Where can you rent a boat for cruising the San Juan Islands

    Renting a yacht is a very viable option.  

We have rented and recommend you consider renting too, why? see below.

Ahoy savings

Lets see why you would rent:

• you may not have a boat
• your boat is not trailerable from Kansas or Kentucky
• your drift boat is trailer ready but it sucks for camping
• renting is a chance to try something different, like a bigger boat
• because it doesn't make sense to own a boat and only use it once a year  (unless your afflicted with  boaters syndrome where you may own many boats you don't use)
• switch from power to sail or sail to power
• because you can't afford to throw your money into a hole in the sea
• to find out if sailing/boating is ok with your family pet, wife, kids, self

Now lets dispel some myths that are true some of the time: 

• renting is cheaper than owning  - yes, with some exceptions
• you must have a competency certificate to rent - absolutely not but you must have your state issued boaters card anytime you operate any boat.
• is it safe to do this as a novice that has good sense - yes
• is it safe to do this as a novice if some relatives that know you well caution you not to - no!
  (listen to friends and relatives) they know if your an idiot and a menace to all around you - just kidding but bring a level headed 1st mate to help with tough choices like - red on the right! or red on left! or red on bottom?
• can a power boater but non sailor rent a sailboat and have a great vacation and learn to sail - absolutely, but the competency thing may come up for bigger boats so bring a sailor friend
• can you rent power and sailboats in the San Juans - yes
• how much will it cost - small boat $100 - $200 a day (power or Sail)
• how much for a bigger rig - $500 and up, up and away
• should I get the added insurance offered - probably talk to your agent
• how many days should I plan for  -  5 / 7 days is very nice but two weeks would be awesome
• only go in mid June to mid Sept. - yes, unless you can save big and don't mind a little snotty weather tossed your way, then go anytime but be prepared for unpleasant things.

The 38 foot boat we rented for about $3000 a week, slept eight and handled bad weather very nice, but as you can see, the weather was not bad. Rental boats should be fully equipped with safety gear and navigation supplies for your travel area but don't assume anything. The boat above came with a 12 foot sailing tender, economical single diesel, thruster, chart plotter and radar.

Rent boats in Anacortes or Bellingham, but do some online research and find private rentals too.

San Juan area campgrounds with boat ramps

      If camping is your primary activity and your boat is for day use such as exploring, fishing and crabbing, 

you will find these parks of interest.

On the mainland:

• Washington Park in Anacortes - located one mile past the ferry landing.

Washington Park boat ramp in Anacortes

Excerpt from their website: In the campground there are 68 campsites, 46 have water and electrical hook-ups. These rent for $27 a night. There are 22 non-utility sites that rent for $21 per night. There are 25 sites available on a first-come, first-served basis. Please note that reservations must be made 14 days in advance. A sewer dump station is located near the park exit. Camping check-in and check-out time is 1 p.m. The campground is open year round. Please note: Maximum stay limit is 14 days. Visit the reservation website.  click here >> Washington Park The boat launch at Washington Park was developed and is maintained for the specific use of recreational boaters. Boat launch parking is $9/day and boaters may stay a maximum of 14 days. The two lane launch ramp is suitable for all trailer-able boats, power or sail.  You may not overnight at dock, but may anchor nearby. Ramp is a short walk to campground.

• Deception Pass State Park - roughly ten miles south of Anacortes.  It is important to note some of the differences between Washington Park and Deception Pass Park.  While Deception Pass camp sites exceed three hundred in three different campgrounds, none are walking distance to the four lane boat ramp at Cornet Bay. However the modern well designed boat ramp claims to have two thousand feet of side tie moorage and overnight at the dock for up to three nights is allowed. Anchoring close by is simple and free. The ramp parking lot is massive and long term is allowed for a fee.

Four lane all tide - Cornet Bay ramp at Deception Pass Park is open 24/7

Lastly, Those putting in at Washington Park will be much closer to the inner island area after simply crossing Rosario Strait, but those putting in at Cornet Bay will have to deal with the pass and a longer run up Rosario or an even longer run through Swinomish Channel.  These are not insignificant differences and should be well considered according to your overall plan before making your decision.

On the Islands:

• Odlin County Park on Lopez Island

Odlin park has thirty one campsites and reservations are a good idea.  The boat ramp is sub parr at best and is not suitable for anything but a small skiff and a four wheel drive. There is no ramp dock and best used at high tide only. The ramp is a short walk to the campground.

• San Juan County Park on San Juan Island

San Juan park is very similar to Odlin park with twenty six sites, they also take reservations.

