Choose Your Own Adventure – Fall 2023

Tue & Thu, Oct 3 & 5
3:30pm – 9pm(ish)

Sessions range from the adventurous with kayaking or sailing to innovative with Nostalgia Coffee, a woman-owned roaster that’s mindfully changing the way the industry does business, and Cooler Heads, a company that has developed a cap that saves hair for chemo patients. There are some old favorites too – we hope that you can find something new that speaks to you, or give you the opportunity to experience your 2nd choice CYOA from the last time we were in San Diego.

Here’s what you need to know:

  • All sessions come with dinner (no $$ required by members)
  • Fri, Sept 15 is the deadline to register your session preferences (you rank your top 3)
  • Each session is assigned on a first-come, first-served basis
  • While we try to give you a break after the day’s meetings, more sessions than usual are departing early on account of the early sunset this time of year. Please make note of the lobby departure times when making your choice.
  • Because we are split into two cohorts, there are fewer people as a whole to spread across these adventures. If the demand for an adventure is too small, we may end up canceling that adventure and assigning you to one of your other choices.
  • Details below


  • Cohort A – Register here
  • Cohort B – Register here

Spouse or Significant Other Joining?

Since many of you have taken our recommendation and are bringing your significant other, we wanted to give an opportunity for them to participate in some of the CYOAs. Naturally, there is a small fee associated with this to cover the cost but we’d love to have them join along! If you’re bringing your significant other, please fill out the Sig Other/Spouse registration (it will be counted for both of you):

  • Cohort A + Significant Other – Register here
  • Cohort B + Significant Other – Register here

Sunset Cruise on the JADA, a Sailing Adventure

Capacity: 28
Dinner: Rubicon Deli

Members will enjoy the fresh ocean breeze upon the deck of a 1930s racing sailboat, the JADA.

You will be accompanied by JADA’s current owner, Carol, who will share the boat’s rich history, including rumored ownership by Marlon Brando, and how the sailboat came by her name. While sailing, members will see the rugged cliffs and historic coastal points.

And of course, keep your eyes out for local marine life: sea lions, dolphins, and occasionally a whale. This adventure will include onboard libations and dinner from one of San Diego’s favorite sandwich shops, the Rubicon Deli.

This group departs from the Estancia lobby at 3:30pm.

Cool Leadership at Cooler Heads

Capacity: 12
Dinner: ¡Salud Tacos!

Get ready to experience the corporate journey with a twist at Cooler Heads! Cooler Heads transforms life for people diagnosed with cancer by empowering them to manage the side effects of treatment. AmmaTM, Cooler Heads’ transportable and affordable scalp-cooling system, brings the innovative therapy to the masses. As the world’s first self-administered scalp-cooling solution, AmmaTM can be used anywhere by anyone, which means less time in infusion centers. The patented system has been cleared by the FDA.

Too often, chemotherapy-related hair loss robs people of the chance to shape their own narrative. By giving people a choice in the matter, Cooler Heads provides a sense of ownership and control, which can positively impact their mental health and their recovery.

Founded by cancer survivor Kate Dilligan, Cooler Heads understands what people dealing with cancer experience on both a clinical and an emotional level. With solutions that address the side effects of cancer treatment, Cooler Heads helps people feel more empowered on their cancer journey. 

Members will have the opportunity to tour HQ, hear directly from patients, and a chat with Kate, their patient-turned-CEO, about her experience bringing an idea to reality. Feel the temperature drop as your scalp gets to therapeutic temperature, cooling sensation rushing at absolute zero. Get set to unwind, connect, and discover the cool side of leadership!

Leaves from the lobby at 4:00pm.

Coffee Cupping with Nostalgia

Capacity: 8
Dinner: Chilanga Mexican Food, onsite

For a world-class coffee experience that will get your innovative java juices flowing *and* tug at your heartstrings, spend your evening with Nostalgia, a woman-owned coffee roastery based in San Diego.

A portfolio company of both Gaingels and Ad Astra Ventures, Nostalgia was introduced to us by our very own CG moderator and partner of Ad Astra Ventures, Vidya Dinamani. Not only does the award-winning team at Nostalgia offer incredible coffee (some of which are rated 95pts by Coffee Review….in other words, some of the best coffee in the WORLD) they also care deeply about people and are systemically changing the coffee industry.

Delicious coffee? Check. Innovation — think coffee in a tea bag, but better! Check. A big-hearted team? Check, check, check. It’s the perfect blend!

Leaves from the hotel lobby at 4:15pm.

Hike Torrey Pines

Capacity: 15
Dinner: Picnic on the Beach

If you’re looking for one of the most beautiful places to hike in San Diego, Torrey Pines is the place for you! You’ll enjoy the stunning coastal views, golden cliffs, and a sandy beach below.

For this adventure, you’ll be hiking the Guy Fleming Trail. This easy-to-moderate hike is about 1 mile long and offers scenic overlooks with panoramic views. The trail also offers the greatest variety of wildflowers, ferns, cacti, and habitat diversity in the reserve. On this docent-led hike, you’ll also learn about the Torrey Pine, one of the rarest and most endangered pine trees in the world.

Come in hiking-appropriate attire, with water in hand.

Leaves from the hotel lobby at 3:30pm.

Sea Cave Kayak

Capacity: 30
Dinner: Shore Rider

This fully guided kayak tour takes you through the Ecological Reserve and along the La Jolla Sea Caves — some of San Diego’s most famous attractions. The La Jolla Ecological Reserve and Underwater Park is a marine protected area that’s a famous destination for snorkelers, divers, and kayakers alike. Home to leopard sharks, Garibaldi (California’s state marine fish!), lush kelp beds, sea lions, and even the occasional pod of dolphins!

Experienced guides from La Jolla Kayak will share fun facts and history about La Jolla, safely guide you along the sea caves, and even lead you through one (ocean conditions permitting). No kayaking experience is necessary!

Afterward, enjoy dinner at Shore Rider Bar — a breezy outdoor eatery with a delicious menu, craft beer & casual, surf-inspired decor.

Leaves from the lobby at 3:30pm.

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