Wander Every Day: Real Talk, Real Trips

Daytona Gilroy-Briand
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  • PLACES & TRAVEL

Wander Every Day is the podcast where real travel stories meet smart recs + great chats. Hosted by Day — a deal-finder, storyteller, and your go-to travel friend — each episode dives into honest conversations with well-traveled friends about where to stay, what to eat, what not to waste your time (or money) on, and how to wander smarter. If you love adventure, good vibes, and learning tips and tricks for planning travel, you’re in the right place. ✈️🌍 Let’s wander.

  1. Episode 12: Tastes of Italy Part 2 - The Sparkle of Florence + the Food Scene of Rome with Al

    SEP 2

    Episode 12: Tastes of Italy Part 2 - The Sparkle of Florence + the Food Scene of Rome with Al

    In the second half of my conversation with Al, we dive into two of Italy’s most iconic cities: Florence and Rome. From cozy agriturismos in the Tuscan countryside to sipping wine at charming Roman bars, this episode is a foodie and culture lover’s dream. In Florence, we talk Air bnbs, sandwiches from All’Antico Vinaio, coffee culture across Italy, exploring the world-famous Uffizi Gallery, and whether Florence has lost a bit of its sparkle under the weight of tourism. In Rome, it’s all about the food and atmosphere: we break down the four classic Roman pastas, debate Roman vs Neapolitan pizza, and talk about what it’s like to explore the Colosseum during the Ryder Cup crowds. Plus, wine bar recommendations, aperitivo culture, and plenty of travel tips for making the most of these vibrant cities. Whether you’re dreaming of your first Italian adventure or planning a return to soak in more pasta, pizza, and history—this episode will give you insider tips and inspiration to experience Florence and Rome like a local. 🎧 Let’s wander. Timestamp: 2:03 Florence: Air B&B, Al Antico Vinaio Sandwiches, Utilitarian Coffee, Uffizi Gallery, Agriturismos + Has Florence Lost its Sparkle? 11:01 Rome: The Ryder Cup, the Four Pastas of Rome, Neapolitan Pizza vs Roman Pizza, Wine Bar Recommendations, Apperitvo Culture, Colosseum Tour + Pre-planning Attractions 25:37 Reflections on Italy Trip and Recommendations 29:36 This or That: Bella Italia Edition 30:34 Listener Questions: Is Rome Overhyped + Best Restaurants in Italy

    34 min
  2. Episode 11: Tastes of Italy Part 1 - Ischia by Boat + Naples by Bite with Al

    AUG 26

    Episode 11: Tastes of Italy Part 1 - Ischia by Boat + Naples by Bite with Al

    In this episode of Wander Every Day, my friend Al joins me to dive into the first half of her Italian adventure – exploring the island charm of Ischia and the bustling streets of Naples. 🌊 Ischia: We chat about staying in Ischia Porto, sipping rucolino, taking a boat tour to see La Mano di Dio and the Green Grotto, riding the island bus, soaking in thermal bath parks, and of course trying the island specialty, coniglio all’ischiatana. Plus, we compare Ischia to nearby Capri and the Amalfi Coast – is it the hidden gem worth choosing? 🍕 Naples: From exploring the Catacombs of San Gennaro to diving deep into Naples’ legendary pizza scene, we review Michelin-recognized favourites like L'Antica Pizzeria da Michele, Gino e Toto Sorbillo, Pizzeria Vincenzo Capuano and Pepe in Grani. We also share a wine-filled stop at Vineria Bandita and chat about Naples’ complicated reputation. ✈️ Italy Travel Tips: We round out the episode with practical advice – from avoiding pickpockets, to navigating Italy’s mix of trains, ferries, and metros, to cost expectations and the best times of year to visit. If you’ve ever wondered whether to put Ischia or Naples on your Italy itinerary (or if you’re just here for the pizza talk), this episode is packed with insight. 🎧 It’s time to experience la dolce vita! Timestamp: 2:47 Introduction to Al: Frequenter of Italy, Lover of Pizza and Wine + Discovering Italy without a Car 12:56 Travel Tips: Planning in Advance, Accommodation Accessibility, Avoid August Travel? + General Review of our Budgets and Cost 25:07 Arrival in Italy, Beware of Pickpockets + Every Mode of Transport in Italy 31:53 Ischia: Getting Around the Island with the Bus, Boat Trip Around the Island, Coniglio all'ischiatana, Rucolino Amaro, Thermal Baths + Comparison to Amalfi and Capri 51:37 Naples: The Grit, Character and Authenticity, the Pizza Journey, the Catacombs of San Genaro and San Genaro Day, and using the Michelin Guide while Traveling (it’s not always super expensive!)