The boat ramp is also sub parr and should only be considered for skiffs being hauled with four wheel drives, again the ramp is in the park and there is no float.

• Moran State Park on Orcas Island is a State Park as is Deception Pass. They boast over one hundred campsites, some suitable for RV's.  Moran park is not ocean front and does not have a salt water ramp, however it is only five miles to the county boat ramp at Obstruction Pass.

          A private park alternative on Orcas Island is West Beach Resort in Eastsound, they have         camping, docks and a boat ramp, suitable for skiffs and four wheel drives.

• San Juan Island:  If you take your skiff to San Juan Island and stay at a private residence, rental or hotel you can put the boat in at Jackson Beach day use park. The ramp is well designed, has parking and a dock. Jackson Beach is about two miles from Friday Harbor.

Ferry's and trailers:
        Don't forget to check the ferry schedules and fares, hauling trailers on the ferry can get expensive and frustrating - very few do it!

My recommendation for mainland camping is that you get a reservation and camp at Washington Park, 

the run time to Friday Harbor is under an hour, the entire San Juan area will be at your door.

First Timers Guide to the San Juan's

Matia Island

 

  From time to time I refresh my thinking and remember our first visit more than twenty years ago. Specifically what a pain it was not knowing the simplest answers to questions many of us take for granted today. This post is written to help new cruisers headed to the San Juan's needing the same simple answers we needed.

     I define the San Juan cruising area not by county or even country, but rather by places we want to visit and spend some time. But that also means, places we have the capability to get to without too much effort or time.  So that being stated, I think of Port Townsend and Deception Pass Park (Cornet Bay), and Swinomish Channel as our loosely defined southern boundary.  I think of Vancouver BC and Nanaimo as our northern most point, and everything in between Vancouver Island and the mainland completing the east west box. Keep in mind, with a day or two extra, you can run down to Olympia or up to Princess Louisa Inlet, but for this discussion, we are sticking to the core San Juan Island area and what you need to get there.

Basics

• You need a boat, but you can rent a sail or powerboat in Anacortes or Bellingham if you prefer, and it doesn't take much experience to qualify.

• Size matters, bigger is more comfy, costly and feels imminently safer in a storm. As size goes up, so do your skill requirements. Once past about thirty five feet you will find you don't fit at some docks and fuel burns at over twenty five gallons an hour. Smaller is  better at times. Eighteen foot ski and fishing boats or day sailors are very easy to get in and out at virtually all places but with all your food and gear, you will be crowded on board.  Above all - don't let your lack of a perfect boat cause you not to go. Take what you have, you can make it work.

• Bring a dinghy, even a two person inflatable kayak is okay.  You need a way to get to shore where there are no docks. You don't have to carry the dinghy on board, you can tow it everywhere you go. Yes you can beach your runabout and let the tide leave you dry but bringing a dinghy is so much easier.

• Sleep on board, at anchor, at the dock, or in the many park campgrounds. (there are about twenty marine campgrounds, you can camp at a different park every night) If preferred, you can spend every night at a marina or resort and sleep on shore.

• The best weather will be in July and August, but the shoulder seasons have less people and okay weather too.

• I suggest you plan a week, but you can make a weekend work.  If you have a comfortable all weather boat, spend the summer.

• If you rent, don't forget you have to park your car(s) If you trailer, plan on a daily parking fee of around $12.  (Squalicum Harbor in Bellingham is free, even long term)

• See this posting for launch ramps. ---launch ramps with long term parking  This is probably the only real planning decision you need to make before you go, but we have changed our planned take off point as we drove up the highway.  Do not start your San Juan cruise down south in Olympia, Seattle or Everett or Port Townsend or Port Angeles. If you do you will spend much of your time motoring long distances (both ways) My advice is to start in Bellingham or Anacortes using one of the ramps from the list above.

• You need with you on the boat, a chart, or you will get lost, count on it. You should have a list of parks, marinas and resources preferably marked on your navigation chart. Get this chart. Noaa # 18421  -  We use noaa chart # 18421 you can see it by clicking here or anywhere charts are sold.  Navigation charts do not show what's on shore, (roads, city's, marinas, parks, etc) so we carry a highway map as well.

• Don't run out and buy an expensive chart plotter. At minimum, you need a paper chart, a  portable GPS and a compass, your smart phone will probably do.  All boats need a depth sounder or you are risking an expensive grounding.

