A Peek Inside a Staycation In Little Italy

And, 5 Reasons Why You Should Vacation In Your Hometown

Avid urban explorer, San Diego blogger, and life coach Christine Tomasello was looking for a special getaway for her one-year anniversary with her boyfriend. Instead of booking flights and expensive resorts, she looked at San Diego neighborhoods for a place that would give her the sense of getting away without flying away. Along the way, she also discovered the bounty of benefits that only a local getaway can give. 


My boyfriend and I just celebrated our one-year anniversary but because of scheduling challenges, we weren’t able to go away to celebrate. We already do the long distance thing (him in LA, me in San Diego), so ‘going away’ would require one of us to travel 120 miles to the other, just to start the journey. Since both of us have packed schedules, it just didn’t seem like a good way to spend our anniversary weekend.

Instead, we decided to stay for a weekend at La Pensione, an adorable boutique hotel, right in the middle of San Diego’s vibrant Little Italy neighborhood. Since I’d never been there before, it seemed like the perfect occasion! We had the most amazing time, and I learned some valuable lessons about why vacationing in your hometown is a fabulous idea.

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  1. It’s really “getting away”

Our one-year anniversary was a BIG DEAL to us and even though weren’t leaving San Diego, I was EXCITED! I researched what we could do and where we should eat, checked out La Pensione’s amenities (was definitely excited about the cool fireplace area in the lobby), I made a list all of the things I want to show him during our stay. Even though he comes down to visit me in San Diego every couple of weeks and we could technically do these things anytime, we usually don’t because life takes over. Now that we were ‘going away’ for the weekend, we had the perfect excuse to do it all.

  1. It’s an easy way to make any occasion special

We could have just as easily spent the weekend in my little apartment in University Heights and gone to dinner to celebrate, but then it would have been like any other weekend. That would have been just fine. Except we were celebrating our first year together and we wanted to make it special. Staying at La Pensione, with its chic rooms and oh-so-perfect location, made the weekend a unique experience that we will always treasure. And much more memorable than dinner at a run-of-the-mill restaurant.

  1. 2013-12-11 16.50.37We didn’t worry about “life”

The fact that we got to stay in a hotel in a fun part of the city made it feel like we were on vacation and it put us in that mindset. We didn’t have to run errands, pay bills, do the dishes, or tackle any items on our “to-do” lists that weekend. Nope. For 3 days it was all about the two of us doing fun things to celebrate our year together. Plus, La Pensione was a cool urban experience that made it so easy to forget that we were only 3 miles from my apartment!

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    Saturday morning Il Mercato, Little Italy’s Farmers Market

    I got to experience my hometown from a fresh perspective

In our year together my boyfriend and I spent lots of time all over San Diego, but we never spent much time in Little Italy. So that weekend, we got to experience this hip and happening ‘hood together. La Pensione couldn’t have been placed in a sweeter spot. Walk in any direction and you’ll run right smack into la dolce vita. We ate at new restaurants, popped into new coffee shops, browsed through new stores, and spent an entire morning at The Mercado, Little Italy’s Farmer’s Market. It was a very different experience than just stopping by for an hour or two one afternoon. We got to really know (and love!) Little Italy.

  1. We did a lot more – got to “see the sights” and do everything like we were tourists

We definitely took advantage of ‘being on vacation’ and did tons of stuff we wouldn’t normally do. We took the ferry to Coronado, we walked along the waterfront, we had breakfast every morning in the little Italian coffee shop downstairs from the hotel. It was a magical weekend that was packed with fun and unique activities that we only did because we were right there to do them!



Screen Shot 2015-03-03 at 1.20.34 PMChristine is a San Diego blogger and avid urban explorer with a penchant for spotting hidden gems in her hometown. A modern-day renaissance woman, she wears many hats and takes on many roles in her life. When she’s not guest blogging about cool finds in San Diego, she helps people thrive in their lives as the founder of Joyful Coaching, where she offers individual coaching and group workshops in the San Diego area. She is also a freelance Executive Assistant and Project Manager for small business and solopreneurs. 



It looks like you need a vacay, too. It doesn’t take much (distance) to get away. Stay with us in Little Italy for a weekend of eating (lots of it), urban exploring, and living la dolce vita.

Book your staycation now.