    1h 9m
  3. Episode 10: Lisbon Food and Winter Travel with Emily

    AUG 12

    Episode 10: Lisbon Food and Winter Travel with Emily

    In this deliciously travel-filled episode of Wander Every Day, I sit down with my friend Emily — culinary school graduate, owner of @ems_treats, and mom of two — to hear all about her 10-day winter adventure in Lisbon, Portugal. Emily, her husband Kyle, daughters Spencer (3) and McKenna (8 months), her mom, and her sister stayed in a cozy Airbnb and explored Lisbon’s charm one cobblestoned hill at a time.  From day trips to the stunning Botanical Gardens, seaside Cascais, and the magical castles of Sintra, to soaking up the culture at LX Factory and Time Out Market, they made the most of their family getaway. Of course, no trip with Emily is complete without a food quest — and this time, it was all about pasteis de nata. Hear how she tried 30 different custard tarts to find the ultimate winner, plus her thoughts on the city’s fresh fish, potatoes, and mouthwatering restaurants. You’ll also get tips for tackling Lisbon’s famously steep, cobblestone streets with little ones. If you’ve ever dreamed of visiting Lisbon, especially with kids, or simply want the inside scoop from a foodie’s perspective, this episode is packed with inspiration, travel tips, and (of course) plenty of pastry talk. 🎧 Listen now and get ready to fall in love with Portugal! Timestamp: 0:00 Introduction to Emily and Wander Every Day 3:30 Camping in New Zealand: Bringing Tents, Unpredicted Rain + Wild Animals of the Region 6:54 Pasteis de Nata with a Culinary School Grad, Emily’s Travel Tips and Style + Shareable Google Maps Map 18:06 Day 1: Down Down with Illness + Air B&B 24:35 Day 2: the Best Cafe in Lisbon (spoiler - it’s vegan!), Botanical Gardens + Beautiful Dinner in Lisbon 30:04 Day 3: Beach in Cascais + Best Gelato in Lisbon 33:31 Day 4: Castle Sao Jorge, the Real Facts about Pasteis di Nata + SOL Restaurant (10/10!) 37:26 Day 5: Timeout Market, Pasteis de Belem + Hilly, Hilly Lisbon 45:47 Day 6: Sintra, Castles like Hogwarts + Quinta da Regaleira 50:12 Day 7-10: Wandering the Cobblestone Streets, LX Factory + Baixa 56:38 Trip Reflections 1:00:38 Rapid Fire 1:03:41 Listener Questions: Balancing Sight-seeing + Parenting, Lisbon Stroller Accessible + Public Transportation Links:Lisbon Sharable Google Map LocationsLisbon Air B&B Recommended Restaurants: Javá, SOL Restaurante e JardimBest Café: Gal Café (Vegan Cafe)Best Gelato: Insano GelatoBest Pasteis di Nata: Aloma

    1h 8m
  4. Episode 9: Aeroplan and Membership Rewards Optimization with Day

    AUG 5

    Episode 9: Aeroplan and Membership Rewards Optimization with Day

    In this solo episode of Wander Every Day, we’re diving into the art of using Aeroplan points and Membership Rewards to make travel more affordable—and sometimes downright luxurious. Whether you're just starting out or looking to level up your strategy, this episode breaks down the essentials of both collecting and redeeming points in Canada. We cover:✈️ What your Aeroplan points are actually worth💳 How to collect more points through sign-up bonuses, strategic credit card spending, and bonus offers 📊 How to optimize redemptions using the Aeroplan Flight Reward Chart, understanding dynamic pricing, and calculating cost-per-point (CPP) 🧠 Tools & experts to help you maximize value—like Roame, Ricky Zhang from Prince of Travel, and Canadian Jetsetters From roundtrip economy to dream-worthy business class flights, this episode is packed with practical advice, real examples, and personal wins that prove points can take you further than you think—if you use them wisely. Links: American Express Cobalt Card Referral Link Aeroplan Flight Rewards Chart Prince of Travel Aeroplan Timestamps: 0:00 Introduction to Point Collection and Redemption 8:03 Optimizing Point Collection: Sign-up Bonuses with the TD Aeroplan Visa Infinite Card 11:32 Optimizing Point Collection: Day-to-day Spending with the Amex Cobalt Card 13:05 Optimizing Point Collection: Bonus Offers and Promotions 12:49 Optimizing Redeeming Points: Star Alliance Price Chart 14:04 Optimizing Redeeming Points: Dynamic Pricing 15:28 Optimizing Redeeming Points:Cost-per-point Ratios 17:37 Closing Tips: Roame, Ricky Zhang + Other Resources

    21 min
  5. Episode 8: Switzerland and North Central Italy (+ a taste of Spain) with Christina

    JUL 15

    Episode 8: Switzerland and North Central Italy (+ a taste of Spain) with Christina

