Plans Are Being Made


I ♥ travel planning! The challenge of scoring a good airfare or getting a great hotel room at a fabulous price or arranging ground transportation and activities – all the necessary pieces to creating a solid foundation for a fantastic trip – is immensely fun for me.

So, with WenYu heading off to college in Massachusetts in just four months, I am heading  once again into the throes of travel planning because, besides making sure WenYu is safely settled in with all her stuff, I’ve been encouraged to add a couple of extras to the itinerary.

One of my dearest friends from our navy days lives in Bath, Maine, and given that I will be so close I am hoping to head up her way for two or three days for a visit (another dearest friend from our navy days used to live in Maine and I so, so wish she were still there to visit too). If we can work out our schedules, I will most likely take the train up to Portland from Boston – it’s very affordable.

After my time in New England, I will head west to Denver to spend three to four days visiting my mom before flying back to Hawai’i.

So, here’s what I have to figure out and arrange (for now):

  1. One-way airfare from Lihue to Boston for WenYu and I
  2. Ground transportation from Boston to Natick, MA
  3. Hotel in Natick
  4. Rental car in Natick (I am NOT driving in Boston)
  5. Transport from Natick to North Station in Boston (maybe)
  6. Round-trip train travel from North Station to Portland, ME (maybe)
  7. Transport from North Station to Logan airport (maybe) with a . . .
  8. Possible overnight hotel stay in Boston
  9. One-way airfare from Boston to Denver
  10. Rental car at Denver airport
  11. Hotel in Loveland, CO
  12. One-way airfare from Denver to Lihue

It all seems like a lot, and I’m sure there’s something that I’ve forgotten or that will pop up, but I know it will all come together. Let the planning begin!

17 thoughts on “Plans Are Being Made

  1. What a lot of logistics! My two cents: Boston is a good city for driving. Despite the volume of traffic, if you need to change lanes, a driver will actually let you in!! And the Mass highways are very manageable too. Now parking and tolls are a different story…


    1. After two years of driving on our small island’s 2-lane highway, I just don’t feel skilled enough anymore to tackle big-city driving while trying to find my way through town and out to the college. Colorado Springs was a real wake-up for me! We have friends in Natick that have offered to ferry us around, but we don’t want to burden them.


  2. My most intricately planned trip was our wedding there up the road from you!

    Two round trip tickets LAX – LIH Friday (am) – Friday (my son and his friend)
    Two one way tickets LAX – LIH Friday (am) for Jim and his younger son
    One round trip ticket SEA – LIH Friday (am) – Thursday for Jim’s older son
    All five guys met up in HNL within an hour of each other and flew together to LIH
    Three round trip tickets CLD (Carlsbad – near San Diego) – LIH connecting through LAX (myself, my daughter, and her friend) Friday (pm) – they had finals and we had to leave later Flight delayed about six hours, almost had to book a hotel in LA.
    Two one way tickets LIH – SEA on Thursday (am) for Jim and his younger son, on same flight as round trip ticket for older son
    Last two boys fly out Friday morning
    Three girls fly out Friday night

    We had: two rental cars, two condo units, one wedding, one Christmas Eve luau, and one Christmas morning. Jim and I ditched the kids for the rest of Christmas, before he had to leave the next morning. I got one extra day to lay by the pool and nurse the cold I came down with on Christmas Eve. Jim and I sat side by side with our computers and booked all the flights together. Priceless, lol.

    Liked by 1 person

    1. And so they were wed . . . .

      Actually, this experience wins for the most involved travel planning I’ve ever heard of. Yikes! I had no idea.

      We’re still waiting to hear the official move-in date from Wellesley, and then I’ll be on it.


