Island Packet 440 (2006)


  • 46 feet

  • 6 guests

  • 2 cabins

  • 2 heads

  • Captained



Prepare to be pampered! Celebrating a special occasion, or just looking for an extravagant getaway at affordable rates? Sailing aboard CAPTAIN SIR! is a unique and luxurious experience allowing you to enjoy the best of Miami.

Available for day or night charters -- the trip departure time and length of your trip is up to you. Sunset charters maximize the romance of the sailing experience, (wedding proposals are our specialty); evening sails allow you to take in the breathtaking skyline of Miami and the city lights. Daytime sails offer our guests time to relax on deck, swim in quiet spots away from crowds and enjoy the scenery of Key Biscayne mansions, historic Stiltsville, nature and so much more that is totally unique to Miami and Biscayne Bay. No matter what time you sail, the photo opportunities are fantastic. Guests are also welcome to participate in sailing the boat and Captain Russ is a patient, competent instructor.

CAPTAIN SIR! is a beautiful Island Packet yacht offering 46 feet of comfort and luxury -- professionally maintained and recommended with confidence by the concierge desks of Miami's five star hotels. You will have all the amenities necessary to make your trip special - you'll leave feeling refreshed and renewed. Enjoy Bluetooth stereo system so you can play music from your phone, Sirius Satellite radio, comfortable deck chairs, a spacious stern platform that allows you to drag your feet in the water while sailing along (plus easy in and out access to swimming), hot/cold fresh water shower on the stern when you come up from swimming, plush towels, plus complimentary bottled water and sodas.

Feel free to bring your own food and beverages aboard or opt for our gourmet food prepared and elegantly served to you. Meals and snacks are customized for your tastes -- this option requires a bit of conversation to plan all the details but also gives you a chance to talk with the captain about any special items you might like to have for your outing. We leave no detail to chance -- our goal is to assure this is the most fun and memorable time of your Miami visit.

From October 15th - May 15th, ask about our stone crab special -- feast on the freshest and biggest stone crab claws as you sail along the skyline of Miami -- that's when you know you have arrived!

*CAPTAIN SIR! is offered with captain and crew for private charters of up to six guests.
*Please contact us in advance for pick up location information.
*Please note that availability is subject to change on a moment's notice. To insure the date and time you would like, please contact us directly for the most up-to-date availability.
*Rates include 7% Florida tax.

We look forward to welcoming you on board!


  • Manufacturer
    Island Packet
  • Model
  • Year
  • Guest Capacity
  • Cabins
  • Single Beds
  • Double Beds
  • Bathrooms
  • Number of engines
  • Horsepower per engine


BOAT OWNER Captain Russ Boley has been sailing his entire life – having grown up around the Chesapeake Bay and sailing that area for his first 25 years. For the last 35 years he has been sailing South Florida’s coast, The Keys, Caribbean and Bahamas. Captain Russ is a U.S. Coast Guard licensed captain, possesses a Master's Degree in Hospital Administration. The added value of booking Captain Sir! is that Captain Russ is also an accomplished chef. He is quality conscious about the food served aboard and makes every effort to assure you not only an enjoyable sailing trip, but also a gourmet culinary experience.


  • Stereo AUX input mp3 hookup
  • Stove / grill
  • Autopilot
  • Microwave
  • Radar
  • WiFi/Internet
Navigation & Safety
  • Autopilot
  • Radar
  • Chart plotter
  • GPS
  • Generator
  • VHF Radio
  • Depth finder
  • Bow thruster
  • Life jackets
  • Fire extinguisher
  • First aid kit
  • Binoculars
  • Stereo AUX input mp3 hookup
  • WiFi/Internet
  • TV
  • DVD
  • CD Player
  • USB Connection
  • Speakers on deck
  • Teak deck
  • Stove / grill
  • Microwave
  • Air conditioning
  • Refrigerator
  • Towels
  • Freezer
  • Inverter
  • Warm water
  • Cockpit table
  • Electricity
  • Outdoor shower
Sports equipment
  • Snorkeling
  • Dining
  • Cocktail parties

Boat Owner


Member since November 2016

I've been sailing ever since I was a child. Grew up in Maryland and sailing on the Chesapeake Bay. I've lived in Miami for the past 44 years and have been chartering for the past 29 years. I have always been the boat of choice for all the 5 star hotels in Miami and keep my guests coming back because they find out that it costs no more to sail first class on CAPTAIN SIR! I'm also the only chef/captain in Miami and am known for providing fine food and custom menus for all my guests. If you want an immaculate boat with fine food served to you while sailing, look no further. If you want a combination of sightseeing and sailing on the protected waters of Biscayne Bay, look no further. It'll be your most memorable day in Miami!

