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PORTLAND

10 Best Private Tours In Portland

Portland's standouts, both coasts.

The 10 standout private tours a Portland traveller will actually book. What each one covers, who runs it, and what it costs from the dock or the trailhead.

10 Best Private Tours In Portland

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks - Why this Portland Harbor charter beats the usual cruise

1.Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

Most Popular 5.0

Private 2-hour charter on a vintage lobster boat in Portland Harbor with four lighthouses, Casco Bay islands, and drinks.

“Tristan and Capt. Nick were great, very knowledgeable. Tristan took a great picture of us with the Portland Head Light centered in the background”

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Private Customized Willamette Valley Wine Maker Tour with lunch

Private Customized Willamette Valley Wine Maker Tour with lunch - Carmine’s guide style: winemaker-level context, not just talk

2.Private Customized Willamette Valley Wine Maker Tour with lunch

5.0

Private Willamette Valley wine maker tour from Portland with an expert guide, about four estate tastings, and lunch included.

“We recently enjoyed a wine tour with Carmine. Despite a hiccup in our plans due to a power outage, he was agile and quickly adapted. His knowledge and network paid off and our day was amazing. His enthusiasm and passion for wine waRead more”

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Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour - Views back to Portland: photos, sea air, and the sense of scale

Private Wine Excursion Willamette Valley, Oregon – Wine Tour

Private Wine Excursion Willamette Valley, Oregon - Wine Tour - Seven Hours and Four Stops: How the Day Actually Flows

4.Private Wine Excursion Willamette Valley, Oregon – Wine Tour

5.0

Private Willamette Valley wine day with four winery stops, picnic lunch, chilled water, coffee on board, and pickup from Portland.

“I was responsible for an executive committee retreat for professionals. Shane did an excellent job of helping me organize a team building experience of wineries, a cidery, chocolate tasting and dinner. He was easy to work with, communicative, and knowledgeable. His expertise and hospitality created a fun atmosphere that allowed us to enjoy the day.…”

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Private Sunset Charter on a Vintage Lobster Boat with Drinks

Private Sunset Charter on a Vintage Lobster Boat with Drinks - The captain-guide touch: local history without turning it into a lecture

5.Private Sunset Charter on a Vintage Lobster Boat with Drinks

5.0

Private sunset cruise on a vintage lobster boat in Casco Bay with drinks, onboard comfort, and guided lighthouse history.

“Best way to see the coastline and lighthouses in Portland! It was nice having the tour all to ourselves. Our guide was very informative and knowledgeable. The boat was nice and clean, and they provided a speaker for us to play our music and blankets. A great experience, definitely recommend!”

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Private Arrival Transfer from Portland Airport PDX

Private Arrival Transfer from Portland Airport PDX - How the Pickup Works at Portland International Airport

Bar Harbor and Acadia Full Day Private Tour from Portland

Bar Harbor and Acadia Full Day Private Tour from Portland - Acadia National Park: Thunder Hole, Schooner Head, Cadillac Mountain, Jordan Pond

Private Wine Tours

Private Wine Tours - From Patricia Green Cellars to Alexana: What Tastings Look Like

8.Private Wine Tours

5.0

A private Willamette Valley wine day from Portland with pickup, bottled water, and a picnic lunch, plus 3 tailored winery stops.

“What a PERFECT day!!! Wayne was an amazing guide and took us to the perfect wineries for our day. He scheduled everything and was so much fun. The wineries were perfect for us and Wayne really knew the locations and owners. Lunch was also excellent. If you’re going to Willamette we highly recommend!!”

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6 Hours Private Lighthouses and Kennebunkport Tour in Portland

6 Hours Private Lighthouses and Kennebunkport Tour in Portland - How the 6 hours actually feel with a private driver-guide

9.6 Hours Private Lighthouses and Kennebunkport Tour in Portland

4.5

Private 6-hour Portland and Kennebunkport tour with lighthouse viewpoints, Casco Bay stops, and a Kennebunkport waterfront stroll for up to 5.

“Our driver didn’t show up. I had no notice though he said he sent a text. He was sick and since we didn’t want to get sick I’m glad we didn’t go.”

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Sunset & Scenic Private Boat Tour of Portland & Casco Bay

Sunset & Scenic Private Boat Tour of Portland & Casco Bay - Portland Head Light from the Water: The Lighthouse You Don’t Need to Hunt

10.Sunset & Scenic Private Boat Tour of Portland & Casco Bay

5.0

Private sunset boat tour around Portland and Casco Bay with Captain Kevin and Sarah, Portland Head Light views, and comfy blankets.

“We had a fun afternoon seeing the islands of Casco Bay. Kevin and Sarah provided a fun, relaxed time and expertly showed us many scenic views. Near the end, we visited a great restaurant for food and drinks then ended the trip right at dusk when the light turned golden.”

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