Island Windjammers Packing Tips & Cruise Insights
By Sarretta McCaslin
My husband and I love to travel, and cruises have become a favored way to do so — we’ve been on over 25 cruises in 33 years of marriage. We appreciate being able to see many different areas or islands during one vacation. As with any vacation or trip, remember that the experience will be what you make of it.
We say that we have never had a bad cruise — we have always found ways to enjoy every ship or hotel or excursion. Not to say there haven’t been little problems (a knocking sound in one room, diesel fumes in a cabin, rain or stormy weather, canceled excursions, and so on), but your attitude and responses to the problems will be what ultimately makes the trip great (or a failure if you choose that mind-set)!

Sarretta and her hubby. *Photo: Sarretta McCaslin
We recently returned from a 12-night repositioning cruise aboard the S/V Vela, operated by Island Windjammer cruises. Although we have sailed on “tall ships” and sailing vessels previously, times have changed, and there are always new strategies and needs for every ship. We researched and asked previous passengers for suggestions, then applied those ideas on board.
Below are some of the things we learned and tried.
Planning Ahead
Taking a cruise on a smaller vessel, like the Vela, is quite different from cruising on a “big” ship, so it is great to have some realistic ideas of what you will encounter and need. Expectations, packing, activities, ports, interactions with other guests and crew — all are completely different. On Vela, for example, you will see every person on board, crew or fellow passenger, on every day of your trip and will likely learn all their names. And the space within your cabin is much smaller than even the smallest cabin on a mega cruise ship — unless you can afford (and are lucky enough to book far, far in advance) the one large Owner’s Suite.
The following list explains our thoughts and advice for deciding on and preparing for a tall ship cruise.
- IMPORTANT: Your physical ability to safely climb into and out of a dinghy (the main mode of transportation to and from the Vela) is a key consideration on whether sailing with Island Windjammers is right for you. These semi-inflatable boats (usually referred to as launches, tenders, or dinghies) can provide either wet or dry landings. For dry landings, the dinghy is tied alongside a dock or pier, and you climb out, assisted by crew members. In wet landings, the dinghy is powered up to a beach, pulled in as far as possible by the crew, and then you climb over the side, usually into ankle- to knee-deep water. Crew will assist you, but being physically able to safely enter and exit the dinghy is vital and can be difficult. (For example, at one rather high concrete dock, several of us had some difficulty: we had to climb up and stand on the side of the dinghy, turn and climb/sit on the dock, then get to our feet from there.)
- We joined the Island Windjammers fan club on Facebook, and used both Facebook and Facebook Messenger to communicate with previous and fellow passengers. This was an amazing resource for information, especially about the ship and suggestions for packing.
- One piece of advice which remains as relevant today as it was 30 years ago is to take enough cash for taxis, tips, and places ashore that don’t take credit cards. US dollars work on most islands, so there’s no need to get EC dollars, but be aware that some of the French islands only accept Euros or credit cards.
- Be sure to check and possibly research your port(s) of embarkation and debarkation (which may be one in the same or may not, depending on your cruise choice). Every island and port is different. On our cruise, we embarked from St. Lucia and disembarked in St. Kitts, which meant some interesting flights to and from those locations.
- If you have the time (and money), it can be wonderful to plan to arrive early at your port of departure, or to stay over for a night or three when you disembark. (For example, we arrived in St. Lucia three days early to get a good taste of the island, and we stayed overnight in St. Kitts after our cruise.)
- Arriving early also reduces the risk of missing your cruise due to missed or delayed flights.
- Speaking of air transportation, sometimes the airport is very close to the port or marina from which you will depart, but it may be quite a distance away. For example, if you fly into St. Lucia, be aware that the main airport is on the southern coast, quite far from the biggest towns, like Castries. Another important thing about departing or arriving in St. Lucia is that IWJ Vela departs from and arrives at Rodney Bay, NOT Castries, where most large cruise ships dock.
- When the airport is distant from the port, staying overnight before and/or after your cruise may be more convenient, or possibly even necessary. (As stated earlier, we chose to get to our embarkation port three days early. We booked a hotel resort in Rodney Bay, then had a 1.5 drive from the airport to the hotel. We took a combination airport transfer plus tour as well as two other tours, including a hike to Venus River waterfall and a North Island beach and rainforest tour, with Island Man Tours — we highly recommend their services and tours!)
- Everyone is somewhat addicted to their cell phones, so plan ahead as to whether you want (or need) to get calls, texts, email, and/or internet service. There is no Wi-Fi connection offered on Vela, but Wi-Fi is often available ashore at restaurants, bars and resorts, as well as through some public access points.
- We used the AT&T International Day Pass for internet, phone calls, and texts, but it only worked if we were on a populated island (or near one, sailing or anchored). Both resorts where we stayed had free WIFI as did many spots we visited ashore. As a cautionary note, research how your phone will charge your usage. For example, we had to be sure to set our phones on “airplane mode” and disable “Wi-Fi calling” on days when we didn’t want to use and be charged for the International Day Pass.
- If you choose to go early or stay longer after your cruise, the cruise line, sites like TripAdvisor.com, and/or other guests can be valuable resources to help you choose where to stay. (We stayed at the Coco Palms Resort which is at a great location in Rodney Bay, within walking-distance of many restaurants, shops, and a beach. If you go there, look for the hummingbirds in the flowering tree next to the pool. The resort also provides a complimentary breakfast buffet that includes authentic local fare.)
RELATED: Here’s a review of Island Windjammers’ Lyra in the Greek Isles.
Things to Know About Sailing on the S/V Vela
Once you book an Island Windjammer cruise, you will receive emails and information detailing much of what you’ll want to know — boarding location and time, travel document requirements, etc. Answering other questions, like “how big is the space under the bunk in cabin #4,” will be more challenging.
Again, Island Windjammers’ Facebook fan club page can help a lot.

