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Portland Getaway 2024

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Portland, ME, USA 3 DAYS

FRI 7 JUN - SUN 9 JUN 2024

From US$899 per person

Overview

Join our Detailed Journey's Getaway to Portland, Maine!

Portland is the perfect destination for a memorable weekend adventure. Whether you're looking for outdoor activities, delicious seafood, or a quaint city to explore, Portland has it all. Our Getaways are less structured than our Small Group Tours, allowing you to customize your visit! We help by providing curated recommendations, as well as offer a few optional experiences you can add on to your trip. We also coordinate participants who want to do the same things, so you can go together. It's another way we help you travel easier!

Upon arrival Friday, you can support the local Portland Sea Dogs minor league baseball team! Or perhaps you might like to head down to Thompson's Point for Summer Sunsets Live, where you can enjoy local food trucks and libations as you take in the beautiful sunset.

Included on Saturday is a private, half-day tour of the three local lighthouses: Portland Headlight, Spring Point Ledge Light, and Bug Light! We'll start by picking up beverages from Burundi Star Coffee to enjoy on the ride. At each lighthouse your Trip Leader and local, Kate, will tell you the history and then you'll have time to take photos and walk through the parks, taking in the coastline, Casco Bay, and the Atlantic Ocean.

You'll have time Saturday afternoon and Sunday to enjoy the city's charming Old Port district, where you can browse art galleries, the Portland Museum of Art, boutique shops, and historic landmarks, taste our local brews, and sample our famous food scene. While in Portland, we also highly recommend getting out on the water as well!

Benefits of Traveling Easier to Portland with Detailed Journeys:

Build community, make new travel friends and sharing experiences together.
Your private trip leader will be onsite for anything you need and act as a local guide as well.
Your included lighthouse tour is private, includes a beverage that supports a local Black-owned shop, takes you right up to the lighthouses, and is less rushed than tours you'd book on your own.
Your pre-trip services include travel consulting for choosing how you'll get to and from Portland and what you'll do while there.
Your included hotel price was locked in months in advance! Hotels in Portland are extremely expensive during the warmer months, so we made sure to book ours ahead of time to help you save. The rate for the one we have booked has already increased $127 for the same dates!
We've organized optional experiences that you can add to your trip and not have to worry about purchasing tickets yourself.

Important Information:

This tour is open to anyone who is 18+.
Your $300 non-refundable deposit is due at booking.

Pre-Trip Planning

Pre-Trip you are provided travel consulting as you plan your travel to and from Portland, as well as what you'd like to do while there. In addition we've planned three optional experiences that you can easily add to your trip: Portland Sea Dogs baseball game, Wine Sail, and Freeport by Train!

Stay at the Hilton Garden Inn Portland Downtown Waterfront

Hotel rooms get very expensive during the warming months in Portland. We've booked ahead of time, locking in a great price for the Hilton Garden Inn Portland Downtown Waterfront hotel. It's location is perfect as a stepping off point to enjoy the food and art scene, as well as embark on one of the many boating experiences on Casco Bay. Plus, it's one of the few downtown hotels that has a pool! There is also a fitness room, plus laundry facilities, valet parking, and breakfast available.

Trip Leader - Kate

While in Portland, Kate is your private trip leader. Not only is she there to assist and guide you, but she's also the founder and CEO of Detailed Journeys, as well as a local! She's excited to welcome you to her hometown and show you all there is to see and do.

Build Your Community!

Whether you join solo or with a travel companion, our group travel experiences are all about building your community. You'll be sharing experiences with others who also love to travel. We will help to coordinate activities and meals for those who are interested in doing the same things. Join us to create new friendships and new memories in beautiful Portland, Maine!

Private Lighthouses Tour

Included in your Getaway is a private tour of the three local lighthouses that guide ships through the channel into Casco Bay! Not only is it private, but you actually get to be right next to the lighthouses (versus a tour by boat) and our land tour is slightly longer, with an included beverage. Your local Trip Leader will be the driver and guide for this experience!

Itinerary

Nothing scheduled for this day, click ALL to see everything

7 Jun 2024

Fri 7 Jun 2024

Day 1

Travel to Portland for your first night! Depending on when you arrive, you'll have time to enjoy activities today as well.

Join our optional outing to see the Portland Sea Dogs take on Akron at Hadlock Field! Or perhaps you might like to head down to Thompson's Point for Summer Sunsets Live, where you can enjoy local food trucks and libations as you take in the beautiful sunset. It's also First Friday, our monthly opportunity for local artists to display their work along Congress Street downtown, plus many local businesses and galleries get in on the fun as well.

Check-in is available at the Hilton Garden Inn Portland Downtown Waterfront hotel starting at 4PM. If you arrive before that time and your room is not ready yet, luggage storage is available.

Getting to Portland:
Train - take the Amtrak Downeaster to Portland, which starts at Boston North Station and also has numerous stops between there and Portland. 8 minute taxi ride to hotel.
Bus - ride Concord Coach Lines from Boston South Station or Boston Logan Airport (BOS). 8 minute taxi ride to hotel.
Plane - fly into Portland Int'l Jetport, which is just a 12 minute cab ride to our hotel. Make sure you are looking at routes to PWM (*not PDX, which is Portland Oregon). You can also fly into Boston and take the bus directly from the airport.
Car - if you drive to Portland and need somewhere to park, the hotel has valet parking for $30/day. Another option is to park off the peninsula in a free zone with no time limits and grab the Metro bus or a cab back to the hotel. Your Trip Leader can provide ideas on where to safely park your car outside of the downtown to save on parking costs.

