How we plan our trips: itineraries, packing lists & the little things that make it work
Twenty years of family trips - from national-park road trips to Iceland's ring road - have turned into a repeatable system. This is that system: how we build an itinerary, exactly what we pack, the checklist we run before we lock the door, and an itinerary library you can borrow from for your own trips.
Every destination below links to its photo diary, and where we've written a longer trip guide we've linked that too. If you just want the pictures, start at all our trips.
⇩ Download this guide (PDF)⇩ Packing checklist (PDF)
Our planning system
We plan the same way every time, and it keeps a trip with kids from turning into a march. Four steps:
1. One shared doc per trip. Every trip starts as a single document the whole family can open. It has a rough day-by-day skeleton at the top and a running list of "places to go / things to eat" underneath. As we research, ideas drop into a day; the ones that don't fit stay in the list as backups for weather or a slow morning.
2. Anchor each day to one big thing. We pin one headline stop per day - a volcano, a waterfall trail, a museum, a beach - and fill in the rest around it. One anchor a day leaves room for the unplanned detours that end up being the best part.
3. Research the specifics that ruin a day if you miss them. Opening hours, timed-entry reservations, whether a cave or attraction is closed that day, how long a drive really takes (always longer than the map says), and one breakfast and one dinner spot per day so nobody is hangry at 7pm. We note confirmation numbers and rental-car codes right in the doc.
4. Build in buffer. The days we leave open are the ones we remember. Wildlife, weather, and tired kids don't run on a schedule, so we plan maybe 70% of the time and let the rest happen.
The packing checklist
This is the master list we copy for every trip and trim to fit. Two versions live in our shared checklist - a full one for 10-day trips and a lighter one for long weekends - but the categories are always the same. Pack by person (we tag each item by name so nobody's swimsuit gets left behind).
Clothing & shoes
- Underwear, socks, sleepwear
- Casual tops & bottoms, pants/jeans, shorts
- Athletic shirts & bottoms
- Sweaters, sweatshirts, a shawl/scarf
- Dresses / nicer outfit for a night out
- Swimsuits & cover-ups, goggles
- Sneakers, sandals, one pair of dress shoes
- Cold-weather: hats, beanies, gloves
- Belts, sunglasses (with a case)
Toiletries & grooming
- Toothbrush, toothpaste, floss, mouthwash, tongue cleaner
- Shampoo, conditioner, body wash, deodorant, body spray/perfume
- Razor & shaving supplies, hair trimmer + charger
- Brush/comb, hair clips, styling tools, hair spray
- Face cleanser, moisturizer, makeup + remover, skincare
- Sunscreen, lotion, nail clippers & file, jewelry
Health & first-aid
- Medications & vitamins, pain relievers (pills + roll-on)
- First-aid kit, thermometer, aloe gel
- Eye drops, contacts + solution + backup glasses
- Insect repellent, hand sanitizer, tissues
- Braces / retainer supplies, hot packs for hands/feet
Carry-on & tech
- Passports / visa / IDs, printed tickets, cash
- Phones + chargers, laptop + charger, Fitbit chargers
- International power adapter, car charger, phone car mount
- Headphones, books / e-books, paper & pen
- Empty water bottle, snacks, gum/mints, lip balm
- Travel blanket, sleep mask, umbrella/poncho
- Big camera (for the ones who like to shoot)
- Luggage scale to check bag weight for the trip home
Before you leave: the door checklist
The five-minute list that saves the trip. We run it every single time:
- Tell the bank - set a travel notice on the credit cards so nothing gets frozen abroad.
- Cash - a little local currency for the first day before you find an ATM.
- House - take out the garbage, set the thermostat for while you're away, arm the Ring/alarm, lock all doors and windows.
- Cars - lock the cars in the garage.
- Adapters & chargers - the one thing everyone forgets; pack them last so they're on top.
- Snacks & empty water bottles - fill the bottles after security; the snacks keep everyone civil on travel day.
Our itinerary library
These are the actual plans we used, boiled down to the highlights. Steal freely.
Iceland - the Ring Road, 10 days
Blue LagoonGolden CircleWaterfallsVik black sandGlacier lagoonAkureyriSnaefellsnes
Fly into Keflavik, hit the Blue Lagoon straight off the plane, then base a night in Reykjavik (Sun Voyager, Hallgrimskirkja, Rainbow Street). Do the Golden Circle - Thingvellir between the tectonic plates, the Strokkur geyser, Gullfoss - then run the south coast waterfall by waterfall: Seljalandsfoss, Skogafoss, Kvernufoss. Reynisfjara's black-sand beach and Dyrholaey near Vik, then the Jokulsarlon glacier lagoon (book the amphibian boat) and Diamond Beach. Loop the north through Godafoss and Akureyri, finish on the Snaefellsnes peninsula at Kirkjufell. Tip: book guesthouses a day ahead of yourself so you're never racing the clock at night.