A view of Island Windjammers’ Diamant & Vela as seen from our dinghy heading into Saint-Pierre, Martinique. * Photo: Sarretta McCaslin
The following are things we learned about various aspects of our cruise:
Embarkation
- Instructions from Island Windjammer will detail the date, time and location that embarking passengers will meet prior to boarding. Getting to the specified location will be up to you. (For example, though our hotel was within hiking distance of the marina, we had to take a taxi to accommodate our luggage.)
- On some itineraries, passengers can fly into the specified island/port and get a shuttle or taxi from airport to marina or dock in time for embarkation, since boarding time is usually in the early afternoon. In other cases, as in St. Lucia, it might be difficult to arrive by plane the morning of your embarkation and still arrive at the marina on time since the drive from the airport to the marina is a couple of hours long.
- I believe that the meeting points for Island Windjammer cruises are usually set in a local bar or restaurant where you can sit in the shade to wait for the cruise liaison. This also gives you the chance to identify and meet some of your fellow passengers. (Example: in St. Lucia, we were told to meet at Cafe Ole at the Rodney Bay Marina — easy walking distance to the dock where we would catch the tender/dinghy which would ferry all the passengers and their luggage to Vela.)
- Many Island Windjammer passengers are repeat guests. Of the 17 guests on our cruise, most had been on several IWJ voyages, while only six (including us) were “first-timers”!
- S/V Vela never actually docked during our cruise — she was always anchored nearby. Dinghies are used to transport everything and everyone from shore to the vessel. I believe that Vela CAN dock at appropriate portages, but did not do so during our itinerary.
Life Aboard Vela
- Any cruise on Vela is going to be rocking! This is a sailing vessel which is powered by diesel engines and which sometimes uses its sails as well. It is always at the mercy of the winds and currents, at least to some degree. Expect for the vessel to be rocking and rolling during your cruise. Even at anchor, you will be swaying.
- In crossings between islands (e.g., from Dominica to Martinique), the seas can become rough. When the power of the Atlantic Ocean is funneled through a deep channel (like between two volcanic islands), the waves can be high. Winds are channeled between the land masses as well, which can lead to lots of “Elvis Presley” sailing — Rock and Roll! Be sure to look for steam from volcanic vents.
- It is a good precautionary practice to bring along something for seasickness. Many folks on our cruise wore the “dots” or patches to prevent nausea. Though neither of us had ever previously suffered from mal de mare, we took along some Dramamine, but never had to use it.
- The crew is immensely helpful especially if anyone needs assistance or has mobility issues. Some disabilities are easier to handle than others, of course. Mobility-assist devices like canes and walkers are not really appropriate on board the Vela, but people often will take them ashore for excursions.
- Note: If you need distilled water for a CPAP machine, you may find it hard to locate on many Caribbean islands — on St. Lucia, it is only sold as “battery water.”
- Most important events will be “announced” on Vela through the use of a very loud bell being rung in the main salon. Many folks used the breakfast bell as their wake-up call.
- Every day, the crew liaison will post the day’s events on a whiteboard in the Main Salon. It will list where the Vela will be (or be going), the “launch schedule” of when/if the dinghies will go to shore, activities and excursions available, and more. (You will want to take a picture of the whiteboard every day.)
- Snorkeling gear is available to anyone who wants it and can be stored on the main deck when not in use (great since cabin space is limited!)

