San Diego · VIP

The 8 Best VIP Experiences in San Diego

8 tours  ·  from $75 a head

The 8 best vip experiences you can book today, with what each costs, how long it runs and who it suits. Number one is top for a reason; start there.

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways - The downtown skyline from the bay
Cruises & Boat Tours, San Diego Sailing Trips, Tour Reviews, Tours, VIP

Luxury Sailing Tour of San Diego’s Bay and Coastal Waterways

1.Luxury Sailing Tour of San Diego’s Bay and Coastal Waterways

★★★★★★★★★★5.0 · 187 reviews · from $119Our pick

Sail San Diego Bay aboard a 34-foot Catalina with a local captain, small groups, skyline views, snacks, and sunset departures.

“My parents and I had a beautiful time sailing the San Diego Bay through Viator. Our captain Peter was wonderful! He had years of sailing experience, was very knowledgeable (and easily answered my parents million questions hahRead more”

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Luxury Private Wine Tasting Tour to Guadalupe Valley from San Diego - First tasting, then a second winery with cheese
Private, San Diego Wine Country Tours, Tour Reviews, Tours, VIP

Luxury Private Wine Tasting Tour to Guadalupe Valley from San Diego

2.Luxury Private Wine Tasting Tour to Guadalupe Valley from San Diego

★★★★★★★★★★5.0 · 171 reviews · 10 hours (approx.) · from $269

Review of a private San Diego to Valle de Guadalupe wine tour with three tastings, BajaMed lunch, border transport, and hotel pickup.

“Mario was awesome. He picked us up right on time and was so helpful. He pointed out spots along the way and knew a lot of history! This was the best tour I have ever been on. Great wineries, and the food was amazing. He sat with us at lunch, helped order and helped us with any and all questions. He was so intelligent, welcoming, friendly and kind. Crossing back from Mexico was super easy! I felt entirely safe and taken care of. I would recommend this tour and plan to do it again myself. So fun and so worth it! Don’t miss out!”

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Luxury Catamaran Sailing Charter of San Diego - Mission Bay to the Pacific Ocean
Cruises & Boat Tours, San Diego Sailing Trips, Tour Reviews, VIP

Luxury Catamaran Sailing Charter of San Diego

3.Luxury Catamaran Sailing Charter of San Diego

★★★★★★★★★★5.0 · 87 reviews · 2 to 8 hours (approx.)

Sail privately from San Diego to La Jolla or Sunset Cliffs on a luxury catamaran with crew service, wildlife views, and flexible trip lengths.

“The whole experience was enjoyable. We plan on doing another trip again. The crew was awesome. They took us out and we saw dolphins up close and personal.”

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San Diego Whale/Dolphin Watching Cruise Aboard Luxury Vessel - What the wildlife search is really like
Cruises & Boat Tours, San Diego Whale & Dolphin Watching, Tour Reviews, VIP

San Diego Whale/Dolphin Watching Cruise Aboard Luxury Vessel

4.San Diego Whale/Dolphin Watching Cruise Aboard Luxury Vessel

★★★★★★★★★★5.0 · 64 reviews · 3 hours 30 minutes (approx.) · from $76

A practical review of San Diego’s Peregrine whale watch, with dolphin sightings, expert narration, comfort, seasickness tips, and honest value advice.

“The crew was amazing from start to finish, seeing the dolphins, whales, tuna, and the birds was an awesome experience, I would definitely do this again.”

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San Diego: Relax on a Morning, Day or Sunset Luxury Sail - Leaving San Diego Bay with the skyline ahead
Cruises & Boat Tours, Evening Experiences, Morning, San Diego Sailing Trips, Tour Reviews, VIP

San Diego: Relax on a Morning, Day or Sunset Luxury Sail

5.Relax on a Morning, Day or Sunset Luxury Sail

★★★★★★★★★★5.0 · 21 reviews · 2 - 3 hours · from $95

Sail San Diego Bay aboard a 40-foot yacht for city views, military ships, wildlife, drinks, snacks, and a relaxed small-group outing.

“Our torn with Greg was amazing. He was super nice and funny and my husband even got to steer for a while. We had always wanted to go sailing, and it was a wonderful experience for us. We can 100% recommend it. Thank you, Greg!”

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San Diego: Luxury Year-round Whale Watching & Dolphin Tour - The first part of the search: open Pacific views
San Diego Whale & Dolphin Watching, Tour Reviews, Tours, VIP

San Diego: Luxury Year-round Whale Watching & Dolphin Tour

Beautiful Luxury Picnic on a Docked Gondola Boat in Coronado - The docked gondola setting
Coronado Island Tours, Cruises & Boat Tours, Tour Reviews, VIP

Beautiful Luxury Picnic on a Docked Gondola Boat in Coronado

San Diego: Bennington Luxury Pontoon Rental - Boarding with a private group of up to 12
Tour Reviews, VIP

San Diego: Bennington Luxury Pontoon Rental

8.Bennington Luxury Pontoon Rental

★★★★★★★★★★5.0 · 4 reviews · 2 hours

Cruise San Diego Bay on a private Bennington pontoon with a captain, cooler, Bluetooth audio, and room for up to 12 people.

“The total experience was great from the booking, to confirmation. The staff was pleasant and helpful. Our Captain Jason was fun and personable and made the trip one of our San Diego highlights.”

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