    This week on Wander Every Day, I’m joined by my sister-in-law Christina, who went on a month-long slow-travel adventure across Switzerland, Italy, and Spain. From postcard-perfect aperitivo moments in Milan to a hidden gem village in Cinque Terre, Christina shares not just where she went — but what it felt like to be there. We talk honestly about the cost of traveling Switzerland (is it worth it?), the simple magic of sipping wine in small Italian towns, and how meeting a local artist in Florence became a highlight of her trip. And when Spain came calling… did she secretly regret leaving Italy behind? 🗺️ In this episode, we chat about: • Why Switzerland’s beauty requires planning to allow for a budget price tag • The perfect aperitivo moments in Milan 🍸• A hidden gem in Cinque Terre (that isn’t where most tourists go) • Meeting a passionate artist in his Florence gallery 🎨 • Second-guessing whether leaving Italy for Spain was the right move • The slower, reflective side of travel — and what Christina would change next time We also talk European trains, review some top bar cafés in Milano, and really dive into whether traveling Europe in summer is worth the price, traffic + heat.  Whether you're mapping out your next Europe trip or wondering if Italy deserves more of your itinerary — this episode’s for you. 🎧 Let's wander. Recommendations: Felix - Milano Mag Cafe - Milano Bar Bello - Montreal Pastaficio di Canneto - Genova Il Gattaccio - Vernazza Timestamp 0:00 Introduction to the Pod2:41 Christinas Travel Style: Travelling with Friends, Authentic Travel Experiences + Preferred Pace of Travel 19:18 Switzerland: Fribourg, Montreux Jazz Fest, Gruyère cheese, Lausanne Beach Day + Marzili Bern 29:25 Switzerland is Expensive: Food + Trains (including the Bernina Express) 37:23 Milan: Appetitivo Hour, Duomo at Golden Hour + Speak Easy Culture 43:03 Genoa: Pastaficio di Canneto Pasta Restaurant, Unexpected Beach Vibes + Castelletto Views 46:47 Cinque Terre: Hidden Gem Town + Hiking Path, Overtourism in the Main Towns + Efficiency of the Train (Unless it’s on strike…) 57:50 Firenze “Florence”: Art Gallery Socials, Surviving the Heat + Day's Flashback to Engagement Pics in the Bardini Gardens 1:02:52 Quick Taste of Bologna: Bolognese, Food and Wine 1:04:37 Madrid: Spain Regrets?, El Retiro Park + Navigating Madrid Train Station 1:10:51 Barcelona: Beware of Phone Thieves, Jamon Iberico + Sitges 1:23:55 This or That: Euro Summer Edition 1:24:47 Listener Questions: People Watching at Apperitivo Hour + Where Would You Go Back

    1h 24m
  6. Episode 7: Travelling with Kids to Barcelona and Costa Daurada Spain with Gates and Laura

    JUL 8

    Episode 7: Travelling with Kids to Barcelona and Costa Daurada Spain with Gates and Laura

    In this episode of Wander Every Day, I’m joined by my friends Gates and Laura, who recently returned from a 10-day family trip to Spain with their two boys — Ian (5) and Logan (3) — and Gates’ mom, Lynn. From the beaches of Salou to family-friendly adventures in Barcelona, they’re sharing the highs, the meltdowns, and everything in between. We dive into what it’s really like to travel Europe with little ones in tow — including what to bring (and what to leave behind), how to adjust to jet lag, and how to balance naps, snacks, and sightseeing without losing your mind. 👶✈️ Perfect for parents dreaming of big trips but unsure if now’s the right time — this is the real talk you need. 🗺️ In this episode, we cover: • 5 days in Salou: beaches, PortAventura World, and a day trip to Siurana • 5 days in Barcelona: Sagrada Familia, a mosaic class, and a kid-focused walking tour • How they planned and booked Airbnbs for 3 generations • Packing essentials: car seats, strollers, carriers & kid entertainment • Managing jet lag, meals, and meltdowns on the road • Encouragement for parents who want to keep traveling with their kids — not wait until they're older 👨‍👩‍👦‍👦 Real advice from real parents who are making it work — one gelato and playground stop at a time. 🔗 Links: Salou Air B&BBarcelona Air B&BBarcelona Kids and Family Walking TourTop 40 Things to Do with Kids in Barcelona 🎧 Hit play and let’s wander.

