Game mechanics can be a funny thing. The first time michelle1963 and I arrived in Monquista, she was in her low-level Marleybone skiff from the Admiral's Bundle and I was in my Sharktooth Ship from the Cutthroat Bundle.
As we stayed in-world to complete all main and side quests, she bought the crown shop (real money) Monquistan skiff - Santa Sofia - which aided me tremendously with broadside combat. When we concluded Monquista and returned to Skull Island to turn in our quests, I was pleasantly surprised to be awarded my own Monquistan skiff!
When I began my secondary character I saved all my gold (in-game money) for the frigate I knew I would need, despite the fact the Sharktooth Ship required assistance from michelle1963's Monquistan skiff. But I quickly grew tired of playing my new character because her class (witchdoctor) was so closely paired with my first character's class (musketeer) insofar as they're both ranged combatants. So I gave her up and focused on something completely unfamiliar, the privateer.
Learning from my previous forays, I bought a crown shop Monquistan skiff right away, knowing it would greatly aid me in timely quest completion. While the ship may have cost real money, I outfitted it with all the best from my previous ship - ships may not be transferable, but ship equipment is. I was well on my way to having my second high-level toon.
As these things turn out, having gotten to the point where our first characters stopped gaining both character xp and nautical xp, we started two characters anew. This had the residual effect of my not playing the two previously created classes. So I created a buccaneer and road-mapped my ship purchases for flawless escalation by purchasing her the Admiral's Bundle while michelle1963 followed my previous strategy of buying a Monquistan skiff right out of the starting gate. Comparing character levels with nautical levels and knowing ahead of time I would be receiving a Monquistan skiff at the end of Monquista and remembering how tough Cool Ranch was before we purchased our Bison frigates I decided to set my Royal Skiff at level 20 and use gold to stair-step my way up the food chain.
From pirate raft to pirate skiff to pirate galleon (skipping that whole ineffective pirate frigate phase) to Monquistan skiff to Marleybone skiff (and more than likely to Bison frigate, Bison galleon...you get the idea). But wait! There's more!
Having a level 50 pirate does not come without its perks. I wondered...While the Pirate galleon isn't nearly as fast or maneuverable, nor, more importantly, as well armored as the Monquistan skiff, how did the stats compare to something I'd never before piloted - the Bison skiff? Last time we were in Cool Ranch the Bison skiff was only incrementally better than the Monquinstan skiffs we were in, so we waited to make level enough to equip the Bison frigates - but I've learned a thing or two about equipping ships since then (Some Things Money Can't Buy)!
Teleporting to michelle1963's level 50 in Cool Ranch, she was able to purchase a Bison skiff. Using my level 50 I battled nearly 100 ships collecting drops in triplicate for each of my girls' ships. Refitted in such a fashion, the Bison skiff is faster, stronger, more maneuverable, and has a greater hull integrity than a fully decked out Monquistan skiff - which will make Monquista a breeze, and battling effortless, in Valencia.
Long live strategy.