The first year following your divorce is going to present many new and possibly frustrating scenarios.  Whether it's the first major home repair, parent-teacher meetings at your child's school or first family vacation, you may not feel totally prepared.   Rest assured most of your concerns are totally normal.

While delving into the unknown will certainly present some challenges and apprehensions, with adequate preparation, research and zeal you and yours will be well on your way to your summer vacation destination!

We put together a DMK Solution Checklist to help you solve many of the problems you may face when planning your first summer vacay as a single parent.

Did somebody say money problems?

Problem:  First, determine how you will be able to afford a vacation following a divorce and generally half the household income.

Solution:  Numerous sites offer hotels at a discount.  Take advantage of earned free days when you reserve 5 or more.  Some sites offer discounts when you reserve a room shortly before travel to a general area without knowing the exact hotel.  You can also earn frequent flyer miles and rewards for frequent business travel throughout the year if you reserve these tickets and rooms on your own reward program or credit card, even though your employer reimburses you.  Driving or taking a train can make the trip fun and exciting with lots of stops to tour or site-see along the way.  It doesn't have to be a long trip, instead make it about the quality of the journey more than the destination.  Save hundreds or thousands compared to flying. 

Top Sites:

Not a train person?  Consider driving to a closer destination, like a neighboring state rather than flying.  In less than 6 hours of driving you can be in what seems like another world.  Just make sure your destination has affordable accommodations and lots of free or low cost sites to see and tour. 

 Tip: Rates on sites like Hotwire® and Expedia® fluctuate a great deal.  So, check frequently and book when you get a rate that works.  Sometimes you can cancel if you find a better deal after you book.  But make sure before you cancel that you secured the new deal and can cancel without a penalty.

 Also, make sure you don't try to book car rentals at a time when the participating rental agency is open (e.g. Searching for a car to be picked up on Saturday at 9:00 am could come back as 'no cars available' if the agency opens at 10:00 am).  It may cause you to have to pay more and drive farther to pickup a car.

Finally, take advantage of pre-booking, months in advance, to get the best rates on airfare if flying is a must-do.  Travel in late summer or fall is often more affordable than spring and early summer.

See our June 2021 article, Best Cheap Vacations in 2021 for destination ideas and March 2019 article, Top Travel Sites to help you get the best deals available.

Resources: Hotwire,, Trivago, Expedia

Will I have the energy to plan, pay, drive, fly and vaca' with the kids?

Problem:  Being a tough broad is all well and good, but the reality is that kids and vacations can be pretty exhausting.  Once the excitement of vacationing wears off two hours into your trip will you wish your vacation money went to a new closet organizer, nanny and a bottle of chardonnay?

Solution:  Don't go overboard on the plans.  Your family has been through a lot this year and while you all need some time away, you will all still be off balance a bit.  The kids will notice dad's not around and will likely behave and feel different.  Pick a location that is super kid friendly, this year more than ever.  No supermom.  Make sure the travel plans aren't too long in the plane, train or car.  Again, consider a destination within your region with some popular sites and parks.

Is it safe to travel alone?

Problem: Traveling alone can present some challenges.  Safety is a primary concern along with planning, packing, airports, rentals and hotels. 

Solution:  Some ideas to avoid traveling alone would be to invite another single mom and her kids along if all the kids get along and know each other fairly well prior to the vacation.  A travel companion could also be a parent, grandparent or sibling.  However, if you are dating someone new, it's best to hold off until the kids have really had time to bond and get to know him before vacationing together.

If you are still interested in traveling alone, you will want to make sure you have your itinerary planned well in advance to avoid any mishaps.  Choose a location that may be all inclusive or provide child care, if needed.  Plan a budget and make sure the hotel room has a kitchenette so that you can plan many meals-in so that you can save money and avoid taking the kids out to eat 3 times a day, which can be challenging.

Your personal security is important, so it's important to share a written itinerary with a close family member back home and phone or text on specific days or times of the trip to let them know you are okay.  Do not post your daily plans and locations on social media. Avoid using public wi-fi since it presents a greater opportunity for hackers.  Be cautious of people who quickly begin to latch onto you or your kids.  Some people are just friendly, but if something seems odd it probably is.  It's not a bad idea to make electronic copies of your i.d.'s, confirmation code for your hotel reservation and passports (if needed), email them to yourself and keep the e-mail accessible should there be any problems.

Don't divulge that you are traveling alone to strangers or staff.  However, it would not be a bad idea to ask some hotel staff members if there are places in the area that they would or would not recommend.

What are common issues that can ruin our vacation?

Problem: Failing to put adequate time into planning your trip will help you avoid nearly all of the problems associated with a bad vacation.

Solution:  Research the area, hotels and amenities with your basic checklist in mind.  The checklist might include: indoor/outdoor pool, beach access or distance to beach, child care, spa, proximity to shopping and tourist attractions, affordable rooms, low cost-family friendly attractions like parks-swimming-museums, etc.

Buyer/renter beware


When booking your hotel make sure you are aware of room and hotel fees, taxes, parking passes and service charges not included in the room charge advertised on-line.  This can add as much as $200-300 to a week’s vacation and can really take a bite out of your fun money!


If renting a car, make sure you have all information related to the type of insurance in the state for which you will be traveling.  In no-fault states you may be liable for the rental vehicle even if you are not at fault and someone hits you.  If your auto insurance does not cover such situations you may elect to add the rental companies added insurance to the rental.  This will increase the cost and should be considered prior to deciding if a rental car is within your budget.  An option would be to plan a vacation that has most attractions within walking distance of your hotel and/or a hotel that offers free shuttle service around town.


Like the hotel, it is important to make sure you are aware of all fees associated with your ticket purchase.  Also, unless a relative will be taking you to the airport or train station, you must factor in an Uber, taxi or parking.  Finally, make sure you have arrangements for either your rental vehicle or hotel shuttle from the airport or station.  Check the list of acceptable items you can bring onto the plane so that you do not have to throw away expensive items when going through security.

Now, get planning your much needed summer vacation!   Even if it isn't a trip to a lush tropical destination, chances are your kids will be happy just being together and getting away from it all.  Of course a swimming pool with a slide doesn't hurt!  So plan well!