September Fall Italy Retreat Dates 2025 (Calabria/Southern Italy)

September Fall Italy Retreat Dates 2025 (Calabria/Southern Italy)

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ITALY 2025 IS CALLING... But This Isn't The Italy You Think You Know

📅 Retreat Dates:

September 14th - 21st, 2025

We’re Going to:

Calabria, Italy

See All The Details + FAQ Below

Still on the fence?Join the waitlist - but honestly, don't wait.

These 3 spots will be gone faster than your first scoop of gelato.

CIAO FOR NOW, BELLA! 💋

Quantity:
Only 3 available
Fill out your Application Here + Complete the Check out process on the Add to Cart Button

THEY SAID I WAS CRAZY TO BUY A HOUSE SIGHT UNSEEN IN ITALY. TURNS OUT, CRAZY WAS EXACTLY WHAT MY SOUL NEEDED.

This isn't some woo-woo nonsense. This is where your nervous system resets, your circadian rhythms align, and you remember what you're actually working toward. The Tyrrhenian Sea calls to you, local Italians shift your perspective, and something magical happens that you can't get anywhere else.

It's the healing you've needed all along.

 

Gals From all walks of life…

The magic happens because: From research scientists to insurance brokers, military women to nurses, young professionals to super moms - women from every walk of life find what they need here. Some are longtime Gals That Brunch members, others have never attended a GTB event and dive in headfirst.

Our roommate matching has a 100% success rate - every 'random' roommate pairing has become lifelong friends.

This is where inside jokes form naturally, secrets get shared about how hard life has really been, and those silly van rides happen where everyone just lets their guard down.

You belong here if you're ready to say YES to yourself, bella. 💌

 

🌟 ITALY IS CALLING, RAGAZZI! 🇮🇹✨

Dream of waking up to sun-kissed mornings, wandering through cobblestone streets, and sipping wine in the kind of place that feels like a hug for your soul? This is your moment to say YES to a journey that blends heart, community, and the magic of Southern Italy.

To get a full break down of the rooms

+ payment plans click down below to be taken directly to shopify landing page:

🌟 THIS ISN'T YOUR BASIC TOURIST TRIP TO ITALY

Why Calabria instead of Rome/Florence/Venice?

Because this is Italy wild and untouched - not overcrowded tourist traps where you're rushing from site to site checking boxes. This is Southern Italy at its most authentic, where locals live the dream and tourists rarely venture.

I'm taking you to my personal hometown in Santa Maria del Cedro. You'll meet my friends, my family, and experience Italy from the inside out. This is a hand-picked, heart-filled, jaw-dropping experience hosted Tiff-style.

🛬 Pro Tip: If you’re already browsing plane tickets, plan to arrive by 3 PM on the 14th—or better yet, come a day early to settle in and soak up the vibes.

🏰 7 nights, 8 days of blissful Italian living, all designed to help you rest, recharge, and connect.

WHAT MAKES THIS DIFFERENT?

This isn’t one of those trips where you’re rushing from one site to the next, checking boxes like a tourist. Nope! This retreat is about giving yourself the time to play and rest. To savor every moment without a single ounce of FOMO.

🇮🇹 YOUR 7-NIGHT, 8-DAY ITALIAN JOURNEY

🏙 1 Night in Naples - Pizza that ruins you for life 🏡 5 Nights in Santa Maria del Cedro - My village, where time slows down 🌊 1 Night in Tropea - The Amalfi Coast's more stunning little sister

What's Waiting for You:

🍷 Private wine tastings in stunning Southern Italian vineyards

🍋 Farm-to-table dining that will spoil you rotten (authentic Italian feasts)

🛶 Boat rides on the sparkling Mediterranean

🏖️ Beach lounging and exploring hidden gems

👩‍🍳 Cooking classes with world-renowned chefs

🌿 Picnicking in our personal olive grove (learn how liquid gold is made)

💆‍♀️ Time to rest and recharge with just the right touch of adventure

Plus: Private chauffeurs throughout (our biggest splurge to make your journey seamless), surprise moments we're keeping secret, and two free afternoons for exploring, shopping, napping in hammocks, or hiking.



💕 WHY THIS RETREAT? WHY NOW?

You deserve this, bella. Italy is calling, and it's time to answer.

