Planning an Anniversary Charter on San Diego Bay

An anniversary deserves more than a dinner reservation. A private yacht charter gives you your own schedule and the San Diego skyline instead of a crowded restaurant. Whether it's your first anniversary or your fiftieth, here's how to plan one on the water.

Why a Private Charter Fits an Anniversary

You book the whole yacht, not a shared table in a shared room. There's no one else's night to work around. A harbor cruise past Point Loma, Coronado, and the downtown skyline gives you a changing backdrop instead of a fixed one. San Diego Bay is generally calm, protected water, which helps if you're bringing along guests who get seasick easily.

A USCG-licensed captain and crew come with every charter, so you can focus on the evening instead of the boat. The typical route runs from Point Loma toward Coronado, with views of the downtown skyline, and can be customized to your preferences.

Choosing the Right Yacht

For two people or a small group, a lot of the same thinking from our guide to proposing on the water applies to an anniversary. The Sea Ray 56 and Sea Ray 52 both offer a flybridge and foredeck, good for a quiet toast away from the rest of your group.

The Beneteau 50 has a forward bow sunpad and a glass-enclosed salon, a relaxed pick for a daytime cruise. For a sleeker look, the Sunseeker Predator 72 is a striking black-and-white sport yacht, chartered as a 4-hour trip, with the option to anchor in Glorietta Bay off Coronado for swimming when conditions allow.

If you'd rather depart from the north side of the city, the McKinna 69 leaves from Mission Bay rather than San Diego Bay. It has an enclosed, climate-controlled Skylounge, a good backup if the evening turns cool.

Picking Your Time of Day

Sunset is a popular choice for an anniversary charter, with the skyline lit up as the sun goes down. A daytime cruise works just as well if you'd rather anchor somewhere to swim, or if older family members are joining and prefer to be off the water before evening. Tell us your preferred time when you request availability.

How Long to Book

Charters have a 2-hour minimum, and most guests book 4 hours or more. The Sunseeker Predator 72 is only available as a 4-hour charter. Use the price estimator to compare rates by yacht and length before you request a date.

Add-Ons to Make It Special

Champagne service and light, vessel-dependent décor are both available — tell us what you have in mind when you book. A photography referral is available too, if you'd like someone capturing the moment, and we can arrange a music setup if you have a specific playlist in mind. If you're planning a surprise, let us know the plan and we'll coordinate timing and any setup discreetly with the crew.

Celebrating a Milestone With More Guests

A 25th or 50th anniversary often turns into a family celebration rather than a quiet night for two. For a bigger guest list, the Westport 100 is certified for up to 134 passengers, with a main-deck lounge and salon suited to a reception-style party. See our large-group charters page for details. If you're planning a vow renewal ceremony on board, our weddings page covers the planning details — we handle the vessel, route, and on-water logistics, but you'll need to arrange your own officiant and confirm any legal requirements independently.

What to Know Before You Book

• Guests may bring their own food and beverages, including alcohol.
• Full payment secures your date, and cancellations at least 5 days ahead are fully refunded.
• If the weather turns unsafe for boating, we reschedule to a mutually convenient date rather than sail.
• The renter must be 18 or older. We accept Visa, Mastercard, American Express, and Discover.
• Public parking for Shelter Island departures is available in the lot across the street near the pier.
• Non-service pets, smoking, and illegal drugs aren't allowed on board.

Plan Your Anniversary on the Water

Tell us your date, guest count, and which yacht caught your eye, and we'll confirm what's available. Request availability to get started, or use the price estimator first if you're still comparing options.