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Montserrat #boatlife #sailingfamily #familyadventure
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Sunset in Montserrat 🌅⚓ Sometimes it’s hard to believe this is real life. Calm water, island views, and another unforgettable Caribbean sunset aboard Isla. ...

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Boat Life in Sint Maarten: Dinghies, Beaches & Island Vibes
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Yes, we’re still in Sint Maarten… and honestly, we’re not mad about it! We’ve been anchored in Simpson Bay for over a week now, and this island is quickly ...

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10 rental cars 10 islands
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We rented a car on every island possible. If we weren’t sailing we were road trippin

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The Ultimate Road Trip Q&A Part 2: Canyons to Grand Canyon, Scottsdale, & Zion National Park. Ep.35
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Welcome to Part 2 of our epic Q&A series! In this episode, we’re answering more of your burning questions while sharing highlights from our unforgettable road ...

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Don’t Watch if You Hate Fun: Family Vacation Q&A Edition Part 1 Episode 34
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Welcome to our most exciting and jam-packed episode yet! Over the holiday break, we took some much-needed time to celebrate, connect, and reflect—and now we’re ...

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Struggles in Nassau & Bittersweet Reunions in Andros
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In this episode, we arrive in Nassau, the vibrant heart of The Bahamas, marking a bittersweet goodbye to cherished friends. While tackling essential fiberglass ...

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Unlocking the Secrets of the Deep with PADI (Open Water Course)
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Join us on Sailing Big Lost as Conor, Finn and Maddie go through the process of achieving their Padi Open Water Diver Certification with Blue Water Divers in ...

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Setting Sail: Our First Adventure Aboard the New Catamaran
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Finally the time has arrived where we get to spend some time on our own catamaran and see for ourselves if we made the right decision purchasing The Big Dog. ...

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