(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 MileValue.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, Ross and Caroline talk about the practical strategies for affordable travel, swapping stories from their journeys across 121 countries. Caroline, an engineer-turned-travel-blogger and Forbes Advisor writer, shares her expert tips on using points and miles, picking the best travel credit cards, and managing loyalty programs like a pro. Together, they reveal how to stay organized with multiple rewards accounts, avoid point expiration, and make the most of tools like AwardWallet, Travel Freely, and Points.com.

Discover how to balance personal preferences with popular destinations, whether it’s finding hidden gems for better value or deciding which hotel and airline programs fit your lifestyle. Caroline’s favorite spots—from Kalala Island in Nicaragua to Canave Suites in Santorini—show how a mix of points, bookings and open-mindedness can unlock memorable adventures. You’ll also hear about her upcoming travels to Italy, where she’ll be claiming her Italian citizenship, and her top food destinations like Japan, Italy, and Trinidad. Tune in for a blend of travel inspiration, money-saving tips, and the motivation to plan your next great getaway!

Affiliate Links:

The Platinum Card® from American Express

American Express® Gold Card

Capital One Venture X Rewards Credit Card

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com⁠

⁠Best Credit Cards for Travel⁠

⁠⁠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

⁠Threads⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Caroline's Socials

• Instagram

• carolinelupini.com

  
  

Some of the links on this site 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 MileValue.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 51, Ross talks about how the Algarve region in Portugal offers a spectacular coastline, rich cultural heritage, and delicious cuisine, making it ideal for a three-day getaway. Ross from “World Travel Made Easy with Itinerary Boss” suggests flying into Faro and using Portimão as a convenient home base. Visitors can enjoy half-day trips to both Albufeira and Praia da Rocha, reserving a full day for Lagos. Must-see experiences include strolling through historic towns, relaxing on pristine beaches, and exploring the famous Benagil Cave—best booked in advance. Renting a car for the first two days is highly recommended for maximum flexibility, before switching to Uber for local transport.

Shoulder season (April–June and September–October) is the perfect time to avoid peak tourist crowds and still enjoy mild weather. Ross shares essential tips such as renting a day cabana at NoSoloÁgua beach club, savoring fresh seafood at restaurants like Caniço and Club Nau, and capitalizing on budget-friendly travel options. He also highlights the value of pre-booking train tickets through Rail Ninja for those looking to explore more of Portugal or Europe. For extra convenience, Ross offers a stress-free travel toolkit featuring checklists, budgeting spreadsheets, and credit card rewards tips—helping travelers make the most of their Algarve adventure.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Capital One Venture X Rewards Credit Card

Capital One Venture Rewards Credit Card

⁠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

Threads

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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 MileValue.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 50, Ross and Danielle talks about discovering the transformative power of travel in this engaging conversation with Ross and Danielle. They explore how adding a human touch to the travel and business industries elevates everything—from personalized service and attention to detail, to the impact of travel on mental health and personal growth. Danielle shares her vision for Inspired Travel Group, highlighting how authentic interactions and thoughtful planning make each journey more meaningful. Together, they offer practical insights on off-peak travel, using points to save money, and the advantages of exploring neighboring regions for a more local, less-crowded experience.

Ross and Danielle also shine a light on trending destinations and the truths behind influencer marketing, illustrating how genuine experiences often beat social media hype. Whether you’re new to traveling or a seasoned jet-setter, you’ll walk away with tips on balancing budget-friendly strategies—like leveraging credit card rewards—with luxurious, unforgettable experiences. Tune in to learn how group trips foster connection, how to integrate personal hobbies into travel, and why the balance of AI and human expertise matters in a service-driven field. Don’t miss out on these valuable insights to make your next adventure both affordable and extraordinary!

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

⁠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

Threads

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Danielle’s Socials:

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

• Facebook: https://www.facebook.com/inspiredtravelgrp

• LinkedIn: https://www.linkedin.com/company/inspired-travel-group

• The Social segment - Off Peak Travel: https://www.youtube.com/watch?v=JzEo7FGJ_yE

Some of the links on this site 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 ⁠⁠⁠MileValue.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 50, Niamh McAnally, a bestselling author and writer on the water, has built a diverse career that spans acting, television direction, scuba instruction, hotel management, and volunteer travel. In this episode she highlights how her oceanic passion and wide-ranging life experiences influence her writing, culminating in a strong desire to keep creating stories for the rest of her life. Niamh’s collaborative project, “Stories of Place,” set to launch in April, connects stories from around the globe through What3Words—a unique mapping system that assigns three-word addresses to locations worldwide. She also shares insights into her own journey, including her volunteer travels, photographing the Taliscore Whiskey Atlantic Challenge rowers for the cover of her book “Flares Up,” and finding personal connections that inform her writing.

