San Diego Cruises, Sailing & Water Tours

67 Results
San Salvador Spanish Galleon Adventure Day Sail with General Admission

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. …More

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon....

4 hours
4.1 (7)
from
$85
San Diego Harbor Speed Boat Adventure

Rev up your excitement with a one-of-a-kind San Diego Speed Boat Adventure! Captain your own speed boat on a guided, narrated tour of San Diego …More

Rev up your excitement with a one-of-a-kind San Diego Speed Boat Adventure! Captain your own speed boat on a guided, narrated tour of San Diego...

2 hours Free Cancellation
4.9 (750)
from
$89
Sunset Sail Along the San Diego Skyline

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from …More

Likely to Sell Out
Likely to Sell Out

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from...

2 hours Free Cancellation
4.9 (658)
from
$99
Daytime Sailing Along San Diego's Skyline

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor …More

Likely to Sell Out
Likely to Sell Out

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor...

2 hours Free Cancellation
5.0 (161)
from
$99
City Cruises San Diego: Buffet Dinner Cruise

Revel in a beautiful evening under the stars with a fun and picturesque Signature San Diego Dinner Cruise on the bay! Turn your dinner into …More

Revel in a beautiful evening under the stars with a fun and picturesque Signature San Diego Dinner Cruise on the bay! Turn your dinner into...

150 to 180 minutes Free Cancellation
4.6 (41)
from
$108
Small-Group San Diego Afternoon Sailing Excursion

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends …More

Likely to Sell Out
Likely to Sell Out

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends...

3 hours Free Cancellation
5.0 (568)
from
$116
2.5-Hour Small-Group Catamaran Sail with Drinks

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. …More

Likely to Sell Out
Likely to Sell Out

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail....

2 hours 30 minutes Free Cancellation
5.0 (370)
from
$119
Deluxe Sunset & Day Sail Small Group

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as …More

Likely to Sell Out
Likely to Sell Out

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as...

2 hours 30 minutes Free Cancellation
5.0 (371)
from
$119
Deluxe Day Sail in San Diego

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego …More

Likely to Sell Out
Likely to Sell Out

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego...

2 hours 30 minutes Free Cancellation
5.0 (82)
from
$119
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat …More

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat...

2 hours Free Cancellation
4.9 (204)
from
$119
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on …More

Likely to Sell Out
Likely to Sell Out

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on...

2 hours 30 minutes Free Cancellation
5.0 (114)
from
$119
2 Hour Whale Watching Kayak Tour for Two

The 2 Hour Whale Watch Kayaking Tour offers the chance to safely view migrating gray whales via kayak in their natural habitat. Each tour is lead by …More

The 2 Hour Whale Watch Kayaking Tour offers the chance to safely view migrating gray whales via kayak in their natural habitat. Each tour is lead by...

2 hours Free Cancellation
4.6 (9)
from
$119
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes Free Cancellation
5.0 (359)
from
$125
San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes Free Cancellation
5.0 (85)
from
$125
Champagne Brunch Buffet

Make the most of your weekend with a 2-hour brunch cruise through San Diego Bay. Capture prime views of the city skyline and harbor from …More

Make the most of your weekend with a 2-hour brunch cruise through San Diego Bay. Capture prime views of the city skyline and harbor from...

2 hours Free Cancellation
4.6 (373)
from
$126
San Diego Harbor Dinner Cruise

Enjoy a 2.5-hour cruise aboard one of San Diego's finest dining vessels. Spend the evening in luxury as you dine on a gourmet dinner , …More

Enjoy a 2.5-hour cruise aboard one of San Diego's finest dining vessels. Spend the evening in luxury as you dine on a gourmet dinner ,...

3 hours Free Cancellation
4.2 (1,299)
from
$126
Small-Group San Diego Sunset Sailing Excursion

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat …More

Likely to Sell Out
Likely to Sell Out

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat...

3 hours Free Cancellation
5.0 (638)
from
$127
City Cruises San Diego: Premier Bottomless Mimosa Brunch Cruise

The most popular cruise in San Diego is the Champagne Brunch Cruise. Sparkling waves and soft breezes set the mood for this relaxing mid-day brunch …More

The most popular cruise in San Diego is the Champagne Brunch Cruise. Sparkling waves and soft breezes set the mood for this relaxing mid-day brunch...

2 hours Free Cancellation
4.7 (326)
from
$128
Harbor Lights Dinner Cruise

Throughout December, Flagship’s fleet of yachts set the stage for unforgettable holiday celebrations. Step aboard for a festive evening filled with twinkling lights, elegant decor, …More

Throughout December, Flagship’s fleet of yachts set the stage for unforgettable holiday celebrations. Step aboard for a festive evening filled with twinkling lights, elegant decor,...

2 hours 30 minutes Free Cancellation
2.5 (4)
from
$145
Whale and Dolphin Watching in San Diego

Step aboard our 22' Zodiac expedition style boat and immerse yourself with wildlife all around you. Our Captains are fun loving, knowledgeable and respectful. We …More

Likely to Sell Out
Likely to Sell Out

Step aboard our 22' Zodiac expedition style boat and immerse yourself with wildlife all around you. Our Captains are fun loving, knowledgeable and respectful. We...

3 hours Free Cancellation
4.9 (156)
from
$149
Spectacular Sunset Sail on San Diego Bay

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas …More

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas...

2 hours Free Cancellation
5.0 (41)
from
$150

Frequently Asked Questions

These answers are based on answers previously given to Key West Private Charters customers' questions.

Recent tour reviews
Activity name

San Diego Tours
Attractions
Guides
Calendar