San Diego Boat Proposals Expert

I'LL HELP YOU FEEL CONFIDENT & PROUD
of the
EXPERIENCE YOU'VE PLANNED

Hi, I'm Jess, and I know what resonates with an on-the-water dream proposal or a next-level date – and I will create it for you.

California Coastal Calm, delivered by a savvy New Yorker

Meant to Be, On the Sea was founded in 2026 in San Diego, but with immersive experience transferred to the West Coast from the East Coast. I founded NYC's most successful private charter company in 2020, at the start of COVID, when outdoor escapes were a true luxury to be had.

I built one of New York harbor’s most successful (and only female-owned) private charter businesses by delivering one engagement at a time, with 376 proposals hosted on my private sailboats over six years.

I KNOW WHAT MAKES FOR A SERENE & UPSCALE EXPERIENCE

Because I created it time and again for hundreds of couples in New York City — one of the greatest cities in the world, filled by people with highly discerning tastes, as well as tourists traveling from around the world, each seeking unique experiences.

I built one of New York Harbor’s most successful (and only female-owned) private charter businesses by delivering one engagement at a time, with 376 proposals hosted on my private sailboats over six years.

In the mix were also many spectacular first dates, wedding anniversaries spanning various decade markers, bountiful baby showers, and intimate family reunions. I’ve seen it all – and done it all in the private charter world, operating within the elevated class (and undeniable chaos) that is New York City.

I moved to San Diego and immediately recognized the need for a luxury cruising experience that delivers against the backdrop of quiet, thoughtful serenity. I wanted once again to channel my passion for boating with my passion for curating memorable private moments for couples to enjoy the peace and undeniable beauty of being together on the water.

Welcome aboard Meant to Be!

xo,Jess

UNDERSTATED ELEGANCE

They are quiet, understated, intimate and built for just you – with thoughtful touches and moments of delight sprinkled throughout.

Aboard our coastal cruising vessel Meant to Be, we deliver...

The most memorable moments and life celebrations aren’t loud, flashy, and made for everyone else to admire.

Upscale intimate moments NOT churn-and-burn cruises

All-inclusive experiences NOT endless extra add-ons

Calm cruising NOT speed boating or heeled sailing

Elevated couples’ experiences NOT group booze cruises

Clean, cozy lounging NOT limited, exposed seating

Chilled premium champagne NOT cans of beer

Plentiful platters of charcuterie NOT bags of chips

Soft Italian linens NOT flimsy paper napkins

Special surprises to help you hold on to the memories

RESERVE NOW

Tim & Kelly

Sean & Robbin

Tyler & Becks

Melanie & John

Peter & Shelly

I’m adept at creating experiences for those with discerning taste – and I deliver only what I expect to personally experience myself.

CUSTOMER-first

My work as a Chief Marketing Officer of a large global corporation includes decades of special-event planning for experiences both large and small – but always delivering for high-level discerning executives, notably for whom exceptional customer service is a non-negotiable.

DRIVEN BY PASSION

I love boating and I love…. well, LOVE! My charter business in New York Harbor was a major passion project for me – quite literally. I thrilled in guiding people of all ages as we planned their perfect proposals, and I delighted in hosting celebrations for families (including the later babies from my engaged couples!) and small groups of friends, marking life moments of all kinds.

DELIBERATE FOCUS

I’ve rolled up all my professional experiences and personal passions into this very niche, very specialized business, combining my passion for discerning experiences, my love for boating and my affinity for creating elevated and curated experiences. I will deliver nothing less for you than precisely what I would personally expect for myself.

CONTACT ME

BOUTIQUE BOATING

It’s like having drinks and a nosh at a boutique hotel …that is floating along on the water, all cool, calm, and collected.

MY INFLUENCE & INSPIRATION

My global career has also sent me country to country, and I’ve been fortunate to frequent the world’s best hotels and resorts. But I have always chosen little luxury boutiques for my own personal travels because I crave intimacy and uniqueness — and I am always delighted by the personal touches afforded by these smaller discerning venues.

REFINED PRIVATE CHARTERING AT ITS BEST

Meant to Be, On the Sea is the quiet luxury that you deserve.

The experience of being onboard Meant to Be is akin to the vibe I seek when staying in a small luxury boutique hotel for those with discerning taste.

For an overall exceptional experience and the memory of a very special place that simply “sticks” with me, I personally look for intimate, cozy, understated elegance, thoughtful touches and polite, proactive service.

This is what you can expect aboard Meant to Be: calm, serene cruising, cozy, intimate spots to curl up and catch the sights of San Diego Bay and the city, champagne, charcuterie — and a few special surprises sprinkled throughout.

We will quite literally roll out the VIP carpet for you in every sense of the word, ensure you are comfortable and have all you need — and then leave the rest to you. Casual, relaxed conversation, laughs shared over some drinks and a nosh. Impeccable memories made.

Only on Meant to Be.

RESERVE →

Speaking of calm, cool & collected…GET TO KNOW OUR CAPTAINS

I am fortunate to have two of San Diego's finest Captains at the helm, who will each take VIP care of you throughout your cruise.

Both Captain Chris and Captain Ray are lifetime residents of San Diego and a longtime sailors, active members of the famed San Diego Yacht Club, and of course, licensed Captains.

Each has a master’s 100-ton license from the U.S. Coast Guard and many years of service on San Diego Bay. Both are the confident and skilled Captains you want at your helm, but also the friendly and relaxed guide you want to ensure your experience is memorable.

Our Captains can share with you however many details you wish to know about San Diego Bay – or he can leave you entirely to your own conversation during your voyage.

Either way, their calm and cool demeanor ensures both a safe passage and pleasurable voyage.