This retreat is intentionally small to keep the vibe intimate and sacred - because the best connections happen when there's space for them to bloom.

Let's go make magic, sip limoncello, and create memories that will live in your heart forever.

Dreams like this don't wait around. 🍋💃

You so deserve this, bella. Italy is calling, and it’s time to answer. 💌

This retreat is intentionally small to keep the vibe intimate and sacred—because the best connections happen when there’s space for them to bloom. Official spots will open later this month, and trust me—they’ll be gone faster than your first scoop of gelato.

And here’s the cherry (or limoncello) on top:

This isn’t your basic touristy trip to Italy. It’s a hand-picked, heart-filled, jaw-dropping experience hosted Tiff-style. Yes, I’m taking you to my personal hometown in Santa Maria del Cedro, where locals live the dream and tourists rarely venture. This is Southern Italy at its most authentic.

Let’s go make magic, sip limoncello, and create memories that will live in your heart forever.



CURRENT PRICING (Because Time is Money, Bestie):

🔥 REGULAR PRICE: $2,499 (Available until June 15th) ⚡ LATE BIRD: $3,799 (June 15th - June 30th)

That's a $1,300 difference for waiting 2 weeks. Your procrastination literally costs you $1,300. Don't let "I'll think about it" cost you more than the trip itself.

Registration SLAMS SHUT June 30th. No exceptions. No extensions. No "but I was going to..."



💰 WHAT'S INCLUDED IN YOUR INVESTMENT:

✅ All accommodations in authentic Italian stays

✅ Nearly every meal (except two free-time afternoons)

✅ Private wine tastings at family vineyards

✅ Hands-on cooking class with renowned chef

✅ Mediterranean boat adventures

✅ Picnics in ancient olive groves

✅ Full ground transportation during retreat

✅ Special Italian-inspired welcome package

✅ All surprise moments and experiences

Payment Plans Available: From $207.50/month with flexible options

IMPORTANT DATES:

  • Transfer Deadline: June 30th, 2025

  • *(if doing payment plans with GTB) Final Payments Due: September 1st, 2025


🚫 WHAT'S NOT INCLUDED:

  • Your flight to Italy (but I'll send you all the tips!)

  • Airport transfers on arrival

  • Specialty cocktails during free time

  • Meals during your two free afternoons

 

🎯 HOW TO SECURE YOUR SPOT (STEP-BY-STEP)

FOLLOW THESE EXACT STEPS - DON'T SKIP ANY!

STEP 1: FILL OUT YOUR APPLICATION 📝

👆 Look for the application form on this page and complete it fully This helps me match you with the perfect roommate and ensures this retreat is right for you

STEP 2: ADD TO CART & CHECKOUT 💳

👇 Click the "Add to Cart" button below

  • Choose your room type (Bunk, Shared, or Private)

  • Process payment through our secure Shopify checkout

  • Payment plans available! From $207.50/month

Need payment plan details? 👉 Click here for full payment options

STEP 3: BOOK YOUR INFO CALL WITH TIFF 📞

This is REQUIRED for all retreat participants

  • Group-based calls happening over the next few weeks

  • Get face-to-face time with Tiff

  • Ask questions and make sure this trip is perfect for you

👉 Book your call here

STEP 4: READ THE FAQ 📚

Scroll down to check out all the details below

  • Travel info, what's included, packing tips, and more

  • This answers 99% of your questions!

🚨 IMPORTANT: YOU'RE NOT OFFICIALLY REGISTERED UNTIL ALL 4 STEPS ARE COMPLETE!

Application ✅ + Payment ✅ + Info Call ✅ + FAQ Review ✅ = ITALY BOUND!

CONFUSED? STUCK? NEED HELP?

Don't let tech troubles steal your Italian dreams!

  • Email us: Hello@GalsThatBrunch.com

  • We'll walk you through every step!

✨ Ready to start your Italian adventure? Begin with Step 1 right now and we'll hold your pinky finger all the way to Italia! ✨

START STEP 1: FILL OUT APPLICATION (at the top of this page: “Fill out your Application Here + Complete the Check out process on the Buy Now Button”)

5. Check out the FAQ section below, hope to answer all your questions and curiosities.

✨ Ready to start your Italian adventure? Begin with Step 1 above now and we’ll hold your pinky finger all the way to italia! ✨

FAQ

  • Here's the best part: from the moment you land in Italy, your only job is to soak it all in. We've handled EVERYTHING:

    • Where to stay (family-run gems we've personally vetted)

    • What to eat or splitting checks (trust us, you'll never want to leave)

    • How to get around (no stress about trains or taxis)

    • Which local experiences you can't miss

    • Even which wines pair perfectly with dinner!

