Reader Holly’s Incredible Italy Trip for 8 With 7 Free Flights!

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Update: One or more card offers in this post are no longer available. Check our Hot Deals for the latest offers. Welcome to the next installment of our Reader Success Series where Million Mile Secrets Readers share how they booked a trip with miles & points to get Big Travel with Small Money! Holly is our newest reader success story to show folks it’s possible to travel without spending a lot of money.
Reader Hollys Incredible Italy Trip For 8 With 7 Free Flights
Waiting for a Train in Pisa. These Kiddos Are Amazing Travelers!
A big thank you to Holly for sharing her story!

Please introduce yourself to everyone and tell us how long you’ve been involved in the miles & points hobby.

Holly Spencer.  My husband Jeremy and I have been collecting miles since we were in college.  We lived 17 hours away from each other when we were dating, so we racked up Southwest points flying to see each other on the weekends.

When we were 24 and 22 and freshly out of college, we opened a coffeehouse and cafe, House Blend, which we have now owned for over 15 years.  We used reward cards for our spending from the beginning.  In those lean first years it was great to still be able to travel a little even though we were poor.

Reader Hollys Incredible Italy Trip For 8 With 7 Free Flights
You Can Never Have Enough Selfies, Right? 😉

A little more than 4 years ago, we discovered your blog and the world of miles and points and began this hobby in earnest.  We had always wondered if it would be a bad for our credit to sign-up for cards for big bonuses for travel.  Turns out it’s a great thing!

Since then we have taken our family of 4 to Europe (twice), Iceland, ski trips to Colorado every year, Quebec City, countless stateside trips, and a 15th anniversary trip to Paris and Amsterdam in Business Class with luxury hotels!

What was the goal of your trip?

We have taken a lot of trips but one of our best was our trip to Italy.  Every time we plan another trip we always seem to think about this one and think “or we could always just go back to Italy!”  I think I could travel in Italy every year and never get tired of it!

Our family of 4 traveled with our close friends (family of 4) – so 4 adults and 4 kids together.  We had plans to take a big trip together, and the 4 of us planned to go mostly free, but we managed together to get 7 out of 8 of our international tickets free – and on the same flights!

How long did you collect miles and points for your trip? 

It took us about 9 months to collect the points for this trip.

Which points did you save to take your trip?

We used a combination of the Chase United Explorer card sign-up bonus (2 per family = 100,000 points) and Chase Sapphire Preferred, and Ink Plus (no longer available).  We do plenty of business spending so we topped off our Chase Ultimate Rewards points with spending to get us to the 240,000 points it took to get 4 round-trips in coach.  We flew on free Southwest tickets (using our Companion Pass too) as positioning flights to get the non-stops we wanted on United Airlines.

Reader Hollys Incredible Italy Trip For 8 With 7 Free Flights
Sitting Down in the Garden to Our Delicious Meal We Prepared With Cooking in Florence: Homemade Spinach Ricotta Ravioli, Bruschetta, and Walnut Biscotti

We used Starwood points for hotel stay in Milan where we began our trip.  Instead of hotels for the rest of the trip we stayed in some great Airbnbs.  We both signed up for the Barclaycard Arrival Plus card and used the credits to pay for Airbnbs and also for train tickets around Italy.

What cards would you recommend to someone starting out with miles & points?

How did you search for and find the award flights?

We started early and booked by November for an end of May/early June trip.  We had to hunt around to find connections where we could all go together on reward tickets!

Reader Hollys Incredible Italy Trip For 8 With 7 Free Flights
Doing a Little Open Water Rowing With ROW Venice!

We ended up flying Philadelphia to Milan and then returning Rome to Zurich to Newark, again positioning from Nashville with our free Southwest tickets.  United Airlines has the best search tools for a novice like me!  Having the Chase United Explorer card also opens up extra award space which is helpful!

How did you find your hotel accommodations?

As anyone knows who has traveled in Europe with kids – you get hit hard by the occupancy requirements.  Most rooms that you can get with points are for 2 people, not 4, so getting 2 rooms on points everywhere can take a ton of points.

For this trip, we opted for Airbnb apartments and loved it!  When traveling with kids, more space almost always equates with a better trip!  We loved having a kitchen and living room as well as separate kids and adults bedrooms.

What was the most challenging part about planning your trip? How did you solve it?

Accommodations for 8 on points is challenging!  And getting 7 award tickets on the same flight was nothing short of a miracle!

Give us a few recommendations or tips for what to do at your destination.  Parks, restaurants, hidden gems, etc.

When we travel with kids we love to have experiences, not just to go to museums and we have a little tradition now of asking the kids to name their “Top 3” of the trip.

Here’s my top 3.

ROW Venice – not just a gondola ride, but a family rowing lesson in the canals of Venice!
Reader Hollys Incredible Italy Trip For 8 With 7 Free Flights
The Amazing Setting for Our Cheese Tasting at the Goat Farm in Tuscany

What we called our “Food Day” in Tuscany – we did a cooking class at a beautiful villa out in the Tuscan countryside (Cooking in Florence) – just about an hour drive outside of Florence – we ate the amazing meal we cooked in the garden of the villa by the pool with the amazing views.  Then we took a tour of a nearby organic goat cheese producer and got to meet the goats and do a cheese tasting.

Hiking in Cinque Terre.  I know it has become popular, but the views are simply amazing and the food we had there we still dream about!

What did you learn about yourself on the trip?

Putting in the legwork and lots of planning beforehand really makes for a great trip.  Since we are traveling with kids we don’t just do the standard tours.  We want to make it memorable for everyone and not boring for the kids.  We always make lots of “contingency plans” so we have alternatives if things don’t quite work out.
Reader Hollys Incredible Italy Trip For 8 With 7 Free Flights
The Amazing Views in Cinque Terre

Also, when traveling with kids overseas, plan for day 1 to be a bust, and if it isn’t, just be pleasantly surprised.  We felt really accomplished in Milan after our international flight that we got lunch, saw the Duomo, had gelato, and went to bed.

What would you say to folks looking to plan a similar trip?  Or to those who haven’t taken a miles & points trip yet!

There’s so much info out there in great blogs like Million Mile Secrets and others, that even newbies can take the plunge.  We have gotten several friends and family members to join the fun, which makes it even better!  Things that used to be “aspirational” are now attainable with the right planning, which is totally amazing.

Miles and points are even easier for us because we spend $30,000 to $40,000 a month with our business, but we still pad our balances with sign-up bonuses several times a year.  If you don’t do a ton of spending, it’s still possible, it just takes a little more planning.

If you own a business and aren’t maximizing your monthly spending on credit cards, you are missing an extra part of your “salary!”  We figure we have accrued roughly $72,000 of free travel in the 4 years since we have been seriously pursuing this hobby.  Worth every bit of effort we put into it!

Want to Share Your Story?

If you’d like to be considered for our reader success story series, please send me a note!  Emily and I would love to hear about how you travel with miles and points!

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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