Ten local wineries will offer sample sips to the grape-stomping throng

Rich Uncle Max is coming for Labor Day. He’s always been one of those old dudes who can hang around young people and somehow not come off as creepy or embarrassing. So we’re a little tempted to set him loose at the Pier Pressure Labor Day Weekend San Diego Mega-Yacht Party, on board the $10 million, 1000-person luxury yacht San Diego Spirit. We could sip at one of the boat’s multiple bars and Max could wander the three decks with their three dance floors and their six DJs, including Donald Glaude, rated a top-100 DJ by DJ Magazine. The cruise runs from 3:30-7:30 p.m. on September 3. Tickets range from $20-$175 (higher-priced tickets include a reserved table on the Sky Deck, but those tables require a minimum bottle purchase, starting at $300).

Make some sand art with lessons from San Diego Sand Castles

But if Max’s dancing feet and sea legs can’t manage to get together and boogie, maybe I’ll take him to war at the Port of San Diego’s Festival of Sail (Sept. 1-4) — the largest tall ship festival on the West Coast. First, I’ll let him pick from one of seven ships — including the California Spirit out of Dana Point — that make up the August 31 Sail Parade ($48 for a child, $60 for an adult). If he’s feeling flush, I might get him to spring for the VIP ticket on the recently recreated San Salvador; $100 for a child, $120 for an adult. Then, once the festival is underway, landlubbers can join a tall ship crew twice daily and engage in a three-hour mock cannon battle (tickets $40-$76). Patrick and kids will watch from the docks, listen to some live music, do a few crafts, and maybe get a photo with some pirates for the old Instagram account.

Speaking of Instagram, Uncle Max recently gave one of his rare likes to a shot of my daughter’s octopus sand sculpture at La Jolla shores. So maybe we’ll visit the sixth annual Sand Sculpting Challenge and Dimensional Art Expo, running Sept. 1-4 at the Broadway Pier and Pavilion. World-class sand sculptors from Italy, Ireland, and Russia will be on hand to challenge ten homegrown heroes on a playing field made from 300 tons of sand. There will be live entertainment from a Beach Boys tribute band, an appearance by Elvis (or a reasonable facsimile thereof), and rides and sandboxes for the kids, but the main attraction will be the roughly 10-ton sculptures. Tickets run $10-$15, depending on the day. (Discounts available for tickets purchased in advance through the website.)

If he gets inspired, we could book some time with San Diego Sand Castles (619-200-0565, book reservations online). They promise to make the lessons as easy or as challenging as we want, and they provide all the tools and equipment. Topics covered include stacking, textures, and how to make such tricky elements as windows, doors, arches, and bridges. We can even send in pictures and designs in advance. Lessons run two to three hours in the morning, afternoon, or evening with a professional instructor at the beach in Del Mar. Cost is $140 for the first two participants and $20 for each additional participant.

There’s always the chance that he’ll disdain anything that resembles touristy gawking or beachy puttering, however, and insist on some serious participation. So we’re looking at the annual Oceanside Labor Day Pier Swim on Sept. 4. Swimmers start at the Oceanside Pier — lifeguard tower 1 — and swim one mile out around a course marked by buoys. Prizes will be awarded for the best times in various age categories, and the $70 registration fee ($60 if paid by August 31) includes refreshments, swim cap, and T-shirt.

All that activity is sure to leave Max with what he likes to call “a parched throat and a powerful thirst,” so we’ll definitely make a little mountain retreat to the 21st Julian Grape Stomp at Menghini Winery, held on September 2 from 11 a.m.-6 p.m. Ten local wineries will be on hand offering sample sips to the grape-stomping throng. Italian music provided by Roman Holiday, plus bocce courts and a Lucy Lookalike Contest. Tickets are $15, $5 for children aged 6-20. It’s a safe bet that Max will want the VIP experience ($50), which includes reserved parking, a fast pass to the stomping vat, two mixed drinks, and VIP seating under a shade tent.