The 26-pax Vela. * Photo: Island Windjammers
Food & Drinks Aboard Vela
- A smaller whiteboard in the main salon will also be updated every morning to show the planned meals for each day. All the food was incredible on our cruise — Robert and George (the chef and cook) made delicious and beautiful meals, often including some local Caribbean dishes.
- Breakfast (7am), lunch (around noon), snack time (5ish) and dinner (7pm) are served every day. Keep in mind, you are always offered seconds, and the afternoon snacks are sufficiently filling that you may not be very hungry at dinner.
- If you know you will not be partaking of lunch or dinner, please inform a crew member — this is always appreciated by the chef and cook.
- Water, sodas, coffee, tea, and beer are always available at no charge. If you bring a water bottle, you can fill it with their purified water (especially nice to have in your bathroom). Hot water is always available for making tea. Rum punch is served at Snack Time, and wine is available at dinner. (You are allowed to bring your own alcoholic beverages on board, and many folks do so and usually share.)
- When you wake up in the morning, there are chef-made pastries and coffee awaiting you in the main salon.
- At breakfast, everyone is offered yogurt with honey and there is dry cereal available on the table. Then the planned breakfast entrees are served to those who want them.
- Unlike the “big” ships, where passengers can order from various food selections, on the Vela there was usually one planned entree, side, and dessert for lunch and dinner. If the planned option was unappealing to some, they could request a reasonable change. (For example, on our cruise, one lady often had peanut butter and jelly sandwiches, while another passenger requested to always have chicken as her protein.)
- Note: there is a lot of seafood served aboard. As someone who usually avoids non-traditional meats and most seafood, I was a little worried at first. In the spirit of adventure, I decided I would try anything I was served — and I am so glad I did! The tuna steak was especially good — and the curried goat was very tasty.

Dining on deck is a delight. * Photo: Sarretta McCaslin
Areas of Vela
- There are several public areas aboard Vela. These include:
○ the Main Salon which is an indoor dining and activity area where you have breakfast (and other meals during inclement weather);
○ the main deck which is an open area forward where lunch and dinner are often served and where folk gather all times of the day;
○ a smaller aft deck which is partially covered and offers seating as well as room for lounges; and
○ the passageways along the main deck and below deck (which lead to the various cabins and crew areas). - On the main deck, tables and chairs are set up and a sunshade/canopy can be raised for shade for lunch and dinner. There are also chairs and lounges which are tied down during sailing, but which can be used for sunbathing and lounging. Guests also use the large lockers and chests around the deck for seating.
- Be aware that there are no “public” or guest restrooms on the main deck — guests must return to their cabin for toilets.
- There are a few off-limits areas where guests are asked to “stay out” unless specifically told otherwise. The forward area of the main deck is usually not available to passengers due to safety concerns and machinery. Crew quarters are private, and all areas which require climbing to reach are off limits (e.g. the roof of the main salon and aft deck, the rigging, etc.). The wheelhouse and galley are “by invitation only,” as is the engine room, except during tours.
- All passenger cabins on Vela are below the main deck and accessible by rather steep stairs, with railings for safety.

