North America Luxury Sailing Trips & Packages Tours & Trips

24 North America Luxury Sailing Trips & Packages trips. Tours from 14 tour companies. 18 reviews.

24 Trips match your criteria (1 - 20 shown)

Mexico (Cabo & Baja): See & Experience it ALL in 6 Days - 1st Class Custom Tours
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By Charlie The Traveler
Local Expert
Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.
Small Group Tour
Why we love them
Travelers report that traveling with CharlieTheTraveler is a life-changing experience, in the best possible way.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Full schedule

Highlights

  • Wine & Jazz Sunset Cruise with an Open Bar
  • Swimming Alongside Whale Sharks (from October to April only)
  • Interacting with Dolphins
  • Horseback Riding on the Beach
  • Rock Climbing
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Themes

High Adventure, Nature & Wildlife

What travelers are saying

"Thank you for reaching out! This trip was absolutely phenomenal—truly the best 10 days of my life. I’m incredibly grateful for everything you arranged. Cindy, in particular, took such good care of me. It felt like she was supporting me around the clock, and I really appreciate her dedication. I’m already eager to recommend your services to my friends and colleagues. On top of that, I realized how much I love the South Island—I’m hoping to visit Queenstown and Mount Cook National Park next, perhaps while participating in some business-related community events. I’d be thrilled if your company could help me plan that trip as well. Thank you again for everything. I look forward to traveling with you in the future!"

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British Columbia Yacht Trip
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Small Ship Cruise
Why we love them
They’ve been recognized by major travel publications for their pioneering adventure travel expertise that spans back to their founding in 1979.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Learn about Haida culture, history and the natural wonders of their homeland
  • Visit multiple UNESCO World Heritage Sites
  • Hike trails that wind through forest floors
  • Enjoy the longer hours of sunlight on waters that attract an abundant and diverse display of marine life
  • Find many varieties of sea stars (formerly known as starfish) and many other marine creatures
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Themes

Cultural, 50 Plus, Sailing, Small Ship Cruise

What travelers are saying

"I have travelled with ROW numerous times, including four trips on the Rogue River. Every trip has been wonderful and every person associated with ROW has been nice, knowledgeable, professional and fun. The Rogue is a great river and the trip is an excellent one for two people or a large group—and I have done both. I’ve taken both of my kids, one time each, and have organized groups of colleagues twice; most recently in 2019 when 14 of us gathered. The guides at ROW are great and help to make the trip very enjoyable. The scenery, lodging and the wonderful outdoors including warm air and refreshing water, make for a wonderful escape from the everyday routine. The fact that this trip offers beds and indoor plumbing is a nice benefit and allows those who have an aversion to camping a chance to see the wilderness. I have recommended ROW and the Rogue trip more times than I can count and my group has already reserved our trip for 2021. What are you waiting for?"

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Memphis to St. Louis
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River Cruise
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • The family recipes of acclaimed Southern chef Regina Charboneau
  • The only steamboat with multiple specialty dining options, all at no additional charge
  • Daily lectures by the Riverlorian, our onboard historian
  • Professional showboat-style entertainment and dancing nightly
  • Our own dedicated fleet of Steamcoaches
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Themes

50 Plus, Small Ship Cruise

What travelers are saying

"We had a wonderful cruise up the Mississippi from New Orleans to St Louis ! Great entertainment, great food , pools, hot tub and visiting interesting places."

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Custom Designed Trip
Lodging level
lodgingLevelName
Physical level
N/A

Highlights

  • Fully customized trip based on preferences
  • Matched with a local specialist
  • From $150 per person per day
Self-Guided / Independent Tour
Columbia and Snake Rivers Journey
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River Cruise
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Follow the path of Lewis and Clark’s expedition through what are today the states of Washington and Oregon.
  • Cruise through the towering canyons of the Columbia River Gorge, and explore the coastline by kayak or motorized landing craft.
  • Hike or bike along breathtaking vistas, and take an exhilarating jet boat ride up the Snake River to Hell’s Canyon.
  • Enjoy locally sourced, sustainable cuisine and nightly beer and wine tastings on board. Also visit a winery for a tasting and tour.
  • Learn about the history of the Nez Perce and other Native American tribes of the area.
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Themes

Nature & Wildlife, Culinary & Wine, 50 Plus, Hiking & Walking, Education / Learning, National Parks

What travelers are saying

"We booked a National Geographic expedition Holland and Belgium by River. The promotional literature promised a 14-day deposit refund window. The “invoice” was marked “non-refundable” deposit. We completed the National Geographic Traveler Information. About 8 days later we received the “Travel Agreement” to be signed. We both approved and signed the National Geographic documents. A Cruise Line Travel agreement was enclosed but had no signature line. This document contained language which was unacceptable. We submitted the signed NatGeo documents. The following day we canceled the trip due to the unacceptable Cruise Line language. Cancellation was made 12 days after booking and no deposit was returned. We were told on the phone that the refund deadline was triggered by the 14 day window OR signatures on the Travel Agreement which ever came first. This was NEW information. To date, we have received NO refund of our $1000. We cancelled our trip within the advertised 14 day window."

