(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 72, former lawyer-turned-creator Jen joins Ross to trace how childhood curiosity and a fearless career pivot led her from courtrooms to full-time travel storytelling. Together they unpack why continuous learning, embracing uncertainty, and treating every trip—near or far—as a chance to reset can unlock both personal fulfillment and entrepreneurial momentum.

The conversation then shifts to hands-on tactics: hacking airfare costs with flexible dates and flight-alert services, planning bucket-list detours, and empowering solo travelers through research and readiness. Alongside tips, they trade anecdotes—from $70 Japan tickets to therapy-dog training—and preview future podcast guests and a new recording setup poised to keep their global-minded community inspired.

Jen Ruiz’s Social Media:

⁠Jen’s Website⁠

⁠Jen on a Jet Plane⁠

⁠Instagram⁠

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

⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠

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 71 Ross explored how strategically leveraging credit-card points and miles can slash travel costs, walking listeners through co-branded cards versus those with transferable currencies and the key perks—travel insurance, lounge access, and generous welcome bonuses—that can justify annual fees. He stressed that the approach only works when balances are paid in full each month, turning everyday spending into free flights and hotel nights while building a solid credit profile.

To keep momentum, he invited listeners to catch next week’s deep dive on choosing the right card, subscribe and leave a five-star review, and download the free Points & Miles Cheat Sheet linked in the show notes. Those eager for tailored guidance can join his weekly newsletter, browse his favorite card picks on the website, or book a complimentary one-on-one consultation for personalized credit-card strategy.

Points and Miles Cheat Sheet⁠⁠

American Express® Gold Card⁠⁠

⁠⁠Capital One Venture X Rewards Credit Card⁠⁠

⁠Chase Sapphire Preferred® Card⁠

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

⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠

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 this episode 70, the Itinerary Boss Ross chats with Ruba, an avid traveler who's visited 46 countries. They reminisce about their shared adventures in Budapest, Prague, Croatia, and more. Ruba shares her recent experience in Mexico City, highlighting the vibrant culture, bustling city life, and memorable activities like hot air ballooning at sunrise. She also recounts her trip to the Stagecoach festival, contrasting it with Coachella, which she found overly commercialized and challenging logistically.

Ruba discusses her travel planning process and how she prioritizes destinations, often influenced by personal recommendations. She shares insights about the benefits of less touristy spots and cost-effective travel strategies, like renting a catamaran in the Amalfi Coast. Additionally, Ruba talks about her early travel experiences, including a solo trip to Egypt at 12, which sparked her lifelong passion for exploring new places.

Ruba’s Social Media:

Instagram

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

⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠

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 68 Ross speaks with Journey with Jake, Ross Alcorn, the founder of Itinerary Boss, explains how he turns the travel ambitions of busy professionals into achievable plans. Drawing on years as the de facto trip organizer for friends while juggling a demanding healthcare-sales career, he built frameworks for everything from weekend snowboarding escapes to 17-day European odysseys. These systems now underpin his company’s service: stripping away the research overload and timing headaches that keep high-achievers from taking real vacations.

Alcorn’s method is rooted in personal experience with burnout, after a year of attending nine weddings without a single personal getaway, he saw how easily adventure slips down a packed priority list. His solution pairs practical strategy with a spirit of discovery: leveraging credit-card rewards, optimal booking windows, and streamlined planning so limited time yields maximum experience. The vivid stories he collects—soaring off a boat in Croatia, chatting with the Croatian president, shepherding quirky Amsterdam souvenirs through airport security, illustrate the lasting impact of stepping beyond routine, proving memorable journeys can coexist with demanding careers.

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

⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠

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 this special solo episode, Ross takes you behind-the-scenes on exactly how to effortlessly plan an unforgettable surprise trip for your partner. He shares the step-by-step details of the perfect birthday getaway he organized for his wife to Turks and Caicos. You’ll discover how you can find budget-friendly accommodations like the Royal West Indies and best strategies for finding the best flights and times to travel with points and miles to Turks.

Join Ross as he shares practical tips and exclusive insights for exploring Grace Bay, top-rated dining experiences (like Coco Bistro and Bay Bistro’s beach dinners), must-do adventures such as horseback riding, catamaran snorkeling tours, Chalk Sound exploration, and unique nightlife experiences at the famous Conch Shack. After tuning in, you'll feel confident and relaxed, equipped with easy-to-follow advice and excited to book your next trip to Turks. Say goodbye to dreading the process of planning, this episode will empower you to effortlessly plan accommodations, experiences, and unforgettable moments.

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

Accommodations:

Royal West Indies

Seven Stars Resort & Spa



Tours:

2 Hour Champagne Sunset Cruise

4-Hour Catamaran Sail and Snorkel Tour

⁠Free Stress- Free Travel Starter Kit

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Travel Freely: Maximize Rewards, travel smarter!

Rakuten: Earn Cash Back on All Purchases

Function Health: Optimize your health, explore the world!