    All you have to do? Get your booty to Italy! We've:

    • Researched the best local spots

    • Made friends with the locals

    • Found the hidden swimming coves

    • Secured the best family recipes

    • Planned every transport detail

    • Arranged all the magical moments

    When you join us, you're not paying for luxury markup or corporate overhead. You're getting an expertly curated experience where every detail has been lovingly planned, so you can focus on what matters: living like a local, making new friends, and creating memories that'll last a lifetime.

    No Googling "best restaurants." No translating menus. No figuring out train schedules. No wondering what to do next.

    Just show up ready to embrace the Italian way of life - we've got the rest covered! 🇮🇹

  • A: You have three options:

    • Naples International (NAP) - Most convenient, direct transfer to our meeting point

    • Rome Fiumicino (FCO) - Take a train to Naples (~1.5 hours)

    • Lamezia Terme (SUF) - Take a train to Naples (~4 hours)

  • A: The retreat Check-In Officially begins at 3PM on Sunday, September 14th, 2024 in Naples. We recommend:

    • Arriving the day before (Sept 13th) to avoid travel stress

    • Using the extra time to explore Naples or rest up

    • If you're flying into Rome or Lamezia, definitely arrive a day early to ensure smooth train connections

  • A: No worries at all! You can join us wherever we are in the itinerary - but you'll be responsible for your own transportation to meet the group. We'll provide detailed instructions and support.

  • A: Oh honey, YES! And here's why with my whole heart:

    This retreat isn't your typical "run around Rome with a selfie stick" experience (though we fully support getting those tourist moments in first! 🤳). Our 7 days together are about letting Italy sink deep into your bones - we're talking cozy lunches that turn into sunset aperitivos, cooking with nonnas who don't speak English but teach you everything with their hands and hearts, and moments that make you forget what time (or even what day) it is.

    So YES, come early! Get those iconic shots at the Colosseum. Toss your coin in the Trevi. Eat gelato for breakfast in Rome. Stand in awe at the Vatican. Do ALL of it! Get your tourist excitement out of your system (it's part of the journey and we love it!)

    Then... come join us with empty cups ready to be filled with something deeper. Because once you're with us, we're not rushing from landmark to landmark - we're living in the gentle pulse of Southern Italian life. We're learning to breathe differently. To taste differently. To see differently.

    Suggestions we love:

    • 2-3 days in Rome for the bucket list dreams

    • A day in Naples to understand why pizza will never be the same again

    • Extra time to let the jet lag melt away and arrive to our retreat with your soul ready to soak in the magic

    Pro tip: Many past guests have said those extra days helped them shift from "vacation mode" to "transformation mode" - and that's exactly what we're after.

  • A: Take the high-speed train (Frecciarossa or Italo):

    • Trains run frequently

    • Journey takes about 1.5 hours

    • Book tickets at trenitalia.com or italotreno.it

    • Cost: €30-50 depending on time/class

  • A: We've got super flexible options! Secure your spot with a $500 deposit, then spread the rest over 6 monthly payments. For example, Super Early Bird rate can be as low as $350/month.

    OR use our shopify function and you can work out a 12 month payment plan :)

  • A: Everything you need for an authentic Italian experience:

    • 7 nights accommodations (1 night Naples, 5 nights Santa Maria del Cedro, 1 night Tropea) check out what they say about tropea here: https://funesahora.com.ar/discover-italys-hidden-gem-the-enchanting-allure-of-tropea/

    • Most meals and wine (breakfast basics, seaside lunches, and 3-5 course dinners) (See meal break down below)

    • All transportation between destinations

    • Cooking experiences with local families

    • Private wine tasting day with farm-to-table lunch

    • Mediterranean boat excursions

    • Welcome gift

    • Daily activities and excursions

    • Group transportation from Naples at start of retreat

  • Q: What's not included?

