Trip to Maui Hawaii 2005

Trip to Maui Hawaii 2005

I took my first trip to Maui, Hawaii, from October 29, 2005, to November 6, 2005. I went with a singles group, and I convinced one of my co-workers to join me soon after I returned from Paris.


I had never traveled so much for pleasure in one year. In April 2005, I got my first passport and my first stamp in London. Then, in September, I flew off to Paris, my dream destination. Two weeks later, I was back on the plane to Hawaii. This was a dream. People often wonder where I get the money to travel so much. When there is a will, there is a way.

When I first started thinking about my next trip, I searched for popular destinations for single people.  To my surprise, Hawaii came up.  At this point, I thought of Hawaii as a honeymoon destination or 20th anniversary trip.  Not for a single woman traveler.  Although the article said plenty of singles, I figured it would be best to go with a group.  I did another search for travel groups for singles.  That’s when I found Singles in Paradise.  The company is based in Los Angeles.  I emailed, found out the room options, and made a deposit.  I was telling a coworker about the trip, and she was interested in coming along, so we planned to share a bedroom within a 2 bedroom condo.  She was coming from Chicago, and I was coming from New York.  We made plans to meet in LA and wait together for our connecting flights to Hawaii.

When we finally arrived in Hawaii, on October 29, 2015, it was dark, and we were driving a rental car along the Hawaiian coast.  Did I mention it was dark?  There were no street lights, and I said I could do it.   Although I didn’t have a car in New York City and didn’t start driving on a regular basis until in my twenties which made about 5 years total at this point.  I’ve never been to Hawaii, but how hard could it be to be right?  I was a little nervous.  We managed to not drive off a cliff and arrived at the hotel and our rooms.

Our two roommates were already in the condo. Our room was small, right by the front door, and looked a little scary. It had been such a long day. After seeing the room, my friend was ready to return to the plane and go home. It was too late to go anywhere, and I said we should just get some sleep and figure things out tomorrow.

The rooms looked much better in the morning.  The beach was just steps away from our room.  We hadn’t plan anything on Sunday but we had a jammed pack week.  My friend had done her researched and got a guide book “Maui Revealed by Andrew Doughty”.  The tour group had optional activities you could sign up for an additional cost but we used the books suggestions.


Our first activity was horseback riding down into the crater of Haleakala in Haleakala National Park.  I had never ridden a horse before.  I didn’t think my first time would be starting at 10,000 feet in the sky.  I almost missed out because I also didn’t realize it was cold on top of that mountain.  Luckily our guide was able to lone me the green pants and blue jacket I was wearing or I was going to be able to go as planned.  I got matched with a horse named Bubba.  He was a more mature horse.  We got on the trail, and I was terrified.  I think I almost killed me and Bubba a few times because I didn’t trust him.  About half way through I realized Bubba knew where he was going.  I also thought this ride was at most 3 hours but it turned into more like 6 hours.  I wasn’t having a good day.  Once we arrived inside the crater and the sun burned my forehead, I could enjoy the beauty.  We also had lunch.  I was much more trusting of Bubba by the end of the day.  

By the time we got back to the condo, we were beat.  It was Halloween, and Maui was known for its Halloween celebration on the island.  We looked at each other and said pass.

The next day, we decided to lounge around the condo and meet up with the group for a boat ride that evening.  It was fun.  It is a lot more relaxing than the day before.


By the third day, it was time for a Luau.  I was excited to wear flowers in my hair and learn about the Hawaiian culture.  The ceremony included roasting the pig in the sand and dancing.  So far, we have been pleased with everything the book has suggested.

On our way to a final full day, we drove the highly recommended road to Hana.  The drive to Hana is one of the most scenic routes in Maui.  It had waterfalls, black sand beaches, and trees.  Ultimately, we would do something a little more adventurous, power hang gliding, and then spend the night.  At this point, I had skydived and gone bungy jumping, so this was the new challenge.  We bought the CD, popped it in, and hit the road.  We stopped and took plenty of pictures and made it to the small airport just in time for our flight.  It was a lot of fun, and I will do something like that again.

We were done earlier than we thought and decided to cancel our hotel room and head back to our condo on the other side of the island.  We had a good time and went out for dinner.

This was our final day in Maui and the weather all week was perfect.  I decided to stay in enjoy the view from the balcony and my friend went to the beach to get some sun.  Maui proved to be a fun destination that singles could enjoy as well as couples.

Bisa Myles

I am a breast cancer survivor and plus-size adventurer traveling the world and capturing every mile as I go. I still have miles to travel.

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