In discussing travel, both Niamh and Ross emphasize the importance of adaptability, gratitude, curiosity, and a sense of humor while exploring new destinations. They highlight the value of cultural exchange and learning from unexpected situations, which can lead to personal growth and compound into lasting life lessons. Niamh also details her enthusiasm for cruise travel, praising the ease of visiting multiple locations without having to constantly unpack, while offering practical advice for first-time cruisers. As they anticipate their upcoming cruise to Japan, they agree on the value of embracing new travel styles and experiences, continually seeking out novel adventures around the globe.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com⁠

⁠Best Credit Cards for Travel⁠⁠

⁠⁠⁠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

Niahm McAnally Socials:

https://www.thewriteronthewater.com/

https://www.facebook.com/TheWriterOnTheWater

https://www.instagram.com/niamh_mcanally/

Itinerary Boss LLC is 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 MileValue.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 49, Ross provides an overview of visiting Porto, Portugal, from transportation options—such as flying (including direct flights from the U.S.) or taking a train—to booking accommodations in the scenic Riviera area. He outlines a recommended three- to four-day itinerary featuring tourist attractions like the Palácio da Bolsa, the Church of São Francisco, and the Praça de Liberdade. Ross also highlights the city’s renowned wine tours in the Douro Valley, advising travelers to plan ahead (book restaurants well in advance) and pack wisely (especially comfortable walking shoes for Porto’s hills). He emphasizes a few budget-friendly brunch spots, including Swallow Decadence and Zenith, and recommends visiting during the shoulder season for better weather and fewer tourists.

Additionally, Ross shares personal experiences from his recent trip, such as dining at Tasco (reserved two months in advance) and sampling various port and tawny wines on a full-day Douro Valley wine tour. He praises Porto’s affordability and walkability, suggests purchasing a fast pass at the airport to avoid long check-in lines, and points out that three or four days allow for a more immersive experience. Ross also mentions creating a free travel starter kit—including a packing checklist and budget checklist—and invites listeners to subscribe for more travel tips and tutorials.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for TravelFree Portugal Itinerary

Blog: The Ultimate 3 Day Porto Itinerary

Manor House Porto

Douro Valley Wine Tour⁠Free 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 is 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 MileValue.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 48, Ross and Linda discuss Linda’s extensive travel-industry background—starting as a child, then working as a travel agent, airline employee, and later in banking—before returning to travel. They focus on practical ways to earn miles, manage rewards, and travel affordably. Linda highlights the importance of picking loyalty programs that align with personal spending habits and being disciplined with credit card usage. She offers specific advice on maximizing points for big-ticket destinations, such as Europe or French Polynesia, and recommends saving points for long-haul flights to get the best value.

They also cover strategies for elevating the travel experience: choosing off-peak seasons, being flexible with dates, and leveraging loyalty programs for flight upgrades, hotel room perks, and other benefits. Linda underscores the value of diligent research, budgeting carefully, and purchasing travel insurance—especially for remote or international destinations. The discussion touches on safety measures like staying alert, avoiding ATMs with high fees, and carrying sufficient emergency funds. Linda describes her recent trip to islands like Bora Bora and Mariah, illustrating the rewards of exploring remote places while respecting local customs and cultures. She concludes by mentioning her book series on Amazon, which shares personal stories and further travel tips.