Hanging out on deck. * Photo: Sarretta McCaslin
Cabins Aboard Vela
- There are 14 passenger cabins on Vela. They range in size from small singles (which feature one bunk with a bit of storage space) to the large (hotel-like) Owner’s Suite (king-sized bed, lots of storage, desk, etc.). Many are mid-sized and have either one large bunk (fits two people) or a lower double with an upper single. All cabins have a private bathroom. Note: Cabins do not have locks or keys.
- There is a door hook at the upper corner of bathroom doors in each cabin — these allow you to secure the door in a partially open position to allow the bathroom and contents to dry out. There is a shelf above the bed and you can find a pair of electrical outlets nearby. There is also a pair of outlets in the bathroom.
- Because cabins are rather tight on space, it is advisable to limit the amount of “stuff” you bring, including clothing. (See list at the end for our packing recommendations.)
- Try to limit the clothing you bring. It saves space to bring a “portable washing machine” or a large, heavy-duty Ziplock bag to wash a few items. Many people use the lines on the main deck to hang up clothes and towels to dry. There are clips and clothes pins available for this purpose. If you bring along your own “portable clothes line,” you can string it up in your cabin or on deck.
- Each cabin has a porthole.
- Cabins are “tidied” daily by crew members, but towels are only replaced as needed.
- Soup, shampoo and body wash are provided in each shower.
- There are hair dryers supplied.
VIDEO: Below, Sarretta gives us a quick impromptu look at her Vela cabin, #5 (unmade beds and all! 🙂
VIDEO: Sarretta shows us cabin #5’s cozy little bathroom, below.
Excursions and Activities
- There are excursions and activities, both ashore and aboard Vela. It is good to know that there are always activities for folks with a wide variety of fitness levels. Keep in mind that transport to and from Vela is almost always by dinghy.
- The onboard activities may include:
- Helping raise the sails (always fun and sometimes competitive).
- Swimming and using the rope swing and playing off the side of Vela (at anchor, of course) with the many inflatables and other toys.
- Multiplayer games like Pictionary, card and board games, scavenger hunts (there are lots of games on board, but feel free to bring your own).
- During our cruise, we had painting materials available (watercolor and acrylic) and we painted rocks, shells, pictures, cards, etc.
- More solitary activities like reading, sunbathing, fishing (one of our crew caught a large mahi mahi), star gazing, photography, and wildlife sighting (Example: we saw dolphins, flying fish, fishing bats, monkeys, tarpon, and much more!).
- Note: if you like astronomy, you should consider bringing an astronomy app like Stellarium to identify stars and planets, and you can also determine satellite passes (like ISS) using Heavens Above.
- An engine tour is often available upon request. (This tour is very interesting, and it is a great opportunity to acknowledge the efforts of the ship’s engineer who does so much aboard the Vela.).

Helping to heave up the sails. * Photo: Sarretta McCaslin
VIDEO: For many passengers, dancing is a fun activity that can be enjoyed on deck, especially around Happy Hour time and after dinner, like below:
- There will usually be one or two activities or excursions offered (or recommended) at each port-of-call. Some of our favorites included:
- Hiking & snorkeling near the town of Anse d’Arlet, Martinque
- Shelling and sea-glass hunting at every beach
- Walking around Saint Pierre, Martinique, known as the Pompeii of the Caribbean
- Indian River Tour, Dominica
- Beach Barbeque prepared by Vela on Dominica
- Fort Napoleon, Isles de Saintes
- Drinks and hermit crabs at Chez Henri, St. Louis Village, Marie Gallant Island
- Jardin Botanique (Botanical Garden), Deshaies, Guadalupe
- Nevis Island Tour
- Monkeys at Shipwreck Bar and snorkeling near Carambola Beach, St. Kitts
- Captain Sunshine 3-hour St. Kitts Tour

Checking out the tropical birds of the Caribbean. * Photo: Sarretta McCaslin

Îlet du Gosier, Guadeloupe. * Photo: Sarretta McCaslin
- Tours and excursions set up by the liaison can often be purchased and charged to your cabin.
- You can also go ashore and make your own adventure, walking through towns, hiking, or strolling down beaches, not to mention visiting local bars and restaurants. Some folks took taxis to various specific locations they wanted to visit.
- Don’t be too worried about “wet landings” — we found them generally easy to manage. While dry landings may sound preferable to wet landings, on occasion dry landings can be more difficult than wet ones, even with the crew’s help. For example, at one rather high concrete dock, several of us had to climb up and stand on the side of the dinghy, turn and climb/sit on the dock, then get to our feet from there.
- On all landings, the crew will hand bags and other carriables out to prevent them from being dropped or getting wet.

