New England to Portsmouth va to Puerto Rico

[Leviathan33]

Retiring and relocating to western Puerto Rico from Connecticut - leaving mid-June 2020. Probably a stop in Portsmouth, VA before heading through the GS to Bermuda or to Bahamas then to Mayaguez PR.

Need help planning the trip and crew for part or all of the voyage.
Hunter Cherubini 33 outfitted for offshore.

Let's start a dialog. I could use your experience and help.

[Orion Jim]

Bermuda is nearly the same distance from any port on the east coast. I’d just run down to Bermuda from your home port, kick back for a few days, and run down to PR. Unless you had some other reason to visit VA.
Running down to Bermuda can be a challenge for a small boat....many times the prevailing wind forgets it should be from the southwest. This year I had three days of strong winds from the east....then it was northeast and west for the next three days....then there have been years of somewhat normal winds. Be prepared for a six to eight day passage in your 33 footer. It can be a lot of fun and always rewarding.

[Sparx]

Connecticut to Portsmouth Virginia in June is likely to offer wonderful weather. There two basic paths. With many variations.

Path1: Long Island Sound to New York City via the East River, then along the New Jersey Shore. Next up Delaware Bay to transit the C&D canal into the Chesapeake, then south through the Bay to Portsmouth. There is much to see and explore along this route, everyone should do it at least once. There are opportunities to anchor or use a marina every night along the way. This route transits sheltered waters, with the exception of the New Jersey Shore.

Path 2: Montauk to the Chesapeak direct offshore. I would plan for three offshore days. With good weather this can be a great trip, and a good shake down before longer offshore passages. Once in the Chesapeake Portmouth is a short run and Portsmouth/Hampton are good places to relax and repair.

A search will yield more forum discussion of these routes.