Website:⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠Amazon Travel Store⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Itinerary Boss Socials:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠Instagram⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠Threads⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠

Linda King's Social(s):⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Website: ⁠https://www.thesmarttravelista.com/⁠

Some of the links on this site 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 ⁠⁠MileValue.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 of World Travel Made Easy with Itinerary Boss, Ross kicks off his solo series, packed with step-by-step travel tips and expert insights. With a special focus on Portugal—particularly the Azores, Porto, Lisbon, and the Algarve—Ross shares his firsthand experiences from a 16-day adventure. From booking direct flights to navigating layovers, checking bags, and even scoring the best stays, this episode is your ultimate guide to making travel stress-free.Ross dives into the must-see spots in the Azores, including Lagoa das Furnas, the stunning viewpoints, and the island’s famous hot springs. He shares essential tips on renting a car, the best places to stay, and how to avoid tourist crowds for a more relaxed experience. Plus, he’s put together a free downloadable itinerary packed with all his recommendations—perfect for planning your own Azores getaway!Blog Link:https://itineraryboss.com/2025/02/the-ultimate-sao-miguel-travel-guide/For Spotify:Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com⁠⁠⁠⁠⁠⁠Amazon Travel Store⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Opinions 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.Itinerary Boss Socials:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Threads⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Some of the links on this site 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 MileValue.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 47, Ross and Silvia share their perspectives on traveling and living in Europe, highlighting the affordability of flights, trains, and hostels—particularly compared to the United States. Silvia, based in Portugal, describes her frequent hostel stays, her love for exploring cities like Prague and London on foot, and her preference for living like a local rather than focusing on tourist attractions. Both note that hostels are more accepted in Europe, often offering amenities like pools, saunas, or even co-working spaces.

They also discuss remote work strategies, such as leveraging time zone differences, ensuring good internet connections, and using co-working memberships to stay productive on the road. Silvia budgets around €200 per month for travel and uses tools like Skyscanner to find deals, while Ross relies on credit card points. Silvia’s freelance approach involves creating user-generated content in niches like tech, pets, and travel. She often reaches out to hotels or hostels for free stays in return for promotional videos. Finally, they touch on Silvia’s passion for language learning and her journey from providing free work samples to landing paid brand collaborations, underscoring how embracing new environments can unlock both travel and professional opportunities.

Website:⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠Amazon Travel Store⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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.

Itinerary Boss Socials:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠Instagram⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠Threads⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Silvia Pinho Social(s): Website: ⁠freelancingwithsilvia.com⁠

Instagram: ⁠https://www.instagram.com/freelancingwithsilvia/⁠

YouTube: ⁠https://www.youtube.com/@freelancingwithsilvia⁠

TikTok: @freelancingwithsilvia

Some of the links on this site 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 MileValue.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 46, Ross and KC discuss how to save on taxes through travel, charitable foundations, and strategic use of credit card rewards. Kc explains that tying travel to business or a private foundation’s mission can create legitimate write-offs. They explore how charitable foundations can own assets (like jets) and cover travel costs if the purpose is aligned with charitable or business goals.

Kc also emphasizes the importance of carefully tracking expenses and leveraging credit card points through partners and brokers, while noting that one should be proactive with CPAs and tax strategies. Both Ross and Kc recommend planning trips based on goals, whether charitable or personal, and using available tax loopholes and point-transfer tactics to maximize benefits.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠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

Threads

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠

KC Chohan Social(s):

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.togethercfo.com

Itinerary Boss LLC is 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.

In episode 43, host Ross and guest Amy Piper talk about their shared love for travel, highlighting memorable destinations like Turks and Caicos and Michigan. They discussed the value of personalized travel experiences, uncovering hidden gems, and utilizing local expertise to enrich trips. From the serene beaches of Turks and Caicos to Michigan’s charming spots like Indian River and Belle Isle State Park, Amy shared her insights and recommendations, including tips for traveling during off-peak seasons and finding unique stays like the Cartier Mansion Bed and Breakfast. Culinary experiences were also a focus, with Amy suggesting Traverse City for food enthusiasts and Fairfield, Iowa, for vegan and vegetarian offerings. Ross appreciated Amy’s suggestions, expressing interest in exploring these destinations further, especially given his own ties to Michigan.

The discussion also emphasized the importance of exploring one’s surroundings and enjoying the process of travel planning. Amy shared her experiences of living in various places and taking the time to appreciate local cultures and hidden gems. They brainstormed potential collaborations, including Instagram reels, guest blog posts, and connecting with other experts in the travel industry.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Connect with Amy:

Instagram

Twitter

Facebook

How to Plan the Perfect Surprise: Free Webinar

2024 Holiday Travel Gift Guide: 31 Gift Ideas⁠

Amazon Travel Store

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠

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.

Itinerary Boss Socials:⁠⁠⁠⁠⁠⁠⁠⁠

Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Pinterest

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

YouTube⁠⁠⁠⁠⁠⁠⁠⁠

Threads

⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Some of the links on this site 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.