You should be able to comfortably make Leverick Bay on Day 1. It's only 18 nm from Roadtown and should take about 2.5 hours. If you're off the dock by 3:30 pm, you're still there 45 minutes before sunset. If you get to North Sound by early afternoon, you could anchor/moor at Prickly Pear island for some beach time and swimming before repositioning to Leverick Bay. Kids will also like the pool at Leverick. Might as well stay at the dock at Leverick using the TTOL special of $35 with bag of ice and water fill.

For Day 2 & 3, I highly recommend a visit to Anegada. We've taken kids in that age group - they enjoyed the 'adventure' of the sail over the horizon, riding the bench seats in the back of the rental pickup, visiting the Anegada iguana sanctuary, beachcombing and snorkeling (if seas are settled) at Flash of Beauty, hanging out at the beach & pool at Anegada Beach Club, lobster dinner on the beach (many restaurants choices), limbo dancing in the sand at Potters.

On Monday, it's only a 20 nm sail from Anegada to Trellis Bay. In the morning dinghy over to Pam's Bakery at Neptune's Treasure for some fresh baked goods such as banana bread, drop off the rental vehicle (or simply arrange to leave it at Anegada Reef Hotel with the keys under the mat), then enjoy a leisurely sail. If seas are settled, make a stop at Great Dog or George Dog for lunch & snorkel or continue directly to Cam Bay and anchor for the afternoon behind the reef, have lunch and snorkel. In the late afternoon, head to Trellis Bay to meet your crew.

Another alternative on Day 4 would be to spend the afternoon and night at the dock at Scrub Island. The summer marina rate is only $2/ft plus 17% service charge. The kids (and likely the adults) will enjoy the two-level pool, waterslide, and hot tub. Your guests can take the Scrub Island ferry from Trellis Bay (10 minute trip, departs 45 minutes after the hour until 10:45 pm). This also allows you and your new guests to take nice long showers ashore, and to start you next leg in the morning with full water tanks ($0.35/gallon).