Most shore visits entail a ride in the ship’s Zodiac. * Photo: Sarretta McCaslin
At the End of the Cruise
The end of your trip, vacation, or cruise is always hard, and leaving the Vela is sad, especially when you’ve made friends. The crew will help make everything as smooth and easy as possible. Both on the day before debarkation and on the day of, the liaison will give lots of information and instructions to make departure as smooth and easy as possible.
The Last Night On Board
- The liaison will gather all snorkeling equipment which was given out to passengers.
- There will be a special Captain’s dinner along with group photos of the crew and the passengers.
- The liaison will provide instructions for luggage handling the next morning (For example, we had to have bags packed and placed either just inside or outside cabin doors by 9am the next day.)
- The liaison will also get passengers set up with taxis to hotels or airport, or will arrange tours (if requested) for those staying longer on the island.
- There will be a sheet for guests to fill out, if desired, listing names, email addresses, and phone numbers. When everyone has filled it out, guests can take a picture of it so they can remain in contact and exchange photos.

Group shot! * Photo: Sarretta McCaslin
Last Morning and Disembarking
- The 7am bell will announce the last breakfast aboard.
- After a last wonderful meal, guests should have any luggage ready for the crew to pick up (by 9am on our cruise).
- Final bills will be totaled up and paid (credit card ONLY) for items purchased and charged to the cabin (cruise gear, jewelry, etc.), excursions, and crew tips.
- Guests have a last chance to photograph the guest information sheet.
- Note: there is a recommended amount for crew tips, but guests may leave as much as they choose. Service aboard Vela was incredible and they deserved their tips!
- The crew will load and transport bags to shore, standing guard over them until passengers can collect their stuff.
- After hugs and farewell, guests are transported ashore to retrieve luggage.
Ashore
- Taxis and shuttles will be waiting for guests — some going straight to the airport for flights home, others to hotels on the island.
- On our trip, some guests joined up for a tour of the island, after which two folks went to the airport for a later flight.
- Several of us ate dinner together at a beachfront restaurant near the disembarkation dock (Zanzi — an excellent establishment offering American, Caribbean and Indian foods).
- No matter when you plan your departure (immediate or after a night or two), be sure you have adequate layover time in your return flight schedule —we missed our connecting flight due to extreme wait times at passport control in Miami.

One of many beautiful sunsets typically seen on an Island Windjammers cruise in the Caribbean. * Photo: Sarretta McCaslin
Other Helpful Suggestions…
Island Windjammers Packing Tips
Most people overpack for a cruise of any kind. Because of the limited space for storage on a sailing vessel, it is more important than ever to forgo unnecessary “stuff” and only bring what you really NEED.
Here are some suggestions for clothes:
- sun-shirts or rash guard shirts
- multiple swimsuits
- a good hat (we had wide-brimmed)
- heavy-duty water shoes (& possibly an extra pair to allow the other to dry out)
- Shorts and shirts or coverups (for onshore)
- Shoes or sandals which you can hike in and can get wet
- a light jacket for cool nights or rain
- possibly a light sundress or dress shirt and slacks
This is a list of nonessential but useful items that were recommended to us (and which we used):
- soft-sided, collapsible bags (backpacks or duffels – NO hard-sided luggage)
- over-the-door shoe/pocket organizer for storage (many pockets!)
- a small, plug-in night light for the bathroom
- a non-surge-protector power strip for charging electronics like phones, cameras, watches, etc. (there are two 110VAC sockets next to the bunk)
- a small bag/backpack to take stuff ashore
- a waterproof pouch for your cell phone
- enough cash for on-shore tips and small purchases
- binoculars
- good sunscreen (although some sunscreen is available aboard)
- insulated water bottle (they supply drinking water)
- Microfiber or Turkish beach towels (fold small, won’t hold sand, dry quickly)
- a lint roller to get inevitable sand out of your bed
- a “portable washing machine” or 5-gallon heavy-duty Ziplock (note: you can use shampoo as laundry soap)
On one final note, let us suggest again that your journey (on Vela or in life) will be as enjoyable as YOU make it. Look for all the wonders! See the good in every event! Enjoy every minute! Don’t waste a moment on dwelling on what might have been or on what went wrong – always look forward with gratitude and joy
Hope you enjoyed my Island Windjammers packing tips!
Despite having an online store and five artificial joints, Sarretta plans to keep traveling and adventuring until something stops her!
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Top photo is not the Vela.
Thank you, you’re right, it’s the Royal Clipper, I fixed the caption, my mistake! And I added a Vela shot. 🙂