Private Sailing
in Sunny Isles Beach
Escape the ordinary on the Intracoastal Waterway aboard a quiet electric sailboat with USCG Captain Alex in Sunny Isles Beach, near Miami.
Romantic Sunset Sails • Learn to Sail • Proposal Experiences • Private Family Adventures
Private Sailing, the Way It Should Feel
Sunny Sailing is private sailing at a slower pace. Step aboard in Sunny Isles Beach for a peaceful experience on the Intracoastal Waterway—no crowds, no noisy engine, just the breeze, the water, and time together.
Up to 4 guests • 2–4 hour private sails • Photos included • Small pets welcome
Sunny Sailing Gift Certificates
Give the Gift of Sailing
Celebrate birthdays, anniversaries, holidays, and new adventures with a private sail or hands-on lesson in Sunny Isles Beach.
Choose Your Perfect Sailing Experience
Whether you're planning a romantic sunset, your first sailing adventure, or a relaxing afternoon on the water, every experience is private, personalized, and led by USCG Captain Alex aboard our quiet electric sailboat.
Private Sailing Escape
2 Hours
From $298
Escape the crowds and discover Sunny Isles Beach from the water aboard our quiet electric sailboat. Cruise the calm Intracoastal Waterway, enjoy beautiful waterfront views, spot dolphins when nature cooperates, and even take the helm if you'd like.
- ⏰ 2 Hours
- 👥 Up to 4 Guests
- 📸 Photos & Videos Included
Private Sunset Experience
3 Hours
From $398
Experience Miami's most beautiful hour from the water. Watch the sky glow with vibrant sunset colors while sailing aboard our quiet electric sailboat. Bring your favorite drinks, relax, and create unforgettable memories with family or someone special.
- 🌅 Best for Sunset
- 👥 Up to 4 Guests
- 📸 Photos & Videos Included
Ultimate Sailing Adventure
4 Hours
From $498
The ultimate private sailing experience. Explore farther along the Intracoastal Waterway, learn to sail with Captain Alex, relax, enjoy lunch onboard, take the helm, and experience South Florida at your own pace.
- ⚓ Hands-On Sailing
- 👥 Up to 4 Guests
- 📸 Photos & Videos Included
Every experience includes
✔️ Private sail — your group only
✔️ USCG Licensed Captain Alex
✔️ Quiet electric sailboat
✔️ Complimentary photos & short videos
✔️ Up to 4 guests
✔️ English, Russian & Hebrew spoken
Learn to Sail with Captain Alex
Have you always dreamed of learning to sail? Now's your chance.
Whether you're stepping aboard for the first time or building confidence at the helm, USCG-licensed Captain Alex provides fun, private sailing lessons aboard a quiet electric sailboat on the calm Intracoastal Waterway in Sunny Isles Beach. Learn at your own pace in a relaxed, hands-on environment with personalized instruction designed just for you.
🌊 Teen Sailing Lessons
Ages 12+
Build confidence, responsibility, and real sailing skills while having fun on the water.
Your teen will learn:
- ⚓ Steering & helm control
- 🌬️ Reading the wind & sail trim
- 🧭 Points of sail & changing direction
- 🪢 Essential knots & line handling
- 🦺 Safety procedures & life jackets
- ⛵ Boat confidence & teamwork
⚓ Adult Sailing Lessons
Beginner • Intermediate
Whether your goal is to sail confidently, prepare for boat ownership, or simply enjoy a new hobby, Captain Alex will customize every lesson to your experience level.
You'll learn:
- ⛵ Sailboat terminology & fundamentals
- 🌬️ Sail trim for different wind conditions
- 🧭 Tacking, jibing & points of sail
- ⚓ Navigation on the Intracoastal Waterway
- 🚤 Docking & boat handling basics
- 🌊 Safe seamanship & confidence at the helm
I CAN SAIL
Learn It. Sail It. Captain It.
Private hands-on sailing lessons for teens and adults, with a maximum of 1–2 students per lesson so each student gets personal attention and plenty of time at the helm.
✓2-hour private sailing lessons
✓Maximum 1–2 students
✓Hands-on from Day One
✓Build confidence and independence
✓Learn real sailing and boat-handling skills
✓Teamwork, focus and decision-making
✓Docking, sail handling and close-quarters boat handling
✓Fun, safe and personalized instruction
This is a hands-on recreational sailing instruction program — not an ASA certification course.
Option 1
Try Your First Lesson
A private 2-hour sailing lesson for up to 2 students total. Start at the helm and learn by doing.
$250
Private 2-hour lesson · up to 2 students
Option 2
I CAN SAIL 10-Lesson Program
Ten private lessons, each 2 hours, with a maximum of 1–2 students. Schedule each lesson individually after purchase.
Package price · Save $500
Included at no additional charge
Lesson 11 — The Graduation Sail
Our Gift to You.
After completing the 10-lesson program and demonstrating the required sailing skills, the student receives a free 2-hour Graduation Sail. Under Captain Alex’s supervision for safety, the student becomes the captain and may invite up to 3 family members or friends aboard.
YOU’RE THE CAPTAIN TODAY.
I CAN SAIL.
10 Lessons. One Goal. Take Your Family Sailing.
🙌 Every Lesson is Hands-On
From the very first lesson, you'll have the opportunity to:
✔ Take the helm
✔ Steer the sailboat
✔ Trim the sails
✔ Feel how the wind powers the boat
✔ Learn by doing — not just watching
No simulators. No classroom.
