Skip to content Sailing Into History: Remembering Our Old Boat
25 Years of Excellence on the Water
The Beginning
Sea Dog Sailing was founded with a passion for providing unforgettable sailing experiences. Starting with a single sailboat, the company quickly gained a reputation for its exceptional service and expertise.
First Fleet Expansion
Due to increasing demand, Sea Dog Sailing added a second vessel, allowing more guests to experience private charters and guided sailing tours.
Award-Winning Service
Recognized for outstanding customer experience, Sea Dog Sailing received its first Best Sailing Charter Award, solidifying its status as a top-tier sailing company.
Specialized Experiences
Introduced
To cater to a growing audience, the company launched sunset cruises, proposal sails, and team-building events, expanding beyond traditional charters.
National Recognition &
Media Features
Sea Dog Sailing was featured in travel magazines and TV segments, highlighting its unique and memorable sailing adventures.
Eco-Friendly Initiative
The company introduced sustainable sailing practices, including responsible waste disposal and promoting ocean conservation awareness among guests.
Adapting to Change
Despite global challenges, Sea Dog Sailing implemented private charters with enhanced safety protocols, ensuring continued operation while prioritizing guest health and comfort.
Luxury Upgrades &
VIP Packages
Sea Dog Sailing was founded with a passion for providing unforgettable sailing experiences. Starting with a single sailboat, the company quickly gained a reputation for its exceptional service and expertise.
25 Years of Sailing
Adventures
Now celebrating 25 years in business, Sea Dog Sailing remains a trusted name, offering expertly guided sailing trips with the same passion and commitment that started it all.
The Beginning
Sea Dog Sailing was founded with a passion for providing unforgettable sailing experiences. Starting with a single sailboat, the company quickly gained a reputation for its exceptional service and expertise.
First Fleet Expansion
Due to increasing demand, Sea Dog Sailing added a second vessel, allowing more guests to experience private charters and guided sailing tours.
Award-Winning Service
Recognized for outstanding customer experience, Sea Dog Sailing received its first Best Sailing Charter Award, solidifying its status as a top-tier sailing company.
Specialized Experiences
Introduced
To cater to a growing audience, the company launched sunset cruises, proposal sails, and team-building events, expanding beyond traditional charters.
National Recognition &
Media Features
Sea Dog Sailing was featured in travel magazines and TV segments, highlighting its unique and memorable sailing adventures.
Eco-Friendly Initiative
The company introduced sustainable sailing practices, including responsible waste disposal and promoting ocean conservation awareness among guests.
Adapting to Change
Despite global challenges, Sea Dog Sailing implemented private charters with enhanced safety protocols, ensuring continued operation while prioritizing guest health and comfort.
Luxury Upgrades &
VIP Packages
Sea Dog Sailing was founded with a passion for providing unforgettable sailing experiences. Starting with a single sailboat, the company quickly gained a reputation for its exceptional service and expertise.
25 Years of Sailing
Adventures
Now celebrating 25 years in business, Sea Dog Sailing remains a trusted name, offering expertly guided sailing trips with the same passion and commitment that started it all.
25 Years of Excellence on the Water
The Beginning
Sea Dog Sailing was founded with a passion for providing unforgettable sailing experiences. Starting with a single sailboat, the company quickly gained a reputation for its exceptional service and expertise.
First Fleet Expansion
Due to increasing demand, Sea Dog Sailing added a second vessel, allowing more guests to experience private charters and guided sailing tours.
Award-Winning Service
Recognized for outstanding customer experience, Sea Dog Sailing received its first Best Sailing Charter Award, solidifying its status as a top-tier sailing company.
Specialized Experiences
Introduced
To cater to a growing audience, the company launched sunset cruises, proposal sails, and team-building events, expanding beyond traditional charters.
Luxury Upgrades &
VIP Packages
Sea Dog Sailing was founded with a passion for providing unforgettable sailing experiences. Starting with a single sailboat, the company quickly gained a reputation for its exceptional service and expertise.