• Sample itinerary:  #1. Begin at Squalicum Harbor in Bellingham (open 24/7).  2. Head for Friday Harbor and get a slip for your first night or every night (they take reservations).  3. Use Friday Harbor as your base, returning every night to your own slip with power, water, restrooms, on shore restaurants and entertainment. This plan will work for virtually all boaters regardless of  gear, experience or creature comfort requirements. None of the Marine State Parks have reserve-able docks or anchor buoys, everything is first come first gets it. This means you should plan on anchoring and using your dinghy,  it also means when someone pulls out you may grab the spot at the dock. Rafting is the term  used when several boats tie together at anchor or the dock.

• Sample itinerary:  #2. Begin at Squalicum again but this time head for Matia or Sucia. Next, Jump over to Stuart and then Roche Harbor or Jones, then to Friday Harbor, then Fisherman Bay. This itinerary will make sure you have a shower and food store available (Roche and Friday) when you really need and want both.  

• Fuel is readily available but you should try to have a minimum range of seventy five miles just to be sure should you encounter adverse conditions.

• How many days you spend at each park is up to you, your car and trailer will be waiting in the free parking lot when you circle back to Bellingham.

• Get my San Juan Islands Cruise Guide, it  has all the parks, marinas, fuel, resources, phone numbers, etc. and is written specifically for visitors coming by boat. My companion book, the San Juan Islands Travel Guide is written for visitors coming by car or boat.

              San Juan Islands Cruise Guide     -----   San Juan Islands Travel Guide

         Don't be cheap, the books cost less than a meal and will pay for themselves in saved frustration,  making your cruise a real success.

• Lastly, I can't address everything you may want to know in a single post, so I suggest you search this site and read some more articles. There are several with detailed day by day itineraries. Next, after becoming more knowledgeable about what and where you want to go and do, set aside a week and go. It really is that easy. The central cruising area is small enough that you can completely change your plans on the fly. You don't need reservations, you don't need a plan, you don't even need to bring food, just grab your gear and boat and hit the road. OH - bring some cash for, fuel and park fees and that food I just said you don't need.

If you happen to see us on Kraken somewhere, please say hello. We hope to be anchored in Fisherman Bay for the Lopez Island 2019 4th of July show.

John and Linda
              feel free to use the e-mail contact form with your questions

Fast Track to the San Juan's and Patos Island State Park

In keeping with this sites purpose to help newcomers get to the San Juan's, you will find listed below selected posts and links.

These posts are the bare essentials needed to get you off on that trip to the San Juan's, the rest is up to you. (click on the links)

1. Where to launch your boat and park your rig!
• Where to Launch your boat and park your rig
• First choice = Bellingham - (Squalicum Harbor)
• Close runner up = Deception Pass State Park (Cornet Bay)
• La Conner city ramp (Swinomish Channel)
• Washington Park - Anacortes
• Cap Sante - Anacortes (sling only)
2. Suggested Itinerary!
• Suggested Itinerary
3. All the Parks with complete descriptions and chart snips!
• All the parks with chart snips
4. Rent if you don't have a boat!
• Rent a boat in Bellingham or Anacortes
5. 12 fuel docks- marinas - resorts - you should know about before you take off into the unknown!
• 12 Places you should know about

Is this all you need?

Of course not, but if you are a competent boater, the above posts will answer many questions you want answered.

Patos Island Anchorage

Did you know you can ask silly questions? Use the e-mail box on the left side somewhere.

Marine Parks of the San Juan Islands and Surrounding Area

Below is the marine parks list
             followed by reviews, charts, and pictures
                         in the order listed.
        This is not all the parks, just the ones you may want to make part of your cruising. It's unlikely you can visit all in one trip and still do a decent job of sightseeing. You should plan multiple visits to the San Juans.
Many people choose Jones as their favorite for just hanging for a few days, so Jones is first.
For hiking, Sucia, or Pelican Beach on Cypress Island are the best, but all the parks have hiking trails.
      Some parks are in a convenient location when you need to spend the night and you're between destinations, Saddle Bag, Eagle Harbor, and Odlin would fit this description.  Most parks with docks have picnic tables on the floats, which are very handy for extending your living area, socializing, and meeting other boaters.
        For marinas/etc. where you can get fuel and provisions try this list >> Marinas - fuel - beer and ice - slips for rent

• Jones Island
• James Island
• Clark Island
• Doe Island
• Obstruction Pass
• Pelican Beach
• Eagle Harbor
• Cypress Head
• Matia
• Patos
• Sucia
• Stuart Island  (Prevost & Reid Harbor)
• Spencer Spit
• Odlin County Park
• Washington Park
• Deception Pass Park
• Saddlebag Island
• Sidney Spit Marine Park (Canada)

Click here to go to complete description and maps of above listed parks

Ten Best Parks of the San Juan Islands

      Picking the best of anything is asking for an argument but I thought folks planning a visit would benefit from the discussion.

