North America Sailing Tours & Trip Packages

North America Sailing Tours & Trips

2,859 North America trips. Tours from 388 tour companies. 3,209 reviews. 4.6/5 avg rating.

13 trips exactly matchall of the the filters you selected. We are displaying some similar trips.
My selections:
Sailing
Greece Sailing Adventure: Corfu to Kefalonia
Save this trip to your favorites or other list
4.5/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Full schedule

Visits

Corfu

Highlights

  • Begin your sailing adventure on one of the most beautiful islands in the Ionian Sea – the island of Corfu, filled with gorgeous Venetian architecture and boasting an azure sea.
  • Spend your nights on a sailing boat and fall asleep to the relaxing undulation of the waves below. Watch sunset every night from a nearby beach and wake up early to catch sunrise on the deck.
  • Explore the finest beaches in the Greek Islands at sister islands Paxos and Antipaxos, swimming in translucent waters and walking along pure white sand.
  • Take a dip near private islands seldom seen, like Skorpios – once home to Jacqueline Kennedy Onassis – and Atokos – uninhabited except by a few wandering goats.
  • Explore the seaside villages, hospitable locals, glittering bays, lush verdant hills and warm tavernas of Meganisi, Kastos, Kalamos and Ithaca – all at the desired pace of your group and friendly skipper.
Show more

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
Save this trip to your favorites or other list

Health Safety +

More
Greece Sailing Adventure: Kefalonia to Corfu
Save this trip to your favorites or other list
4.5/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate

Visits

Corfu

Highlights

  • Begin your sailing adventure on the biggest and one of the most beautiful islands in the Ionian Sea – Kefalonia, famous for its delicious wine, sheer white cliff faces and world-famous beaches.    
  • Spend your nights on a sailing boat and fall asleep to the relaxing undulation of the waves below. Watch sunset every night from a nearby beach and wake up early to catch sunrise on the deck.    
  • Explore the finest beaches in the Greek Islands at sister islands Paxos and Antipaxos, swimming in translucent waters and walking along pure white sand.   
  • Take a dip near private islands seldom seen, like Skorpios – once home to Jacqueline Kennedy Onassis – and Atokos – uninhabited except by a few wandering goats.  
  • Explore the seaside villages, hospitable locals, glittering bays, lush verdant hills and warm tavernas of Meganisi, Kastos, Kalamos and Ithaca – all at the desired pace of your group and friendly skipper.
Show more

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
Save this trip to your favorites or other list

Health Safety +

More
British Columbia Yacht Trip
Save this trip to your favorites or other list
5/5 Excellent
81 reviews
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
Show more

Themes

50 plus, Cultural, Small Ship Cruise, Sailing

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?"

Trip dates & details
Save this trip to your favorites or other list

Health Safety

More
Hawaiian Island Hopping Adventure
Save this trip to your favorites or other list
4.9/5 Excellent
100+ reviews
Private Guided
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Full schedule

Visits

Hawaii, Hawaii Volcanoes National Park, Los Angeles, Maui

Themes

18 - 30's, 50 plus, Cultural, Cycling & Biking, Eco, Sustainable & Green Travel, High Adventure, Hiking & Walking, National Parks, Nature & Wildlife, Sailing

What travelers are saying

"It's hard to describe how lucky we are to have been able to work with Stephanie in planning our honeymoon to Japan. From the very beginning, Stephanie was friendly, flexible, and an absolute wealth of knowledge. We had several meetings with her leading up to our trip to come up with the perfect itinerary. Throughout this, Stephanie was mindful of our budget, without sacrificing anything. During our trip, Audley was available at all hours to help with anything and everything which was such a relief to know we had that resource available to us. I truly cannot imagine having planned this trip without all of Stephanie's guidance and knowledge- and cannot imagine taking another big trip like this without the help of Audley. Thank you again!"

Trip dates & details
Save this trip to your favorites or other list
More
Discoverers Glacier Country
Save this trip to your favorites or other list
4.9/5 Excellent
100+ reviews
Small Ship Cruise
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Alaska, Baranof Island Sitka, Glacier National Park, Icy Strait, Juneau

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

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."

Trip dates & details
Save this trip to your favorites or other list
More
Fall Semester In Baja
Save this trip to your favorites or other list
4.7/5 Excellent
28 reviews
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Strenuous
Trip pace
Balanced schedule

Visits

California

Highlights

  • This is an outdoor leadership course designed for 23 years and older
  • Explore the stunning, contrasting environments of the Baja Peninsula
  • Develop outstanding leadership skills
  • Huge canyons and thick vegetation

Themes

High Adventure, National Parks, Nature & Wildlife, Rafting, Kayaking, Canoeing, Sailing

What travelers are saying

"Great Wilderness courses!"

Trip dates & details
Save this trip to your favorites or other list
More

Unlock Community Benefits

Travel better together

  • Save favorite trips and itineraries
  • Get insider insights
  • Receive personalized recommendations
  • ... and much more
Join community
Baja Women's Coastal Sailing
Save this trip to your favorites or other list
4.7/5 Excellent
28 reviews
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • This is an outdoor leadership course designed for 23 years and older
  • Cherish the opportunity to strengthen your confidence and leadership skills
  • Get learned about technical sailing and wilderness expedition skills
  • Explore Baja’s unique natural history and landscapes

Themes

High Adventure, Hiking & Walking, National Parks, Nature & Wildlife, Rafting, Kayaking, Canoeing, Women Only, Sailing, Scuba Diving

What travelers are saying

"Great Wilderness courses!"