Adapting to Change
Despite global challenges, Sea Dog Sailing implemented private charters with enhanced safety protocols, ensuring continued operation while prioritizing guest health and comfort.
Eco-Friendly Initiative
The company introduced sustainable sailing practices, including responsible waste disposal and promoting ocean conservation awareness among guests.
National Recognition &
Media Features
Sea Dog Sailing was featured in travel magazines and TV segments, highlighting its unique and memorable sailing adventures.
25 Years of Sailing
Adventures
Now celebrating 25 years in business, Sea Dog Sailing remains a trusted name, offering expertly guided sailing trips with the same passion and commitment that started it all.
Testimonials
Andria Crawford-Whitehead
Sailed with Capt. Matt this summer and had a wonderful time! It was our kids first time sailing and they were able to be very hands on. Capt. Matt was generous with his time and very kind. Would sail with him any time!
Lorin Heinert Lewis
Captain Bob is the best! He is knowledgable, charismatic, and always has the best crew. The Sea Dog team will always go out of their way to ensure you have the best experience. Our fourth year sailing with him – this will be a summer tradition as long as he’s out on the water!
Spencer Hellman
We had a wonderful time sailing with Capt. Bob and crew. They are easy going and can cater the sailing experience to your preference. The views alone are worth the trip, let alone the sailing experience itself. Highly recommend!
Maria Ponzi Luce
Perfect day out on the water! Captain Bob is so knowledgeable and shared that knowledge with us during the sail. We even got to take the wheel during some pretty crazy waves! His crew did a fabulous job as well. Would highly recommend!
Jessica Ramirez
Had so much fun today! It was my first time to sail and an experience I will never forget. Captain Bob and his crew is amazing. Great conversation, laughs and music. Highly recommend, you will not be disappointed
Lea Kolkmeier
This is an amazing sailing experience for the whole family. Totally reccomend it and Captain Bob is a great friendly guy!!
Jennifer Perreault
This is the third time I have been sailing and the third time I went with Captain Bob! And I will continue to do so until I either can’t or he is no longer in business (which better not happen fir quite a few years
). Thanks for a great adventure on a very rough water!!! And THANK YOU for making your customers’ well-being a priority!
Andria Crawford-Whitehead
Sailed with Capt. Matt this summer and had a wonderful time! It was our kids first time sailing and they were able to be very hands on. Capt. Matt was generous with his time and very kind. Would sail with him any time!
Lorin Heinert Lewis
Captain Bob is the best! He is knowledgable, charismatic, and always has the best crew. The Sea Dog team will always go out of their way to ensure you have the best experience. Our fourth year sailing with him – this will be a summer tradition as long as he’s out on the water!
Spencer Hellman
We had a wonderful time sailing with Capt. Bob and crew. They are easy going and can cater the sailing experience to your preference. The views alone are worth the trip, let alone the sailing experience itself. Highly recommend!
Maria Ponzi Luce
Perfect day out on the water! Captain Bob is so knowledgeable and shared that knowledge with us during the sail. We even got to take the wheel during some pretty crazy waves! His crew did a fabulous job as well. Would highly recommend!
Jessica Ramirez
Had so much fun today! It was my first time to sail and an experience I will never forget. Captain Bob and his crew is amazing. Great conversation, laughs and music. Highly recommend, you will not be disappointed
Lea Kolkmeier
This is an amazing sailing experience for the whole family. Totally reccomend it and Captain Bob is a great friendly guy!!
Jennifer Perreault
This is the third time I have been sailing and the third time I went with Captain Bob! And I will continue to do so until I either can’t or he is no longer in business (which better not happen fir quite a few years). Thanks for a great adventure on a very rough water!!! And THANK YOU for making your customers’ well-being a priority!
Pictures
Stories from the Sea
Real adventures, real smiles — hear from those who made waves with us.