurous, so I will try anything at least once!

    • O&A says:

      It will be a vacation experience you’ll never forget! The reviews of our Windjammer sailings have been unprecedented high marks.

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