Just real sailing on the beautiful Intracoastal Waterway.
Ready to learn to sail?
Lessons are private, flexible, and scheduled around you. Contact us for availability and pricing.
What's Included
Everything you need for a perfect day on the water — at no extra charge.
Photos Included
Captain takes photos throughout your sail — shared with you after.
USCG Licensed Captain
Safe, professional, and knowledgeable. Your safety is always first.
Pet Friendly
Small pets welcome. Jenny the sailing dog may join too.
100% Private
No shared sails. Just your group, the boat, and the waterway.
Bluetooth Speaker
Set the mood with your favorite playlist on the water.
Kids Life Jackets
Properly fitted life jackets for young sailors, available on board.
Silent Electric Motor
No engine noise. Just the wind, the waves, and good company.
Hands-On Lessons
Want to take the helm? Alex will teach you the basics.
Small Pets Welcome
Well-behaved small pets are welcome on board our private sailing experiences. Bring your best friend along for new views, new adventures, and unforgettable memories on the water.
Don't have a pet? Jenny — our resident sailing dog and official first mate — is available to join you on your experience.
Bring Your Pet Aboard
Pearson Ensign
A classic American sloop built by Pearson Yachts — fiberglass, hand-laid, and designed to handle beautifully in all conditions. The Ensign is one of the most beloved one-design sailboats ever built, making it ideal for private sailing experiences, sunset sails, and lessons on the ICW.
Length Overall
22' 6"
Beam
7' 0"
Draft
3' 0"
Sail Area
235 sq. ft.
Displacement
3,000 lbs
Cockpit Length
8' 8"
USCG Licensed Captain · Up to 4 guests · Electric-assisted for silent sailing
Meet Captain Alex
Alex is a USCG Licensed Captain with a passion for sailing and sharing the beauty of the Intracoastal Waterway with guests of all experience levels. Whether you're stepping on a sailboat for the first time or looking to sharpen your skills, Alex brings patience, knowledge, and genuine enthusiasm to every experience.
Based in Sunny Isles / North Miami Beach, Alex knows these waters intimately — where the dolphins like to play, the best spots for photos, and how to make every two hours feel like a full day away from the world.
A Glimpse of the Journey
Real moments. Real people. Real memories.
What Our Guests Say
5.0 stars · Verified Google Reviews
Private Sailing Proposals in Miami, Florida
The Most Romantic Way to Propose — on the Water
Imagine sailing through the calm waters of Sunny Isles as the sun sets over the Miami skyline. The golden light reflects across the Intracoastal Waterway, the breeze is gentle, and it's just the two of you. When the moment feels right, you ask the question that changes everything.
💍 Reserve Your ProposalPrivate • Romantic • Unforgettable
Kosher Proposal Packages — Miami & Sunny Isles
Captain Alex speaks English, Hebrew, and Russian, making Sunny Sailing a top choice for the Jewish community across Sunny Isles, Aventura, Hallandale Beach, and North Miami Beach. We have proudly hosted dozens of kosher-friendly proposal sailings and understand the importance of discretion, timing, and meaningful moments.
Whether you're looking for a quiet sunset proposal or a full celebration sail, we'll work with you to create an unforgettable experience that honors your culture and your love story.
What's Included in Every Proposal Sail
Why Propose on a Sailboat in Miami?
A sailboat proposal offers total privacy, natural beauty, and a setting that no restaurant or public venue can replicate. Sailing the Intracoastal Waterway between Sunny Isles and Aventura, you'll have the Miami skyline, open water, and a golden sunset all to yourself.
The silence of a sailboat — no engine noise, just the wind and waves — makes the moment even more intimate and memorable.
We Speak Your Language
Simple Proposal Sail
A private, romantic sailing experience on the Intracoastal Waterway — perfect for an intimate proposal moment.
Most Popular
Sunset Proposal Experience
Our most popular package — a private sunset sail with stunning views of the Miami skyline and golden-hour photos.
Premium Proposal Experience
Fully customized planning, special decorations, photography coordination, and personalized touches for your big moment.
Serving South Florida
Sunny Isles Beach • Aventura • North Miami Beach • Hallandale Beach • Miami Beach • Bal Harbour
Ready to Plan Your Proposal?
Contact us to check availability and start planning the perfect moment.
Frequently Asked Questions
Everything you need to know before your sail.
Book a Sailing Trip
Let us know what you're looking for — we'll make it happen.
Or call us directly: (305) 676-5176
Tell us about your perfect sailing experience, and Captain Alex will personally get back to you within 24 hours to confirm availability and answer any questions.
Photo & Video Release
Captain Alex loves capturing your experience on the water. Please complete this release to allow Sunny Sailing LLC to use photos and videos from your sailing experience on our website and social media.
Photo & Video Release Agreement
I hereby grant Sunny Sailing LLC and its captain(s) the irrevocable right and permission to use photographs, videos, and other media taken during my sailing experience for any lawful purpose, including but not limited to:
- Website content (sunnysailingflorida.com)
- Social media platforms (Instagram, Facebook, Google, etc.)
- Promotional and marketing materials
- Google Business profile and reviews
I understand that no compensation will be provided for this release. I waive any right to inspect or approve the finished product. This release applies to myself and any guests in my party.
I confirm that I am 18 years of age or older, or am a parent/legal guardian signing on behalf of a minor in my party.