     Let's start by listing my choices in order of best first, first because they have overnight docks,  followed by some pros and cons and a few real world comments.  (hopefully I haven't omitted your favorite)  Keep in mind, we go to all the parks and don't dislike any but  there is no doubt some parks are five star and some are not depending on what we are doing or the weather during that particular cruise.

     For a more detailed review of the San Juan area marine parks including maps try this post.  marine parks

• parks with docks

• Jones Island   
• Matia
• Fossil Bay on Sucia 
• James Island
• Stuart Island  (Prevost & Reid Harbor)
• Sharpe Cove and Cornet Bay at Deception Pass

• parks without docks

• Saddlebag Island
• Pelican Beach
• Turn Island
• Eagle Harbor
• Cypress Head
• Patos
• Sucia   (Echo and Shallow bays)
• Spencer Spit
• Odlin County Park  (has 2 hr dock)
• Clark Island
• Doe Island
• Obstruction Pass
• Sidney Spit Marine Park (Canada) (has overnight dock)
• Washington Park  (launching ramp only dock)
• San Juan County Park
• Shaw Island Park
1. Jones Island is my number one choice and here's why.

                Pros:

• bigger but not biggest dock
• protected bay 
• great dinghy beach with a couple tidepools
• anchor buoys and lots of room to anchor
• running water and four nice nearby composters
• hiking the many loop trails at Jones never gets boring
• tiny deer, many tame, are unique to Jones
• dock is very close to camp sites for evening fires
• close to Deer Harbor for supplies

                Cons:

• crowds sometimes
• long ways back to the mainland
• open to north wind
• no bicycle trails

     2.   Matia Island never disappoints us.

             Pros:

• very small intimate dock for four boats
• usually room when we arrive
• small protected bay holds about four more boats
• great gravel beach
• multiple coves for beachcombing
• puffins, seals and eagles and great sunsets
• unique rain forest one mile or less loop trail
• somewhat close to Squalicum Harbor (2-3 hours)
• restroom at top of gangplank
• Matia is a peaceful quiet special place

click here for the rest

Cruise the San Juan Islands – Sample Itinerary, Trip Plan, Info Guide

      Talk to ten San Juan Island cruisers and you will get ten different answers to the question, "What's the best place to go or thing to do in the San Juan's."   Each will be correct, mostly. To support their answers, they will offer first-hand exciting personal experiences.  That is why you must gather the best information, inject your wants and quirks, and then chart your own course to the San Juan's.  

Our experiences and local knowledge have been earned the old-fashioned way – one cruise at a time. Sailing, hiking, biking and gunkholing, all while immersed in nature has been our reward. 

     This website is a compilation of our travels in five sailboats and two trawlers spanning over two decades.

     Along the way we published a cruising guide, “San Juan Islands Cruise Guide,” followed later with a Land and Sea Guidebook, “San Juan Islands Travel Guide.”  My goal for this website and these books is to help boaters, travelers, sailors, and families enjoy the good times we have enjoyed for many years.

     What is the best five-day itinerary?  That's like asking what's the best color.  But there are certain things that our experience and local knowledge will help with.  Sometimes, one just needs a little push in the right direction to get on the right tack, so to speak.  It is impossible in an essay or article to cover everything important to everybody or all the possible places to go.  However, this website does cover every state park, every county park, every public dock, and much much more.  You will find many links to pictures and specific posts, all composed for San Juan Island boaters.  Be sure, while reading to click the links and follow your interests. Be sure to use the search box at the top of this page on the left side.

You're invited!

     To help you muddle through this dilemma and provide some interesting reading, please come along with us on our summer cruise in the San Juan Islands.  Of course, you will be taking your own boat since ours is full.  

     Today, we use our laptop as a chart plotter, I only use the GPS function. The program was free online Free chart plotter software but I had to buy a USB antenna for $19.95.  You can get by with a small handheld GPS or even your cell phone but I enjoy the big screen.   I don't want you to get lost if we get separated, or your battery is dead, so you should pick up a paper chart and a compass.   chart #18421 I carry a colorful roadmap with us as well.

    Let's get on the same page and assume this is your first boat trip to the San Juan's, and you are in a trailerable sailboat with a 5-6 mph speed.  There are five or six starting points we have used but only three are preferred.  They are Cornet Bay in Deception Pass, Cap Sante in Anacortes or Squalicum Harbor in Bellingham.  If you have a fast powerboat or are coming up from the Seattle direction you will want to make time and distance adjustments.  We will plan to sleep on board but use bathrooms on shore. Okay, let's go. ----- We have narrowed it down to about twenty parks to choose from for the first night, and that's not counting the marinas at Friday Harbor, Roche Harbor, or Rosario.   Not to worry, I have a plan >>>  all the parks and then some

      Sometimes when we plan a vacation trip to the San Juan's,  we try to make a great circle route because it saves time and resources. But this time we're going to decide where we go, as we go. We will see how that non-plan works out.  Certain people on the boat have expressed a desire for hot showers, I guess we will see how that works out too. Since we may travel all the way across the San Juan's and back, your boat will need a minimum 75-mile range. Fuel is readily available everywhere but smart skippers figure one-third of the miles out, one-third back, and a third as a cushion.  If your fuel tank is a little small you can tie a five-gallon can on deck.  Knowing you have reserve fuel will ease anxious thoughts and ensure you have a great visit.  Shall we also assume that you have a seaworthy vessel with all safety gear?  If not, correct it before we head out, or stay home.  Life jackets for all

Plan as we go itinerary:

Cornet Bay Launch Ramps

        Let's begin at Cornet Bay in Deception Pass Park.  However, after reading this post, I suggest that you search this website and check out the other launch locations. Some may fit your plans better. launch points Also, search the other parks and marinas and things to do.  It is easy to overlook a great place or mini adventure that will make your cruise the best of all.  I chose to launch at Cornet Bay this time because I really enjoy the pass scenery.  The dock and the long-term parking are ideal.  Plus being able to take off or return from both directions 24/7 opens up even more possibilities when not having a firm plan. If I was heading for the Sucia area first off, I may have chosen Squalicum Harbor in Bellingham but where we end the cruise may dictate where to begin.

Read the rest?

16 public floats and docks you should know about in the San Juan's

          Obstruction Pass           Blakely's                   Deer Harbor          Roche Harbor                 

          Friday Harbor               Jackson Beach           Hunter Bay           Prevost Harbor

          Washington Park           La Conner                 Eastsound             Odlin Park

          West Sound                   English Camp           Orcas Landing      Olga

     When visiting the San Juan's many of us  head for the great marine state parks and for good reason, that's where the floats, campgrounds and amenities are located that vacationers desire.

   

    However,  if you want to get off the boat and see something other than campers and boat people you have two choices. #1 dinghy ashore somewhere or #2 find a public dock and head out.  This list and description of San Juan area docks excludes the state parks because most marine state parks are landlocked or waterlocked leaving visitors with no opportunity to explore beyond the park.

Sixteen  public docks organized and listed in no particular order.

     Obstruction Pass, this county float and boat ramp is located just inside Obstruction Pass on the southern tip of Orcas Island.  Nearby pass traffic wakes make this a punishing place to tie up even for just the two hours allowed, however rendezvousing with friends on shore or heading out on bicycles for a strenuous ride to the top of mount Constitution may be just what's needed to round out a perfect cruise. Tip: For longer visits, anchor nearby after dropping off passengers and bikes, then drag dinghy up onto float or shore. Your boat will thank you when you return.

Obstruction Pass county dock in red circle at top
Blakely's at bottom

     Blakely's is a conveniently located fuel dock about halfway between everywhere we go in the San Juan's. They are just inside Peavine Pass on Blake Island. On shore is a small store and deli bar famous for ice cream cones to savor on the lush waterfront lawns. Grazing deer share the lawn so watch your step. The dock is rather long with plenty of room on both sides to tie up big and little yachts and still not interfere with those getting fuel. They offer overnight marina slips in a very protected tiny cove. The island and roads are private so boaters may not leave the resort property.

Fuel and store dock at Blakelys is long and you may tie up on either side to avoid wind or current issues.

     Deer Harbor,  on the west end of Orcas Island at the end of the road is diminutive Deer Harbor community and  marina.  You may purchase fuel and snacks, get ice and rent a slip. The county dock is actually the same dock as the fuel float. Simply tie up out of the way just past the fuel dispenser.  The county section is painted yellow and accommodates several runabouts or one large yacht. This is an excellent jump off point for kayakers heading for Jones Island or dropping off people catching the San Juan Transit mini bus. The bay out front is calm and rogue wakes are few, anchoring room is abundant, restrooms, showers and laundry are on wharf.