    • Flights to/from Italy

    • Travel insurance (required)

    • Some meals during free time (2 lunches)

    • Optional additional excursions

    • Shopping (trust us, you'll want to!)

    • Speciality Cocktails

  • A: Our retreat officially concludes around 130PM on Saturday, September 21st, with group transportation to Naples Centrale. Here's what you need to know:

    • Group Departure (Included):

      • 130PM departure

      • Assistance with train connections to Rome, Naples, or other destinations

    • Early Departures:

      • Need to leave earlier? We get it!

      • You'll be responsible for your own transportation

      • We'll provide trusted taxi recommendations

      • Expect €20 for taxi to Scalea station

      • We'll help you plan but cannot provide transportation before group departure

  • A: Welcome, solo traveler! About 80% of our guests come solo. We'll pair you with an awesome roommate, or you can grab a private room.

  • A: For 8 days (7 nights):

    🍝 INCLUDED MEALS:

    18 INCREDIBLE ITALIAN MEALS:

    • 8 Traditional Italian Breakfasts

      • Start each day like a local with a fresh cornetto and perfectly crafted cappuccino

    • 4 Long, Lazy Lunches

      • From seaside feasts to farm-to-table experiences

      • (2 free lunches for your own exploring!)

    • 7 Memorable Dinners

      • Multi-course evening meals where time stands still and conversations flow like wine

    What to Expect:

    • Breakfast: Traditional Italian style - light and sweet with coffee

    • Lunch: When included, these are proper Italian lunches (no quick bites!)

    • Dinner: 3-5 course experiences with wine

    • Wine included with lunch and dinner

    • Any meals or snacks during free exploration time are on your own

    • Specialty drinks beyond included wine are extra

  • A: From Scalea station, here are your best train + flight planning options:

    NAPLES (NAP):

    • Fast train: 1.5 hours to Naples Centrale

    • Airport transfer: 20 mins to Naples Airport

    • Security/Check-in: 2 hours recommended → Don't book flights before 6PM from Naples

    ROME (FCO):

    • Fast train: 3 hours to Roma Termini

    • Airport transfer: 30 mins to Fiumicino Airport

    • Security/Check-in: 2 hours recommended → Don't book flights before 7:30PM from Rome

    LAMEZIA (SUF):

    • Local train: 2 hours to Lamezia

    • Airport transfer: 15 mins

    • Security/Check-in: 2 hours recommended → Don't book flights before 5:30PM from Lamezia

    Pro Tips:

    • Book fast trains (Frecciarossa/Italo) in advance for best rates

    • Consider spending an extra night or two in your departure city to avoid travel stress

    • Many guests extend their trip into Northern Italy via Rome or Milan

    • We're happy to help you plan your post-retreat Italian adventures! 🇮🇹✨

    Remember: Group transfer leaves for Naples at 130PM. Early departures will need to arrange their own transportation to the station.

  • A: After deposit confirmation, payments are non-refundable. This retreat requires extensive advance planning and reservations. We strongly recommend comprehensive travel insurance that covers trip cancellation, medical emergencies, and travel delays. We're happy to recommend trusted insurance providers!

  • A: We’re asking everyone to book an Italy Discovery Call before or after signing up—it’s a heart-to-heart chat about experiencing Italy the way it’s meant to be lived! We’ll talk about what draws you to Italy, answer your questions, and make sure you’re excited about our style of travel—think long dinners where conversation flows like wine, mornings at the local café where the barista knows your order, and afternoons diving into the crystal-clear Tyrrhenian Sea.

    Even if you’ve been on a previous Italy trip, we’d love to hear from you and see your beautiful faces! This call helps us connect, share all the exciting details, and ensure this experience is the perfect fit for you. And if we decide it’s not, your deposit will be 100% refundable. We want everyone on this journey to be ready to embrace the authentic Italian way of life!

  • A: We'll send you our detailed "Dress Like a Local" guide, but here's the essence:

    • Comfortable walking shoes (those cobblestones are no joke!)

    • Swimwear (multiple sets recommended)

    • Mix of casual and smart-casual outfits

    • Light layers (Calabrese evenings can be breezy) We'll send you our curated outfit suggestions for each day, including our favorite "blend in like a local" tips. No tourist vibes here!