See it: Iceland photo diary · full Iceland guide
Portugal - Lisbon, Sintra & the Algarve
AlfamaTram 28Sintra palacesBelemAlgarve beachesPorto
Base in Lisbon: wander the Alfama, ride Tram 28 up to Sao Jorge Castle, the Santa Justa elevator, Rossio and Praca do Comercio. Give Sintra a full day - the Pena Palace, the National Palace, and the Initiation Well at Quinta da Regaleira. In Belem, be at Pasteis de Belem when it opens at 8, then Belem Tower, the Monument to the Discoveries, and Jeronimos Monastery. Work south to the Algarve's beaches (Praia do Camilo, Ponta da Piedade) and north to Porto. Eat: pastel de nata, caldo verde, piri-piri chicken, and a port tasting. A minivan beats a compact SUV for a family of five with bags.
See it: Portugal photo diary
Puerto Rico - San Juan, the islands & El Yunque
Old San JuanEl MorroViequesBio BayCulebraEl Yunque
Start in Old San Juan - Castillo San Felipe del Morro, Paseo de la Princesa, Castillo San Cristobal - with mofongo and a pina colada where the drink was invented. Ferry to Vieques for black-sand and Sun Bay beaches and the can't-miss bioluminescent bay kayak tour after dark. Day-trip Culebra for Flamenco Beach. Back on the main island, give El Yunque rainforest a full day: La Coca Falls, the Yokahu Tower, Juan Diego Falls, and the Caimitillo / El Yunque trail (about 2.4 miles each way - it took us 3.5 hours and 20k steps, so start early).
See it: Puerto Rico photo diary
Oregon - Portland, the Gorge, Mt Hood & the coast
Columbia GorgeMultnomah FallsMt HoodCannon BeachSilver FallsPowell's
Day one, the Columbia River Gorge - Multnomah Falls, Vista House, and the short, pretty Latourell Falls loop. Day two, Mt Hood National Forest and the Mirror Lake trail (about 4 miles). Day three, the Oregon Coast: Cannon Beach and Haystack Rock, the drive-on-the-sand beach, Ecola State Park, and the Wreck of the Peter Iredale at Fort Stevens. Save time for Portland itself - Powell's Books, the food carts, Voodoo Doughnut - and the Trail of Ten Falls at Silver Falls (the 9-mile loop, or just the half-mile to North and South Falls, where you can walk behind the water). Portland eats well: Screen Door, Pine State Biscuits, Mother's for brunch.
See it: Portland & Oregon photo diary
Texas - the big triangle road trip
DallasFort WorthHoustonGalvestonSan AntonioAustin
Loop Dallas - Houston - San Antonio - Austin over a week. Dallas: the Sixth Floor Museum at Dealey Plaza, the JFK Memorial, the Dallas World Aquarium, the Cattle Drive sculptures at Pioneer Plaza, and Fort Worth's Water Gardens and Stockyards. Houston: the Waterwall, Hermann Park, the Museum of Natural Science, Space Center Houston, and the Kemah Boardwalk, with a beach-and-pier day in Galveston. San Antonio: the Alamo and a River Walk cruise, plus Brackenridge Park and the missions. Austin: the State Capitol. It's a lot of miles - anchor one headline stop per city and don't over-schedule the drives.
See it: Texas photo diary
Shawnee National Forest - a hiking long weekend
Garden of the GodsCamel RockLittle Grand Canyonwaterfalls
Three days of southern-Illinois sandstone. Day one, Pomona Natural Bridge (0.3 mi, easy) and the Little Grand Canyon trail (3.4 mi). Day two, the star: Garden of the Gods and Camel Rock, then the Rim Rock trail (1.7 mi) past Ox-Lot Cave, and Cave-in-Rock State Park. Day three, chase waterfalls at Ferne Clyffe. Cliff-top hoodoos, slot canyons and mossy grottoes an easy drive from home - our best low-key nature weekend.
See it: Shawnee photo diary
The lake-house getaway - planning a group trip
Multi-familyShared costsBoat & ferry
Renting a big house with other families is its own kind of planning. What worked for us: a shared sheet with two tabs - a supply list (who's bringing the drinks, snacks, chai/coffee, sports gear, bug spray, sunscreen, homemade food) and an expenses tab that logs every shared cost so it splits evenly at the end. Assign categories to people up front, keep receipts in the sheet, and settle per-adult on the last night (ours came to about $240 a head after the boat rental, ferry, and group meals). Book the boat and any ferry early - they sell out on summer weekends.
See it: browse all trips
Want the longer version?
Several destinations have their own detailed, day-by-day family guides: Costa Rica, Iceland, Rome, Paris, Prague, Glacier and the Grand Canyon. P