Every island-hopping trip starts the same way: a list of islands you want to hit and a fixed number of days to do it. The Exumas in a week. Four Greek islands on a flotilla charter. The San Juans over a long weekend. And every experienced skipper knows where these trips go wrong - not in choosing the islands, but in the order. Visit them in the wrong sequence and you burn a day of your week recrossing the same passage, usually into the wind. This guide is about sequencing an island itinerary properly: the geometry, the weather logic, and how to compute the order instead of sketching it.
- Island order is the itinerary: the same five islands can be a lazy loop or a punishing zigzag depending on sequence.
- Water distance between islands is not chart distance - reefs, banks, and cuts force real routes that differ sharply from straight lines.
- Chains (Exumas, Cyclades) favor a linear sweep; clusters (San Juans, BVI) favor a loop - and mixed groups are where computed ordering beats eyeballing.
- Weather bends the best order: the exposed crossing goes on the calmest day, and downwind beats upwind for the long legs.
- An optimizer that checks every order over real sea distances turns an evening of chart-squinting into a minute of typing.
#Chains, clusters, and why the shape decides the plan
Island groups come in two shapes. A chain - the Exumas, the Florida Keys, the Cyclades on a north-south line - wants a linear sweep: start at one end, work to the other, position for the exit crossing. Backtracking in a chain is pure waste, and the classic mistake is starting in the middle because that is where the airport is. A cluster - the San Juans, the BVI, the Abacos cays - wants a loop that visits each island once and comes home without recrossing the sound. The hard cases are mixed: a chain with an outlier (say, a must-visit island 10 miles off the line) where the right answer depends on exactly where along the chain the detour costs least. That is an ordering computation, and it is precisely where intuition starts guessing.
#Real water distances, not ruler distances
Between islands, the straight line is usually not a legal or sensible route. Banks too shallow to cross, reef lines with only charted cuts through them, and channels that funnel all traffic through one gap mean the true distance between two anchorages can be double the ruler distance. Any ordering decision made on straight lines gets exactly these cases wrong - it happily routes you "6 miles" across a bank that carries 3 feet of water. Sequence decisions must be fed by routed distances over the sea-lane network, the same way you would actually run the legs.
Once you have the shortest order, bend it for weather, not the other way around. The rule: the most exposed crossing of the trip goes on the best forecast day, even if that shuffles the sequence; short protected hops can absorb a windy afternoon. In the trades, plan the long legs downwind - an itinerary that saves 5 miles but puts your 25-mile crossing dead upwind saved nothing.
#A worked example: five stops in the Abacos
Say you are staging out of Marsh Harbour with four targets: Hope Town, Man-O-War Cay, Great Guana Cay, and Treasure Cay, then home. Typed in that order the day zigzags across the Sea of Abaco - southeast to Hope Town, back north past your start to Man-O-War, north again to Guana, west to Treasure, then the long run home. Sweep it instead - Hope Town, Man-O-War, Guana, Treasure as one arc - and every leg is a short hop to the next cay. The stops are identical; the difference is a third of the distance and most of an hour at trawler speed. Multiply that across a week and a bad sequence quietly costs you an entire island.
This is what the Marine OS Multi-Stop Optimizer computes. Enter the anchorages or marinas (up to eight), mark it a round trip, and it measures real sea-lane distances between every pair, checks every possible visiting order, and returns the shortest as one editable route with stops numbered in visit order - plus how many miles it saved versus the order you typed. Then the Voyage Timeline puts an ETA and a forecast on every stop, which is where the calmest-day-for-the-crossing decision gets made with numbers instead of hope.
Marine OS is marina management software, and its route planner includes a Multi-Stop Optimizer that sequences up to 8 island stops over real sea-lane distances, plus a Voyage Timeline with ETA and forecast at each stop. Part of Boater Pro.
Type the islands, get the order
Enter your island stops and the optimizer returns the shortest visiting order as one editable route - with the miles saved versus your original sequence shown plainly.
#Frequently asked questions
Frequently asked questions
Pick the islands freely; compute the order coldly. For the general method see the multi-stop trip planning guide, for shorter outings the day cruise guide, and for the ordering math the shortest multi-stop route explainer.
Get the next post in your inbox
Monthly marina operations briefing. 2,400+ subscribers.