The trip was excellent. Pedro was amazing!
Private Sail Sunset or Bay Tours with Free Drinks & Tapas

Short Description
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.
Description
? Overview
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
⚓ Full Description
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
? What to Bring
? 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!
❤️ Why Travelers Love It
? 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.
Important Note
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:
- 📞 Barbara (WhatsApp): +1 829-318-9463
- 📞 Dary (WhatsApp): +1 829-754-6322
- 📧 Email: [email protected]
We look forward to welcoming you! 🌴✨
Choose what to book
Reviews
What struck me most about this tour was the guide's genuine connection to the land. He shared stories passed down through generations, painting a vivid picture of the region's history and its people. It wasn't just about reciting facts from a textbook; it was …
The local insight really made this tour special. The guide was extremely knowledgable. The best tour ever.
Its well worth the cash and some you just all need to see this. You never go to see this much its all up to all and you what to do just book.
This tour blew my expectations. We really were looking for something we could enjoy and the whole team made it.
You might also like…

Carolina: ATV Adventure at Campo Rico Ranch with Guide

Carolina: ATV Adventure at Campo Rico Ranch with Guide

San Juan - Arecibo: midwest expedition waterfalls and beach

San Juan - Arecibo: midwest expedition waterfalls and beach

Morning Old San Juan Walking & Food Tasting Tour

Morning Old San Juan Walking & Food Tasting Tour

San Juan: WATER JET CAR-Red Bugatti Experience

San Juan: WATER JET CAR-Red Bugatti Experience

Carolina: Beginners Surf Lesson & Extended Surfboard Rental

Carolina: Beginners Surf Lesson & Extended Surfboard Rental

Caribbean Driftwood Making in San Juan

Caribbean Driftwood Making in San Juan

San Juan: sea trek tour explore beneath the waves

San Juan: sea trek tour explore beneath the waves

San Juan: Surfing Class with Professional Instructors

San Juan: Surfing Class with Professional Instructors

San Juan: El Yunque Rainforest and Luquillo Beach Day Tour

San Juan: El Yunque Rainforest and Luquillo Beach Day Tour

Puerto Rico: Cave & Beach Hopping Tour

Puerto Rico: Cave & Beach Hopping Tour

San Juan: Visit 10+ towns PR-10 Mountain drive

San Juan: Visit 10+ towns PR-10 Mountain drive

Hydroventure Luquillo: 1HR Guided Jet Ski Tour Las Picuas

Hydroventure Luquillo: 1HR Guided Jet Ski Tour Las Picuas

Puerto Rico: Old San Juan Guided Private Walking Tour

Puerto Rico: Old San Juan Guided Private Walking Tour

San Juan: El Yunque National Rainforest Sightseeing Tour

San Juan: El Yunque National Rainforest Sightseeing Tour

San Jose : Best Street Food Tour With A Local Guide

San Jose : Best Street Food Tour With A Local Guide

From San Juan: Cave of the Taino Indian Trek and Beach Tour

From San Juan: Cave of the Taino Indian Trek and Beach Tour

Puerto Rico: UTV and Can-Am Sightseeing Tours

Puerto Rico: UTV and Can-Am Sightseeing Tours

picnic san juan puerto rico

picnic san juan puerto rico

Puerto Rico: Toro Verde Adventure Park- The Monster Zipline

Puerto Rico: Toro Verde Adventure Park- The Monster Zipline

Urban Park: Pico del Toro Climbing wall

Urban Park: Pico del Toro Climbing wall

San Juan: Sunset Glow Kayak Tour and Salsa Experience

San Juan: Sunset Glow Kayak Tour and Salsa Experience

Old San Juan: Make Your Own Perfume Workshop

Old San Juan: Make Your Own Perfume Workshop

San Juan: El Yunque Waterfalls & Scenic Beach Buggy

San Juan: El Yunque Waterfalls & Scenic Beach Buggy

Rincon: Beginner Surf Lesson

Rincon: Beginner Surf Lesson

Toro Verde: Zipline + The Beast with Transportation

Toro Verde: Zipline + The Beast with Transportation

From Fajardo: Icacos Island Boat Trip and Beach Day Package

From Fajardo: Icacos Island Boat Trip and Beach Day Package

Latin Zumba Beach Class in San Juan, Puerto Rico

Latin Zumba Beach Class in San Juan, Puerto Rico

Vieques: Bioluminescent Bay Boat Tour
