New England Road Trip: Solo Vacation Tips & Itinerary

While it would have been fun, and at times less stressful, to have someone to travel with, I wanted to go on this trip no matter what and I am so glad that I did! I would absolutely go on another solo trip!! I could do the things I wanted, when I wanted, at the pace I wanted, how I wanted, and change my mind if I wanted. It was great :)




There were some parts of the trip that I was a little apprehensive about being on my own but they turned out fine. Here are few tips if you are planning a solo vacation.


  1. Don't worry about eating in restaurants by yourself. Lots of people do it, especially people on business trips, and it's not awkward like I feared it may be. Either the wait staff or other customers were chatty, if you are sitting at the bar, or I could catch up on my journaling while I was waiting on my food. Also, when you are a party of one you either get seated right away or there is very little wait time. (Even if you don't drink, it's absolutely fine to sit at the bar and order food. You will not be the only one, trust me.) 
  2. Just because you are traveling alone does not mean that you won't talk to other people for the duration of your trip. Every time you purchase an admission ticket, order food, buy something from a shop, etc. you interact with other people. 
  3. If you are not on the same schedule or time zone as your loved ones back home, check out the video apps available for communication. My best friend introduced me to the Marco Polo app before I went on my trip and I love it! It's free, works on wifi, and works on androids and iphones (a huge bonus for me because I usually turn out to be one of the few people who use an android in this iphone world of ours). You can record a message of yourself talking or of your surroundings and send it to one or multiple people in your contact list who also have the app. It was nice to be able to show people where I was during my trip, send and watch videos sent to me whenever I had free time (instead of trying to coordinate a phone call), and to be able to see their faces and hear their voices when they replied with their own video messages. 
  4. If you pack your itinerary as full as you possibly can, there will not be time to get lonely. Seriously, if you are only in your hotel/air bnb to sleep and spend the rest of your time exploring you will not have time to be lonely. 
  5. It's better to over plan than to under plan when traveling solo. For example, that foodie friend of yours isn't going to be with you to find the perfect restaurants to eat at during your trip. So before you leave, do some investigating and come up with a list of restaurant options for the cities you are visiting. Nobody wants to be standing on the sidewalk hot, hungry, and angry because it's lunch time and you have no idea where to get a good meal that isn't an expensive tourist trap. It's always easier to cull a list than to add to it.
  6. Don't be afraid to ask for help. For example, if you are in Boston and your Google Maps gps freezes up because everyone else in the city is trying to use it you need to ask for directions (not that I have any experience with that). However, be selective about who you ask, safety first people. If you can, pop into a store and ask one of the employees for the directions you need. If they work in the shop they are probably a local and can give you correct directions.
  7. Dress to blend in. We all want to look cute, but traveling alone is not the time to stand out. Leave the eye catching jewelry at home and don't flash you cash or other valuables around. You don't want to be an easy target for a pick pocket. 
  8. Don't tell anyone you don't know that you are traveling alone. When people asked me during my trip, I told them that I was meeting different friends throughout my trip. Actually, I only met one friend at the end of my trip, but they didn't need to know that. In reality, the majority of people are nice and you don't need to worry about them. However, for the few people out there with sinister intentions you just let them know that multiple people know where you are, where you should be next, and thus you became a less desirable target.
  9. Look confident. If you look confident people and walk with a purpose, people assume you know what you are doing, where you are going, and they generally will not bother you.
  10. Use common sense and trust your instincts. Just like your home town/city, there are certain parts of town you wouldn't visit after dark. The places you are visiting are the same. If you stick to the main touristy areas you should be fine, but to be on the safe side don't stay out too late, stay in well lit areas, and trust your instincts. If you need to walk back to your hotel or where you parked your car, it's dark, and something doesn't feel right stay on the safe side by ducking into a well lit place with other people around and call an Uber to pick you up. Even if you are only going a short distance, it's worth the extra money to stay safe. 

Now on to the fun stuff! Below is my itinerary for my New England road trip. Normally, I like to have between 2-4 activities planned for each day. Since I was traveling alone, I did more research and planning than I typically do and I planned out restaurants I wanted to try as well. 



However, even with the most thorough planning you need to be flexible. It may rain the day you planned to go on a boat tour and the company needs to reschedule your tour or a restaurant may have a two hour wait, because it's Saturday night in Boston...who knew?, and you just want to eat and then crawl into bed. Needless to say, the itinerary below is what I actually did on my trip and not how I originally planned it, but everything worked out and I had so much fun!