If you squint, looking under the main wharf at Deer Harbor, you can see the yellow painted county dock.

Where are the Public Boat Ramps in the San Juans - just the basics to get your boat in the water

      Buried in this website are itineraries, helpful hints and everything you need to get going to the San Juans.

         And that's the problem, it's buried.


Some of us don't need anything but to be pointed to the boat ramp.


This post points the way.
BOAT RAMPS TO THE SAN JUANS   << hot link, clickety click!


Should you take your boat trailer on the ferry and get off somewhere?  NO! - I don't recommend it unless you are going to a resort that has a ramp and you plan to rent a cabin -- plan on spending substantial time waiting in  ferry lines.  Be forewarned, some so-called local ramps are simply sandy beaches with no docks. Plus the ferry rates for trailers - ouch.

If you carry kayaks on the roof, riding a ferry makes good sense.  My #1 suggestion for kayakers that don't want to paddle across Rosario Strait -- go to Deer Harbor on Orcas Island, park your car and paddle two miles to Jones Island for a night or two camping.

Let's say you carry a kayak on the roof or trailer a day-sailer and plan on camping on shore, and you don't want to deal with ferries - do this.  Drive to Washington Park in Anacortes, (campground and ramp) set up your camp, splash your boat and sail or paddle to either Pelican Beach on Cypress or Saddlebag Island.  Spend the night or come back each evening.  Using the currents, you can avoid difficult paddling or  fluky sailing if that's what works for you.

Hint, use the search box and search Saddlebag or Cypress or Pelican Beach or Deer Harbor, or Jones.

Public ramps with floats and parking open 24/7

Step by Step guide and Itinerary for making that Dream Boat Trip to the San Juan Islands

     This cruise itinerary is for the first timer with the boat on a trailer. The novice skipper with family for crew will find this article contains just what's needed to get going on that long talked about trip to the San Juans. While this is a step by step action plan to follow, some skippers do not need all the steps and prodding and so they should skip ahead to      Day #1.  for the daily itinerary  

For the rest of us, these steps are important, so I've numbered them.
  Before you go

1. Right now, go put two marks on the calendar. Mark the day of departure from home and one week or so later mark the day your returning. Do it now or forever hold your peace and admit your not really going boat camping in the San Juans.
2. Go to your local chandlery or go online and purchase a big color map or chart of the San Juans. I'm not telling you which one, it doesn't matter, just big and one you like to look at.
3. Got the map? Good now nail it to the wall where you can see it all the time. Do it now!  OK, the hardest part is over, you have now made a commitment to yourself and crew. Your really going.  Kick back a little, relax, do some day dreaming.  Your trip (cruise, vacation, what ever you want to call it) is already well underway. By now you should be  getting into the  excitement that comes with planning and preparations.    Note:   Don't let worry and stress build up, your really going to enjoy this outing and it will be easy, trust me  (heh, heh, heh)  Relaxing good times should be part of the  process that started when you made the X on the calendar. Remember, on this cruise there are no deadlines to meet, no times to beat, no "sorry no vacancy's" to worry about. You are on your own schedule to do as you please. What could be better besides a gourmet chef and staff.  Study the map with your crew, locate Friday Harbor, Jones Island, and Squalicum Harbor in Bellingham. Do some internet searches, read peoples reviews.
4. Start compiling a list of supply's and provisions that you think you need. Click here for help with that list >>  Cruisers Packing List this list may be a little too much, so pick and choose.
5. Start making a list of boat and trailer, must do's (like greasing the wheel bearings) I mention wheel bearings because there are a few "must do's" that will potentially ruin your plans, having a bearing go out from your neglect is avoidable, so are boat motor issues. We once went with an untested, worrisome diesel motor, and sure enough it quit, but because of suspected problems I had mounted an outboard bracket and brought my trusty 7.5 hp Honda along which not only saved the trip, but allowed us to extend it a few days.  Another time with a different boat I towed a dinghy which sole purpose was to carry a spare outboard just in case.   Another mistake not to make is inadequate packing for inclement weather, (hope for warm sunny days, but plan for cold windy rain).  Don't forget seasickness pills (Dramamine)  or other medication, one persons needs could ruin the trip. There must some other must do's that are particular to your family??? Spare tire for trailer! Hmm!
6.  #5 was a downer, lets lighten up.  You need to bring an ice chest if your boat has none, maybe two, plan on ice lasting 3-4 days and then resupply time.  For a food menu, you should plan to eat well, especially if you have bad weather when hot food hits the spot and improves spirits. Sandwiches are easy to prepare and bring lots of trail mix and snacks.  You will need lots of water, don't plan on any being available once you shove off. We bring our water in 5 gallon jugs and pour it into smaller bottles
7. You will need a propane cook stove and fuel bottles to last entire trip (propane is $7+ in the islands)
8. Garbage:  I need to mention it now after suggesting you bring all the junk food.  Your little boat will quickly become overrun with trash, bring bags, the outside islands have no garbage service. Think about all that convenience food packaging material I just told you to bring.  Some of the packaging may be left at home. Prepare things in advance and freeze meals ready to go as they thaw (2-4 days in ice chest)
9. Under boat equipment, the list is very subjective so lets just list a few must haves.  PFD's all around and all coastie required equipment (whistle, type 4, fire ext., registration, lights, etc) Plus I think you need a minimum of two anchors and extra rode, extra fuel if your tank is small.  Your boat should have a range of 75 miles. The rule is 1/3 outbound, 1/3 to get back, 1/3 for reserve. It could be 25 miles between fuel stops, so a 75 mile range gives a good cushion. Many boaters simply tie 5 gallon jugs on deck.  If your boat is open and it really rains hard, bring a tarp and ropes to lash it down. You may sleep on shore so a tent is needed. You need a hand bilge pump and a bucket (they look like a big suction tube and flex hose.
10. Bring a GPS,  You can get by without one but they are fun and really are useful. Some phones have apps available. Bring your cell phone (they work good almost everywhere) Bring the map or chart nailed on the wall or better yet go buy a real navigation chart with depths and rocks all located.  Bring a compass (hand held is OK) Bring a vhf marine radio (you can buy a portable battery one for about $100.   
11. The boats loaded your ready to go. Don't forget to tell someone where your going, and when to call for help if you don't check in as planned. That person could be a friend or relative that doesn't panic over  icky weather reports.  They should call the San Juan County Sheriff or Coast Guard if needed, or someone you have prearranged to call, 911 works too. Remember, your plans may change as the week progresses, but you can check in with a cell phone call most of the time.

