Custom adventure itineraries for people who want more than a vacation.

Adventures with Alyssa helps families, couples, and curious travelers plan nature-forward road trips, hiking getaways, scenic routes, local restaurants, shops, and memorable stops, without spending weeks buried in research.

Start planning my trip See how it works

Not sure where to start? Take the 1-minute adventure style quiz

Planned from wherever you're starting. You book, Alyssa maps.

View from a kayak on a calm mountain lake with a snow-capped peak ahead
Toes up on a mountain lake
Hiker walking through a narrow red rock canyon
Red rock, cool shade
Hiker waving from a snowy summit in the clouds
Worth the climb
Turquoise river winding between forested mountains
Yes, it's really that color

You tell Alyssa where you want to go, what kind of trip you want to have, and what matters most. She shapes the route, the stops, the pace, and the details that turn a trip into a memory.

Free · about a minute

What's your adventure style?

Seven quick questions about how you like to explore. Get matched to the itineraries, trails and weekend escapes that fit, and the full Field Guide opens up for you.

Already know your style? Tap it to skip ahead.

What goes into every plan

The scenic stops worth pulling over for, and all the small details you'd otherwise spend weeks researching.

  • Scenic road trip routes

    Mapped drives with the overlooks and detours built in.

  • National parks & nature stops

    Timing, entrances, and the corners most visitors miss.

  • Hiking ideas

    Trails matched to your group's real ability, from easy walks to summit days.

  • Kid-friendly stops

    Short trails, playgrounds, ice cream, and the breaks that keep everyone happy.

  • Restaurants & coffee shops

    Local spots worth planning a stop around.

  • Local shops & small-town finds

    Main streets, makers, and markets that give a trip its texture.

  • Lodging area recommendations

    The right towns and basecamps for your route and budget.

  • Backup rainy-day options

    A plan B for every stretch, so weather never wrecks the day.

  • Pacing & day-by-day flow

    A rhythm with room to breathe, so nobody needs a vacation from the vacation.

What a planned day looks like

An excerpt from a sample itinerary. Every plan is built around how your group actually travels, including what happens when the weather doesn't cooperate.

Sample itinerary, day 3 of 6

Seward, Alaska

Trip
Kenai Peninsula family road trip
Travelers
Family of four, kids 5 and 8
Pace
Moderate, one big outing a day
Basecamp
Cabins just outside town

Plans also include drive times, lodging zones, packing notes, and a route map.

  1. Coffee before the crowds

    Drinks for the car, cocoa for the kids. The harbor is quiet this early.

    Coffee cup held up against a small-boat harbor

  2. Glacier-view hike

    Easy to moderate with a big payoff. Pack layers; it's colder near the ice.

    Green valley leading up to a glacier between mountains

  3. Galleries and the aquarium

    Swap the trail for a walkable indoor morning near the waterfront.

    Wood-shingled gallery building with a red door

  4. Seafood lunch

    Crab for the grown-ups, something simple for the kids, window seats if you can get them.

    Platter of king crab legs with vegetables

  5. Main street wander

    Murals, small shops, and a bakery stop, all walkable and stroller-friendly.

    Building covered in a colorful painted mural

  6. Cozy early dinner

    Warm up somewhere casual, then board games back at the cabin.

    Exterior of a casual bar and grill with a neon sign

  7. Back to basecamp

    Quiet nights and room for the kids to run before bed.

    Red cabins along a trail in a green mountain valley

This sample is illustrative. Your plan is built from scratch around your dates, crew, and pace. See all six days of this Kenai trip in the Field Guide →

Free from Alyssa

Explore the Field Guide

Sample itineraries from four corners of the country, weekend escapes from Louisville and the planning tools Alyssa uses herself. Collect a passport stamp at every stop.

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Open the Field Guide

From trip idea to mapped adventure

You share the dream, Alyssa maps it, you go live it.

  1. 1

    Share your trip idea

    Fill out the inquiry form with your destination, starting point, dates, budget, travelers, and dream experiences.

  2. 2

    Alyssa builds the direction

    She reviews your goals and recommends the best path: a curated destination framework, a custom route, or a fully custom itinerary.

  3. 3

    Receive your adventure plan

    A polished itinerary with routes, stops, food, shops, activities, timing, and notes.

