My First Solo Trip – Nantucket, MA

The destination of my first ever solo trip was Nantucket, Massachusetts.

I highly recommend Nantucket for beginning solo female travelers. The island is safe, clean, and a perfect place to build confidence in yourself about figuring things out on your own. I spent 4 days by myself: 2 days of travel and 2 days/3 nights on the island. For me, this was the ideal length of time to dabble in solitude.

I went to Nantucket the summer after I graduated from college. I was nervous and excited. I had never stayed in a hostel before, and I didn’t know what to expect.

For a brief moment, I considered canceling my trip. I thought, ‘Is it weird to visit Nantucket alone?’ and ‘Why don’t I wait until next summer and plan to go with a friend?’

But as fate would have it, the following summer I worked full time and didn’t have enough vacation days to visit Nantucket. I won’t be going this summer either because of COVID-19 travel restrictions.

I’m thankful that I traveled when I could. Life is crazy and unpredictable, and that’s why I’ve learned to go for it, even if that means going alone!

I took the scenic (most affordable) route to Nantucket. I took a train from my apartment in Allston to Boston’s South Station. Then I caught a Peter Pan bus to Hyannis, a town on the Cape. At the Hyannis bus station, I was instructed to use a pay phone to call a shuttle for a complimentary ride to the ferry. The shuttle arrived and took me and other travelers to the ferry. I boarded the boat and got a seat by the window. 2 hours later, we arrived on Nantucket!

Arriving in Nantucket via ferry

As a first-time solo traveler, I was VERY nervous that there would be a problem with my hostel booking. My greatest fear was that the reservation didn’t exist, and I would have no place to sleep. The front desk person would squint at me and go, “We don’t have you in our system,” then the Earth would swallow me whole. Even though I received a confirmation e-mail AND spoke on the phone with the hostel staff to confirm my reservation, I was still nervous that there would be a problem, and I would end up with nowhere to stay.

When I stepped off the ferry, all I wanted to do was find my hostel and check in ASAP. So I rented a bike, picked up a map, and peddled furiously in the direction of my hostel. When I arrived, I discovered there were no issues with my reservation, and I was guaranteed a safe and clean place to sleep. I wanted to hug the front desk person! Relief washed over me and my vacation officially began.

I stayed at the Nantucket Hostel on Surfside Beach. I didn’t expect Nantucket to have a hostel, but let me tell you: THIS PLACE IS A HIDDEN GEM. It is BY FAR the most affordable place to stay on the island. I saved literally hundreds of dollars by staying here instead of a hotel.

The Nantucket Hostel, which used to be a lifesaving station

Nantucket is an expensive place. Bostonians love to say, ‘Martha’s Vineyard is for millionaires and Nantucket is for billionaires.’ While there is some truth to this, you can definitely have a great time in Nantucket without spending a fortune.

I saved a boatload of money on lodging by staying at the hostel. I didn’t go to any of Nantucket’s fine dining restaurants, either. Instead I enjoyed delicious and affordable meals at local cafes.

My favorite cafe on the island is ‘Yummy.’ Yummy is a short bike ride (1.8 miles) away from the Nantucket Hostel. They serve sandwiches, wraps, smoothies, and acai bowls. Everything is fresh, delicious, and affordable. You can visit their website here.

Smoothie from Yummy

My favorite cafe in downtown Nantucket is Provisions. They serve coffee, sandwiches, and pastries. Everything is affordable and high quality. The turkey sandwich I ordered ($12) came on the softest bread I’ve ever eaten in my entire life. It was like eating a cloud.

If you’re on a budget and plan to stay in Nantucket for an extended period of time, I recommend going to the grocery store and cooking at home. There are two Stop & Shop grocery stores on the island. I didn’t cook on my 2-day vacation, but I went to Stop & Shop to purchase some fresh fruit and nuts to snack on between meals.

This museum is totally worth a visit! Historians give interactive presentations throughout the day and there is a lookout tower on top of the museum. I felt more connected to the island after learning about its unique history. Adult tickets are $20 and student tickets are $18.

After visiting the Whaling Museum, I rode my bike to the Cisco Brewery. As I walked towards the brewery, it suddenly dawned on me that I was going to a bar… alone. I had never been to a bar alone before. I entered hesitantly.

I saw food trucks and families picnicking. Everyone was having a great time. And no one stared at me like I was weirdo for showing up solo!

Amongst the food trucks, I saw a classmate from college! She was busy at work but we were able to chat for a minute. It felt great to see a familiar face.

With renewed confidence in my decision to travel solo, I purchased a lobstah roll with fries and a Grey Lady Ale. It was HEAVEN.

Lobster roll, golden fries, and Grey Lady Ale at Cisco Brewery

After lunch, I rode to Cisco Beach. The water was FREEZING, so I didn’t swim, but I enjoyed watching the surfers. The waves are bigger here than anywhere else on the island, which makes it the best beach for catching some waves.

After relaxing at Cisco Beach, I got back on my bicycle and rode over to Madaket, on the far west side of the island. Madaket is mostly residential. You won’t find many cafes or shops over here, but you will find Madaket Beach and Smith Point, which I LOVED. There was hardly anyone at Smith Point. The water was flat calm and there was a light breeze. I embraced the quiet. I put away my phone, looked out over the horizon, and reflected on my summer.

Smith Point

Smith Point

As far as I know, Millie’s is the only restaurant in Madaket. They serve Tex-Mex dishes in a casual environment. I stopped here to fuel up on chips and guac before the long (9 mile) bike ride back to my hostel.

A peer from college was living and working on the island while I was visiting. She was working crazy long hours as an event planner, but she still made time to meet with me for brunch, which I greatly appreciated. We went to the Island Kitchen and feasted on Eggs Benedict with bacon and iced coffee. Everything was excellent!

After brunch, Maddie gave me a ride to Siasconset, a village on the east side of Nantucket. I wanted to visit Siasconset because the Siasconset (‘Sconset) Bluff Walk is a popular tourist attraction. Visitors can walk along the nature trail and admire pretty ocean-front cottages and their charming gardens. It’s all very ‘instagrammable.’

Classic Nantucket cottage on the ‘Sconset Bluff Walk

Cosmos flower on the trail (I did not pick this flower – I strive to LEAVE NO TRACE)

After the Bluff Walk, I decided to walk to the Sankaty lighthouse. The lighthouse is only a mile and a half from the Bluff Walk but the path was entirely on the beach. Have you ever walked in sand? If so, you know it’s not easy. This walk would have taken me 30 minutes on pavement but it took ages in the sand.

Time became meaningless as I haphazardly trudged through the sandy desert. There wasn’t a soul in sight, and I began to feel like Tom Hanks in Castaway. Finally, FINALLY, I saw the candy cane striped lighthouse.

At the lighthouse, I met a friendly woman and she offered me a ride back to the Bluff Walk. I’m eternally grateful for her hospitality. (Of course I don’t recommend hitch-hiking, but I knew that she genuinely wanted to help me, and I accepted her offer).

I cherish my time in Nantucket. It’s where I first discovered the joys of solo travel. I’d love to return someday with friends, someone special, or maybe even on my own again.

I’m sure some of you reading this have been to Nantucket. What do you like most about the island? Please let me know in the comments. I value your input!

– Travel Alli