Here we are to talk about travel. Specifically, how my wife Christy and I lead our three teenagers and an old guy, her dad, through all kinds of adventures. I’m going to tell you where we went, what we did and show you how we paced ourselves to avoid meltdowns
and mutiny. If you're trying to plan a trip anywhere with your family or alone, this show will be helpful. If you’re looking to stay at home and let us do the traveling for you, that works too.
Basically, travel is good and we do it well. And I want to share that with you.
Meteora Greece travel guide, How to get from Athens to Meteora, Monasteries, Meteora Greece hotels
Steve and the fam take a road trip from Athens to Meteora, from chaotic city driving in a rental minivan to the geographical wonders that make even teenagers look up from their phones. We share how the monasteries hit as art, nature, and something bigger than religion, plus the practical tips that keep the whole crew positive. • getting out of Athens with broken map apps and narrow alleys • why Meteora makes our month-long trip highlight list • what we learned from the Greek...
24 Sept 2026
Best things to do in Athens, Greece. Why Athens is worth visiting. Athens 3 day itinerary. Monastiraki, the Plaka, Psirri. Greek food and restaurants. Acropolis, Parthenon.
Steve, Christy and family head to Athens and learn that the difference between wonder and misery is often a snack, a nap, and the courage to change the plan. Along the way we bail on a bad Acropolis tour, stumble into a better sightseeing rhythm, and somehow get teenagers to love an opera in an ancient Greek theater. • Choosing an Airbnb next to the Acropolis and letting location do the heavy lifting • Learning the hard way that “I feel weird” usually means “I’m hungry” • Using Monastiraki fo...
3 Sept 2026
Greek Island Hopping, Greek Islands Itinerary, Greek Islands beyond Santorini and Mykonos, Best Greek Islands that aren't Touristy
Steve and the fam go sailing through the Greek islands on a week-long catamaran charter, from the heat of Athens to tiny harbors cruise ships can’t touch. Along the way they share how we pace the days, keep logistics simple, and enjoy the moments that don’t fit in a photo. • Choosing trains vs rideshares based on group energy and cost • Handling Athens heat, time-zone hunger • Why a Greek islands catamaran charter can be more affordable than it sounds • Meeting our ca...
27 Aug 2026
Things to do in London. First time in London guide. Best 4 day London itinerary
The Gaggle's first stop in season 2 is London. Walk through how they handle big sights, crowds, and jet lag with three teenagers and a Grampy in the mix. They keep the trip fun by pacing, staying flexible, and choosing good vibes over checking every box. • blending a new family dynamic while traveling together for the first time • using the London Underground with tap-to-pay, Oyster options, and Google Maps • first London moments that hit hard • walking London well, wi...
18 Nov 2025
Our Approach to Planning. Ten steps to the perfect trip: travel itinerary, flights, accommodations
Steve shares the 10-step framework for planning trips, from choosing destinations that truly fit to pacing days so the fun lasts. Anchors, alternation, and a single shared Google Doc turn daunting into ease without losing the spark. • choosing a destination by connection, food, climate, culture, relaxation • using guidebooks and searches to find anchor experiences • building a shared Google Doc with confirmations and backups • alternating city and country to manage energy • one main activity...
11 Nov 2025
Travel Bangkok, Thailand. Pt 2: itinerary, markets, street food guide, river cruise
The gaggle returns to Bangkok to land the final days of a month across Thailand and Cambodia, trading checklists for pacing that keeps joy alive. A missed palace, a Michelin detour, a neon river cruise, and a noodle farewell show how small choices turn fatigue into celebration. • managing energy and expectations at trip’s end • navigating Sukhumvit with kids and avoiding nightlife zones • poolside reflections on Thailand’s modernization and Cambodia’s scars • Thai Niyom Cuisine and why Miche...
Steve and family head to Siem Reap and find more than temples: hard history, true art, and everyday resilience. Between jeep tours, hero rats, and student-run kitchens, the city shifts from chaos to compassion in real time. • visa prep tips for Cambodia and arrival logistics • first impressions from Pub Street to quiet side roads • Angkor Wat, Ta Prohm, and Bayon highlights • guides’ personal histories and unfiltered context • pacing kids through heat, history, and long days • where to eat w...
28 Oct 2025
The Elephant Nature Park. An ethical Sanctuary just outside Chiang Mai, Thailand.
Steve and crew head out to The Elephant Nature Park in Northern Thailand and learn how ethical sanctuaries center animal needs, not tourist schedules. Between river rituals, calf chaos, and quiet kitchen work, they find a better way to travel as a family and a deeper respect for elephant lives. • why they chose an ethical sanctuary in Chiang Mai • first encounters with Granny and her world • baby elephants, caretakers and safe distance • river swims, mud as sunscreen and comfort • rescue his...
21 Oct 2025
Chiang Mai, Thailand: travel tips, itinerary, night bazaar, markets, cooking class, how to get around, best temples
Steve and Fam explore Chiang Mai with a steady pace, from khao soi and night markets to river tubing with elephants, Monk’s Trail quiet, and a cooking class that wins over the teens. He shares practical tips, honest laughs, and why travel keeps minds open. • choosing a calm base near Tha Phae Gate • anchoring days with food, markets, and rest • Sunday night market strategy at 5 pm • river tubing turning magical with elephants and buffalo • waterfall hike, slides, and safe footwear • Monk’s T...
14 Oct 2025
Travel Koh Samui, Thailand: luxury accommodations, Boat tour, night market, jungle tours, beaches, temples, best time to visit
Steve and Fam head to Koh Samui’s quieter north shore, trade big itineraries for smart pacing, and find joy in jungle ridgelines, hidden lagoons, and night markets. A cliff-edge scare, a storm pivot, and an airport save sharpen how they travel together and why it works. • choosing the north shore for calm, walkable food, and fewer crowds • villa setup with beachside pool, house chefs, and settling rituals • pacing rules: one anchor activity per day, rest and room to roam • atv jungle tour, s...
11 Oct 2025
Where We're Gonna Go season 1 Trailer
11 Oct 2025
Travel Bangkok, Thailand: best itinerary, temples, street food, markets, river cruise
Four days in Bangkok with three teens and Grampy. See how Steve and Fam pace a big city, savor street food, and find calm inside the noise. Tricks that saved their sanity, the moments that floored them, and the choices that turned detours into family lore. • setting expectations for long-haul flights and arranging first rides • using Grab, landmark pins, and cash strategies for smooth transit • morning markets in Watthana and simple Thai phrases that help • jet lag reset using sunrise, sunse...
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
8 ratings
Spotify
4.5 / 5
2 ratings
Contact Where We're Gonna Go with Steve Webb
Guest appearances
Does not typically book guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Pod Engine is an independent podcast discovery and analytics service and is not affiliated with or endorsed by this podcast. Artwork and show content belong to their owners. Full legal notice.
Explore this show Podcast research with Pod Engine