    1h 26m
  7. Episode 6: The Ultimate African Safari in Tanzania (+ Beaching Around in Zanzibar) with Francesca

    JUN 24

    Episode 6: The Ultimate African Safari in Tanzania (+ Beaching Around in Zanzibar) with Francesca

    This week on Wander Every Day, I’m joined by my cousin-in-law Francesca, to review her action-packed and unforgettable trip through Tanzania and Zanzibar — a journey that had everything: wildlife, wonder, and a few unexpected bumps (literally). She takes us along on her 6-day Serengeti safari, where she: 🦓 Witnessed the legendary wildebeest river crossing 🚙 Survived a couple of safari vehicle breakdowns 🎈 Soared over the plains on a sunrise hot air balloon ride 🦁 Explored the incredible Ngorongoro Crater — home to some of Africa’s densest wildlife Then it was off to Zanzibar for some well-earned rest and exploration: 🌴 Beachfront chill time in Kendwa 🌶️ A deep dive into culture on a Stone Town spice tour Oh, and did they see a kill on safari? You'll have to listen to find out 👀 Whether you’re dreaming of a Big Five safari, craving clear turquoise waters, or just curious what it’s like when your safari truck breaks down in lion territory — this one’s got stories. 🎧 Hit play and let’s wander. 00:00 Introduction to Tanzania and Zanzibar 3:07 Even Experienced Travellers Make Mistakes - the Soon-to-Expire Passport Story 9:24 African Safari Planning: When To Go, the Great Migration + Preparatory Info 15:20 Francesca’s Trip to Tanzania + Zanzibar: Ethiopian Airlines, How to Choose A Safari Tour + Cost Expectations 26:58 Serengeti Safari Day 1: Truck Breakdown Part I, Seronera + Overview of the Camps 35:55 Serengeti Safari Day 2: Truck Breakdown Part II + Safari Meals 41:52 Serengeti Safari Day 3: Hot Air Balloon, Up Close Lions + Flash Flooding Dangerous River Crossing 52:09 Serengeti Safari Day 4: Wildebeest Crossing + Elephants 55:05 Serengeti Safari Day 5: The Kill!? + Pamoja African Lodge 1:01:36 Serengeti Safari Day 6: Ngorongoro Crater + How Many Gazelle are There?!? 1:04:55 Zanzibar: Arusha Airport, Italian Invasion in Kendwa + Stonetown 1:14:54 Respecting Culture, Diving + Canadians Owning the Zanzaibarian Resort 1:22:52 Rapid Fire Round 1:24:57 Listener Questions: Other Safari Locations in Africa, Bathrooms?, and the Beaches in Zanzibar

    1h 30m
  8. Episode 5: Budget Review of the Golden Route (+ Nikko, Okinawa & Hakone) in Japan with Maddie

    JUN 17

    Episode 5: Budget Review of the Golden Route (+ Nikko, Okinawa & Hakone) in Japan with Maddie

    This week on Wander Every Day, I’m joined by my wonderful friend Maddie, who’s no stranger to Japan — she’s traveled there three times, spent over six weeks exploring the country, and just so happens to be married to someone who grew up there. In this episode, Maddie takes us along on her most recent trip: ✨ Visiting her husband’s hometown of Misaki in Chiba 🌸 Exploring Nikko and sipping morning coffee by the river 🎤 Singing karaoke and missing the last train in Tokyo 🦌 Traveling solo to Nara with a peaceful day trip to Minoo waterfall 🚄 Experiencing her first bullet train ride 🍱 And of course — the food: tonkatsu, konbini snacks, and all-you-can-drink beer She also reflects on highlights from previous visits to Kyoto, Okinawa, and Hakone, sharing tips, funny stories, and favourite off-the-beaten-path moments. If Japan is on your list — or you just love hearing honest, thoughtful travel stories — this episode is packed with inspiration, laughs, and seriously great recs. 🎧 Press play and let’s wander. 00:00 Overview of Travel to Japan 4:00 Japan Working Holiday Visa 8:11 Overview of Maddie: Previous Trips to Japan, Solo Travel + Budget Style and Planning Approach 18:51 Chiba: Authentic Japan, Socializing Customs + Surfing 22:50: Nikko: Dewy Mountain Vibes, Hostel Coffee by the River + See No Evil, Hear No Evil, Speak No Evil 30:32 Tokyo: Overview of Tokyo Regions, Tonkatsu/Ramen + Missing the Last Train 38:27: Nara: Aggressive(ish) Deer, Japanese Customs + the Shinkansen 48:48 Osaka, Kyoto + Tokyo: General Overview of the Golden Route 54:46 Okinawa: Beaches, Mazemen + Zamami Island 57:17 Hakone: Onsens, Mount Fuji + Japanese Food Talk 1:03:55 Final Review of Japanese Activities and Reflection on Trip 1:06:42 This or That: Japan Edition 1:07:52 Listener Questions: Luggage Forwarding, Where to Revisit in Japan + Is Cherry Blossom Season Worth It?

    1h 13m
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Wander Every Day is the podcast where real travel stories meet smart recs + great chats. Hosted by Day — a deal-finder, storyteller, and your go-to travel friend — each episode dives into honest conversations with well-traveled friends about where to stay, what to eat, what not to waste your time (or money) on, and how to wander smarter. If you love adventure, good vibes, and learning tips and tricks for planning travel, you’re in the right place. ✈️🌍 Let’s wander.

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