Sail, Swim, Repeat: A Three-Hour Escape on Shelter Island
Private Charter • Up to 6 People • All Ages • Everything included
The bow parts the water like a deliberate thought. Salt air fills your nostrils, the bay’s surface glittering with a dozen sunlit scissors of wake as Shelter Island slides free of the city’s skyline. For three hours you trade streets for spray: 90 minutes of sail, then an hour to jump in, paddle, and drift. The formula is simple and small enough to feel intimate—a private charter for up to six people that puts the Pacific in reach without asking for a full day.
Trail Wisdom
Bring a light wind layer
Even warm San Diego afternoons get breezy on the water—pack a windbreaker to stay comfortable.
Use reef-safe sunscreen
Protect skin and marine life by choosing reef-safe SPF; reapply after swimming.
Secure motion-sensitive items
Bring a waterproof case or dry bag for phones and cameras when jumping in.
Kids need lifejackets
Children 12 and under must wear lifejackets on board at all times—bring appropriately sized ones if you prefer.
Local Knowledge
Hidden Gems
- •Harbor Island seawall walk for skyline photos
- •Point Loma tide pools (at low tide)
Wildlife
Common dolphins, Brown pelicans
Conservation Note
The bay includes sensitive eelgrass habitats—avoid anchoring in marked areas and use reef-safe sunscreen to reduce impacts.
Shelter Island is a man-made peninsula formed with fill and dredged material in the early 20th century; it evolved into a recreational marina district.
Seasonal Guide
spring
Best for: Dolphin sightings, Cooler sails, Fewer crowds
Challenges: Unpredictable light winds, Variable water temperatures
Spring offers mild air temperatures and active wildlife; the water may still be cool, so plan on a wetsuit for extended swims.
summer
Best for: Warm water swims, Long daylight, Flat seas
Challenges: Peak demand on weekends, Stronger midday sun
Summer delivers the most consistent warm-water conditions and calm afternoons—book early for weekend slots.
fall
Best for: Warmer ocean temperatures, Clear skies, Great photo light
Challenges: Occasional marine layer mornings, School schedules limit weekdays
Late summer into early fall is often the warmest water and clearest sailing—ideal for combining sail and swim.
winter
Best for: Quieter marinas, Dramatic skies, Less competition for bookings
Challenges: Cooler air and water, Potential for stronger winds
Winter brings fewer crowds but cooler conditions—good for brisk sails and dramatic coastal views if you dress for it.
Photographer's Notes
What to Bring
Reef-safe sunscreenEssential
Protects skin and fragile marine ecosystems while swimming and paddling.
Light wind shellEssential
Blocks spray and wind once the sails are up—useful year-round in the bay.
Water shoes
Make getting in and out of the water and walking a marina safe and comfortable.
Dry bag for phone/cameraEssential
Keeps electronics safe while you swim or paddle off the stern.
Common Questions
Are towels provided?
Towels are not included—bring your own or rent/buy locally.
Is food and drink provided?
Soda, water, champagne, and snacks (including gluten-free and vegan options) are provided onboard.
Can we bring alcohol?
Champagne and some drinks are provided; check with the operator about outside alcohol policies before booking.
What’s the policy for children?
All children ages 12 and under must wear a lifejacket on board at all times.
Do you provide paddleboards and snorkel gear?
Paddleboards are provided; bring your own snorkel gear for the best fit and hygiene.
How many people can the charter accommodate?
The private charter accommodates up to six people.
What to Pack
Swimsuit (for the hour in the water), Reef-safe sunscreen (protects you and the bay), Light wind layer (keeps off spray and breeze), Dry bag (keeps phone and valuables safe)
Did You Know
Shelter Island was created using dredged material and landfill in the early 20th century, transforming a shallow bay shoal into the recreational peninsula it is today.
Quick Travel Tips
Book weekdays to avoid weekend crowds; Arrive 20–30 minutes early for check-in; Bring your own mask if you prefer snorkeling; Have a light layer for wind on the water
Local Flavor
After your sail, walk the Shelter Island promenade to Bali Hai for a Mai Tai and waterfront views, or head to Point Loma’s local seafood spots and breweries for tacos and craft beer.
Logistics Snapshot
Closest airport: San Diego International Airport (SAN) / Driving from downtown San Diego: 10–20 minutes / Cell service: Good near shore, intermittent further from marina / Permits: None for guests; children must wear lifejackets
Sustainability Note
This bay contains eelgrass beds and marine life—use reef-safe sunscreen, avoid stepping on submerged habitats, and pack out all trash.
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