Your Crew
CAPTAIN Tim Montgomery & MATE/CHEF Jessica
Captain Tim and Chef Jessica bring an easygoing blend of local knowledge, thoughtful hospitality, and genuine island spirit to every charter aboard GET ALONG. Tim’s extensive experience throughout the Virgin Islands and Lesser Antilles pairs naturally with Jessica’s warm service and fresh, approachable cuisine. Together, they create a relaxed, personalized atmosphere where guests can unwind, explore, eat well, and enjoy the best of Caribbean life.
Click each crew profile to learn more about their background, experience, and personal story.
July 2025
I cannot express to you how amazing our crew was. First, Captain Tim worked his ass off for the entire trip to ensure that things went smoothly for our families. Second, his suggestions for cool side trips were all spectacular. From our stop at the Bitter End to Water Island, his choices and suggestions made our vacation even better. Point is, Tim was legendary.<br />
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Our chef, Ashley, also amazing. Her food was top notch from our opening lunch all the way through our final breakfast together. I cannot say enough about these two.<br />
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-Brendon
March 2025
Six days in paradise! Tim and Peta came to our rescue with 24 hrs notice when our Bahamas charter canceled on us. Things happen for a reason! We couldn't have been more pleased with how the trip turned out. We can't wait to do it again some day. Hopefully, Tim's pool game improves!<br />
- Brian & Jess<br />