  3. You may think this is crazy but I am a 62 year old female who stayed at the HI hostel in Boston last fall, I stayed in a four bed dorm which was spotless very comfortable and the hostel had the look of a boutique hotel. I was there a couple of days, my first hostel experience and could not have been more pleased! I chose this because I was shocked at the price of a hotel in Boston ( at that time even compared to NYC, Chicago etc). My room was about forty dollars, was across from a big medical center, near the theater district and two blocks from the park. Boston transit made it no problem getting around (FYI it was about four blocks from the Amtrak station which was what I came in on) also I had two roommates at that time one was a resident Dr. In pathology who was in town several days for a medical conference and another girl doing masters work at a museum, they were friendly but no over some and were usually in bed when I got back from my touristy roaming:). I thought it was funny that the resident said that she had not told her husband that she was stayin in a hostel because she thought he’d have a fit but that the hotel prices were outrageous (I don’t think residents make a lot). Sorry this is so long but this may help your budget if needed.


    1. Thank you for this wonderful tip! I am hoping to not have to pay for a hotel in Boston, but this sounds like it would fit the bill perfectly, both for location and price, if I do have to do an overnight there.

      Hotels in Loveland are all surprisingly expensive, but the B&B where my youngest daughter and I stayed four years ago is still affordable, plus you get a 3-course gourmet breakfast! It’s a little bit more of a drive to get to where Mom lives, but not enough to disqualify it so I’m going to book there.


  4. I went to Wellesley and often took the commuter rail from Wellesley into Boston and then transferred to the T which goes out to Logan. Depending on how much you two are flying with that might be a pain, but worth looking into. Or even taking a cab from Logan to south station which puts you on the commuter rail lines is another option. And I feel like the commuter rail goes to Natick and maybe the hotel has a shuttle or could connect you with a taxi service. While at Wellesley, my boyfriend, now husband, lived in Maine and I often took Concord trail ways from south station to Portland or further north depending on schedules. It used to have a stop in Bath. It might be called Concord Coach Lines now but I remember it being so easy. I would avoid driving in Boston if at all possible; it is brutal and compared to Kauai, even more so. I hope WenYu loves Wellesley as much as I did!


    1. Luggage is going to be the BIG determining factor for which type of transportation we use getting from Boston out to Natick/Wellesley. WenYu will have several big pieces as she has to bring everything along with her, and I’ll have my carry-on as well, so we’re going to need something that can hold all our stuff. I honestly cannot see us wrangling it on and off a train. So, we will probably have to spring for some sort of van on that one leg of the trip.

      I checked out Concord Coach Lines and they do have a bus that goes right to Bath! Same price each way as the train, but more convenient. Thanks for the tip!

      WenYu is so excited about attending Wellesley, and we feel it will be a great fit for her. She is already in a Facebook group for new Wellesley admits, and is communicating with others, and can’t wait to go! She’s especially excited about being so close to Boston, and the opportunities to explore the city and outlying areas.


    1. I’m still in the research phase, but will keep things updated as they come together!

      (P.S. For some reason your messages always go to spam and I have to ‘rescue’ them – I have no idea why. So that’s why it takes a while for them to show up.)


  5. This is exciting! Maybe WenYu could bring less stuff with her and buy what she needs when she gets there? I’m assuming she doesn’t currently own any winter/fall clothes so she’ll have to buy those there anyway or order online. Is she living in a dorm room? I don’t know how big they are at Wellesley, but usually they are quite small so you want to be careful not to bring too much stuff.

    It’s so tough to find the college that is the right fit for the kid, their personality and what they want to achieve and it’s great that WenYu worked so hard and was able to go to the college that’s the best fit for her. You must be very proud!


    1. We will be traveling with 1 extra large suitcase, 1 large, and 2 carry-on bags as well as her (cheap) guitar – she doesn’t plan to take her good guitar, at least not yet. We do plan on doing some shopping in Massachusetts, particularly for winter clothes and accessories, but she’ll be bringing linens from here (she’s going with a Hawaiian theme). Thank goodness for Space Bags!!

      I follow Wellesley now on Twitter, and today they posted pictures of the Wellesley “Scream Tunnel” at the Boston Marathon, and I burst into tears because I know WenYu will be there next year, having the time of her life. She’s a runner, and getting to cheer on the marathon runners will be a huge thrill for her. She’s already communicating with other admitted students on Facebook and is making connections. We are all sooooo excited for her!


      1. Does WenYu plan to run track/cross country in college? It’s great that they have social media these days to connect with other new students. I’m sure that really helps them feel a part of the campus even before they get there.


  6. Hi Laura,
    Congratulations on WenYu’s well-deserved opportunity to attend Wellesley College! As a parent of a son who is off to Columbia University in NYC in August, I commend you and Brett as well for doing the due diligence in figuring out how to help make that amazing opportunity happen.
    As you probably know from your friends, staying in Natick is a far better choice than Boston in terms of cost and traffic. There are 3 or 4 hotels located on Route 9 (Worcester St/Rd) that are a straight shot to Wellesley in about 15 minutes. They are also close to the Boston Express bus station in Framingham, (the town adjacent to Natick) where you can catch a bus to South Station. If there is no drop fee for a one-way rental (and you probably know to use your Costco membership for the best car rental rates) you may be better off returning your van in Framingham and taking a shuttle or cab to the Boston Express station where you can head to South Station for your bus transport to Maine. As someone who also dislikes city driving, I would suggest that this may be less stressful than driving back to Logan to return your rental.
    I have a sister who lives in Natick and I live about an hour north, so am very familiar with the Boston metro-west area. I can offer shopping suggestions – both retail and second-hand (Burlington Coat factory is a great place to find winter gear and is located close to the Natick hotels). Please feel free to email if you have any questions!


    1. Thanks for all the great tips! They are greatly appreciated. It looks like I won’t be going up to Maine after all because my friend is both having her house remodeled AND her daughter is getting married the same time I would arrive! Not a great time for me to visit. So, it will be just WenYu and I into Natick, then me on my own back to Boston and on to Denver to see my mom.

      If you’re interested and have time, I would love to meet up when I’m back there!


      1. I would love to meet you if we could arrange it. Hopefully we won’t be headed to NYC to move our son into his dorm at the same time that you are in Massachusetts! I too have been ready to start making travel plans for move-in, as finding well-located hotels in NYC that aren’t prohibitively expensive can be a challenge.
        I was thinking about your transport from Boston to Natick. For the leg out you will probably need a limo if you have luggage concerns. I reread your post more carefully and now see that you don’t want to rent a car at Logan (I don’t blame you!) Keep your eye on Groupon Boston as they are always running limo specials from Logan to the Boston metro-west area. The zip code for Natick is 01760 and it’s about 15 miles outside of Boston. You will need this info to determine if your trip is within the service area for the limo companies. Also pay attention to Groupon expirations, some expire in less than 3 months so they can’t be purchased too far in advance. It should cost about $60-$80 for a ride to Natick, less if you can snag a deal. As far as returning to Boston, if you stay at one of the Route 9 hotels I imagine that they would have shuttles to the Logan Express bus terminal. A one-way fare to the airport is $12, and the buses run frequently. You can find info about this option at (Logan Express/Framingham). My niece’s fiancé travels frequently and uses the Logan Express all the time.
        There are some car rental locations in Natick, but the closest to the Route 9 hotels would be Thrifty, which is located on Speen St (it shows the same address as the Hampton Inn in Natick). If you choose one of the other hotel options they are located less than a mile away from Thrifty.
        As I mentioned before, feel free to ask if you need more info about logistics in the Natick/Wellesley area. I don’t know if I can/should post my email address here or if you already have access to it through WordPress. Just let me know the best way to get it to you. I’ll keep me eye on orientation dates for August – fingers-crossed we can get together while you are visiting!


      2. As soon as the dates are firmed up (we’re waiting for confirmation of her move-in date) I’ll email you. Hopefully we can work something out. And, thanks again for the GREAT tips!


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