(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In episode 62, Harrison sheds light on key points-and-miles misunderstandings and shows that you don’t need to spend extravagantly to earn meaningful rewards. By choosing the right credit cards, even moderate expenses can rack up significant points. He also underscores the idea that any travel redemption is valuable, no matter how simple. Recommended options include the Capital One Venture X card for its strong earning rate and transferable points, and the Bilt Mastercard for earning points on rent without fees. In addition to debunking these myths, Harrison pinpoints lesser-known destinations perfect for remote work: Bulgaria offers budget-friendly adventures, Athens caters to digital nomads, and Singapore serves as a vibrant stopover hub. Whether it’s Salvador, Brazil for a solo escape or Bulgaria for a road-tripping adventure, there are plenty of ways to explore the world without breaking the bank.

Beyond destinations, Harrison offers practical strategies for anyone considering a remote work lifestyle. He advocates experimenting with short-term stays before making bigger moves, managing boundaries to maintain work-life balance, and tapping into local events and resources like Meetup to integrate into new communities. Harrison also highlights the potential of credit cards in a freelancing context, business cards can help separate personal and professional expenses while earning extra points. Lastly, he reassures travelers that bringing a pet abroad is often simpler than expected, showing that with the right preparation, pets don’t have to hold you back from a flexible and fulfilling remote work journey.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

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⁠Rakuten⁠: Earn cash back/rewards on every purchase!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

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Carry: The modern Solo 401(k) for business owners

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Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.

Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In episode 61, Ross shares his insights on the ideal times to visit Greece, spotlighting the advantages of traveling during the shoulder season (April, May, September, or October) for fewer crowds, pleasant weather, and more budget-friendly prices. He lays out a clear plan for first-time visitors, suggesting Athens, Mykonos, and Santorini as top destinations, with Milos as his personal favorite for a more intimate experience. Ross recommends visiting the mainland or hopping between islands, depending on each traveler’s preference and budget, and references resources like Santorini Dave, the “Greece Travel Secrets” podcast by Sandra Pappas, and his own downloadable guides for further exploration and planning.

To help travelers organize a stress-free Greek adventure, Ross underscores the importance of factoring in time off, finances, and personal travel styles. He encourages listeners to utilize points and miles for flights and accommodations, including the availability of direct flights from Charlotte to Athens. Ross also suggests exploring additional islands like Zookynthos (for its famous Shipwreck Beach) and Paros or Naxos as alternatives to more crowded locales. He wraps up by directing his audience to a previous episode for an in-depth itinerary guide, urging them to take advantage of his free downloadable travel resources and share the podcast with fellow Greece enthusiasts—topped off by a request for a 5-star review if they find the content valuable.

Athens Accommodation:⁠ ⁠⁠https://booking.tp.st/fWHinVgc⁠

Santorini Accommodation:⁠ https://booking.tp.st/CGRTOJIp⁠

Santorini Catamaran Cruise:⁠ https://booking.tp.st/dybB9qvy⁠

Mykonos Accommodation:⁠ https://booking.tp.st/bh1kpo1Y⁠

Milos Accommodation: ⁠ https://booking.tp.st/hIrFjxLJ⁠

Milos Catamaran Cruise: ⁠ https://booking.tp.st/46BOfK7l⁠

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

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TravelPayouts: Turn your trips into income and earn!

Gondola AI:⁠ Find better hotels, earn more points, travel for free!

⁠Rakuten⁠: Earn cash back/rewards on every purchase!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

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Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In episode 60, Ross and Midwest travel expert Sara Broers as they explore the hidden gems and unique experiences waiting to be discovered in America's heartland. Sara shares insider tips on authentic storytelling, local cultural attractions, and must-see destinations in Iowa, South Dakota, North Dakota, Missouri, Indiana, and beyond. Learn about iconic sites like Iowa's Frank Lloyd Wright hotel, a memorable Midwest road trip itinerary, and top recommendations for unforgettable adventures—from ice fishing at Devil's Lake to visiting historic Medora and the vibrant community of Branson.

Sara also highlights the value of family travel, encouraging listeners to seize opportunities for multigenerational trips and create lasting memories through shared experiences. Whether planning a road trip, exploring off-the-beaten-path destinations, or seeking inspiration for your next family adventure, this episode is packed with practical advice and fascinating stories that showcase the Midwest’s unique charm. Follow along to rediscover your own backyard with Sara’s insightful guidance.

Sara’s Social Media and Links:

https://travelwithsara.com

https://www.facebook.com/travelwithsara

https://instagram.com/travelwithsara

https://www.pinterest.com/travelwithsara

https://www.tiktok.com/@travelwithsara

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

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Transfer Bonus Notifications

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TravelPayouts: Turn your trips into income and earn!

Gondola AI:⁠ Find better hotels, earn more points, travel for free!

⁠Rakuten⁠: Earn cash back/rewards on every purchase!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

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Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.

Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In episode 59, Ross’s Greek Islands Travel Guide provides an in-depth look at an 11-day itinerary through Athens, Mykonos, Santorini, and Milos. He begins by noting the convenience of direct flights from Charlotte to Athens—especially beneficial for those able to use rewards points and miles—and underscores the importance of leaving ample time for layovers and customs. While in Athens, Ross suggests staying in the Plaka area to enjoy its central location, historic charm, and quick access to highlights such as the Parthenon and the Acropolis. He emphasizes the value of planning ahead by booking ferries in advance for island hopping, as well as scheduling ground transportation, particularly in Santorini and Mykonos where rides can be in high demand.

Beyond Athens, Ross’s tips concentrate on beach clubs and restaurants in Mykonos, recommending reservations at popular spots like Santa Ana Pool, Bar Negrita, and Cavo Paradiso. In Santorini, he suggests staying in Imerovigli for scenic caldera views without the premium prices of Oia, plus activities like a sunset catamaran cruise and dinner at Argo. Milos is a highlight for explorers who enjoy renting four-wheelers to discover secluded beaches, and Ross cites O! Hamos as a can’t-miss dining experience. For overall stress reduction, Ross recommends not checking luggage and using the Priority Pass app to locate lounge access—particularly at Athens International Airport—ensuring a smoother journey between destinations.

Athens Accommodation: https://booking.tp.st/fWHinVgc

Santorini Accommodation: https://booking.tp.st/CGRTOJIp

Santorini Catamaran Cruise: https://booking.tp.st/dybB9qvy

Mykonos Accommodation: https://booking.tp.st/bh1kpo1Y

Milos Accommodation: https://booking.tp.st/hIrFjxLJ

Milos Catamaran Cruise: https://booking.tp.st/46BOfK7l

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI:⁠ Find better hotels, earn more points, travel for free!

⁠Rakuten⁠: Earn cash back/rewards on every purchase!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

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Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.

Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In episode 58, Ross and Glen dive deep into the world of personal finance, sharing insights from Glen’s experience as a deputy editor at Fortune, specializing in credit cards, mortgage rates, and financial literacy. They discuss common misconceptions about credit card usage, effective strategies for building a strong credit score, and personalized approaches to leveraging rewards and cash-back benefits. From avoiding financial pitfalls to making strategic decisions about annual fees and credit card applications, this conversation provides practical guidance to help listeners optimize their financial health.

The discussion also explores budgeting techniques, strategic use of credit card rewards for travel—including Ross and Glen’s upcoming trip to Estonia—and the essentials of managing personal finances through helpful tools and apps. Whether you're planning to invest in real estate, start a rental business, or simply enhance your credit strategy, Ross and Glen offer valuable advice to empower your financial journey.

Glen’s Social Links:

https://fortune.com/section/personal-finance/

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

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Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

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Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In episode 57, Ross presented a concise packing checklist designed to streamline travel preparations by focusing on a “less is more” philosophy. He emphasized the practicality of carry-on luggage from reputable brands like Samsonite, Away, or Monos, coupled with the use of packing cubes to maintain organization. Ross also provided tips on choosing versatile clothing items that are easy to wash and pair, ensuring travelers can minimize their overall luggage without sacrificing essentials. Alongside this, he recommended key accessories such as noise-canceling headphones, portable chargers, and international adapters to help maintain comfort and convenience during any trip.

Beyond packing guidance, Ross highlighted the value of subscribing to his weekly newsletter on itineraryboss.com, which contains travel tips, expert interviews, and important updates on credit card offers and travel tools. He underscored the newsletter’s objective to help readers travel stress-free, inviting them to engage further by sharing feedback and suggestions for future content. Ross also encouraged attendees to download his stress-free travel starter kit and expressed enthusiasm for additional expert interviews and solo tutorials, signaling ongoing support for those aiming to travel more efficiently and confidently.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI:⁠ Find better hotels, earn more points, travel for free!

⁠Rakuten⁠: Earn cash back/rewards on every purchase!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

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Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.

Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In episode 55, Ross introduced his ultimate travel planning checklist as a comprehensive guide to help listeners organize trips and avoid common mistakes. He highlighted the significance of thorough pre-trip preparation, such as using Google Docs for collaborative checklists, Google Maps for route planning, and Tripit for itinerary management. Ross also emphasized collecting and arranging necessary documents, shared strategies for maximizing rewards with travel credit cards, and recommended opting for Euros instead of US dollars during credit card transactions for potential savings. Additionally, he underscored the need to secure an international plan when traveling abroad and selecting luggage that meets both airline and traveler requirements.

