2023 Cruising Calendar

Events aren’t just for racers – here are some upcoming cruising events you should have on your 2023 calendar!

Whether you’re a pencil-and-paper planner or use a digital calendar, there are plenty of upcoming events this year for cruisers to get together and share in the joy of sailing. Rendezvous are a great way to meet like-minded sailors from all over the world and to build a robust network of friends. 

Before we get to planning, here are a few tips to make the most out of a rendezvous or cruising event — whether you’re looking for your first or fiftieth event:

  1. Once you’ve decided on an event that works best for you, let the pre-planning begin. Like any other trip, you’ll want to do some research into where you’re going and what the itinerary is, as well as any other equipment you might want to bring along, like snorkel gear or fancy threads for a night on the town.

  2. Take advantage of the entire itinerary while you’re in the rendezvous. Whether you’re leveraging another attendee’s expertise to try a new activity or attending a cocktail party, just showing up with a positive attitude can lead to fun and memorable adventures with new friends that will greatly enrich your experience.;

  3. Observe and learn from other sailors. One of the great things about a rendezvous is that it provides a low-pressure opportunity to glean knowledge from more experienced sailors from a variety of backgrounds. If offered, take advantage of the experts and seminars. Refresh your skills, and soak up as much new information as you can.

  4. If it fits in your schedule, take a few days off after the event and enjoy some downtime with your family or crew. You can flex your new sailing muscles with a little more cruising, or spend a couple of extra days at the final stop enjoying the scenery or some hobbies you might not have fit into the rendezvous schedule.

Feeling inspired? Here are a few dates cruisers should make sure to note on your calendars. Comment at the end where you’ll be headed this year!

Yesteryear Regatta, May 13, 2023

Headquartered at the Southwestern Yacht Club in San Diego, the racing portion of this regatta is open to sailboats of ancient vintage or classic design. But even if your cruiser is a bit more modern, it’s worth the trip to San Diego to watch these gorgeous boats in action. If the date doesn’t work for you, check out other Ancient Mariners Sailing Society events for some vintage eye candy.

Marion Bermuda Race, June 16, 2023

While it’s an offshore race, the Marion Bermuda Race is designed for cruising boats and their crews ready to try their hand at ocean racing. Spanning a handful of days, the race starts in Marion, Massachusetts, and finishes in gorgeous Bermuda. For those looking for an additional challenge, the race offers a celestial class, where navigators utilize sextants and plotting rather than GPS/AIS to find their way to the finish. The alternate-year Newport Bermuda Race also offers a cruising division.

Hunter Sailing Rendezvous, June 15-18

Hunter Yachts is celebrating 50 years this summer with a rendezvous in Baltimore, Maryland. Attendees will enjoy a program offering speakers and experts from Hunter and across the sport, as well as live entertainment, gourmet food and drinks, kids’ activities and optional tours of the nearby attractions. It’s definitely a must-do for East Coast Hunter owners.

Salty Dawg Rallies, various dates

This non-profit organizes bluewater rallies throughout the Caribbean and US. Salty Dawg Rallies seek to educate sailors, build camaraderie, and facilitate offshore passages. With preparation assistance, daily forecasts, and more, these are a great way to get from point to point as safely as possible within a group of boats. “Quantum Sails is proud to be the official sailmaker for the Salty Dawg Rallies,” says David Flynn from our Annapolis Loft. “For each event, Quantum provides free evaluation of existing inventories, and discounts on new sails and services.” The 2023 calendar includes an early season Homeward Bound Rally in May to help boats headed back to the East Coast from various Caribbean destinations, a Downeast Rally from July 6-11 from Virginia to Rhode Island, a Maritime Rally in July from Massachusetts to Maine, and an end-of season Caribbean Rally, departing from the East Coast and heading south to warmer climes. If longer journeys are on your list for this season, find safety, security and plenty of fun with a Salty Dawg Rally.

West Coast Multihulls/Denison Yachts Rendezvous, July, 2023

Usually slated for the end of July (specific dates to come soon), this cruising rendezvous takes over Catalina Island for a weekend of social events and sailing. Past events have included raft-ups, open houses, an on-shore disc golf tournament, and a boat decoration contest. Keep an eye on the West Coast Multihulls website for more details and date announcements.=

Beneteau Cup, September 16-17, 2023

San Diego Yacht Club’s Beneteau Cup is a great opportunity for cruisers to get their feet wet with racing. In years past, South Coast Yachts has provided coaching for novice racers, and, of course, the weekend wouldn’t be complete without some post-race social gatherings and events. Sponsored by our San Diego loft, check out this event and get expert input from our San Diego team, too.

As you prepare plans for this year’s cruising season, be sure to also check out some of our recent pieces, like tips for greener cruising and keeping your cruising crew happy. If you’re in need of new sails, repairs, or just want to chat about your upcoming cruising adventures, reach out to your local Quantum loft.

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