Ashley Hesseltine is on the road for about four months of the year performing live shows as the co-host of the top-rated comedy podcast Girls Gotta Eat.
When Hesseltine’s not traveling on tour, there’s a good chance she’s figuring out an itinerary for her next getaway with friends.
“I have somehow fallen into the role of planner with my friends over the last few years, and while it takes work, the upside is that you get to do all the dope stuff you want to do,” says Hesseltine, who recently took group trips to Hawaii and Mexico.
Here, she shares where to eat and what to do in Kauai, which travel credit cards she currently swears by, and more.
What was the last place you traveled? What was a highlight of the trip?
My last vacation was Kauai! I’ve always wanted to visit Hawaii, and I checked it off the bucket list with a girls trip in April. I lived on the East Coast for most of my life, so Hawaii just felt like this exotic, faraway land. When I moved to L.A., it was much more accessible.
We wanted to experience both the north and south coasts, so we stayed in an Airbnb in Princeville for the north half of the trip, and Sheraton Kauai Villas for the south half. Food highlights were the casual breakfast and lunch spots around the island — Hanalei Poke, Nourish Hanalei, The Musubi Truck (my first time eating Spam!). We also had an incredible dinner in the most stunning setting at Tidepools Restaurant in the Grand Hyatt Kauai; if you go, make sure to request a table on the lagoon.
A favorite activity was the Smith’s Family Garden Luau, where we got to experience Hawaiian culture, learn about the island’s history, and leave no crumbs at the buffet. We also did a catamaran trip around the Napali Coast where everyone (as in, the entire boat) got seasick, so embark on that at your own risk.
What is the most memorable vacation you've taken and why?
My 40th birthday trip to Cabo last year was the best four days of my life. It was all my closest friends and my boyfriend (who was brand new at the time). We stayed in the most stunning villa on the ocean that came with a wonderful staff (read: margaritas and guac around the clock). The A+ itinerary ranged from fancy meals overlooking the water to partying at El Squid Roe. 12/10 recommend.
What destination or trip/hotel is on your bucket list?
Japan is high on the bucket list, but I have no plans to visit as of now. I did cross off another bucket list hotel last summer when I stayed at the Fairmont Chateau Lake Louise in Banff. I was so excited to finally see this lake IRL instead of just gawking at it on Instagram.
What has been your favorite hotel stay and why?
This is a tough one — touring for the last six years, I have stayed in so many hotels in so many places. Memory/sentiment-wise, it’s the W Boston. Energy/vibes, it’s The Ned in London. As a second home, the Marriott Stanton in South Beach. And I love a Thompson Hotel.
What is your go-to luggage?
I’m a Béis girlie! The suitcases are elite, but I especially love the Weekender and mini Weekender bags.
What's your travel uniform?
Black Lululemon Align leggings, black Cuts tee, Anine Bing oversized denim jacket or cashmere trench (depending on the season), and Nike Air Maxes.
Are you a planner or spontaneous when you travel? What are the benefits of your approach?
I don’t make rigid itineraries with every minute and meal planned out — and I do love the spontaneous moments — but I need to have activities and dinner reservations booked. I don’t understand how people just show up to a new place with no plans (but to each their own!). TikTok has actually been a great resource for travel recommendations.
Any tips for fighting jet lag?
Everyone has different schools of thought, but I always try to sleep on the flight (hot take!). If I’m not in a lay-flat seat, I bring a blanket or big scarf to wrap up in. And magnesium + melatonin gummies have been working for me lately. Aside from jet lag, I’m big on keeping your immune system strong when you travel a lot. Leading up to a trip, I always take a few doses of echinacea mixed with elderberry syrup, and I bring Emergen-C packets with me.
What makes you a smart traveler?
I’m huge on credit card perks and points: I compare cards before committing, and then make sure to actually read about all of the perks and take advantage of them. It was a little overwhelming at first, but now I’m the friend who’s schooling people on their perks.
My current cards are the Amex Platinum for work purchases and Chase Sapphire Reserve for personal ones. They have perks like 3 to 5X points on travel, airline lounge access, Uber credits, and hotel upgrades. Amex also offers free Clear membership and has top-tier customer service. They both have great intro offers (points when you sign up), and I think they pay for themselves between the perks and points.
More and more, I’ve been doing “off season” travel because so many popular places have gotten so crowded and pricey. If you can, take that summer destination trip in June or September instead of July or August.
Lighting Round
Packing cubes, rolling method, or neither? Neither. Sometimes I’m sort of rolling, but there’s no real method to my madness. I need to get into the packing cube culture.
Window or aisle seat? WINDOW! So I can keep the shade DOWN. Don’t get me started.
Morning, afternoon, or night flight? I do them all, but 8 a.m. to 9 a.m. is my sweet spot.
Airline loyalist or least expensive flight? I’m a Delta girl.
Beach or mountains? Beach.
City or nature? A mix of both.
Hotel or house rental? Hotel solo or as a couple, house with a group always.