At first, despite our guide’s insistence, I didn’t see anything.

There were about ten of us in the small group who opted for this excursion into the Curú Wildlife Refuge in Costa Rica. All of us were hoping to set eyes on the variety of creatures promised – everything from scarlet macaws to howler monkeys. But not one of us could see the baby crocodiles that he swore were right in front of our eyes.

This was our first excursion on this sailing aboard Windstar’s Star Seeker – which, after its inaugural season in the Caribbean, was making its way to Alaska by way of Seattle. Ours was a repositioning cruise, an out-of-the-ordinary itinerary that allows passengers to hop on board the ship as it switches locations for a new season. Which meant we’d spend time in ports to which the Star Seeker might never return.

All the more reason to make sure we were seeing all there is to see. But why this man was pointing at brown leaves in the water and insisting they were something more, I had no idea. Until. Movement!

I zoomed in with my camera for a closer look. And there they were. At least a dozen baby crocodiles resting on the water’s edge. Small enough to be more cute than dangerous – but not worth sticking a finger in the water to test the theory. Our little group bubbled with joy at the sight. Each of us wondered what other new experiences might lie ahead.

It may be a while, if ever, before other Windstar guests are able to duplicate this cruising experience. Our route was chosen by the cruise line for its ability to get the ship from Point A to Point B as efficiently as possible. The lush beach landscapes and cultural experiences we enjoyed along the way are secondary. But that doesn’t mean they were less exciting. Many of our port stops and excursions were one-offs, never to be repeated, which makes passengers feel more like intrepid explorers than tourists.

This was my first time on a repositioning cruise, and I discovered there are some very good reasons I’d do it again. If you’ve never done one, here are five things you should know before you commit.

Unlike typical cruise segments, repositioning cruises aren’t designed for their attractive ports or popular routes. The goal here is to get the ship from one region to another. Cruise lines don’t want to sail empty so, to attract guests, cabins often go for a fraction of the cost. It works. Many of my fellow passengers told me they often choose these sailings, which give them more bang for their buck. However, they are one-way sailings. This can add to costs since you’ll need to fly in and out of different destinations. And longer sailings may also mean extra add-on expenses like wifi and cocktails.

Small-ship and expedition cruising tend to skew older, and on this cruise almost all the guests were retirees. It makes sense. They have time. My husband and I hopped on in Puerto Caldera, Costa Rica and cruised for eight nights to Puerto Vallarta, Mexico. But there were people who’d been on board for weeks before that, journeying through the Panama Canal. There were others who planned to stay on until the ship reached Alaska weeks later. And there were others, still, who decided to add additional nights to the trip while they were on board.

Unlike a traditional Caribbean or Mediterranean sailing, the ports we stopped in during our cruise were often new – even to the crew. And many of them are ports that the ship won’t call at in the future. For some passengers, the reason to choose this sailing was exactly that. It added a must-see vibe to excursions. But that also brings some risks. There are never any guarantees with ports on an itinerary, as weather or geopolitical situations can easily change your route. And sometimes, the ports themselves – despite the cruise line’s best efforts – simply aren’t well matched for the level of luxury guests are used to. On a repositioning cruise, that’s all part of the adventure.

On the flip side, travellers who love ships – either for their technical specs or their luxurious offerings – will love repositioning cruises, as sea days are plentiful. (We had three). It’s the kind of time on board that could drive someone to out-drink their drink package if they aren’t prepared for it. But if you love the time-slowing nature of a day out on the open water, and can picture yourself leisurely sipping cocktails, completing puzzles, and finishing that new book, it's a relaxing pace to travel.

Star Seeker seemed made for this life. On a typical day, I would start with a latte in The Yacht Club, a bright, roomy observatory at the front of the ship with large, comfortable couches. Then the day would unfold with meals at one of the four restaurants on board (one of which features James Beard Award-winning chefs); quiet time in one of the shaded loungers on the aft decks four through seven; trivia matches and informative lectures in the afternoon. (We had astronomer Greg Redfern and Costa Rican naturalist Karla Taylor on board with us.) Plus, Windstar’s open bridge policy allowed guests to meet and greet with the captain and his officers throughout the cruise for an insider peek at how the sausage gets made.

Star Seeker's 112 spacious suites nearly all have private verandas or floor-to-ceiling infinity windows

You’ll enjoy a repositioning cruise most if it’s with a line you know and love. It’s probably not the best time to take a gamble on something new. Aboard our sailing, 102 of the 168 guests had travelled with Windstar before. And while Star Seeker is new (it launched in January), these guests had a good sense of what to expect from the cruise line while they were on board, making them less worried about rolling the dice on this trip.

Following their lead, trusting the Windstar team is what ultimately allowed me to submit to – and enjoy – the unpredictability of this special sailing. So, when my guide at Curú swore that the heavy lump draped over the branch of a Ficus tree in the distance was actually a howler monkey drunk on fermented fruit, I not only trusted him. I saw it too.

This article was first published on Condé Nast Traveler.