Response rate: 70%
Response time: within 11 hours
Message owner

Location and Destination Guide

Usually this boat operates around Miami, FL.

It’s always party time in Miami! If you’re looking to for year round sun, fantastic beaches and a huge choice of things to do, you’ll find all kinds of party boat rentals in Miami with Sailo.

Miami truly is a year round destination, blessed with perfect sandy beaches, stacks of local culture and a sunny disposition that brings back visitors again and again. Whatever brings you to Miami, one of the best things to do in the city is hit the water on board your own private yacht rental.

Customer Questions & Answers

Ask general questions about this boat. For questions related to a specific booking request click here to Message the Boat Owner directly.


Can the boat accommodate more than 16 people?


0 votes
No, the maximum guest capacity for this boat rental is 6 person according to US Coast Guard regulations.
by Simon on January 16th 2019
Please select dates:
Boat From $695 per half day
Total* Select dates
*excludes Sailo's service fee
per half day (4h)


What type of yacht should I charter?

No matter what type of yacht you choose to charter, we know that you will have a fantastic time on the water. If you are more about the journey, and want a relaxing time aboard, then choose from one of the many sailboats on the platform. If you are more about the destination, and going fast, check out the powerboats on Sailo. For an exclusive experience, Sailo recommends chartering a luxurious yacht for the day. Finally, Sailo has access to many event boats as well for group outings from 50 - 1,000 guests. If you are still unsure, then just ask! more...

What should I bring?

Bring yourself, and some comfortable clothes suitable to the season you are going to be out on the water. Please keep in mind that it is often 10 degrees cooler out on the water, so a jacket or windbreaker is never a bad idea. We also recommend bringing a hat, sunscreen, and sunglasses, as well as a swimsuit if appropriate for your charter location. Please coordinate with your captain regarding any food or drinks that you wish to bring aboard. For term-charters, Sailo recommends using soft-sided luggage, and keeping it simple. more...

How long does a rental last?

The basic daily rental is structured as either a quarter-, half-, or full-day. A quarter-day is two hours, a half-day is four hours, and a full-day is eight hours. You can also discuss a custom trip with the boat by contacting the owner through Sailo. Most term charters (weekly rentals) are from Saturday to Saturday. Keep in mind that the boat generally needs to be back at the dock by Friday evening, and you will need to be off the boat on Saturday morning so they can prepare the boat for the next guests. more...


Welcome to one of the most famous year-round boating destinations in the world! Hop aboard your yacht charter in Miami, FL and enjoy this amazing floating playground for both beginners and experienced sailors. The boat rental in Miami, FL you have selected is a Island Packet Sail boat - a popular choice to explore the natural beauty of Florida’s coast. Sailing on a FL, Miami yacht charter is an experience you should not miss if you decide to visit the boating capital of the world. Picture yourself on romantic  sunset cruise on this FL, Miami boat rental, or having fun with your family or friends on a sightseeing tour along the coast. For more ideas about things to do on your boat rental or yacht charter in Miami, FL, make sure to check our destination guide for Sailing in South Florida!

We invite you to browse through hundreds of Sailo boats perfect for sailing in Florida, and choose the dream Sail boat rental or yacht charter for your nautical adventure. Whether you are looking to spend a relaxed afternoon on a classy motorboat or sailboat, or have a fun on a sporty catamaran, our team here to make sure you will be making the best out of your time on the water.  For details about this Island Packet 46.0 boat rental in Miami, FL, or to make special arrangements for your trip, please click on the “Message Owner “ blue button to send a direct message to the boat representative.