THE WHYCATION PLANNING CHECKLIST

How to Plan Your First Purpose-Driven Trip

🧭 What is a Whycation?

A Whycation is a trip where you decide your motivation BEFORE your destination. Instead of asking “Where should I go?”, you ask “Why do I want to travel?” and let that answer guide you.

This checklist will help you plan your first intentional, purpose-driven trip in 2026.

STEP 1: DISCOVER YOUR “WHY”

Before you book anything, identify what you truly need from this trip. Check the box next to the motivation that resonates most:

☐ RECHARGE – I need rest, silence, and disconnection from daily stress

☐ RECONNECT – I want to deepen relationships with family or friends

☐ REDISCOVER – I want to trace my roots and explore my heritage

☐ LEARN – I want to develop a skill or explore a passion

☐ EXPERIENCE – I want to attend a specific event or cultural moment

☐ ADVENTURE – I want raw nature and physical challenge

☐ NOURISH – I want to focus on food, wine, or wellness

STEP 2: DEFINE YOUR WHYCATION TYPE

Based on your “why,” choose the type of Whycation that fits:

PASSION-CATIONS (Travel built around a hobby or skill)

☐ Wine-cation

  • Research vineyard regions (Napa, Tuscany, Mendoza, Bordeaux)
  • Book winery tours with blending workshops
  • Consider harvest season timing (August-October)

☐ Photography Retreat

  • Choose landscape destination (Iceland, Patagonia, New Zealand)
  • Book workshop with professional photographer
  • Research best seasons for lighting

☐ Culinary Journey / Grocery Tourism

  • Identify must-visit local markets
  • Research cooking classes with local chefs
  • Make list of ingredients/tools to bring home

☐ Run-cation / Active Adventure

  • Find destination marathons or trail runs
  • Book accommodations near routes
  • Plan rest/recovery days into itinerary

☐ Wellness Retreat

  • Research yoga/meditation centers
  • Look for hot springs or spa destinations
  • Consider digital detox options

INHERITOURISM (Travel to trace your family roots)

☐ Genealogy Research Trip

  • Use Ancestry.com or FamilySearch.org to identify ancestral towns
  • Contact local genealogy societies or archives in destination
  • Request access to church records, immigration logs, or cemeteries
  • Bring printed family tree and old family photos
  • Book accommodations IN the ancestral town (not nearby)

☐ Heritage Destinations

  • Ellis Island (NYC) – for immigration records
  • Irish villages (county-specific)
  • Eastern European towns (Poland, Ukraine, Czech Republic)
  • Scottish Highlands (clan research)
  • Italian regions (regional ancestry)

MULTIGENERATIONAL TRAVEL (Three or more generations on one trip)

☐ Family Connection Trip

  • Survey all generations on mobility needs
  • Choose destinations with varied activity levels
  • Book accommodations with common gathering space (villa, large Airbnb)
  • Plan “together time” AND “alone time” into schedule
  • Assign one meal per day where each generation chooses the activity

☐ Comfort Considerations for Mixed Ages:

  • Wheelchair/walker accessibility at key sites
  • Nearby medical facilities
  • Bathrooms at regular intervals on excursions
  • Flexible cancellation policies
  • Shorter travel days (max 4-5 hours)

HUSHPITALITY TRIPS (Travel for silence and peace)

☐ Silence-Focused Destinations

  • Kyrgyzstan (remote yurt stays in Tian Shan mountains)
  • Patagonia (Chilean/Argentine wilderness lodges)
  • Scottish Highlands (isolated cottages)
  • Iceland (off-season countryside stays)
  • U.S. National Parks (backcountry lodges)

☐ Digital Detox Preparation:

  • Set up out-of-office email auto-reply
  • Download offline entertainment BEFORE departure
  • Notify family/friends you’ll be unreachable
  • Consider leaving phone in hotel safe for portions of trip

BIG-TICKETING / GIGTRIPPING (Travel around one major event)

☐ Event-Based Trip

  • Identify the event (concert, Olympics, festival, reunion tour)
  • Book tickets to event FIRST (before flights/hotels)
  • Build 2-3 extra days around event to explore destination
  • • Research event-specific transportation (shuttles, parking, public transit)

Examples for 2026:

  • 2026 Winter Olympics (Milan-Cortina, Italy)
  • Major music festival (Glastonbury, Coachella)
  • Historic concert or reunion tour
  • Cultural festival (Running of the Bulls, Carnival, Diwali)

STEP 3: MATCH YOUR “WHY” TO A “WHERE”

Use this quick reference guide to pair your motivation with destinations:

YOUR WHY SUGGESTED DESTINATIONS

Raw Nature & Awe Dominica, New Zealand (South Island), Patagonia, Iceland

Culture & Connection Georgia (country), Guatemala, Morocco, Peru

Silence & Peace Kyrgyzstan, Scottish Highlands, Patagonia, Faroe Islands

Wine & Food Tuscany, Napa Valley, Bordeaux, Mendoza (Argentina)

Heritage & Roots Ireland, Poland, Italy (regional), Ellis Island, Scotland

Learning & Skill Iceland (photography), Thailand (cooking), France (painting)

Family Connection U.S. National Parks, Portugal, Costa Rica, Canadian Rockies