With cushioned decks and cockpits, ample shade, and excellent performance, these sailboats in Cabo are among the best. Iti is VIP service all the way with the premium open bar and delicious snacks on board. Top that with an incredible team of captains and crew with over 20 years’ experience, and you know you will be getting the best sailing experience in Cabo. Your only task is to choose which sailboat to charter, and what you would like to do on board! All our sailing trips in Cabo can be customized just for you!
VIP Snorkeling & Sailing Charter
One of the great things about departing from the Cabo San Lucas marina is its proximity to a wealth of amazing snorkeling spots just outside the marina. You can cruise around seeking out the best snorkeling spots, or relax on board and sip cocktails while taking in the sites of the famous Cabo Arches as you navigate around Lands’ End. You can even spot sea lions who love to all hang out on the rocks right in view of the arches. (Maybe they enjoy the view as well!) Some of the larger sailboats and catamarans even have SUP boards and paddles you can use to explore the beaches and inlets on your own.
Sailing with Whales December Through March
Are you heading to Cabo in the winter? December through March is whale watching season in Cabo San Lucas. There is no better vessel for whale watching than a sailboat. Whales and dolphins love to play in the wake. Since we are sailing and not using a motor, they tend to come a lot closer so you have some incredible photo ops. It is a truly incredible experience. And when sailing with us, it will be a VIP whale watching experience too!
Choice of 5 Cabo Sailing Charters Perfect for Small Groups
We offer 3 sailboats ranging in size from a 30' sail boat perfect for a small group of up to 6 friends, all the way up to a 44' sail boat perfect for celebrating special occasions up to 18 passengers. And for those that prefer a bit steadier sailing vessel, we have 2 catamarans that comfortably hold groups between 16 to 20 guests. Click on each tab below to see more information on each boat.
Best of all, we offer the best deals on the best sailing charters in Cabo San Lucas. So choose your favorite boat and book your private Cabo sailing charter with The Real Deal Tours today!
This is our favorite Cabo sailboat rental for couples looking for that perfect romantic sailing cruise in Cabo San Lucas. Sail past the arches, Lovers Beach and Lands’ End into the great Pacific while sipping a drink from the open bar. The 30' Sol Mate sailboat is perfect to share a day on the water with your soul mate.
30' Private VIP Sailboat Charter in Cabo San Lucas Details
30' Private Cabo Sailing Charter Includes:
Departures: Sails twice daily from the Cabo San Lucas Marina at 9:00 am or 12:30 pm. Exact meeting instructions will be provided on your confirmation voucher. If traveling between December and March, we recommend the 9:00 am tour for the best whale watching experience.
Length: The boat is yours for up to 3 hours!
30' Private Cabo Sailing Charter Recommendations:
Children: All ages are welcome. Children under 12 years old are free of charge. If you are traveling with a toddler, we recommend you bring an appropriately sized live vest with you on your trip to Cabo.
Cruise Ship Passengers: This is the perfect shore excursion in Cabo San Lucas for those traveling in with family or small groups. We can cater your departure time according to your cruise ship schedule since it is private. Our check-in office is a short walking distance from the tender boat pier (exact instructions to be provided on your confirmation voucher).
Restrictions: Expectant mothers may want to consider one of the more stable trimaran charters instead.
Insider Tip: This sailing charter company has hosted birthday celebrations, anniversaries and family reunions. They’ll do their best to accommodate any special requests you may have. We can customize the sailboat with a bouquet of flowers, bring a cake, and even provide some champagne to celebrate that special occasion. Contact us if you’re interested!
Retail: $600.00
Real Deal: $540.00
The 33' sailboat aptly named Alegria, meaning joy or happiness, is sure bring you joy too as you sail around the arches, Lovers Beach & Lands End! Comfortably seating 6 people with a cabin below and restrooms on board make this the perfect sailboat charter in Cabo for families or small groups of friends. the captain and crew will make sure your Cabo sailing experience is a memorable one.
33' Private VIP Sailboat Charter in Cabo San Lucas Details
33' Private Cabo Sailing Charter Includes:
Departures: Sails twice daily from the Cabo San Lucas Marina at 9:00 am or 12:30 pm. Exact meeting instructions will be provided on your confirmation voucher. If traveling between December and March, we recommend the 9:00 am tour for the best whale watching experience.
Length: The boat is yours for up to 3 hours!
33' Private Cabo Sailing Charter Recommendations:
Children: All ages are welcome. Children under 12 years old are free of charge. If you are traveling with a toddler, we recommend you bring an appropriately sized live vest with you on your trip to Cabo.
Cruise Ship Passengers: This is the perfect shore excursion in Cabo San Lucas for those traveling in with family or small groups. We can cater your departure time according to your cruise ship schedule since it is private. Our check-in office is a short walking distance from the tender boat pier (exact instructions to be provided on your confirmation voucher).
Restrictions: Expectant mothers may want to consider one of the more stable catamaran charters instead.
Insider Tip: This sailing charter company has hosted birthday celebrations, anniversaries and family reunions. They’ll do their best to accommodate any special requests you may have. We can customize the sailboat with a bouquet of flowers, bring a cake, and even provide some champagne to celebrate that special occasion. Contact us if you’re interested!