Listeners were advised to set up flight alerts, create vacation checklists for clarity, and download useful apps to streamline their travels. Ross advocated for travel credit cards to accumulate valuable points, suggested creating a dedicated email folder for all travel-related communications, and advised storing both digital and printed copies of critical documents. He further recommended sharing itineraries with trusted individuals, researching visas and travel insurance, and preparing backup plans for essentials. Finally, Ross encouraged subscribing to the Itinerary Boss Insiders Newsletter for continued travel tips, specialized tools, and exclusive credit card offers.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

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TravelPayouts: Turn your trips into income and earn!

Gondola AI:⁠ Find better hotels, earn more points, travel for free!

⁠Rakuten⁠: Earn cash back/rewards on every purchase!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

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Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.

Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In episode 56, Ross and confidence & relationship coach, Tzara, in a powerful conversation about overcoming anxiety, cultivating deeper relationships, and transforming your life through travel and adventure. Tzara shares how her personal journey—sparked by workplace anxiety during Covid—led her into self-development, confidence coaching, and traveling the world chasing solar eclipses. She reveals her unique experiences refitting a van, exploring Australia's stunning Nullabor landscape, and explains why embracing risk and setting clear intentions can unlock profound personal growth.

From creative date-night tips to the psychological benefits of frequent travel, Ross and Tzara explore practical ways to break daily monotony, reconnect with nature, and maintain meaningful relationships amidst busy schedules. Whether you're looking to improve your confidence, foster healthier connections, or find inspiration for your next big adventure, this episode offers powerful insights to help you grow personally and professionally.

Tzara Social Links:

https://www.Myconfidencecoach.com.au/IRL

https://myconfidencecoach.com.au/52dates/

https://www.Myconfidencecoach.com.au/ec-call

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI:⁠ Find better hotels, earn more points, travel for free!

⁠Rakuten⁠: Earn cash back/rewards on every purchase!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.

Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In Episode 52, join Ross as he chats with Autumn—flight attendant, travel photographer, and author of “Traveling in Wonder.” She takes us through her journey from a teen photographer studying abroad in England to earning her wings as a flight attendant, revealing what really goes on behind the scenes of every flight. From monitoring able-bodied passengers to soothing nervous flyers, Autumn’s role goes far beyond simple beverage service. Discover how these experiences fueled her passion for adventure and shaped her perspective, ultimately inspiring her to write a book capturing her travels to 30 countries before the age of 30.

In this conversation, Autumn and Ross also dive into practical tips for anyone hoping to travel smarter. Learn how to pack like a pro, repurpose everyday items (yes, even shower caps!), and maximize your points and miles through credit cards. Autumn highlights how small, deliberate steps—like joining the right Facebook groups or using the right apps—can build confidence in exploring new places. Whether you’re a frequent flyer or someone easing into your first international trip, you’ll walk away with fresh insights on budgeting, planning, and cultivating a mindset that lets you embrace the wonders of travel.

Autumn's Socials

• Website: https://www.autumncarolynn.com

• Instagram: https://www.instagram.com/autumncarolynnphotography/

• NEW BOOK: https://autumncarolynn.com/my-book-traveling-in-wonder/p/tiw

  
  

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Best Credit Cards for Travel

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Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI:⁠ Find better hotels, earn more points, travel for free!

⁠Rakuten⁠: Earn cash back/rewards on every purchase!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

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Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.

Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In episode 53, Ross talks about how to make the most of a three-day trip to Lisbon, Portugal, emphasizing the convenience of flying directly into the city from U.S. airports like New York or Miami. He suggests timing your visit for the shoulder seasons (April–June or September–October) to avoid heavy crowds while still enjoying pleasant weather. Once in Lisbon, Ross recommends staying in central districts such as Baixa, Chiado, or Alfama, ensuring easy access to must-see attractions. He highlights key landmarks like Belém Tower, Padrão dos Descobrimentos, and the Jerónimos Monastery, all within a short distance of each other. Ross also underscores the importance of trying local cuisine at spots like Mercado da Ribeira, Cervejaria Ramiro for seafood, and neighborhood eateries in Alfama—including a memorable stop at Audrey’s (made all the more special because his fiancée shares the same name).

Throughout the episode, Ross provides practical tips for transportation, advising visitors to use rideshares or hotel shuttles upon arrival and take advantage of the city’s extensive public transport network. He also mentions the Lisboa Card for convenient, unlimited travel on trams, buses, and the metro—plus discounts on popular sights. Ross outlines a sample itinerary that begins with settling into your accommodation and exploring Alfama, followed by a day in Belém for culture and history, and finishing with scenic city views from famous miradouros. He wraps up by recommending day trips to Sintra or Cascais, noting that extending your stay can unlock even more of Portugal’s charm, including a trip to the picturesque Algarve or the city of Porto.

Accommodations:

Pousada Alfama

Vincci Ponte de FerroAndo Living - Santa Justa 77 House

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI:⁠ Find better hotels, earn more points, travel for free!

⁠Rakuten⁠: Earn cash back/rewards on every purchase!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

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Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.

Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.