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Twin Outings

Written by The Twin Source

Travel With Toddlers 

When you're vacationing as a couple, you can enjoy sleeping late, lounging by the pool, and exploring your destination at will. Things change when you begin vacationing with toddlers, but it doesn't mean you can't still have fun!

When you transition to a family vacation, your days are typically structured around what to do pre-nap, what to do post-nap, and what you can squeeze in before bedtime. This may be different from what you were used to pre-babies, so here are some tips for getting the most out of vacationing with toddlers.


Remember that you are escaping for a week or two—not moving out—so pack light and rent or acquire must-have baby gear when you get to your destination. A few ideas:

  • Rent car seats. Arrange with the rental car company to have car seats waiting for you upon arrival. Be sure to specify the type of car seat (infant, convertible, booster, etc.) when booking your reservation. Hertz rental car has a good service.
  • Rent baby gear. You can rent everything from a crib and/or a pack and play to a jogging stroller to a highchair—and everything is waiting for you when you arrive at your accommodations! Check out these baby gear rental sites: www.babysaway.com, www.babiestravellite.com, and www.akamaimothers.com (Maui).
  • Buy supplies locally. After you arrive, make a stop for diapers, wipes, and other supplies instead of trying to pack it all in your suitcase.
  • Take advantage of amenities. Check with your concierge ahead of time to see what amenities (cribs, pack and play, etc.) can be provided—often for free. If your accommodations include laundry, pack less and do a load or two of laundry while on vacation.



You want to find a place that offers the space you need and the entertainment you want. You don't want to be the only family at a honeymooners' resort!

  • Book a condotel, house, or suite. Having separate rooms allows you and your partner to enjoy some downtime while the kids are napping or sleeping. You might also have in-room laundry and a kitchenette, allowing you to travel light. Bonus: Multiple rooms mean you won't have to dodge cribs or pack and plays, which take up a lot of space.
  • Know what's included in your rate. When shopping around for accommodations, find out what activities and amenities are included in the per-night rates. Sometimes a rate that is slightly higher includes free activities and other perks, making it worth the extra cost.
  • Look for family-friendly accommodations. You want to find a place with a great balance of adult and kid activities. Trip Advisor has fantastic reviews of resorts and features great family recommendations.



Don't let mealtime become a big ordeal. Some ideas: 

  • Eat where you are staying. If you're staying at a resort, having lunch or an early dinner served to you poolside is a great luxury and a relaxing time-saver that the kids will enjoy just as much as you will. Many resorts offer a breakfast package for free or for a small daily fee, which means less meal preparation for you. Score!
  • Make reservations when dining out. Don't ruin your dinner waiting 45 minutes for a table. If the restaurant you want to patronize doesn't take reservations, go early. Yelp is a great resource for finding inexpensive local fare for families. (Bonus: Check out Twin Mom Carrie's tips on dining out with twins!)
  • Eat after the kids. Consider feeding your kids dinner in your suite or condotel before heading out to dinner. Once at the restaurant, get the kids a simple dessert like a bowl of ice cream. They will be excited and engaged, and you will get more time to enjoy and eat dinner.
  • Eat off hours. You don't have to avoid fine dining. Just go for lunch instead of dinner! The food is typically half the price, lunch is a more casual atmosphere, and service is a bit quicker.



Most toddlers require an afternoon nap and must go to bed at a decent hour—or else everyone suffers. Sleep is the key to a successful vacation, but sleeping away from home can be tough. These tips can help:

  • Keep your sleep routine. Chances are, your kids will stay up a little later, nap a little later, and hopefully sleep in a little later when you're on vacation. This is fine so long as you keep a consistent, predictable routine that your toddlers can rely on. It's less about sticking to the clock and more about keeping the routine. For example, if you give the kids baths and then read to them before tucking them in at home, do that on vacation as well.
  • Bring an item from home. A blankie or sheet with the smell of home can be comforting to your little ones when they go to sleep. Note: Even though you want to pack light, you don't want to skimp on bedtime supplies!
  • Use naptime to travel. If your kids nap well in the car, go for a drive during naptime. Time it so they wake up when you get to a fun destination. If the kids don't nap in the car as you hoped, though, make sure you avoid a big night out!


Miscellaneous Tips

Here are a few extra ideas to help you enjoy your vacation to the fullest:

  • Plan for some adult time. Bring a nanny with you or meet with your concierge to hire a nanny so that you and your partner can slip away for some quiet time. Most nanny services are reputable and can be researched in advance.
  • Share parenting duties. Take turns with your partner bringing the kids back to the room for daily naps. This way, each of you will get some quiet time by the pool, at the beach, and/or at the gym.
  • Take long walks with your family. This is a great way to explore your destination by foot, get some exercise, and keep your kids entertained for an hour or so. You may even want to rent a jogging stroller at your destination.
  • Enjoy and take lots of pictures. You will be surprised—your children will slip into vacation mode just as easily as you do!


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