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How to Plan Your Summer 2021 Vacation

This is a guest post from Jen Terra Travels!

As I sit down to write this in late March, the birds are chirping and the trees are starting to form those red buds which will eventually transform into chartreuse green new spring leaves. This Thursday in Connecticut vaccinations will be available for every adult over the age of 16. I have finally finished planning and booking last minute spring break vacations for the subset of people willing and able to travel now. And now I am taking a deep breath before the inevitable rush of inquiries for summer 2021 vacations!

After a year of little or no travel for most of us, wanderlust is at an all-time high. But for many of you, the questions dominate the answers. Will it be safe to travel this summer? Which destinations can I travel to? What do I need to do to prepare for travel? Do I need to be vaccinated? And then there is the million-dollar question- will travel to Europe be possible this summer??

Considering I have traveled extensively during the pandemic, I do have some tips on how to effectively plan travel for Summer 2021 as well as strong opinions on the best places to travel within the U.S. and if you are willing, internationally. Are you ready to plan your ‘vaxication’? If so, read on!

Summer 2021 Vacation Considerations

How to get there?

Last summer most of us were very happy to have the opportunity to travel anywhere- even to a driveable location in your home state. Visits to the National Parks, weekend getaways to local inns and camping trips provided a much-needed respite from the WFH/distance learning grind. In 2021, many of us will get on a plane and travel for the first time in over 12 months but many are understandably nervous about it. So, before you decide where to go, consider if you are ready to fly. If the thought still causes extreme anxiety, it may be better to hold off until later this year or 2022. Vacation and travel should bring excitement and joy, not fear.

Where can I actually go? And Where should I go?

For those ready and willing to jump on a plane, the question is, where can I actually go? There are indeed many international options for US travelers on the table at the moment. Mexico, Belize, Peru, Costa Rica, Dubai, The Maldives, Egypt, Turkey, Croatia, Montenegro, Greece, Iceland, South Africa, Uganda, Morocco and much of the Caribbean is or will be welcoming travelers this summer. Other beloved European destinations, such as Italy, France and Spain, hit hard with a second wave of Covid, are still determining if they will open their borders this summer. Add to that the many amazing US destinations and analysis paralysis can easily set in.

If this is the first time you’ve traveled anywhere significantly since last year (or earlier), my recommendation is to not overthink it. Select an uncomplicated itinerary to a destination that is meaningful to you. Whether that means you finally want to journey to that spot on your bucket list or you’d rather laze on a beach at a resort with an excellent kid’s club and great spa- now is the time to listen to your gut.

Additionally, just because you can travel to a destination doesn’t mean you should. Do your research first. How are they managing tourism? What testing and safety protocols are in place? What is the quarantine policy? Are most restaurants open and activities available? Is there a curfew? Reach out to a trusted travel advisor or other friends & family who have traveled to the location to get real time information on what it’s like now.

When to Book?

If you have your heart set on an international destination not yet open (Italy we see you!) I’d recommend that you book your accommodations now with a generous cancellation window. I would also recommend that you book a domestic or international plan B that is currently open which also has favorable terms and decide closer to your date. Inventory at popular resorts and hotels is already restricted by 2020 trips that were pushed forward and by bookings made by Nationals who can’t travel far from their home country. In addition, because many travelers aren’t willing yet to travel internationally, top US resorts are filling quickly. The good news: right now most hotels and resorts are offering flexible cancellation & deposit policies!

Ok, now for the fun part! Here’s my curated list of some of my favorite destinations and resorts to spend your much-needed summer vacation~

My top Summertime US destinations


This is the US State on many a bucket list that gets pushed off for other international destinations. Now is the time to visit friends! Alaska’s vast wilderness creates the perfect environment for social distancing. And because extreme temperatures make much of its terrain inaccessible during the winter months, summer is the best time to visit. For those who love an active adventurous vacation, pristine natural landscapes and prefer to view wildlife in their natural habitat, consider Alaska. Stay at Tutka Bay Lodge located near Homer or the remote eco luxe Stilllpoint Lodge in Halibut Cove.


There is a reason why Hawaii’s residents rank as the happiest population in any US state! This island archipelago is literally paradise on earth with its stunning white and black sand beaches, lush mountains, and aloha spirit. Whether you want to learn to surf, love to hike, or simply want to relax on your lanai while sipping a Mai Tai and viewing some of the most vibrant sunsets you’ve ever seen, Hawaii has something for everyone. Stay at the newly renovated Turtle Bay Resort in the North Shore of Oahu, Mauna Lani on the Big Island or The Four Seasons Lanai.