Fri 7 Jun 2024 5:30PM - 8:00PM

Portland Sea Dogs Game

Add-on +US$17

Our Red Sox minor league affiliate team, the Portland Sea Dogs, don their special "Maine Whoopie Pie" jerseys tonight in honor of our official state dessert. You'll have the opportunity to enjoy a whoopie pie or Rising Tide's special "Wicked Whoopie" stout during the game. Plus, our National Hall of Fame mascot Slugger will be joined by Sweetie Pie tonight (the Whoopie Pie mascot). Walk through the stadium concourse to learn about the team's history - there are some big names who have taken the field here!

*Our tickets will be in the bleachers so that everyone is comfortable as the seats with arm rests can be tight.
*Tickets are nonrefundable unless the game cannot be played.

PC: Portland Sea Dogs

8 Jun 2024

Sat 8 Jun 2024

Day 2

A full day to take in the sights, sounds, and tastes of Portland! A suggestion - start your day with a tasty treat from Standard Baking Co. or Holy Donut, both of which are just down the street.

At 9AM we head out on our private, half-day Lighthouse tour! First we'll stop at Burundi Star Coffee to pick up your beverage of choice to enjoy in the van. Then we'll journey to Bug Light with it's picturesque view of the Portland city skyline. We often spot one of the Casco Bay Line ferries sailing past as well. Next up is Spring Point Ledge Light, where you can journey out onto the breakwater and all the way out to the lighthouse. You'll be surrounded by the waters of Casco Bay and want to keep an eye out for sea birds and fishing boats. And last, but certainly not least, we'll visit Portland Head Light, the first lighthouse commissioned in the U.S. and one of the most photographed in the world. While taking in the history at the surrounding Fort Williams you may be tempted by a lobster roll or gelato sold at local food trucks.

Arriving back into downtown Portland by noon, the afternoon is free for you to customize! If you're craving local seafood: High Roller, Portland Lobster Co, Luke's Lobster, and Becky's are all open for lunch!

We absolutely recommend getting out on Casco Bay, one way or another. You could rent a kayak, sup board, or sailboat to take out yourself. There are also boat tours that take you out in search of whales and seals or others with wine tastings, cocktails, and brews. We're offering our favorite wine sails with Wine Wise Events as an optional experience because they're truly amazing and worth every penny!

For dinner, we advise you make a reservation ahead of time because even with so many options to choose from, our food is famous! We'll help to coordinate a group booking at an establishment within walking distance of the hotel if folks want to dine together!

Sat 8 Jun 2024 2:45PM - 5:15PM

Wine Sail

Add-on +US$155

Join us for a wine sail with Wine Wise Events aboard the Frances! We depart from the Maine State Pier, just across the street from our hotel. This sail features Delicious Whites, and sommelier Erica Archer will talk us through each of the five pours as we sail across Casco Bay. Your local Trip Leader and founder of Detailed Journeys absolutely loves these wine sails and can't recommend them more highly!

These wine sails sell out far in advance. We highly recommend adding this when you book if you're interested and paying for it at the same time. We cannot book your space until you've made the payment to cover this experience.

*Tickets are nonrefundable unless the operator can fill your spot (there is no guaruntee), and notice must be given more than 24 hours in advance.
*Space is limited and based on real-time availability.

9 Jun 2024

Sun 9 Jun 2024

Day 3

While today is your last in Portland, we hope you'll make the most of it! There is still so much to see and do! Check-out is at 12PM, and luggage storage is available if you are sticking around after that!

Stroll through the Old Port, visit some of our fun shops, grab brunch at one of the dozens of restaurants within walking distance from the hotel. You might also join us on our optional experience by train up to Freeport, known for the famous L.L. Bean outdoor brand!

Sun 9 Jun 2024 11:00AM - 6:30PM

Freeport by Train

Add-on +US$15

We'll board the 11:25AM train to Freeport, arriving at 11:55AM. You'll have time to walk through the village, enjoy a bite to eat, marvel at the L.L. Bean flagship store, and shop at the outlets. We'll take the 5:58PM train back and arrive in Portland at 6:33PM. **You can also request to return on the 1:08PM train, arriving in Portland at 1:43PM if you need to return earlier, please let us know if you prefer this schedule.

*train times are based on the current schedule, posted as of 12/11/23.
*Tickets are refundable if canceled before train departs.

PC: Amtrak Downeaster

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Select a Package:

One person - shared room

US$899 per person

Only 4 left!

This package is for one person in a shared room, there are 2 queen beds.

If you have a roommate you are signing up with, please list their name in the Traveler Profile form so we can match you together. If you don't, we will match you with another single traveler to share the room.

Pricing

Included:

2 nights in a 3-star, downtown hotel, located in the Old Port with a small pool
Private Trip Leader
Private 3 Lighthouses Tour
Small group, maximum 12 travelers
Travel Consulting for getting to and from Portland, as well as planning your time while there
Coordination of participants who want to do similar activities
Google map with pins showing recommendations for free time and meals
Access to YouLi mobile app

Not Included in package:

Travel to & from the tour
Transfers to your Hotel
Travel insurance: required for anyone who is not a U.S. citizen per our terms & conditions
Most meals
Tips, which are recommended, but not required, for:
- Your Trip Leader
- Housekeeping
Optional Experiences

HOW TO BOOK:

1. Read through the trip details to make sure it's is right for you!
2. Click on "Book Now", then fill in your Traveler Profile and review and accept the terms & conditions.
3. Make your $300 non-refundable deposit.
4. You'll now have access to the trip portal where you can see pre-trip tasks, the itinerary, and more.