Time to go 

The blue line indicates general route, red dots are overnight stops. 80 miles

Squalicum Harbor Marina - red dots = boat ramp, restaurant, showers, parking, guest docks

1.   Day #1  Your destination is Squalicum Harbor in Bellingham. (not Anacortes) Squalicum has the best boat ramp around, and free long term parking for your trailer and tow rig. Cap Sante in Anacortes has a sling and pay to park.  You can arrive and take right off but I would plan to spend the first night at the guest dock or in your parked rig. Do not cast off unless you are sure you will have enough light to make it to your anchorage or marina. Navigating in the dark is risky business and requires more of you than you bargain for, and may easily become a really stressed vacation.  Its still daylight until around 9pm, so if you arrive around  6pm there is plenty of time to get the boat launched, go shopping, eat in a restaurant, hang out.  The marina has bathrooms, showers, lots and lots of parking.  If your the worrier on this trip and need to talk to people, you can call them during regular business hours.  The launch fee and guest dock payments are made at a self serve kiosk, you could arrive at midnight, its a 24 hour deal.  No stress, just show with your boat.
2.   Day #2   In the morning, you can eat at the restaurant overlooking the marina next to the bathrooms, (the food is good and priced right) jump in the car and run to Walmart or just cast off at sun up. I like to walk around and talk to other boaters coffee cup in hand.
3. Your destination is Echo Bay at Sucia Island, its about 20 miles so you will have plenty of time even if you hang around Squalacum until early afternoon.   If you get there a little earlier you will have time to hike and explore, or maybe first go to Fossil bay where you may get a spot at the dock.  Of course tying up to an anchor buoy or the dock requires a fee whereas                                                                                   anchoring is free.

4. 

   Sucia Island with Echo Bay and Fossil Bay marked with red dots

5.   Day #3   On this day you may want to stick around Sucia for some exploring, fishing, or kayaking if it suits you. You could easily spend several days just hiking.  
6. Lets up anchor at noon, our destination is Jones Island, a distance of only 12 miles.  On the way to Jones you may want or need to stop at West Beach resort/marina on Orcas.  West beach is right on the way and wont add much time or distance to this leg.  At West Beach you can get fuel, waffle ice cream cones, ice and groceries. West Beach is just past Point Doughty on Orcas (check your chart/map and find pt Doughty) Did you bring binoculars, they will be helpful in spotting some far off places across the water and West Beach is one of those places? Once again, like Sucia, if you get to Jones early you may get a space at the dock, but you can always snag a buoy or anchor for free. Jones is pretty small but about perfect, you can beach comb, explore, kayak or hike trails, circling the island in about an hour.
7. Jones Island
   