Jackson Hole, Wyoming

Many of us have visited Yellowstone National Park but those in the know prefer its more picturesque neighbor, Grand Teton National Park. Just at the foot of GTNP is the western town of Jackson Hole, WY- the perfect base to explore this wide-open space brimming with glacial fed lakes, jaw-dropping mountain peaks, and wildlife galore- think bears, moose, Bighorn sheep, wolves, Pronghorn (these are cool!) bison and elk. Who needs Africa when you have Wyoming? Add to all of this a lively downtown with great shopping and an amazing food scene. Stay at the Four Seasons Jackson Hole or for larger groups the Caldera House. In town Hotel Jackson is your best boutique option.

Lake Tahoe, CA

Being an outstanding ski destination, Lake Tahoe is often mistakenly overlooked for its summer allure. Located on the California/Nevada border, this Alpine dreamland is the perfect spot for families looking to relax and adventure. Its giant lake is home to a variety of beaches, each with its own personality and water sports galore. Hiking, biking, fly fishing and golfing will also keep you entertained if gambling isn’t your thing. At the North Shore’s Northstar ski area, stay mid-mountain at the Ritz Carlton. On the South Shore, stay close to casino action in Stateline, NV at Edgewood Tahoe.

South Carolina’s Low country

Experience southern charm, hospitality and mouthwatering cuisine in this summertime haven. From Bluffton to Hilton Head and the Kiawah Islands, there is something here to suit every summer vacation desire. Recreational pursuits include fishing, sailing, beaching, birding, golfing and tennis. History lovers will enjoy perusing lighthouses and historic buildings. Stay in Bluffton at Montage Palmetto Bluff, in Kiawah at the Sanctuary or in Hilton Head at Sea Pines Resort.

My top Summertime International Destinations:


For those based on the East Coast, Bermuda is the best way to experience those blissful island vibes in the summer without having to head south to the hurricane-prone Caribbean or to other far-flung international destinations. If pristine pink sand beaches, crystal clear grottos, an array of water based activities and lively harbor side towns are your thing, Bermuda may be the perfect summer choice. Stay at Rosewood Bermuda or the newly opened St. Regis.

Costa Rica-The Peninsula Papagayo

I am going out on a limb here but I will argue that summer in the Peninsula Papagayo is a very good idea. In Costa Rica, the rainy season stretches from May-October but the microclimate of Papagayo (the driest part of Costal Rica) is less rainy than other portions of the country. Located in the North Pacific ,this sliver of paradise flanked by ocean and bay is a natural playground for children & adults alike. Expect to see white-faced monkeys and giant iguanas. Zip lining, whale watching, deep sea fishing, surfing and golf are some of the many activities to occupy your time. Base yourself at The Four Seasons Peninsula Papagayo or the Andaz Costa Rica Resort.


There has never been a better time to visit this Balkan dreamland! While much of Europe is still off limits, Croatia has begun to welcome back tourists with proof of vaccination or a PCR test. Explore the historical towns of Dubrovnik and Split, island hop to Hvar and Korcula, tasting fine wines along the way, hike through its 8 National Parks or simply sunbathe by day and spend your nights sampling its diverse Dalmatian cuisine. Stay at Hotel Excelsior in Dubrovnik, Maslina in Hvar or indulge yourself in Montenegro at the newly opened One & Only Portonovi.


A Greek summer vacation is looking more promising each day as Greece just announced a re-opening mid-May. This summer, take advantage of expectedly lower crowds to explore Athen’s archeological sites and Greece’s many gorgeous islands dotting the Mediterranean. Start off in Athens with a stay at Athens Capital then set off to Mykonos and stay at Mykonos Blu. End your journey in Santorini with a stay at the iconic Canaves Oia Epitome.


One of the first countries to accept visitors who can show proof of vaccination, and a short plane ride from the East Coast, the wide open landscapes of Iceland should be on everyone’s bucket list for summer 2021. Summer in Iceland brings more milder temperatures and almost endless daylight to allow for ample opportunity to explore it’s natural wonders- think snow-covered lava fields, majestic glaciers, natural hot springs and the chance to see sunshine loving puffins! Split your time with a stay in downtown Reykjavik at The Sand Hotel and then pamper yourself at The Retreat at the Blue Lagoon.

Big Thank You to Jen Terra for this super informative article and I cannot wait to chat about summer travel plans with you! Please head over Jen Terra Travels for more details on how she can help you with your next adventure!

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8 thoughts on “How to Plan Your Summer 2021 Vacation”

  1. I wish that we could plan any sort of travel for the summer, but it’s not looking like that will happen this year. We want to wait until we are all vaccinated first.

  2. My family and I can’t wait to travel again. We are thinking maybe next year or the year after. We have no idea where we want to go yet though.

  3. Good for you that you are able to travel guys. As for us. I want it to be super safe to be doing a lot of travel. But thanks for the good vibes. 😘

  4. What a great post. My family and I were just talking about visiting Hawaii for my youngest daughter’s 15th birthday. Which we celebrate like a SweetSixteen. I was wondering were to even start on my research.

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