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Portland Discovery provides trolleys for wedding parties, shuttling of wedding guests, rehearsal dinners, or private tours of Portland. We also own and operate 3 sightseeing boats that can be used for cocktail receptions, rehearsal dinners, private island transportation, or even wedding ceremonies!

Trolleys can be open-air or enclosed and accommodate up to 34 people per trolley. Boats accommodate up to 130 guests and feature fully enclosed cabins as well as plenty of outside deck space with 2 bathrooms and full bars.

  • Woman-owned
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Frequently asked questions

What types of vehicles are in your fleet?


Do you offer special types of transportation?


Schedule permitting, which of the following driving services do you provide?

Round Trip
One-Way Trip

Typically, what is the minimum rental time required to book your services during peak season?

4+ Hours

Which of the following amenities are your vehicles equipped with?

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Reviews of Portland Discovery Land and Sea Tours

4.9 out of 5 rating
4.9 out of 5 rating
7 Reviews
99% recommend it
  • Quality of service
    4.9 out of 5 rating
  • Average response time
    4.9 out of 5 rating
  • Professionalism
    4.9 out of 5 rating
  • Value
    4.9 out of 5 rating
  • Flexibility
    4.9 out of 5 rating

Latest reviews

Dlm Sent on 12/19/2021
5 out of 5 rating

When you need reliable transportation...

SO happy we chose Portland Discovery for our transportation to our rehearsal and rehearsal dinner. At a busy time when things can go wrong and you're being pulled in 100 directions, it was a blessing that we hired Portland Discovery! Customer service is extremely responsive and the driver was prompt and friendly. There were zero issues, and I regret not hiring them as our wedding day transportation. It is a breath of fresh air when you don't have to babysit a vendor (oh yes, that happens!) When you need reliable transportation...hire these folks!
Meg Sent on 09/09/2019
5 out of 5 rating

Wedding Day Trolley

We were looking for wedding transportation that was affordable, unique, and met the needs of our complicated wedding and we couldn't have been happier with Portland Discovery Land and Sea tours! We booked a trolley with Portland Discovery Land and Sea Tours first to transport the groom to the wedding, and then to drive the wedding party to and from our ceremony venue around Portland for photographs.
When I first reached out, Jake was able to answer all of my questions and helped me plan the schedule and logistics for our wedding. He was really helpful in making sure our schedule would work with our key events throughout the day. He was extremely responsive as well! The trolley is very well priced - much cheaper than other options we were looking at such as limos and buses. We were able to fit our entire wedding party and parents without being squished together as well as take advantage of the beautiful weather by opening the windows!
On the wedding day, the driver was on-time, very friendly, and made sure that we made all of our events! She also was flexible as well, when we need to adjust the schedule due to the ferry from Peaks Island being late.
The trolley made for some unique wedding photos and wonderful moments before and after wedding. I would highly recommend Portland Land and Sea Trolley for your wedding transportation for a unique, cost effective, organized and beautiful way to transport people for your wedding!
Kaitlyn Sent on 10/21/2018
5 out of 5 rating

A Wonderful Experience!

We were looking for a way to transport our wedding guests from hotel-to ceremony-to reception, all located in downtown Portland. We were so fortunate to contract with Portland Discovery Trolleys. They were wonderful to work with and Jake was very accommodating. They made the timeline and multiple stops all flow so perfectly. Our guests loved the experience! Our Maine wedding day was fun, unique and complete with Portland Discovery Trolleys!
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Real Weddings

Sarah & Dave
98 photos · 10/06/2018


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