New England Coast Road Trip Itinerary: 16 days, 17 states, and 4,462 miles
·         OK, MO, IL, IN, OH, PA, NY, MA, NH, ME, RI, CT, NJ, MD, VA, TN, AR

·         Saturday, September 22 – drive Norman, OK to Columbus, OH
  14 hours
·         Sunday, September 23 – drive Columbus, OH to Portland, ME
  13 ½ hours
·         Monday, September 24 – Portland, ME
o   Recover from driving
o   Main Historical Society Walking Tour 1:30pm
o   Lunch @ Eventide
o   Shopping
  Exchange Street
  Commercial Street
  Old Port District
o   Drive to see the Winslow Homer Studio
o   Dinner @ Duckfat
·         Tuesday, September 25 – Portland, ME
o   Portland Discovery Land & Sea Tour
  Peek at Portland Trolly Tour @ 12:45pm
  Harbor & Sights Cruise @ 10:30am
o   Lunch @ Otto
o   Portland Museum of Art
o   Dinner @ Nosh
·         Wednesday, September 26 – Portland & Rockland, ME
o   Victoria Mansion
  Rockland to Portland = 1 hour 40 minutes
o   Olson House
  Tour 12pm
o   Snack @ Atlantic Baking Co.
o   Farnsworth Museum
o   Dinner @ Café Miranda
·         Thursday, September 27 – Gloucester, MA
  Portland to Gloucester = 2 hours
o   Beaufort, The Sleeper-McCann House 10am
o   Lunch @ Last Stop
o   Seven Seas Whale Watching @ 1pm
o   Dinner @ Latitude 43
·         Friday, September 28 – Boston, MA
  Gloucester to Oak Grove T Station = 42 minutes
  Oak Grove T Station to Old North Church = 23 minutes
o   Old North Church
  Behind the scenes tour 11:30am
  Regular tour
  Captain Jackson’s Chocolate Shop
o   Lunch @ Boston Public Library (afternoon tea)
o   Isabella Stewart Gardner Museum
o   Dinner @ Eatly
·         Saturday, September 29 – Boston, MA
o   Beacon Hill PhotoWalks Tour 10 am
o   Lunch @ Tatte Bakery & Café
o   Boston Public Gardens
  Make Way for Ducklings sculpture
o   Boston Tea Party Museum 1:30pm
o   Quincy Market (next door to Faneuil Hall)
o   Dinner @ Chowda in Faneuil Hall
·         Sunday, September 30 – Boston, MA
o   National Park Service walking tour Freedom Trail: Meetings, Mobs, & Martyrs 11 am
o   Lunch @ Boston Sail Loft
o   Historic Harbor Cruise @ 3 pm
  Boat: REGENCY, dock: 2, 1 Long Wharf
o   Dinner @ Carmelina’s Boston (North End)
o   Dessert - Cannoli at Modern Pastry
·         Monday, October 1 – Newport, RI
  Melrose to Newport = 2 ¼ hours
o   Town walking tour
  Road to independence 10:30am
o   Lunch @ The White Horse Tavern
o   Chateau-sur-Mer
o   The Breakers
  Beneath the Breakers tour @ 4:30pm
o   Dinner @ Malt on Broadway
·         Tuesday, October 2 – Newport, RI
o   The Elms
  Servant Life Tour at The Elms @ 10:30am
o   Lunch @ Mooring Seafood Kitchen & Bar
o   Shopping
  Thames St.
  Long Wharf Mall
  Bowen’s Wharf
  Bannister’s Wharf
o   Dinner @ Brick Alley Pub
  Newport to Mystic = 1 hour
·         Wednesday, October 3 – Mystic, Groton, New London, & Norwalk, CT
o   Lunch @ Captain Scott’s Lobster Dock
o   Lighthouse Cruise 12:30pm
o   Lyman Allyn Art Museum
o   Shopping downtown New London
o   Dinner @ The Spice Club
·         Thursday, October 4 – Mystic, Norwalk, & New Haven, CT
  Mystic to Norwalk = 1 hour 20 minutes
o   Lunch @ Chick-fil-a
o   Lockwood Matthews Mansion 12:00pm
o   New Haven
  Yale University Art Gallery
  Dinner @ Prime 16
  Les Miserables @ Shubert Theatre 7:30pm
·         Friday, October 5 - Mystic, Groton, New London, & Norwalk, CT
o   Breakfast @ B.F. Clyde’s Cider Mill
o   Olde Mystic Village
  Sofia’s Mystical Christmas
o   Lunch @ Oyster Club
o   Dessert @ Sift
o   Drive by old Groton places
  Church, apartment, and libraries
o   Mystic Seaport
o   Dinner @ Red 36
·         Saturday, October 6 – driving from Mystic, CT to Knoxville, TN
  13 hours
  Breakfast @ The Cure Café in Stroudsburg, PA
  Chocolate World factory tour @ Hershey, PA
·         Sunday, October 7 – driving from Knoxville, TN to Norman, OK
  13 hours 

Be on the lookout for my next post about my first day of exploring in Portland, Maine!


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