The sailing component of this plan serves three purposes simultaneously: it's a genuinely wonderful lifestyle (Puget Sound summers, Baja winters), it keeps us connected to the water community around Port Townsend, and it maintains a capability that doubles as emergency transportation if things ever get truly bad. But the primary pitch is simple: this is how we want to spend our time.
The Annual Rhythm
May – August
Puget Sound & San Juan Islands. Some of the best cruising waters in North America. Protected, scenic, endless anchorages. Orcas Island, Friday Harbor, Sucia Island, Desolation Sound (BC). The boat lives at Port Townsend and we sail from there. Weather is mild (60s–70s), winds are reliable, currents are manageable with planning.
September – October
Southbound passage. Depart Port Townsend, transit the Washington and Oregon coasts (inside stops at Neah Bay, Westport, Astoria, Newport, Coos Bay), continue to San Francisco, then Channel Islands, then San Diego. 10–14 days of coastal cruising with the prevailing northwesterlies at your back. This is the adventurous leg — open ocean, big views, real sailing.
November
Baja Ha-Ha Rally. Depart San Diego with 150+ boats heading to Cabo San Lucas. Two weeks, three stops (Turtle Bay, Bahía Santa María, Cabo). Social, supported, festive. This is how the cruising community migrates south each year — potluck dinners on the beach, shared sundowners, instant friends.
December – March
Sea of Cortez. La Paz as home base. Cruise to Isla Espíritu Santo, Isla Partida, Los Islotes (sea lions), Loreto, Agua Verde. Water temperature 70°F+, air dry and sunny, daily highs 75–85°F. La Paz itself is a wonderful walkable city — great Mexican food, cheap marina fees ($500–800/month), large expat sailing community. This is the antidote to PNW winter.
March – April
Return north. Either "Bash" back up the Baja coast to San Diego (7–10 days of motoring into headwinds — unpleasant but doable), ship the boat via yacht transport ($10–15K), or leave it in La Paz and fly home. Then reposition to Port Townsend by May for summer sailing season.
Home Base: Port Townsend
Port Townsend is the natural hub for this plan. It's a historic maritime town on the Olympic Peninsula — Victorian architecture, working boatyards, a wooden boat school, excellent marina facilities, and a community of serious sailors. The town has good restaurants, a food co-op, galleries, and a year-round cultural calendar. Population ~10,000.
Why PT Over Anacortes or Bellingham
Port Townsend has direct access to the Strait of Juan de Fuca and the Inside Passage without transiting Puget Sound's shipping lanes. The maritime infrastructure (boatyards, sailmakers, riggers, marine electronics) is world-class for a town its size. And critically for the long-term plan, it's the most direct staging point for an Inside Passage trip to Alaska — just follow the coast north. Anacortes is a close second (better for San Juans access). Bellingham is farther from open water.
A cottage or small house in Port Townsend ($500K–$700K) serves as: a place to stay when visiting the boat, a launching point for summer cruising weekends, a gathering spot for the whole family, and in an emergency, a staging area close to the boat.
The Boat
The boat needs to handle three very different jobs: comfortable Baja living for two people, bluewater passages down the Oregon/Washington coast, and manageable sailing for a two-person crew. The sweet spot is 40–45 feet, center cockpit or pilothouse, moderate to heavy displacement.
Island Packet 445 — Top Pick
$180K–$280K used (2000s vintage). Designed for exactly this mission. Full keel (stable, forgiving, handles rough seas without drama), center cockpit with hardtop dodger option, enormous fuel and water tankage (150+ gal fuel, 200+ gal water). Interior feels like a small apartment — critical for months of liveaboard life. Not fast, not flashy, but built like a tank. Huge owner community for parts and knowledge. The best tool for the job.
Hallberg-Rassy 43 or 46 — Best Sailing
$200K–$350K used (late 90s–2000s). Swedish-built, beautifully finished, with a signature integrated windshield that makes the cockpit almost enclosed — perfect for PNW weather. Sails notably better than the Island Packet (Dad will appreciate this). Gorgeous teak interiors, exceptional build quality. Holds value stubbornly. The tradeoff: European parts cost more and they're priced at a premium on the used market.
Hylas 44 or 46
$180K–$300K used. Taiwan-built to American designs. Serious offshore cruiser, center cockpit, beautiful hand-laid fiberglass construction. Sails well for a heavy cruiser. Excellent aft cabin (queen berth, private head). Less common than Island Packets but devotedly followed by owners who know them. Worth the search.
Outbound 46 — Modern
$250K–$400K used. Modern design with carbon-fiber reinforcement, clean deck layout, and better sailing performance than traditional cruisers. Built in Annapolis. Systems are newer (less rewiring needed). Fin keel with skeg-hung rudder — sails great, slightly less bombproof than a full keel for grounding scenarios.
Catalina Morgan 440 — Value
$140K–$200K used. The pragmatic choice. Roomy center-cockpit 44, comfortable for liveaboard, adequate offshore. Not the build quality of the others, but perfectly capable and leaves significantly more budget for everything else. Enormous aft cabin. Your dad may call it a "production boat" — he's not wrong — but it gets the job done.
Budget Overview
| Item | Amount | Notes |
|---|---|---|
| Portland main residence | $1.3–1.5M | Primary home, climate-hardened |
| Port Townsend cottage | $500–650K | 2BR, walkable to marina |
| Sailboat (used, refit) | $200–300K | Including survey, safety upgrades |
| Annual sailing costs | $20–30K/year | Marina, insurance, maintenance, Mexico cruising |
| Reserve fund | $100–150K | First 5 years carrying costs |
| Total | ~$2.3–2.5M |
Where Should the Parents Land?
If they're relocating from Nashville and want liberal community, comfort, fine dining, and proximity to the boat, there are two strong options:
Bainbridge Island
35-minute ferry to Seattle. Refined, artsy, established. Great restaurants, galleries, wine bars. Retired professionals and creative types. Quiet daily life with urban access. Feels like upscale Aptos/Capitola. $850K–$950K median home.
Bellingham
College-town energy (WWU), ~95K people. Outdoorsy, progressive, vibrant. Fairhaven district is charming. More affordable ($600–700K median). Younger demographic — may feel energetic rather than peer-group. Think Santa Cruz vibes, colder and rainier.