Long Weekend Boat Trip Planning: The Dockhead Checklist
Memorial Day weekend is behind you. The next long weekend is July 4th. In between are the trips that happen because someone made a plan, not because the calendar handed them one. Here's the checklist the Dockhead crew uses for a proper long weekend boat trip — from the planning stage through the last morning on the water.
The People
Start here. The trip is only as good as who's on it. Long weekends on a boat require people who can coexist in close quarters, contribute to the logistics rather than just consuming them, and have the same general understanding of what kind of trip this is. A mismatch on any of those three things can be corrected in a day trip. A long weekend is long enough that it becomes a defining characteristic of the trip.
Confirm commitments early. People who say yes to a trip idea in March and then back out in late May are a pattern, not a surprise — the earlier you lock in dates and get explicit confirmations, the more accurate your crew count will be.
The Boat
Checklist before departure, not the morning of:
- Engine service current
- Safety equipment checked: life jackets, flares, fire extinguisher, horn, first aid kit
- Navigation lights tested
- Bilge pump functional
- Fuel calculation done with reserve margin
- Charts or chart plotter updated
- Float plan filed with a contact ashore
None of these are exciting. All of them matter.
The Gear
Long weekend gear needs to cover the full temperature and activity range. Here's the Dockhead packing list:
Swimwear: At least two suits. The Summer Fun Swim Trunks or Coral Reef Swim Trunks for men; the Floral Recycled String Bikini, Sunflowers High-Waisted Bikini, or any of the other women's recycled-material styles. Quick-dry matters on a multi-day trip.
Sun protection: The Buoy Call Women's Rash Guard ($44.95) or Drunk On Waves Men's Rash Guard ($44.95) for extended sun exposure. The Dockhead Trucker Hat ($29.95) every day, all day.
Layers for morning and evening: The Rock The Boat Long Sleeve ($32.95) and Essential Dockhead Hoodie ($44.95). Even in late May, mornings and evenings on the water earn these.
Graphic tees for dock-to-bar transitions: The Iconic Dockhead Tee ($24.95), Boney Booze Cruise Tank ($24.95), Grab My Dock Tee ($24.95). One for each evening.
Drinkware: The Kiss My Aft Travel Mug ($29.95) for morning. Everything else is your department.
The Logistics
- Marina reservations confirmed (long weekend slips fill early)
- Grocery and provisioning run done before departure
- Ice or refrigeration plan settled
- Fuel dock location known at each stop
- Weather checked and rechecked through departure day
- Everyone knows the departure time and has acknowledged it in writing
The Intangibles
The best long weekend boat trips have one quality in common: nobody is in a hurry. The whole point of being on the water for three days is to let the water set the pace. Overplanning the itinerary kills it. A loose framework — a destination, a marina or two, a rough daily shape — is enough. The rest fills itself in.
All Dockhead gear is made to order through Printful and available at TotalDockhead.com. If any of the pieces on this list aren't in your bag yet, order now — 2–7 business days for production and you'll have everything before the trip.
Documenting the trip? Tag @TotalDockhead and check out the Dockhead Collabs program if you want to make something more formal out of it.
Frequently Asked Questions
What should I pack for a long weekend boat trip?
Pack multiple swimsuits, a rash guard for sun protection, a trucker hat, graphic tees for evenings, a long-sleeve layer for mornings, a hoodie for cold evenings, and an insulated travel mug. Dockhead covers the full boat trip wardrobe at TotalDockhead.com.
What safety equipment do I need for a multi-day boat trip?
Required equipment includes USCG-approved life jackets for all aboard, visual distress signals (flares), a fire extinguisher, a sound-producing device (horn), and navigation lights. A first aid kit and float plan filed with a shore contact are strongly recommended.
How far in advance should I reserve marina slips for Memorial Day weekend?
At least 4–6 weeks in advance for popular destinations during holiday weekends. Some marinas book months in advance for Memorial Day, July 4th, and Labor Day. Call the marina directly to confirm availability and reservation policies.
What is a float plan?
A float plan is a document left with a contact ashore that describes your trip — the vessel, the crew, the route, and the expected return time — so that authorities know where to look if you don't return as planned. It is not filed with the Coast Guard, but leaving one with someone reliable is standard safe boating practice.
Is Dockhead swimwear good for a multi-day boat trip?
Yes. Dockhead's quick-dry swim trunks and recycled-material women's swimwear are designed for actual water use — multiple swims, extended dock time, and the dock-to-marina-bar transitions that define long weekend boat trips.
What Dockhead products are essential for a boat trip?
The trucker hat, a rash guard, swimwear, a graphic tee for evenings, and the Kiss My Aft Travel Mug. For multi-day trips, add a long-sleeve layer and a hoodie for mornings and cool evenings. All available at TotalDockhead.com.
Does Dockhead ship in time for a last-minute boat trip?
Dockhead orders require 2–7 business days for made-to-order production through Printful, plus standard shipping time. The Virtual Gift Card is available instantly if timing is tight. For planned trips, ordering 2–3 weeks in advance is recommended.
