Member Success Story: Saving $1,500+ on Bucket-List Girls’ Trip Through the San Juan Islands!

by Kelly Green | Aug 22, 2023 | Member Success Stories
Two women boarding a small plane and sitting at an outdoor table. Text: Success story for member Kelly, $1,500+ saved! On a girls’ trip to San Juan Islands! Logos: Travel Freely and airplane icon.

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Welcome to another inspirational success story with Travel Freely member, Kelly! Along with her husband and two teenage daughters, Kelly has been harnessing the power of points and miles for free travel for the past six years. From exploring the Pacific Northwest to wandering through Rome, Italy, Kelly and her family have been on numerous adventures, making the most of their points. Today, we delve into one of her most enjoyable escapades – a summer getaway to the San Juan Islands in Washington State, a trip that was as cost-effective as it was unforgettable. Let’s dive in and explore how Kelly turned her miles into memorable moments! Psst… Have you seen our latest points & miles update? Click here to unlock your dream vacation like Kelly.

Tell us a bit about yourself. How long have you been using points and miles towards free travel?

My name is Kelly and I live in Maryland with my husband and two teenage daughters. I have been using miles and points for free travel for about six years now. Our first year in this hobby, we booked trips to the Pacific Northwest and Rome, Italy almost entirely on points for our family of four. And we’ve been exploring much of the U.S. and the occasional overseas trip this way ever since.  Two people smiling in a tandem kayak on a sunny day. The person in front wears sunglasses and a green cap, while the person in back waves, wearing a straw hat and gloves. A canoeist is visible in the background on the lake. Please tell us about your trip. Where did you go? These days, my girls compete in travel sports and it’s hard to find time for my family to get away for fun, especially altogether. So, I carved out some time to travel with one of my dearest friends to a bucket-list destination – a kayaking trip through the San Juan Islands in Washington State. An archipelago off the coast of the U.S. Pacific Northwest, the San Juan Islands are known for their pristine natural beauty and abundant wildlife – think seals, orcas, harbor porpoises, bald eagles. We chose a highly regarded outfitter (Discovery Sea Kayaks) to lead us on a 3-day kayaking tour so we could not only enjoy ideal weather but also tack on a bioluminescent tour. The image shows a serene sunset over a calm body of water, with the sun casting a golden reflection on the surface. A silhouette of a tree is in the foreground, and distant hills are visible under the hazy sky. We spent our days kayaking the Salish Sea and camped overnight on Jones and Stuart Islands in primitive campsites. All food/drink and kayaking/camping equipment was included. The weather was outstanding and the views were gorgeous! Kelly tent camping

How much money did you save by using points and miles for your trip?

We saved $1,500 on this trip by using miles and points! I live on the East Coast so booking this trip required loads of logistical planning (fortunately, both Heather and I get a thrill from challenging itineraries!). Heather had Southwest points and a companion pass so she covered our roundtrip flights from BWI to SEA (approximately $1,100) and I covered the hotels. With taxes and fees, the Hampton Inn Seattle Airport hotel should have cost us around $400 for two nights.  Two women smiling and posing in front of a maroon van with Discovery Sea Kayaks written on the side. They are dressed casually and appear to be outdoors, with a wooden building and trees in the background. Because this was a once-in-a-lifetime experience for us, we did have to spend some cash but we did so as wisely as we could. Our tour cost $689/person for 3 days and included all meals, equipment and lodging. To pay for this and my bioluminescence tour ($143/person), I used my husband’s Citi Premier® Card (this card is no longer available) as he was working on achieving his minimum spend requirement at the time of purchase.  A person in a yellow life jacket is kayaking on a calm body of water. In the background, a dog is standing on a cluster of rocks. The shoreline with dense trees is visible in the distance under a clear sky. To maximize our experience (and because we had a tight timeline), we flew Kenmore airlines (an approx. 35 min flight) from Seattle-Boeing Field to Friday Harbor airport. We spent about $363 total for the two of us to fly which was a splurge but the ride and the views of Seattle and Puget Sound were totally worth it. My seat was directly behind the pilot which was SO cool! Heather purchased our tickets with her Chase Sapphire Preferred® card (she then used her accumulated Ultimate Rewards points toward her family trip to the Smokey Mountains a few weeks later). 
View from inside a small aircraft cockpit showing a pilot in uniform flying towards a runway for landing. The dashboard shows various controls and displays, while the runway extends through a grassy field under an overcast sky.

Landing at Friday Harbor

Accommodations on San Juan Island are mainly boutique hotels and B&Bs so I covered the cost of our Friday Harbor hotel (The Earthbox Inn & Spa) using my Chase Sapphire Preferred card (and applying accumulated points toward hotel stays in New England the following week.) We also used our Chase Sapphire Preferred cards to cover Ubers/Uber Eats delivery while staying in Seattle (which totaled about $100 between us.) To get back to Seattle from Friday Harbor after our tour was complete, we took the FRS Clipper, a high speed boat that takes you through the Puget Sound. This mode of transport is quicker than the Anacortes ferry/drive back Seattle. And BONUS – we were able to see an orca pod from the deck of the ship! Watching them breach with a view of Mount Baker in the background was absolutely priceless. As a transportation cost, I was again able to use my Chase Sapphire Preferred card to book our seats (total $130), earning 2x points on this expense.

What kind of points did you use for this trip?

We used approximately 35,000 Southwest miles for flights, a stash my friend was more than eager to use since she had stored them up for a fun trip. She also has a companion pass good through this year and covered my flight using that. My tickets were $11.20 total. I used 37,000 Hilton Honors points per night for the two nights we stayed at the Hampton Inn Seattle Airport, points I had accumulated from my American Express Hilton Honors Surpass card. Our rate included free breakfast and a free shuttle to and from the Seattle-Tacoma (Sea-Tac) International airport. Two women sitting at a table on a waterfront balcony, smiling at the camera. They have drinks and napkins on the table. In the background, numerous boats are docked at a marina, and theres a scenic view of the water and distant trees.

What advice would you give to someone who is interested in using points and miles to book a trip like yours?

Be realistic with your money-saving expectations. I knew that even with miles and points, this trip was special and would still require some out of pocket cost. As I booked my itinerary, my husband and I jokingly said this would be my birthday gift for a few years to come! That said, I made sure I put my out-of-pocket expenses to use. Any cash purchases I made, I did so thoughtfully and with additional travel in mind. A week later, my family took a trip to an area MANY folks were visiting this summer – Acadia National Park in Maine. Using Chase Ultimate Reward Points I had accumulated through this trip, I was able to book accommodations on Mount Desert Island, ME, solely through points at a time when finding and booking hotel rooms for less than $500/night was not possible. Make your purchases count! 👉 Inspired by Kelly’s story? Start tracking your cards with Travel Freely today – it’s free, beginner-friendly, and built to make stories like this possible. Have a success story you’d like to share? We’d love to hear it! Reach out to us at or fill out our form here. Cards used for this trip: