New England Travel with Kids

by Melania Mitchel
New England Travel with Kids

Trip Planning

For most, vacation travel is a high-stakes activity. You’ve saved your money, banked your vacation time and cleared your calendar. If things don’t go well, there’s little you can do beyond waiting another year and learning from your mistakes. And even if you’ve put the best plans in place, vacation doesn’t become vacation until you start enjoying the experience. Which begs the question: Can you do something to help increase the odds that you’ll enjoy your vacation; especially with kids in tow?

For families who allocate more of their annual budget towards vacation travel, a poorly planned trip can leave mom and dad feeling even more tired–and bummed–when they return home. Yes, we’ve been there several times–absolutely no fun–which is why the stakes of a poorly planned vacation are higher as the cost of the trip increases and the amount of one’s paid time off decreases. Furthermore, for most of us, we’re exceptionally lucky if we get more than 3-4 weeks a year of uninterrupted paid time off from our employer, which leave most with a week or two for “bigger” trips. Good pre-trip planning can help you maximize your paid time off (PTO) and will ensure you leave your kids with lifelong memories.

The 3 Principles of Travel Planning for Families

Before we get into the nuts and bolts of family travel planning, I wanted to share three basic principles that inform how we go about our planning. You can skip this section if you’re traveling solo or as a couple sans kids.

Principle #1: Vacation is Not About You

Well, it’s kind of about you, but you get the idea. Embrace this and everything else will fall into place. The more you test the limits of this presupposition, the more this principle will become the foundation for all your family travel planning. And really, it’s not a bad thing since the great secret of travel is to set appropriate expectations and to realize that travel is more about the people you meet than the landscapes you traverse. When it is about you, figure out how to involve your spouse and kids–unless your goal is time alone. With your new mindset, you’ll most likely find your own level of enjoyment going up as you bond with your kids, spouse and more intentionally identify what your own “recharge” needs are and work those into the larger set of plans and activities. Do you fish, jog, knit, eat out? Bring one or more of your kids along with you. Since alone time is a priority for my wife during vacation, we build that into our travel planning as a scheduled activity. In short, the larger your group, the more structure you might need to protect the more important priorities you’ve identified. When we recently traveled to Acadia National Park with 12 people, I was careful to draft an adaptable itinerary and then jettison parts of the plan when it didn’t serve its purpose. Having said that, I estimate that I spent about 5-6 hours of research for our 3-day camping trip. While that may seem like a lot of time to devote to planning, I tend to spend more time on planning when the cost is higher, more people are joining us or if there is more complexity around the location or getting there.

Every travel agent and travel industry expert would like to have you focus on high-end luxury or “can’t miss” sights, but most of our top travel moments we’ve had in New England have been tied to people and things we’ve seen or done off the beaten path. For most of us, this simply means figuring out what your priorities are: a Broadway musical, exotic sushi, a whitewater kayaking trip or simply strolling along a winding river? Start there and then jump back into principle 1: prioritizing the needs of the rest of your family. In the photo below, we traversed a rocky section of the Maine coast to find a beautiful area (Land’s End on Bailey Island, Maine) filled with sea glass–one of our niece’s top requests for her stay with us. And, yes the rest of us had fun as we joined her.

Family Travel

Ultimately, unless you’re staying in an all-inclusive hotel and your spouse is willing to give you an open-ended pass to pursue your own interests during your time off (not likely), you’ll need to think about how you’ll share the responsibility of caring for your kids. And if you’re the one who isn’t typically keeping the trains running at home, I’d highly recommend you do your best to shift roles and give your partner a break during your vacation; which leads me to principle #2 and #3. And don’t forget to clarify this before you leave for your trip.

Principle #2: Keep it Simple

Hanging out in York Maine with a classic Westfalia bus


There’s much more to be said about this principle, but our tip is to keep the main thing the main thing: memories, quality time, people first and respecting the budget. In many cases, camping and time spent outdoors is a great way to vacation while your kids are young. Even if you’ve never camped before, give it a try. If tent camping is too much for your initial foray into the great outdoors, rent a yurt or find one of the many “glamping” options where you can stay in a cabin or some other structure.

If you’re interested in renting a VW bus or vanagon in New England, check out Firefly Vans or Vintage Van Adventures. You should also consider a Mercedes Sprinter if you’re traveling with children and need increased reliability. And don’t forget to stay with friends and family who live in interesting locations when your kids are young and less mobile. Staying close to home will ease the burden on managing your supply chain (my humorous way of referring to transporting cribs, food, etc.) and give you more quality time with the important people in your life. Save your travel dollars for when your kids are older and more adventurous. In New England, there are almost unlimited options if your goal is quality time with your family.

Principle #3: (For kids) Clarify Roles (For adults) Switch Roles

If your kids are old enough to understand, sit them down and explain their roles during vacation. This might include some of the following responsibilities:
Boy in charge

  • Packing their lunch
  • Cleaning up their room/space
  • Cooking one or more meals (for older kids)
  • Looking out for one or more siblings—looking for ways to encourage/help them
  • Behaving well during technology free periods (more about this later)

If your spouse is responsible for cooking meals at home, switch roles during your trip. If he or she manages the laundry or carries a heavier share of cleaning, take on more cleaning and take over the laundry. Where possible, have your older kids chip in. In short, give your spouse a break from their daily duties. You may be the primary bread winner, but don’t assume that gives you a free pass. Of course, the all-inclusive vacation is an easy way to solve this problem, but for the rest of us who have more moderate travel budgets, do your best to give your significant other a break from their day-to-day chores.

Principle #4: Ditch your Technology

It will be hard. Your kids might even revolt. They may think that you are the worst person in the world. But, please don’t let your kids’ phones and devices destroy your family dynamic.

There is no quicker way to short circuit the quality of your vacation than letting your technology usurp your group time and hinder your communication. When in transit between destinations, we do let our kids play their games, but once we close in on our destination, the devices turn off. We also periodically let them play video games at the end of a long day–but, use this privilege sparingly. If you’re on a much longer trip and can afford the expense, an iPad or Amazon Fire loaded with e-books (or audio books) makes a strong companion.

Travel Planning Tools

On one hand, planning a successful vacation is about knowing how to use the most current planning and research tools. In today’s web-connected world, there are numerous web-based tools that can be used to help plan a trip. Since there are so many players in the travel industry: airlines, vacation rentals, car rental companies, campgrounds, restaurants, credit card companies, travel review websites, etc–it’s no surprise you’ll need to use a host of different tools to get at the best prices and most compelling places to visit.
Travel Tools
Figuring out how to use these tools along with crowd-sourced reviews will give you much of what you need to successfully plan you vacation. While some suggest you should use the incognito mode on your browser to hide your identity from an airline, knowing when to purchase your airline ticket is the better tactic. When I have 4 or more flights booked in any given year, I also use the Tripit Pro tool to track on my purchased airline tickets so notifications can alert me to price changes after I’ve already purchased my ticket. In most cases, you can then follow up with your airline to receive credit for the price difference. As of 2018, TripIt Pro tracks on price changes for the following airlines: Alaska Airlines (AS), American Airlines (AA), Delta (DL), Frontier (F9), Hawaiian Airlines (HA), Jetblue (B6), Southwest (WN) and United Airlines (UA).
Some other helpful travel planning apps you may want to check out: Google Trips and Packing Pro. I’ll share more about trip search tools later.

Travel Preferences and Perspective

Technology aside, travel is also about managing human factors: decision making, emotions, expectations and biological needs. Throw large amounts of money into the mix if you’re purchasing airline tickets and hotel tickets and the stakes are indeed high. While some of the travel information you can find online is helpful, there’s also a lot of information that is inaccurate, overly influenced by commercial interests or too generic to be helpful. I’ve always found that the best travel writers have strong opinions about the places they’re reviewing and aren’t afraid to share their unfiltered thoughts.

When traveling with children, you’ll also be managing the needs of others. You’ll need to be flexible and expect the unexpected. In the photo below, we couldn’t find an unused picnic table, which led our kids to throw a boogie board on our bike rack so they could prep our dinner.

Sea Wall in Acadia National Park

Prepping dinner from the back of our van.

STEP 1 – Pick Your Destination

For some of us, this might be the most enjoyable part of the vacation. There are numerous considerations you should have on your radar at this point. Below are some helpful tools and criteria you should rely on or keep in mind as you pick you travel destination(s).

  • Planning Tools: AirBnb, VRBO, Expedia, Turo, Costo Travel, GoCity/Coupon, Tripit, Tripadvisor
  • Packing: How much clothing and gear can you or should you carry based on your destination, luggage restrictions and hoped-for level of mobility.
    • Helpful accessories: chargers, extra cables, headphones, dramamine, aspirin, small towel, water bottles, good camera/light room (print photo books after trip), extra credit card, cash, photocopies of your identification documents, wrinkle remover spray
  • Weather considerations: How will the weather determine how much you need to pack, what type of activities you’ll be engaged in and what type of housing you’ll be comfortable in?
  • Kids needs: Do you need access to childcare, medical support, access to bathrooms, etc.
  • Budget and length of trip: Figure out how much you can spend and how much time you can take off. If you’re creative and flexible, it’s not hard to reduce your expenses, but you won’t be able to stretch your vacation window unless you bank your PTO hours or arrive at some kind of agreement with your employer. For those living a location independent lifestyle, this won’t be an issue.
  • Clothing: Don’t overpack! Bring layers and bring your most comfortable item for each layer. You can always wash your clothes somewhere, so don’t overdo it with bringing too many clothes.

When traveling without kids, picking a vacation destination is usually straightforward. Ask some friends which places they’ve enjoyed, spend some time searching for destinations on Google and check your bank account to see what your budget supports. In today’s world, you can also search your Facebook account using a destination to see if any of your friends have traveled there recently. If they have, reach out and ask them what they thought. You live in the 21st-century, so if you’re fortunate enough to have financial means, the world is your backyard. Although X-generation people like me were once dependent on Rick Steve’s travel guides and a pre-Internet, pre-sharing economy, we now have Airbnb, VRBO, Expedia, Google, Turo and a host of other tools to help stoke your imagination and narrow your travel options. So, take the opportunity to see the world while you have fewer responsibilities and expenses.

Sand Beach - Acadia National Park

Hanging out at Sand Beach, Acadia National Park

New technologies are helpful, but there’s still a lot to consider before booking flights or making reservations: How old are your children? What are their interests? What is their level of stamina? Do they have allergies? What time of the year can you vacation without adversely impacting their sports or schooling? Will their friend(s) be joining the trip? And perhaps most importantly, how much vacation time do you have and what will your budget support?

Destination Assessment – Tips and Tricks

In addition to TripAdvisor and Yelp, we also use Google to search for by a location name. We’ll then use the “image” tab in Google search to view the top 100-150 images of the location. This gives us a general idea of what a city’s highlights look like and when you encounter an image that interests you, Google allows you to click on that image so you can view the story or webpage that used the image. For more visual information, Google’s street view and YouTube provide additional help. You’ll typically find numerous travel videos on YouTube as well.


If you’re fortunate, you will have accrued frequent flier points during the year via your credit cards or from your other travel activity. If you’re a business traveler, it’s time to cash in your points. Here are some of our favorite frequent flier programs. I also use Google Flights to help me quickly compare the lowest flight pricing on a calendar. When possible, avoid purchasing your tickets over Expedia or other online platforms as you may lose the opportunity to make changes to your itinerary.

Car Rentals

There are numerous car rental agencies, but our favorite mainstream rental agency is National Car Rental. Their customer service is excellent, they reward repeat customers with free rentals and we’ve always found their vehicles to be in good condition. While I was a frequent business traveler, I was always impressed with their customer service. Costco also has a solid car rental service and if you have an account, you’ll be qualified for their discount. If you’re looking to save even more money, Turo will most likely save you even more money, especially if you need to rent a minivan or a large vehicle. As a comparison, we recently booked a minivan in Tampa, Florida for 10 days using Costco’s rental service. Our price was about $1,100 since our dates spanned over the holidays. On Turo, we found a minivan for just under $600 for the same period. While our vehicle had over 100,000 miles and wasn’t the newest Chrysler Town and Country specimen, it got the job done and saved us almost $500.
Rental Car

Pricing and Pre-Booking Your Travel

To reserve vacation rental properties, you can use Airbnb, VRBO or a number of other tools. We prefer AirBnb and VRBO for their simple interface and for the size of their rental property pool. Tripadvisor is our go-to tool for identifying restaurants, hotels and things to do. It’s helpful to see how others have ranked a restaurant, hotel or experience. Since TripAdvisor is supported by unpaid reviewers, it’s often the most helpful and unbiased tool you can find for travel planning. We use Yelp from time to time to double check Tripadvisor restaurant reviews.

STEP 2 – Departure – Game On!

If you’re flying to your destination, for the love of all things good, please leave early! I can’t stress this enough. If you can swing it, plan on getting to the airport at least two hours before your departure time. If you have multiple legs prior to your arrival at the airport or if you’ll be dealing with possible storms or heavy traffic, arrive at the airport the night before and sleep at an airport hotels. When traveling to Florida from the Northeast over Christmas, we arrived at the airport with almost three hours to spare. We enjoyed some nap time as we waited in the terminal. And, as we made our way to security, NBC News interviewed us to ask what we thought about the holiday traffic. We laughed and encouraged the world to arrive at the airport early. To help you arrive at your destination with as little drama as possible, I’m sharing some of our most helpful travel tips.

1. The pilot is in charge
This is a maxim I’ve embraced after traveling for so many years via different flights around the world. As I’ve watched travelers complain about flight delays and other issues, I’ve always told myself, “the pilot is in charge.” Essentially, this just means the professionals who manage commercial airplanes know what they’re doing. It’s in nobody’s interest for them to rush things when they’re assessing the health of the airplane, waiting for repairs or waiting to taxi. Sure, it’s a hassle for everyone involved, but I’ve learned to respect the professionals who are obviously doing their best. And of course, I’ve had some negative experiences with flight attendants and other passengers, but I’ve handled those situations as one-off scenarios that required a call to the airline or a discussion with another passenger. I’d like to think that when I’m positive and easy to get along with, the people who are helping me make my way to my destination are more likely to return the favor.


2. Verify/confirm!
Be paranoid about your flight times. Typically, your airline will email you any flight changes, but not always, And get into the habit of confirming your flight time the night before your departure and the morning of. It’s amazing how often flight times change. Double check your ticket information and review any stop overs you might have in transit. Do you have enough time to get something to eat in between or do you literally need to run to your next gate. Look at a map of the airport if you’re unfamiliar with how far you’ll need to walk. If you need assistance, call the airport directly. If you’re traveling with a family, it’s a good idea to confirm your hotel, camping or hostel reservations. Yes, there have been times when we’ve arrived at a hotel to find they mixed up our reservation in some way. If you’re really on the ball, make sure you’ve given the airline or hotel your reward program information.

3. Print out of itinerary
Yes, this is essential. Print out your entire itinerary and give a copy to your spouse. I also give a copy to my kids periodically. Plan on having no Internet access from time to time. Include your hotel addresses, phone numbers, key contacts, etc. Having all of your essential contact information included on a printed document is important. You should also have copies of your birth certificates and passports if you’re traveling internationally.
Travel Papers
Include contact information for your parents, friends, etc., if you think you won’t be able to remember their phone numbers. It may sound far fetched, but the idea is to plan for a scenario where your phone, identification and other things are lose or stolen. It’s happened to me once when I was in France and thankfully, I had money and my ID in a passport bag around my neck.

4. Cash
Cash is always helpful when you’re on the road. Fewer vendors accept only cash, but you’d be surprised. And, if you need to hop on a taxi, some taxis will not accept credit cards.

5. Your First Day – Getting Settled
Respect and protect your first day after you’ve landed. You’re not doing much when you travel, but it does take a lot out of you–and your kids. Sit at a pool, lay down on the beach, take a nap in your hotel and then watch some TV before you go to sleep early. Even if you go out and hit the town, plan on getting back early so you can all unwind and recharge.

walking on log in montana

Don’t forget to slow down and smell the roses.

6. Traveling with Kids
There’s a lot to say about traveling with kids. Each child will have their own comfort zone and unique needs. My oldest son (now 17) has traveled with me on longer trips to North Africa and Europe. Even from a young age, he was more flexible and resilient than most of the adults who traveled with us. He still is. Our middle child (13) can be moody and is much more sensitive to new things around him. When traveling with any or all of our three kids, we let them know what we expect of them before, during and after the trip. We’re gently remind them that we’ll be changing our daily routine and we expect them to be helpful and kind with each other. This behavior shouldn’t be any different than at-home expectations, but there will definitely be new stressors and they’re typically stretched in various ways during our longer trips. With your youngest child, train your older kids to keep an eye out for him/her so everyone in the family in tracking on the little (one)s.

Active kids are happy kids

Active kids are happy kids

Taking your oldest child with helping take care of your younger kids (within reason) is also helpful. Some other helpful tips:

  • Bring lots of snacks
  • Pack some small games (cards, coloring books, etc.)
  • Bring a map or copy of a map so they can see where you’re going and track on your progress
  • Technology for transit–we depend on this for the “in between” times

7. Responsible for Your Own Stuff
Make sure each child packs their own stuff, and then check and correct as needed. During transit, stress the importance of each child caring for their own things. Yes, we’ve had an iPad left behind in Madrid and numerous other objects left by a child. We do our best to verify everything has been packed and included when we move, but having your children co-own this responsibility is helpful. It’s also a good life lesson for them to learn they’re individually responsible for their own things.

Step 3 – Return to the Real World

Re-entry is difficult regardless of whether you’ve had an enjoyable vacation or a good one. If possible, give yourself a full day to unpack, unwind and re-enter in your normal routine. Kick your feet up if you went all out and minimize your chore list if at all possible. In short, take care of yourself so you don’t return to work or your home community as a short-tempered zombie. If you’re a hard core planner like me, you might even use your re-entry time to debrief and organize your travel notes.

Other Travel Resources

Below are links to some resources you should find helpful, especially if you’re traveling with children.