  4. 4

    Book and go

    You book your own lodging, activities, and transportation using Alyssa's recommendations, then hit the road.

Three ways Alyssa can help

Not sure which fits? Tell her about your trip and she'll recommend one.

Free samples in the Field Guide →

Curated destination guides

Experience frameworks for places Alyssa knows well, with hikes, overlooks, food, shops, lodging zones, photo moments, and rainy-day backups, then adjusted to your starting point.

Best forClassic trips like the Tetons or the Smokies.

Custom road trip itinerary

A personalized route from your driveway to your destination, with the stops, meals, and overnight towns planned along the way.

Best forDrive-there trips and multi-stop routes.

Fully custom adventure planning

A bespoke plan built from scratch for your family, couple, or group, down to the day-by-day pacing.

Best forMilestone trips and bigger groups.

Trips Alyssa loves to build

Starting points, not packages. Every itinerary is shaped around where you're coming from and how your crew likes to travel.

Rainbow over a forested mountain valley

Teton & mountain road trips

Peaks, overlooks, and quiet valley mornings.

Kayakers floating over a manatee in clear spring water

Beach & nature trips

Springs and shorelines like St. George Island.

Waterfall cascading down a mossy rock face beside a trail

Smoky Mountain family getaways

Waterfalls with kid-approved stops.

Red storefront with an open sign on a small-town street

Small-town food & shop routes

Main streets worth the drive.

Hiker with a backpack crossing an alpine meadow

Family-friendly hiking

Trails everyone can finish.

Fog rolling over a rocky ocean coastline

Cross-country scenic adventures

The long way, on purpose.

Kayaks pulled up in a red rock canyon

National park routes

One park or a string of them.

Bridge spanning a forested river gorge

Weekends from the Midwest

Big scenery, a tank or two away.

Don't see your trip here? Most of Alyssa's favorite plans started as "somewhere with mountains."

Alyssa smiling outside a market stand in the mountains
Always scouting the next stop
Muddy hiking boots with traction spikes

Travel that feels lived-in, scenic, and full of small discoveries

Alyssa Lindsey has always loved the kind of travel you remember in details: the trailhead at golden hour, the diner the locals swore by, the pull-off nobody else stopped at. Her love of nature, her children, and life outside the ordinary shapes the way she thinks about every trip.

Adventures with Alyssa was created to help people spend less time researching and more time experiencing the places they came to see.

  • Nature first
  • Kid-tested
  • Room to breathe
  • Local over famous

Less research, more real-life adventure.
— Alyssa

From the road

Every photo in this strip comes from Alyssa's own trips.

Mountain reflected in a forest-ringed lake
Lakeside, early
Orange kayak nose pointed into a sandstone canyon
Into the canyon
Glacier edge above an icy blue lagoon
Ice and blue water
Person sitting in a forest rock shelter
A dry spot to sit a while
Alyssa standing on a snowfield under a blue sky
Top of the world, briefly

Good to know

Quick answers before you start.

Do you book the trip for me?

No. Adventures with Alyssa is an itinerary planning and experience curation service. Alyssa recommends routes, stops, lodging areas, restaurants, and activities, and you book your own lodging, transportation, tickets, and reservations.

What if I don't know where I want to go yet?

That's a great place to start. Tell Alyssa what you love, like mountains, water, or small towns, and how far you're willing to travel. She'll suggest a direction.

Can you plan around kids, pets, or mobility needs?

Yes. Share who's coming along in the form, and Alyssa will build the pacing, stops, and activities around them.

What's in the free Field Guide?

Four sample itineraries (New River Gorge, Acadia, Oregon and Washington, and Alaska's Kenai Peninsula), four weekend escapes from Louisville, a kid-friendly trail finder, a park booking calendar and a drive-day planner. Day 1 of every guide is open to everyone; add your email to unlock the rest.

What will I receive?

A polished itinerary with your suggested route, stops, food, shops, activities, timing, notes, and backup options for bad weather.

Tell Alyssa what kind of adventure you want to take

Share a few details about your dream trip, and Alyssa will review your request to see what kind of itinerary or planning support makes the most sense.

  • Three short pagesAbout you, trip basics, and trip style.
  • Read by Alyssa herselfEvery request is reviewed personally.
  • A reply by emailWith the planning path that fits your trip best.

Prefer email? Write to youradventureplan@gmail.com.