How much does a Sail & Swim charter cost in San Diego?

The 3-hour Sail & Swim is $950 and the 4-hour version is $1,200. Both are fully private for up to 6 guests and include paddleboards, drinks, snacks, and champagne with a USCG licensed captain.

Is the water clean and safe to swim in at the anchorage spots?

Yes. The anchorage locations we use — off Point Loma and Coronado — have consistently clean, clear water. We monitor conditions before every charter and choose the best anchorage for that day.

Do I need to know how to swim?

Life jackets are available on board for anyone who wants one, and you don’t need to be a confident swimmer to enjoy the paddleboard and deck experience. We make sure everyone is comfortable and no one feels pressured to get in the water.

What should I bring for a Sail & Swim charter?

Swimsuit, towel, sunscreen, and whatever food and additional drinks you want. Paddleboards are provided.

Can kids participate in the Sail & Swim?

Absolutely. Sail & Swim is one of the most popular charters for families with older kids and teenagers. Children’s life jackets are available on board.

Can we bring food to grill on the 4-hour charter?

Yes — the 4-hour Sail & Swim includes a grill on board. Bring whatever you want to cook.

What if someone doesn’t want to swim?

No problem at all. The deck is a fantastic place to spend the afternoon in the sun with a drink while other people swim. Everyone finds their version of a great time on a Sail & Swim charter.

Guests with champagne on a Sail & Swim charter in turquoise San Diego water

Sail & Swim · San Diego Bay

Sail & Swim San Diego

Name: Sterling Sails
Address: San Diego, CA, US
Telephone: (858) 999-9895
Price range: $$$

Anchor off Point Loma, jump in, and paddleboard — the full active day on the water, drinks already cold before you get in.

Book a Sail & Swim Charter Where You Swim

Paddleboards Included

Anchor at Point Loma or Coronado

Grill on 4-Hr Charter

From $950

Some people want to sail. Some people want to swim. The correct answer is: you shouldn’t have to choose.

Sterling Sails offers Sail & Swim charters on San Diego Bay — private sailing adventures that end with Mojave dropping anchor in calm, clear water off Point Loma or Coronado so your group can jump off the boat, grab a paddleboard, and spend the afternoon actually in the water. Fully private boat. Real paddleboards. Drinks already cold before you get in. This is what summer in San Diego Bay is supposed to feel like — and it’s available year-round.

What Happens on a Sail & Swim Charter

All charters depart from Harbor Island with drinks and snacks ready when you board. The sail out takes you through San Diego Bay past the Navy ships and Coronado Bridge, heading toward Point Loma or Coronado depending on conditions and your group’s preference. Along the way you’ll pass the sea lion colony at Point Loma and have clear views of the lighthouse on the bluffs above.

Once Mojave drops anchor, the paddleboards come out and the swim portion begins. The anchorage water off Point Loma is calm and clear. Your group can swim from the boat, paddleboard, or just chill — there’s no set agenda and no pressure to do anything in particular. The 4-hour charter includes a grill at anchor: bring your own food and cook it on board while the paddleboards are out.

Anchorage Spots

Where you'll jump in.

Point Loma

Our most popular anchorage — protected by the peninsula, so the water is calm and clear. The lighthouse stands on the bluffs above, sea lions bask on the rocks, and it feels genuinely remote just minutes from downtown.

Paddleboards + swim from the boat

Sail & Swim Options

Half day or full float.

3-Hour Sail & Swim

$950

Sail to Point Loma, anchor in calm water, swim + paddleboard, sail back. Paddleboards included.

Book this charter

4-Hour Sail & Swim

$1,200

Everything above plus a grill on board and more time at anchor. Point Loma or Coronado.

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Who Books Sail & Swim Charters

Families with older kids and teenagers who want to actually do something on the water rather than just look at it
Friend groups visiting San Diego who want a full active day rather than a cruise vibe
Birthday and bachelorette celebrations that want the swimming, paddleboarding, and sunshine energy
Couples looking for something more adventurous than a traditional sunset sail
Anyone who has always wanted to jump off a sailboat into the Pacific and has finally decided to do it

Every Charter Includes

Complimentary drinks, snacks, and champagne
Paddleboards — included on both charter lengths
JBL Party Box speaker with karaoke
A restroom and refrigerator below deck
USCG licensed captain
Up to 6 guests — fully private charter
Grill on board (4-hour only — bring your own food to cook)
Life jackets available for all guests
All safety equipment and required permits

A group relaxing on deck during a Sail & Swim charter

The Mojave under full sail heading out on San Diego Bay

A guest with arms outstretched on the bow under sail

The Mojave near the Point Loma lighthouse and anchorage

Before You Dive In

Good to know.

The 3-hour Sail & Swim is $950 and the 4-hour version is $1,200. Both are fully private for up to 6 guests and include paddleboards, drinks, snacks, and champagne with a USCG licensed captain.

Sail in Peace. The paddleboards are ready.

Book a Sail & Swim Charter (858) 999-9895

Keep Exploring

Not sure which sail suits your group? Compare every option on all charters & prices, see the boat and the bay in the Sterling Sails photo gallery, read what past guests said in our guest reviews, or get to know Captain Liz, our USCG-certified captain.

For seasons, timing and local tips before you book, browse the Sterling Sails sailing journal, or read the press coverage of Sterling Sails.