Vacationer of the Week: Alysse Dalessandro

Alysse Dalessandro is a fun plus-size fashionista who always gives us life on Twitter and Instagram. She embodies everything we love at Vacationer Magazine – an out queer traveler who lives her truth and owns it! The lifestyle blogger and influencer uses her website, Ready to Stare, as a platform to spread a body-positive and LGBTQ+-inclusive. And we’re always here for it! So, it’s no surprise that we wanted to feature her for our Vacationer of the Week. 

So, we decided to catch up with the Ohio native and see what travel wisdom she had to drop on us. Dalessandro Santiago reveals why she has a strong connection to Sicily, her favorite LGBTQ+ friendly destinations, what she never forgets to pack, and what 90s boy bands are at the top of her music playlist when she’s traveling.

Vacationer Magazine: At what age did you receive your first passport? What was your first trip?

Alysse Dalessandro: I got my first passport at the age of 20 when I studied abroad in Rome, Italy. I was in college at Loyola University Chicago, and they had a campus in Rome that made it really easy to study abroad without losing any traction on my double major.  They also structured their program so there were no classes on Fridays. I was able to have no classes on Mondays too, so I traveled every weekend ultimately visiting nine countries and 15 cities across Europe during that time. 

What trip or travel experience sparked your passion for travel? 

I knew that I had a passion for travel before my semester abroad but actually having the opportunity to immerse myself in another culture really solidified that passion. Seven years later, it was another trip to Italy that ended up changing my life forever! Although I was very close to Sicily during that semester abroad, I never visited it, and I vowed to return when I could come with my parents. 

I ended up traveling to Sicily in 2015 with my parents, godmother, and cousins. For the first time, we met our family in Sicily, and making that connection to my heritage was a life-changing experience. I was able to see my great-grandmother’s childhood home before she immigrated to the US. I’ll never forget that moment. 

What inspires you to travel?

I am inspired to travel because I crave adventure and new experiences. It really excites me to explore new places and try different foods. I love meeting locals when I travel, especially fellow LGBTQ+ folks in other places, and learning about their experiences being a part of the community where they live. I also recognize the value of sharing my experiences of traveling as a plus-size queer person. My audience looks to me for travel advice on accessibility, safety, and inclusivity. It inspires me to be able to use my experience in travel to help others have a more enjoyable and comfortable trip. 

Please tell us how you identify yourself on the LGBTQIA spectrum. Tell us if how you identify influences the way your travel. 

I identify as a queer femme and that certainly informs the way that I travel. I want to go to places that are not just gay-friendly but welcoming to the full LGBTQ+ spectrum. If your branding features only fit cisgender gay white men in speedos, I will assume you are not interested in a customer that looks like me. I want to travel to destinations where queer women, non-binary folks, and trans travelers are not only accepted but celebrated. 

What domestic and international destinations do you feel comfortable visiting as an out queer traveler?

Domestically, Fort Lauderdale has got to be one of the most welcoming destinations for LGBTQ+ travelers. Not only is the city home to the Stonewall National Museum and Archives which connects us to our history, but the city has always been at the forefront of representation. They regularly host Southern Comfort, one of the largest trans conferences. 

Internationally, I was absolutely blown away by a recent trip to Stockholm. They pride themselves on being an open city and in my experience, that was absolutely true. There’s no set gayborhood because everywhere is generally LGBTQ+ friendly. This is a place where it was really easy to find LGBTQ+-owned hotels, restaurants, and nightlife that felt welcoming for all. 

Is there a travel destination that most queer travelers would think isn’t safe to visit, but you’ve visited and enjoyed it? If so, where? What made it a memorable experience?

If I am visiting a place that isn’t typically safe for queer travelers, then I like to try and find a FabStayz. They are a vacation rental site that ensures all of their hosts are LGBTQ+ friendly. When I went to stay at a cabin in the Smoky Mountains, it’s really in the heart of the bible belt. I think I may have been afraid to out myself to my host but staying with FabStayz, I knew I would be safe to be myself! 

We love your fabulously colorful fashion pics! How would you describe your fashion style?

My style is gaudy, bold, and over-the-top. It’s loud. This might be hard for people to believe but I am shy by nature, so I like to let my outfit do the talking for me first. I often find that my loud style is a great icebreaker especially when traveling. 

What’s the best tip you’d offer travelers?

The best tip that I would offer travelers is to be open. I have done trips that were overly planned down to the minute and that doesn’t leave much time for spontaneous exploration. Be aware of your surroundings but also give yourself some time to just walk around and explore. 

What are your top 3 favorite places to visit?

1. Anywhere in Sicily especially Modica, Taormina, and Palermo. I can’t pick just one city! 
2. San Juan, Puerto Rico 
3. Stockholm, Sweden 

What three places are still on your bucket list to visit?

1. Bali, Indonesia 
2. La Fortuna, Costa Rica 
3. Cappadocia, Turkey

What’s one thing you never forget to pack in your suitcase?

I have made the mistake of not packing my Zone Naturals Chub Rub stick and I’ll never make that again. If it’s hot where you are headed and you are planning on doing a lot of walking, this is a fat babe MUST! I also always bring my own seat belt extender whenever I fly. I’ve been denied an extender before so having my own makes me feel safer. 

You’re going on a road trip? What singer or band is always on your playlist?

Honestly, I love the 1990s/2000s throwbacks, so it’s probably Boyz II Men or Backstreet Boys. 

What travel trend or travel industry change would you be excited to see happen?

In LGBTQ+ travel, we have seen a tendency for travel to be segregated. Gay men over here. Lesbians go there. I would love to see inclusive spaces where everyone in the community is welcome. We don’t all have the same needs when we travel but we can certainly be more mindful of ensuring our spaces are safe and welcoming for all. 

Keep up with Alysse Dalessandro’s most recent travels and more on her Ready to Stare website. You can also follow her on Facebook, Twitter, and Instagram.