  • A: Get ready for a true Calabrese food journey! All your meals are included, featuring:

    • Farm-to-table feasts

    • Cooking experiences with local families

    • Wine tastings at family vineyards

    • Traditional multi-course dinners

    • Local market visits You'll enjoy set menus showcasing Calabrese specialties, with plenty of options at each meal. Have dietary restrictions? Let us know when booking so we can ensure you're well taken care of!

    • A: Absolutely! Whether you're vegetarian, gluten-free, or have other restrictions, we'll make sure you're well-fed and happy. Just communicate your needs when booking - we'll work with our local partners to ensure delicious alternatives are always available.

  • A: US citizens don't need a visa for stays under 90 days, but your passport must be valid for at least 6 months after your return date. For our international friends: Visa requirements vary by nationality. Check your country's specific requirements for entering Italy/Schengen Area well in advance. We recommend starting this process at least 3 months before travel. Need help? We can point you toward reliable resources for your specific situation!

  • A: Absolutely! Private rooms are available for an extra charge. They're limited though, so book early if you'd like your own peaceful retreat space!

  • 🏃‍♀️ This is truly go at your own pace. Stay back if you need to or gallop ahead. We'll be walking on cobblestones and hilly villages, but it's designed for everyone to enjoy at their comfort level.

  • This retreat is all about FUN, personal healing and sisterhood - exploring Italia like a local!

    However, if you're looking for something more business-focused, Tiffany also runs a Prophetic Business Retreat every year in Italy just a few weeks after this one. It's where soul-led entrepreneurs gather to align their purpose with profit in the most magical setting.

    Check out all the details at youhadmeatitaly.com 💫

  • A: From the official start of our trip until our 1 PM Sunday departure, ALL group ground transportation is fully covered. We'll drop you off at Naples central station or you're welcome to stay in the Santa Maria del Cedro area.

  • A: No worries if you don't speak Italian! While we'll teach you some fun local phrases (perfect for ordering your morning caffè!), our English-speaking hosts and local guides will ensure you're well taken care of. Plus, there's nothing better than bonding with locals through hand gestures and smiles - it's part of the magic!

  • A: Nothing brings us greater joy than introducing the magic of Italy's countryside to kindred spirits who become family. Every detail of this retreat is priced at cost because our mission is simple: to share the real Italy we've fallen in love with.

  • How to Sign Up for the 2025 Gals That Brunch Italy Retreat

    Your Retreat Payment Options

    Option 1: Shopify SHOP Store (Recommended)

    1. Fill out the application on the Gals That Brunch website

    2. You'll be directed to our Shopify store: https://galsthatbrunch.myshopify.com/products/gals-that-brunch-retreat?variant=50153641640152

    3. Select your preferred room option:

      • Bunk It Up Bestie Experience (share a bed with your bestie): from $2,499

      • Shared Room (your own bed): from $2,799

      • Private Room (ultimate privacy): from $3,499

    4. Choose any add-ons:

      • Mini Branded Photo Shoot: $350

      • Private Arrival Transfer: $140

    5. Proceed to checkout

    6. Select "Shop Pay" as your payment method

    7. After clicking "Complete Order," set up Shop Pay installments

    8. Choose a payment plan of up to 12 months with Shop Pay

    9. No additional admin fees!

    10. Manage your payments easily through the Shop app

    Option 2: $500 Deposit + GTB Payment Plan

    1. Visit the Gals That Brunch website

    2. Fill out the Italy Retreat application

    3. Select the "$500 Deposit" option to secure your spot and lock in early bird pricing

    4. Our team will set up a 6-month payment plan for your remaining balance

    5. Important: Full payment must be completed by August 30th, 2025

    6. Please note: This option includes an 8% admin fee and has limited flexibility

    Pricing Tiers (Book Early & Save!)

    • Super Early Bird (Now through February 29): Save $700

    • Early Bird (March 1 through March 31): Save $500

    • Regular Price (April 1 through April 30): Save $300

    • Late Bird (May 1 through June 15): Full price

    Group Discount Codes

    • Book with 1 friend: Use code TWINSIES to save $100 each

    • Book with 2 friends: Use code WETRIPLETSNOW to save $150 each

    Need Assistance?

    If you have any questions during the registration process:

    Email us at Hello@GalsThatBrunch.com

  • 💕 THIS IS FOR YOU IF YOU'RE...