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠

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 66, Tony Perkins, lead editor at Forbes Advisor, shares her enriching travel journey, from her initial adventures with her husband to navigating solo travel experiences in Europe with her four children. Highlighting both triumphs and setbacks, Tony recounts memorable stories such as an eventful family trip to Turkey, underscoring the importance of adaptability when unforeseen challenges arise. Through personal anecdotes, she emphasizes how travel, despite occasional mishaps, fosters resilience, adaptability, and lasting family bonds.

Additionally, Tony provides valuable insights on maximizing travel through strategic use of points, miles, and credit cards. Addressing common misconceptions about credit and travel rewards, she advocates for flexible reward strategies and recommends tools like "Word Wallet" to efficiently manage multiple reward programs and travel itineraries. Her practical approach underscores that travel can be accessible and affordable, even for larger families or those on limited budgets, ultimately encouraging listeners to embrace travel's transformative potential.

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

Toni's Social Media:

Instagram

https://www.instagram.com/tonisoutham

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠

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 this solo episode, Ross guides you through a stress-free, detailed 10-day Costa Rica itinerary expertly blending remote work, adventure, and relaxation so you can confidently travel without feeling overwhelmed. Discover how to effortlessly plan productive remote-work trips, find accommodations with reliable Wi-Fi, manage logistics seamlessly, and maximize travel rewards, leaving you feeling excited and fully in control of your next journey.

Come along as Ross shares practical tips for exploring Playa Hermosa, Monteverde, and La Fortuna, including unforgettable experiences like ziplining, ATV tours, cloud forest hikes, standout restaurants, and hidden gems you won't find elsewhere. By the end of this episode, you'll have clear, actionable advice to avoid common mistakes and decision fatigue empowering you to effortlessly book accommodations, tours, and experiences that provide exceptional value and lifelong memories.

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

Accommodations:

Playa Hermosa Casa de Encanto Tropical Villa

Playa Hermosa Private Villa

Playa Hermosa Dreamy Villa Near the Beach

Playa Hermosa

Monteverde Sunset Vista Lodge

Monteverde Sunset Paradise House

La Fortuna, Tabacón Thermal Resort & Spa

La Fortuna, Hotel Lomas del Volcán

Tours:

ATV La Fortuna

La Fortuna Waterfall

Ziplining in Monteverde

Monteverde Cloud Forest

⁠Free Stress- Free Travel Starter Kit

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Travel Freely: Maximize Rewards, travel smarter!

Rakuten: Earn Cash Back on All Purchases

Function Health: Optimize your health, explore the world!

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠

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 64, family travel expert Dia Adams shares how her love for global adventures—from Mexico to Cuba—evolved into mastering points and miles to travel smarter with kids. A key moment? Scoring a 100% AMEX transfer bonus that helped fund a family trip to Guatemala. From riding trains across Europe to planning a $5,400 dream vacation packed with fireworks at the Eiffel Tower and kissing the Blarney Stone, Dia proves travel memories don’t need to break the bank.

She also dishes out smart tips for visiting Disney parks abroad—like Paris and Tokyo—as affordable alternatives to Orlando. From scoring discounted train tickets to bidding on upgrades and booking off-site stays, Dia’s advice blends cost-efficiency with comfort. Whether you’re planning around school calendars or choosing travel insurance, her approach focuses on flexibility, intentional planning, and keeping travel fun for the whole family.

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

Dia's Social Media Links:

Instagram

https://thediaadams.com/

Disney World Hacks Book

YouTube:

https://www.instagram.com/thediaadams?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==

https://thediaadams.com/

Disney World Hacks Book: https://www.amazon.com/Disney-World-Hacks-Proven-Vacation-ebook/dp/B077H6F7P3

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠

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 this special solo episode, Ross helps you eliminate overwhelm and stress by sharing an effortless, step-by-step guide to his ultimate 16-day itinerary through Portugal and the breathtaking Azores Islands. You’ll go behind the scenes as Ross reveals exactly how he turns decision fatigue into confident, easy decision-making highlighting smart accommodation choices like the luxurious yet affordable Verde Mar Hotel and Spa, leaving you relaxed and fully in control of your travel plans.

Join Ross to discover practical, time-saving advice on car rentals, must-see attractions, hidden gems, standout dining experiences, and unique adventures that make the Azores the "Hawaii of Europe." Packed with exclusive recommendations and insider tips to avoid costly mistakes, this episode equips you with everything you need to confidently plan your own unforgettable trip. Tune in to start effortlessly booking tours, accommodations, and experiences that deliver maximum value, excitement, and lifelong memories.

Azores (Ribeira Grande): Verde Mar Spa

Azores (Ponte Delgado): Hotel Gaivota Azores

Porto Manor House

Porto Historic Center Porto - Passeio das Cardosas

Douro Valley Tour 

Portimao Rocha Seaview 

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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

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.