Trip dates & details
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Hawaiian Seascapes
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Small Ship Cruise
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • 8 days Hawaii cruise
  • Watch for whales off Maui and the Big Island of Hawaii
  • You will have opportunities like snorkeling, paddle boarding, kayaking, hiking and other activities
  • Explore Molokai Museum, discover the history of this ancient homeland as you enjoy

Themes

Nature & Wildlife, National Parks, High Adventure, Scuba Diving, Small Ship Cruise

What travelers are saying

"We particularly wanted to do this trip because of the abundance of wildlife we expected to encounter and selected this ship because they offered the kayaking experience. Overall, the weather was very good. Most people seemed like minded and were there for the adventurous experience. Accommodations Review They upgraded our cabin and we were very pleased with the amount of space and the amenities in the room. We appreciated the twin windows and being able to see humpbacks diving from our cabin. It was kept very clean and it was a treat to have our bed turned down with chocolates on the pillow each night. Meals Review We liked the variety and the quality of the food. There was always something new to try. The dining room staff was very professional and personable. Crew & Guides Review Solon was our Principal Trip Leader. He was incredibly professional and it seemed like he was constantly working to maximize the encounters with wildlife and scenery, taking advantage of all the weather opportunities and going to places that they don't often go. He worked very closely with the captain who was very accommodating and caring about us having a memorable voyage. Aymie and Andrew were our kayak guides. We went out to kayak 10 different times and were able to get to know both of them well. They worked hard to keep us safe and well informed. They made sure that we didn't miss out on any land excursions. We've had quite a few kayak guides over the years that we've paddled and we loved these two. Marla was the marine biologist aboard the ship. She was very enthusiastic and had a passion for marine mammals that was infectious. We loved listening to her presentations and looked forward to hearing her voice on the PA saying that there was another whale sighting. Colin, the geologist aboard the ship, was very knowledgeable and able to make difficult subjects understandable to the passengers. Itinerary Review The trip far, far, far, far, far, far exceeded our expectations. I had one "far" in the sentence when we left South Georgia Island after seeing 250,000 King Penguins at St. Andrews Point and added the second when we saw blue whales on two different days. The third "far" was added when we saw hundreds of whales for 6 hours along the iceberg, A68a. I added another "far" when we kayaked for over an hour with humpbacks all around and another "far" when minke whales were all around the kayaks the next day. The last "far" was added the day we didn't paddle since a leopard seal was all around the kayaks and then an orca came close. We had so many incredible experiences that we could never experience all of them in the same trip again. The guides told us that the close encounters that we had didn't happen very often and that we were very lucky that they all happened on our trip. The only thing that we didn't like was portions of the Drake Passage when it was a tad rough, but that experience gives us something to talk about. Transportation Review We made our transportation arrangements through another travel agency. Traveler Advice Make sure that you take sea sickness meds. Take advantage of every opportunity to see wildlife."

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Discoverers Glacier Country
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Small Ship Cruise
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • View Alaska's massive glaciers
  • Kayak and small boat explorations
  • Visit Glacier Bay National Park
  • Enjoy whale watching in Frederick Sound and bears near Icy Strait and Chichagof Island

Themes

Cultural, Nature & Wildlife, Family Friendly, Sailing, National Parks, Small Ship Cruise

What travelers are saying

"We particularly wanted to do this trip because of the abundance of wildlife we expected to encounter and selected this ship because they offered the kayaking experience. Overall, the weather was very good. Most people seemed like minded and were there for the adventurous experience. Accommodations Review They upgraded our cabin and we were very pleased with the amount of space and the amenities in the room. We appreciated the twin windows and being able to see humpbacks diving from our cabin. It was kept very clean and it was a treat to have our bed turned down with chocolates on the pillow each night. Meals Review We liked the variety and the quality of the food. There was always something new to try. The dining room staff was very professional and personable. Crew & Guides Review Solon was our Principal Trip Leader. He was incredibly professional and it seemed like he was constantly working to maximize the encounters with wildlife and scenery, taking advantage of all the weather opportunities and going to places that they don't often go. He worked very closely with the captain who was very accommodating and caring about us having a memorable voyage. Aymie and Andrew were our kayak guides. We went out to kayak 10 different times and were able to get to know both of them well. They worked hard to keep us safe and well informed. They made sure that we didn't miss out on any land excursions. We've had quite a few kayak guides over the years that we've paddled and we loved these two. Marla was the marine biologist aboard the ship. She was very enthusiastic and had a passion for marine mammals that was infectious. We loved listening to her presentations and looked forward to hearing her voice on the PA saying that there was another whale sighting. Colin, the geologist aboard the ship, was very knowledgeable and able to make difficult subjects understandable to the passengers. Itinerary Review The trip far, far, far, far, far, far exceeded our expectations. I had one "far" in the sentence when we left South Georgia Island after seeing 250,000 King Penguins at St. Andrews Point and added the second when we saw blue whales on two different days. The third "far" was added when we saw hundreds of whales for 6 hours along the iceberg, A68a. I added another "far" when we kayaked for over an hour with humpbacks all around and another "far" when minke whales were all around the kayaks the next day. The last "far" was added the day we didn't paddle since a leopard seal was all around the kayaks and then an orca came close. We had so many incredible experiences that we could never experience all of them in the same trip again. The guides told us that the close encounters that we had didn't happen very often and that we were very lucky that they all happened on our trip. The only thing that we didn't like was portions of the Drake Passage when it was a tad rough, but that experience gives us something to talk about. Transportation Review We made our transportation arrangements through another travel agency. Traveler Advice Make sure that you take sea sickness meds. Take advantage of every opportunity to see wildlife."