Retail: $600.00
Real Deal: $540.00
If you love a good monohull sailing experience but want to share it with a larger group of friends, the 44' Espiritu Santi is the perfect sailboat charter for you. This is our favorite for celebrating special occasions with smaller more intimate groups, but this sailboat comfortably holds up to 18 guests. And with the captain and crew at your beck and call, this is sure to be a memorable day of snorkeling and sailing in Cabo for everyone. Did we mention it is 100% eco-friendly too!!
44' Private VIP Sailboat Charter in Cabo San Lucas Details
44' Private Cabo Sailing Charter Includes:
Departures: Sails twice daily from the Cabo San Lucas Marina at 9:00 am or 12:30 pm. Exact meeting instructions will be provided on your confirmation voucher.
Length: The boat is yours for up to 3 hours!
44' Private Cabo Sailing Charter Recommendations:
Children: All ages are welcome. Children under 12 years old are free of charge. If you are traveling with a toddler, we recommend you bring an appropriately sized live vest with you on your trip to Cabo.
Cruise Ship Passengers: This is the perfect shore excursion in Cabo San Lucas for those traveling in with family or small groups. We can cater your departure time according to your cruise ship schedule since it is private. Our check-in office is a short walking distance from the tender boat pier (exact instructions to be provided on your confirmation voucher).
Restrictions: Expectant mothers may want to consider one of the more stable trimaran charters instead. Also, because this boat is 100% eco-friendly, it runs on wind and solar power. We do not recommend this boat for whale watching which requires us to motor out instead of sailing.
Insider Tip: This sailing charter company has hosted birthday celebrations, anniversaries and family reunions. They’ll do their best to accommodate any special requests you may have. We can customize the sailboat with a bouquet of flowers, bring a cake, and even provide some champagne to celebrate that special occasion. Contact us if you’re interested!
Retail: $690.00
Real Deal: $590.00
Retail: $100.00
Real Deal: $90.00
There are several motor catamarans in Cabo San Lucas. But if you love sailing catamarans, our 35' Trimaran, Sea Amore, will remind you what you love about sailing the sea. Trimarans offer a bit more stable sailing experience making this private trimaran charter perfect to celebrate events with small groups up to 16 guests.
35' Private Sailing Trimaran Charter in Cabo San Lucas Details
35' Private Trimaran Charter Includes:
Departures: Sails twice daily from the Cabo San Lucas Marina at 9:00 am or 12:30 pm. Exact meeting instructions will be provided on your confirmation voucher. If traveling between December and March, we recommend the 9:00 am tour for the best whale watching experience.
Length: The boat is yours for up to 3 hours!
35' Private Trimaran Charter Recommendations:
Children: All ages are welcome. Children under 12 years old are free of charge. If you are traveling with a toddler, we recommend you bring an appropriately sized live vest with you on your trip to Cabo.
Cruise Ship Passengers: This is the perfect shore excursion in Cabo San Lucas for those traveling in with family or small groups. We can cater your departure time according to your cruise ship schedule since it is private. Our check-in office is a short walking distance from the tender boat pier (exact instructions to be provided on your confirmation voucher).
Restrictions: This vessel is great for the whole family!
Insider Tip: This sailing charter company has hosted birthday celebrations, anniversaries and family reunions. They’ll do their best to accommodate any special requests you may have. We can customize the sailboat with a bouquet of flowers, bring a cake, and even provide some champagne to celebrate that special occasion. Contact us if you’re interested!
Retail: $990.00
Real Deal: $890.00
Retail: $100.00
Real Deal: $90.00
This beautiful 37' catamaran is the largest of the small sailing charter fleet, but holding a maximum of 20 guests, it is still perfect for smaller more intimate group celebrations. For the snorkeling tour, the trampoline is the perfect place to spend the day soaking up the sun and cool breeze. The French built 37' Ave Maria sailing catamaran will have your heart praying for more sailing time in Cabo! (Not to worry, you can book extra hours, just ask)
37' Private Sailing Catamaran Charter in Cabo San Lucas Details
37' Private Trimaran Charter Includes:
Departures: Sails twice daily from the Cabo San Lucas Marina at 9:00 am or 12:30 pm. Exact meeting instructions will be provided on your confirmation voucher. If traveling between December and March, we recommend the 9:00 am tour for the best whale watching experience.
Length: The boat is yours for up to 3 hours!
37' Private Catamaran Charter Recommendations:
Children: All ages are welcome. Children under 12 years old are free of charge. If you are traveling with a toddler, we recommend you bring an appropriately sized live vest with you on your trip to Cabo.
Cruise Ship Passengers: This is the perfect shore excursion in Cabo San Lucas for those traveling in with family or small groups. We can cater your departure time according to your cruise ship schedule since it is private. Our check-in office is a short walking distance from the tender boat pier (exact instructions to be provided on your confirmation voucher).
Restrictions: This vessel is great for the whole family!
Insider Tip: This sailing charter company has hosted birthday celebrations, anniversaries and family reunions. They’ll do their best to accommodate any special requests you may have. We can customize the sailboat with a bouquet of flowers, bring a cake, and even provide some champagne to celebrate that special occasion. Contact us if you’re interested!
Retail: $990.00
Real Deal: $890.00
Retail: $100.00
Real Deal: $90.00
