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Weddings

About

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
illustration popular

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Frequently asked questions

What types of vehicles are in your fleet?

Trolley

Do you offer special types of transportation?

Boat

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

Round Trip
One-Way Trip
Multi-Locations

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?

Bar

Reviews of Portland Discovery Land and Sea Tours

Kristina
Kristina Sent on 08/18/2024
5 out of 5 rating

Communicative, Proactive and Dependable Vendor

Look no further for transportation for your big day! We got married on 8/16/24 and had the best experience working with Portland Discovery Land & Se a Tours. When emailing before the event, Ben, Jake and Jamie were so lovely and responsive. They worked to help customize our route, helped contact a hotel on my behalf to ensure our guests could be picked up easily and were always quick to respond to emails. On the day of our event, Wendy was our driver when we had to make a last minute change to our route, she was able to act quickly to help us pivot without missing a beat. I would highly recommend trusting this vendor on your big day!
DLM
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!
MegHitTheZachPot
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!
K
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!
E
Emily Sent on 09/05/2017
5 out of 5 rating
We used Portland Discovery for our wedding: we had two trolleys come pick up our guests and take us to their dock after dinner, where we went on a reception cruise. The whole thing was simply fabulous. They were super easy to work with and very accommodating- they gave me an early tour of the boat, worked with my fiancé to organize two signature drinks, and were happy to provide some narration before the sunset and then let us use their sound system to play music and give toasts. The cruise around Casco Bay was delightful, and the crew was really nice to my husband and me and our guests. Our guests adored it. And I'd booked the trolleys simply as convenient transportation (they were cheaper and much easier to book than a bus), but they ended up being a wonderful experience in themselves. The drivers were very punctual, and riding around on these cute little things with wooden benches and windows down was just heavenly. My mom said the trolley ride home was one of her favorite parts of the day! I would highly highly recommend working with Portland Discovery Tours for a boat, trolleys, or just one of their scheduled tours!
N
Nicole Sent on 09/07/2016
5 out of 5 rating
We loved the trolley service for our wedding! It was such a treat getting to ride around Portland for our big day. Everything from pickup to drop of times ran smoothly and we couldn't have asked for a better experience! Steve was our driver and he was amazing! We had so much fun and would recommend this service to anyone in need of a fun way of transportation!
M
Miranda Sent on 07/08/2012
5 out of 5 rating
Jake was such a huge help!! He was so polite and such a pleasure to work with! The trolley was so much fun and such a nice touch for our wedding day!! So comfortable and very elegant! Huge thanks to Jake (and Roy of course) for helping to make our wedding day flow seamlessly!

Portland Discovery is the best ride in town hands down!

J&M
E
Emily Sent on 11/02/2015
4.5 out of 5 rating
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 around Portland for photographs. The trolley was unfortunately a little late picking up the groom due to a miscommunication between the company and the driver as well as some bad traffic on our wedding day. Everything worked out in the end, however, and the driver was otherwise funny and professional. The trolley also made for some unique wedding photos!
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