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Northern Passages and Glacier Bay
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Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Visit to Glacier Bay National Park
  • Sail between Juneau and Sitka
  • View Alaska's massive glaciers
  • Areas explored include Icy Strait, Chichagof Island and Peril Strait

Themes

Nature & Wildlife, Family Friendly, Birding, National Parks, Small Ship Cruise

What travelers are saying

"We particularly wanted to do this trip because of the abundance of wildlife we expected to encounter and selected this ship because they offered the kayaking experience. Overall, the weather was very good. Most people seemed like minded and were there for the adventurous experience. Accommodations Review They upgraded our cabin and we were very pleased with the amount of space and the amenities in the room. We appreciated the twin windows and being able to see humpbacks diving from our cabin. It was kept very clean and it was a treat to have our bed turned down with chocolates on the pillow each night. Meals Review We liked the variety and the quality of the food. There was always something new to try. The dining room staff was very professional and personable. Crew & Guides Review Solon was our Principal Trip Leader. He was incredibly professional and it seemed like he was constantly working to maximize the encounters with wildlife and scenery, taking advantage of all the weather opportunities and going to places that they don't often go. He worked very closely with the captain who was very accommodating and caring about us having a memorable voyage. Aymie and Andrew were our kayak guides. We went out to kayak 10 different times and were able to get to know both of them well. They worked hard to keep us safe and well informed. They made sure that we didn't miss out on any land excursions. We've had quite a few kayak guides over the years that we've paddled and we loved these two. Marla was the marine biologist aboard the ship. She was very enthusiastic and had a passion for marine mammals that was infectious. We loved listening to her presentations and looked forward to hearing her voice on the PA saying that there was another whale sighting. Colin, the geologist aboard the ship, was very knowledgeable and able to make difficult subjects understandable to the passengers. Itinerary Review The trip far, far, far, far, far, far exceeded our expectations. I had one "far" in the sentence when we left South Georgia Island after seeing 250,000 King Penguins at St. Andrews Point and added the second when we saw blue whales on two different days. The third "far" was added when we saw hundreds of whales for 6 hours along the iceberg, A68a. I added another "far" when we kayaked for over an hour with humpbacks all around and another "far" when minke whales were all around the kayaks the next day. The last "far" was added the day we didn't paddle since a leopard seal was all around the kayaks and then an orca came close. We had so many incredible experiences that we could never experience all of them in the same trip again. The guides told us that the close encounters that we had didn't happen very often and that we were very lucky that they all happened on our trip. The only thing that we didn't like was portions of the Drake Passage when it was a tad rough, but that experience gives us something to talk about. Transportation Review We made our transportation arrangements through another travel agency. Traveler Advice Make sure that you take sea sickness meds. Take advantage of every opportunity to see wildlife."

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Ultimate Adventure
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Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Flexible schedule

Highlights

  • Explore “wild and woolly” wilderness, glacial landscapes, old growth and rainforest
  • Kayaking, paddle boarding, and skiffing in remote scenic bays
  • Enjoy wilderness hikes, massive icebergs, and calving glaciers
  • Discover isolated coves and dramatic Misty Fjords National Monument
  • Visit Wrangell's Kiksetti Totem Park and Chief Shakes Tribal House
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Themes

Nature & Wildlife, National Parks, Small Ship Cruise

What travelers are saying

"I love your tour program. I may think of visiting other locations you offer, but I'm really invested into Ukraine for a lifestyle. I want to make additional trips to Ukraine as roles beyond tourism."

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North America Luxury Sailing Trips & Packages Reviews

D

Derrick

Oct 2022

Written on

"Well-planned’

"Well-planned’ is the first thing which comes to my mind when I remember the Cabo/Baja area trip I took with CharlieTheTraveler. We did not have to think about much ...

B

Brittany

Oct 2022

Written on

Most memorable moments

The Cabo/Baja California tour CharlieTheTraveler offers is diverse in regard to the destinations we visited and the activities we engaged in. The whole tour was grea...

L

Luke

Oct 2022

Written on

This tour is perfect for adventure-seekers.

This tour is perfect for adventure-seekers. Paddle boarding, zip lining, rappelling, ATV riding, parasailing…We were given so much in a relatively short period of ti...

D

Devin

Oct 2022

Written on

The experience was very good

The experience was very good. We did a lot in our time there which is what we wanted.

A

Abigail

Oct 2022

Written on

Had a great time

What I really liked is that we were doing a different thing every single day. It is almost impossible to get bored on this tour. We had a great time for sure, with n...

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