Planning a bucket-list trip to Iceland and Ireland might seem out of reach for a family of five, but what if you could score flights and hotels using mostly points and miles? Jess recently returned from this exact adventure, navigating the tricky world of Iceland flight bookings and European hotel room occupancy limits with strategic planning and some insider knowledge.

Jess takes us through her 10-day journey, breaking down exactly how she used points and miles for flights from Chicago to Reykjavik with a stopover, then onward to Dublin. She shares the specific redemption strategies for Hilton points at the Canopy Reykjavik and how she creatively solved the challenge of fitting five people into European hotels that typically accommodate only two per room. From working with local trip planners to maximize their limited time in each country to discovering hidden gems like private cliff tours in Ireland, this episode provides the roadmap for making it all happen without breaking the bank.

You can find links to resources mentioned in this episode plus the transcript here: travelmomsquad.com/137

Ready to get started with NEARLY FREE travel? Click here for the exact offers we would sign up for this month: travelmomsquad.lpages.co/bestoffers/

The Travel Mom Squad is also on YouTube! You can watch this episode here: youtube.com/@travelmomsquad

Let us know what you want to hear on the podcast by sending us a DM on Instagram: instagram.com/travelmomsquad

In this episode, Jess and Alex are joined by Kelsi Sullivan, one half of PointSisters on Instagram, who has mastered the art of solo travel using points and miles. Kelsi brings a unique perspective shaped by her international upbringing and her discovery of the financial independence community. Her journey from casual miles collector to strategic points optimizer shows how solo travelers can thrive in the points and miles world.

Throughout the conversation, Jess, Alex, and Kelsi explore how solo travelers can approach earning and redeeming points while traveling alone, safety considerations for solo female travelers, and specific strategies for maximizing value without a traditional "player two." Kelsi shares concrete examples from her adventures in Tanzania, India, Sri Lanka, and beyond, revealing how she stretches her points across multiple international trips each year.

You can find links to resources mentioned in this episode plus the transcript here: travelmomsquad.com/136

Ready to get started with NEARLY FREE travel? Click here for the exact offers we would sign up for this month: travelmomsquad.lpages.co/bestoffers/

The Travel Mom Squad is also on YouTube! You can watch this episode here: youtube.com/@travelmomsquad

Let us know what you want to hear on the podcast by sending us a DM on Instagram: instagram.com/travelmomsquad

Getting a discounted stay at a luxury Maui resort sounds too good to be true, especially when the catch involves sitting through a timeshare presentation. After receiving a letter from Marriott Vacation Club offering a discounted five-night stay at a Westin property, Alex decided to see if the savings were worth the 90-minute sales pitch.

In addition to hearing the pros and cons of attending a timeshare presentation, this episode gives you an inside look at popular Maui resorts such as Andaz Maui, the Westin Nanea Ocean Villas, and Hyatt Regency Maui. Hear the Travel Mom Squad's differing recommendations for visiting Maui based on your travel needs, and whether or not they recommend sitting through a timeshare presentation for the discounted stay.

You can find links to the hotels, tours, and other resources mentioned in this episode plus the transcript here: travelmomsquad.com/135

Ready to get started with NEARLY FREE travel? Click here for the exact offers we would sign up for this month: travelmomsquad.lpages.co/bestoffers/

The Travel Mom Squad is also on YouTube! You can watch this episode here: youtube.com/@travelmomsquad

Let us know what you want to hear on the podcast by sending us a DM on Instagram: instagram.com/travelmomsquad