   

   Jones Island

8. Plan to stay a day or two at Jones it could easily be your favorite stop, it is mine.
9.   Day #4   But it could be day 5 or 6 if your getting into the boat traveling thing.
10. Once again there is no need to take off early, but by now you may have noticed that currents play a big roll in passage times, and fuel used. I check my current charts and then ignore them mostly, but at least I know what to expect. Leave Jones Island in your wake and set course for Friday Harbor, no need to rush, its only 5 miles and they never turn boaters away. You can make a reservation for a slip in advance but there really is no need and its nice to not have a rigid schedule.  You can also just stop by for a few hours for free and walk around town, buy souvenirs and provisions and then move on.  I recommend on your first trip that you spend the night at Friday Harbor, visit the Whale Museum, hang around town and waterfront goings on, eat at the many places, and above all by now you will be wanting a shower, which is available right on the docks.  When you arrive near the breakwater, you can call the Harbormaster on the radio or use your cell phone, or simply tie up at the outer dock, sometimes they have a little harbormaster shed office out on the end and you can talk across the water.  It's all very simple and low key, even after hours  when the security people will take care of you. One visit we rented a slip for two nights while we bicycled around San Juan Island.
11. Friday harbor 

    

    Friday Harbor 

12.   Day #5    Check out time is after lunch sometime so again, no rush. Set course for Rosario in East Sound on Orcas Island.  The distance is about 11 miles and you may end up with a modest current either for or against your plans, you may want to arrange your transit according to favorable currents.  See current guide info right here  >> Current Atlas  <<    Around Friday Harbor is a lot of boat traffic and you will see more than one ferry for sure, don't worry, just use your common sense.  On your way to Rosario you may want to take a little side trip over to Olga for a short stop over at the public dock, (Olga is also on Orcas just south of Rosario) when you get to Rosario you will be able rent a slip, hang on a buoy or anchor out. Rosario resort has some nice grounds, restaurants, provision store, fuel, and tours of the Mansion turned museum. Because you will probably have time to kill I would seriously consider showing up later in the day or making your visit a two hour stop over and then move on to another stop for the night.
13. Rosario picture 

    

    Rosario (Mansion/Museum is in lower left, marina restaurant at top

14. An alternate stop would be past Rosario at East Sound where they have a public dock.
15. Another alternate stop just a little further, but heading more toward your car at Squalicum would be Pelican Beach on Cypress Island.  Pictorial  >> Pelican Beach pictorial  << Pelican Beach has about 4 or 5 buoys and we have always been able to squeeze in and anchor.  In a pinch you can run half a mile down to Eagle Harbor where they have 18 or so buoys. BTW Cypress is DNR land so everything is free (no buoy or camping fees) If your into hiking this is probably the best around. The beach is a favorite for kayakers from Bellingham and Anacortes, expect to enjoy good conversation around the many campfires lining the beach.
16. Pelican Beach map here  

    

    Pelican Beach on northeast end of Cypress Island

    
    
17.   Day #6   Today's destination is Squalicum Harbor and head for home. Its about 15 miles so it will take a some time.  By now you should have a pretty good idea of your boats ability to get around and deal with wind and currents. Bellingham Bay seems to go on forever, especially when the elements are lined up against you. 
18. If you have time for a quick lunch stop on the way, you should really consider dropping hook in Inati Bay on Lummi Island
19. Inati bay map 

    

    Inati Bay on southeast side of Lummi Island

20.   Plan your departure from Cypress so you arrive back at Squalicum with time to load up and head for home, or I recommend you plan one more night on the boat at the visitor/guest docks at Squalicum Harbor.  This way you will be showered, fed and refreshed in the morning and have the whole day to load up and drive towards home. In my opinion driving home in the dark after a long last day of boating is no way to wind up a relaxing vacation.

That's it

• I hope I was able to give you the incentive, motivation and pertinent information to get going on that first trip to the San Juan Islands.  My recommendations are by no means all that there is to see and do. Please do some research and modify my suggestions to suit your situation, for instance it is entirely possible to stay at resorts and eat in restaurants every night. The more budget minded may choose to anchor out everywhere.  (yes you can anchor next to the docks at Friday Harbor and then paddle over to their dinghy dock, no charge) You may also start and end at Cap Sante, La Conner, Deception Pass, or even start out far far south in Olympia like we did once.