Experience a luxurious private sailboat tour in San Juan Bay, Puerto Rico; enjoy complimentary charcuterie, sangria and drinks while you sail past Old San Juan’s historic forts at sunset—perfect for celebratory occasions.
Set sail on a private luxury sailboat through the sparkling waters of San Juan Bay, Puerto Rico. Whether you choose a morning, day, or sunset departure, this exclusive experience offers the perfect blend of relaxation, adventure, and Caribbean charm. Enjoy the breathtaking skyline of Old San Juan while sipping homemade sangria and savoring a charcuterie platter prepared just for you. It’s the ultimate way to see Puerto Rico from a new perspective — peaceful, private, and unforgettable.
? Highlights
✨ Enjoy a completely private sailboat charter for your group (no strangers on board!)
? Sip on complimentary homemade sangria and indulge in local tapas and charcuterie
? Cruise by iconic landmarks like Castillo San Felipe del Morro, La Fortaleza, and the walled city of Old San Juan
? Choose to swim or use water toys during your sail (optional)
? Connect your own playlist with Bluetooth speakers onboard
? Witness a Caribbean sunset from the deck for the perfect photo moment
Step aboard your elegant private sailboat and feel the ocean breeze as you glide across San Juan Bay. Your friendly captain and crew will welcome you with refreshing drinks and light bites as you begin your journey past the colorful streets and historic fortresses of Old San Juan. Depending on your chosen time, you’ll enjoy either the bright, tropical daylight or the golden glow of a Caribbean sunset painting the skyline.
This relaxing experience lets you customize your sail — unwind on deck with a drink in hand, take a dip in the clear waters, or simply soak in the panoramic views. With only your group onboard, this is an intimate and luxurious way to experience Puerto Rico’s capital city from the sea.
? What’s Included
✅ Private sailboat charter (up to 6 guests)
✅ Professional captain and crew
✅ Homemade sangria, local drinks, and light tapas/charcuterie platter
✅ Bluetooth sound system for your own music
✅ Option for swimming or snorkeling (on request)
✅ Safety gear and onboard facilities
? Comfortable clothes or swimwear
? Sunscreen, sunglasses, and a hat
? Camera or smartphone for photos
? Flip-flops or boat shoes
? Towel (if you plan to swim)
? Positive vibes and a sense of adventure!
? Exclusive & Private: You’ll have the whole sailboat to yourself — perfect for couples, families, or friends.
? Stunning Views: The vistas of Old San Juan, its historic walls, and forts from the water are truly magical.
? Delicious Touches: Free sangria, fresh fruit, and tapas make the trip extra special.
?✈️ Professional Crew: Guests rave about the friendly captain and personalized service.
? Perfect for Any Occasion: Great for birthdays, anniversaries, or simply a sunset escape on the Caribbean Sea.
After completing your reservation, our team will contact you one day before your tour to confirm your exact hotel / Airbnb pickup time or meeting point.
If you selected a meeting point during your booking, please note that your reservation is fully confirmed — simply arrive at the chosen location at the scheduled time.
Please ensure the WhatsApp number, phone number, or email you entered during booking is correct so we can reach you smoothly.
For any changes to your reservation, weather questions, or special requests, feel free to contact us:
We look forward to welcoming you! 🌴✨
This tour was an invitation to connect with the spirit of the region, to immerse ourselves in its culture, and to embrace its unique way of life. We attended local festivals, participated in traditional ceremonies, and learned about the history, art, and music…
An unforgettable adventure! Our guide was fantastic and made sure we were having a good time. We will tell our friends about this must-do!
This day was well made from this tour and we just can say we can. It has been fun and the tour was so very good well well done team good.
The food was amazing and catered for everyone. Plenty to see and do! The whole team are very accommodating and looked after me well!
I loved this tour! Our guide provided us with many recommendations for places to visit after the tour! It was a must see!
