How to Plan a Maine Vacation with Family and Friends

Are you thinking about taking a Maine vacation with family and friends? You’re in good company. According to the VRBO Trends Report, 44% of travelers plan to travel with four or more people. Millennials and Gen Xers are leaders in group travel, with 58% of millennials and 50% of Gen Xers are vacationing in groups of four or more.

Join the trend by planning a successful Maine vacation with family and friends. From choosing the right destination to giving yourself flexibility, here’s how to get started. 

Pick Your Maine Vacation Destination

Maine offers something for everyone from a beachside retreat to hiking, paddling, and fishing in a wooded escape. The best strategy for choosing the right destination is looking for flexibility.

Unless you’ve got diehard hikers and campers in your group, a remote oasis isn’t going to be a crowd-pleaser. Instead look for options that blend a little of everything. Portland, Maine offers fine dining, pubs, and hiking along Maine’s waterfront.

Or head to the Old Orchard Beach and Saco area for family-friendly fun on beautiful beaches, The Pier and Palace Playland, and Funtown/Splashtown. 

Coordinates Your Travel Dates

Picking the right schedule comes with some challenges, with 34% of travelers saying coordinating timing is the hardest part of planning vacations. Kick-off the conversation with a few emails or a shared Google calendar to stay organized. Ask everyone to specificity their top three dates, and a few dates that absolutely won’t work. 

It may take some finessing to get the schedule right. It can help to decide on a season to visit Maine, like summer or early fall, when the foliage is peaking out.

Set Your Budget Expectations

A Maine vacation is affordable and packs in value for any budget. Collect feedback on how much your group wants to spend on accommodations, as well as food and entertainment. Your family and friends should also come to a flexible agreement on how often to eat out, whether to cook a group dinner from a vacation rental and if their budget is impacted by road trip or airfare costs.

Choose Your Maine Vacation Rental

Find a Maine vacation rental in your favorite destinationWhen it comes to traveling with a group, a Maine vacation rental is your best bet. A vacation rental that holds 5 to 12 people or beyond gives your group the opportunity for intimate togetherness with the flexibility to shut your bedroom door or head out for a solo excursion.

Remember to think about sleeping and bathroom configurations in advance. Someone who requires their own bathroom should snag the master suite with a compromise. Get creative with configurations like a bunk bed room for kids to give adults more privacy. 

Create a Flexible Itinerary

Flexibility is non-negotiable when it comes to a successful Maine vacation. With so many personalities from friends to cousins or grandparents in one space, everyone will arrive with different ideas of a fun vacation.

Create a flexible itinerary to venture out together for a beach day, walk to Old Orchard Beach’s Pier, go on a hike, or take in an outdoor concert. Leave the rest of the day open to spontaneity and freedom for everyone to choose their own adventure or break off as a group. The more flexibility you create, the higher the chances that everyone comes home with even closer relationships than before.

Get Out of Your Comfort Zone

A group Maine vacation is about togetherness but doesn’t mean sitting around doing the same things you do at home. Get your group out of their comfort zone by planning one or two things during your vacation like an adventurous hike, a tour somewhere new, or an amusement park, like Monkey Trunks or Funtown/Splashtown in the Old Orchard Beach and Saco area. 

Plan  Maine Vacation Day Trip

Plan a Maine vacation with friends and familyDay trips are an ideal way to see more of your vacation destination and mix up your routine. For ideas within 30-minutes of Old Orchard Beach and Saco, try Portland’s “Old Port” for an afternoon of exploring. You can also opt root for the home team at a Seadogs baseball game, visit a nearby lighthouse, or take a sunset Casco Bay Bayline cruise.

Stretching past your comfort zone keeps your group from getting restless and provides a new bonding experience and memories. You’re more likely to remember that exciting, engaging, unique thing you did on your Maine vacation than the squabbles over what to make for lunch.

Ready to get started? Make your next Maine vacation a success starting with the right rental that accommodates the space and flexibility you need. Browse our listings in Southern Maine here.


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