    The woman who's been:

    Grinding so hard you forgot what rest feels like You know that bone-deep exhaustion that sleep doesn't fix? When you wake up already tired because your mind never stops running? That's your nervous system screaming for the kind of reset that only happens when you're completely removed from your daily grind. Italy doesn't just give you permission to rest - it makes rest inevitable.

    Putting everyone else first (again) while your dreams collect dust How many times have you said "maybe next year" while booking everyone else's vacations, paying for everyone else's experiences, making sure everyone else's dreams come true? Your dreams aren't selfish, gorgeous. They're necessary. And they're waiting for you in a sun-drenched Italian village where the only person you need to take care of is YOU.

    Scrolling Italy pics thinking "someday..." while that someday never comes Those Pinterest boards full of Tuscan sunsets and cobblestone streets? That Instagram save folder labeled "travel goals"? Stop torturing yourself with someday. Someday is a thief that steals your dreams while you're busy being "responsible." September 14th is your someday. It has a date, a flight number, and 3 spots left.

    Craving REAL connection beyond surface-level small talk You're tired of "How's work?" and "Fine, how are you?" You want the conversations that happen at 2am over wine, where masks come off and souls connect. You want to laugh until your stomach hurts with women who GET IT. You want friendships that start with "Remember that time in Italy..." This is where those connections are born.

    Ready to invest in yourself without the guilt spiral, honey That voice in your head calculating what else you could do with $2,499? IGNORE HER. She's the same voice that's kept you small, kept you last on your own priority list, kept you believing that everyone else deserves beautiful experiences but you don't. You've spent more than this on other people's happiness. It's your turn.

    You might be:

    A super mom juggling everyone's needs (like our Nebraska queen with 7 kids!) Seven kids, y'all. SEVEN. And she still said yes to herself. If she can carve out a week for her soul, what's your excuse? Your kids need to see you living fully, not just surviving. They need to see what it looks like when mama chooses herself too.

    A boss babe feeling burned out from the hustle The 5am wake-ups, the endless Zoom calls, the "crushing it" that's actually crushing YOU. Success without joy is just expensive misery. You didn't build your empire to become a prisoner in it. Italy will remind you why you started - and give you the clarity to remember what actually matters.

    Someone serving others who rarely gets served back Nurse, teacher, caregiver, therapist - you pour into everyone else's cup until yours is bone dry. When's the last time someone served YOU? When's the last time you were pampered, prioritized, taken care of? In Italy, you're not the giver - you're the receiver. And honey, you've earned it.

    Single and ready for adventure, or married and craving sisterhood Single? This isn't about finding a man in Italy (though Italian men are... chef's kiss ). This is about finding YOURSELF in Italy. Married? This isn't about escaping your life - it's about remembering who you are outside of being someone's wife, someone's mom, someone's everything. You're allowed to have an identity that's just YOURS.

    In transition - new chapter, new you, new possibilities Divorce papers signed? Kids off to college? Career pivot? Life just threw you a curveball? Transitions are terrifying and beautiful and messy. Italy doesn't fix everything, but it gives you space to breathe, to dream, to remember that endings are also beginnings. Your new chapter starts in Calabria.

    Done waiting for permission to live your most beautiful life You've been waiting for the right time, the right bank balance, the right circumstances. But here's the truth: there's never a perfect time to choose yourself. There's only NOW. And now is asking you to be brave enough to say yes to the life you've been dreaming about.

    🌍 WOMEN FROM AROUND THE GLOBE ARE SAYING YES

    Some are longtime GTB members who've been waiting for THIS moment - the chance to go deeper with their global fam bam beyond a 2-hour brunch.

    Others are brand new to our sisterhood and ready to dive in headfirst with the most beautiful introduction possible.

    From research scientists to insurance brokers, military women to nurses, young professionals to super moms - our roommate matching has a 100% success rate. Every 'random' roommate pairing becomes lifelong friends.

    This is where inside jokes form naturally, secrets get shared about how hard life has really been, and those silly van rides happen where everyone just lets their guard down.

    You belong here if you're ready to say YES to yourself, bella. Whether you've been part of our global fam bam for years or you're about to become our newest sister - Italy is calling your name. 💌