Trip dates & details
Save this trip to your favorites or other list
More
Discoverers' Glacier Country
Save this trip to your favorites or other list
4.9/5 Excellent
39 reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Alaska, Glacier National Park, Icy Strait, Juneau

Highlights

  • Two exclusive days in Glacier Bay National Park accompanied by a Park Ranger
  • Discover scenic coves and fjords by kayak, paddle board, and skiff
  • Beachcombing and wilderness hikes in the Tongass National Forest
  • View stunning glaciers and listen for the “white” thunder
  • Watch for whales and wildlife in Frederick Sound and Stephens Passage
Show more

Themes

High Adventure, National Parks, Nature & Wildlife, Rafting, Kayaking, Canoeing, Small Ship Cruise, Sailing

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."

Trip dates & details
Save this trip to your favorites or other list
More
Travelstride Gift Card
One card, thousands of extraordinary trips
Gifts Card

Want a tailor-made trip instead?

Your trip, your way, planned by an expert:

  • You choose budget, destinations, activities, transport & lodging type
  • Expert designs the itinerary for you, and once approved, takes care of logistics
Design custom trip
Other trips you may like [sponsored]
Maryland: Eastern Shore & Chesapeake Bay
Save this trip to your favorites or other list
4.9/5 Excellent
100+ reviews
Group Tour
Why we love them
Their unique emphasis on immersive cultural experiences combined with active exploration with personalized cycling experiences.
Lodging level
Premium - 4 star
Physical level
Strenuous
Trip pace
Full schedule

Visits

Belleview, Cambridge, Chesapeake Bay, Chestertown, Eastern Shore, Easton, Maryland, Oxford, St. Michaels

Highlights

  • Sail the eastern shores with Captain Ed aboard the skipjack HM Krentz
  • Feast on the region’s famous seafood
  • Ride through the Blackwater National Wildlife Refuge, a haven for more than 250 bird species, and learn about Harriet Tubman at the newly opened Underground Railroad State Park and Visitor Center
  • Travel on the country’s oldest privately owned ferry (since 1760), across the Tred-Avon River between Oxford and Bellevue
  • Cycle the quiet country roads leading to the charming small towns of Oxford, St. Michaels, Rock Hall, and Easton

Themes

Birding, Cycling & Biking, Nature & Wildlife, Photography

What travelers are saying

"This was the first organized tour my husband and I have ever joined, so we were not sure what to expect , but it turned out to be the best vacation we've ever had. The scenery and food were amazing. We stayed in beautiful hotels. Most of the riding was on paved bike paths so we hardly ever had to deal with car traffic. Our leaders, Andrea and Martin, were funny, informative , and so helpful. We are already planning to go back to Italy with VBT this summer."

Trip dates & details
Save this trip to your favorites or other list
More
Mexico Unplugged
Save this trip to your favorites or other list
4.5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Basic - 2 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Central America, Chichen Itza, Mexico City, Palenque, Playa del Carmen, San Cristobal

Highlights

  • Visit the community of San Pedro Tlahuac, home to Nahuatl descendants who practice traditions like chinampa farming, fiestas and ancient ceremonies.
  • Wander the stalls, snap some photos and pick up traditional handicrafts at the markets in Mexico City and Puebla.
  • Escape the Mexican heat in the highlands of San Cristobal de las Casas and explore surrounding villages where traditional customs and roots are thriving.
  • Explore the stunning Mayan temples of Palenque dating back to AD600 and stroll through Chichen Itza, one of the New Seven Wonders of the World.
  • Finish off your epic journey and recharge with a little beach time in the beachside hub of Playa del Carmen.
Show more

Themes

Cultural, High Adventure, Local Immersion & Homestays

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
Save this trip to your favorites or other list

Health Safety +

More
Iceland: See & Experience it ALL in 9 Days, 1st Class Custom Tours
Save this trip to your favorites or other list
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.
5/5 Excellent
100+ reviews
Private Guided
Why we love them
Travelers report that traveling with CharlieTheTraveler is a life-changing experience, in the best possible way.
Lodging level
Luxury - 5 star
Physical level
Moderate
Trip pace
Full schedule

Visits

Akureyri, Blue Lagoon, Dettifoss, Eyjafjallajokull, Fimmvorduhals Volcano, Geysir, Godafoss, Gullfoss, Gunnuhver, Jokulsarlon, Lake Myvatn, Reykjanesfolkvangur Reserve, Reykjavík, Reynisfjara, Seljaland, Skaftafell, Skogafoss, Svartifoss, Thingvellir National park, Thorsmork Nature Reserve, Vatnajökull National Park, Viti

Highlights

  • Witnessing Aurora Borealis/Northern Lights (seasonal)
  • Hiking a Caldera, Craters, Glaciers & Volcanoes
  • Bathing in a Natural & Steaming Spa (a.k.a. the Blue Lagoon)
  • Geothermal Attractions: Geysers, Lava Fields, Mud Pools, Sulphur Springs & Hot Springs
  • Exploring an Ice Cave (seasonal)
Show more

Themes

Family Friendly, Nature & Wildlife

What travelers are saying

"Thank you guys for setting up this trip. We spent 7 days in Palawan and Coron island and enjoyed every day. The remote coordinator worked very well for us through Whatsup, and the daily itineraries were exactly what we expected. Not too much and not too short. We recommend this tour for every one who wants to explore these locations"

Trip dates & details
Save this trip to your favorites or other list

Health Safety

More
Western Trails
Save this trip to your favorites or other list
5/5 Excellent
47 reviews
Group Tour
Why we love them
They discover the best local partners, providing trips that are both efficient and authentic.
Lodging level
Premium - 4 star
Physical level
Very Easy
Trip pace
Balanced schedule

Visits

Bryce Canyon, Grand Canyon, Lake Powell, Las Vegas, Los Angeles

Themes

Family Friendly

What travelers are saying

"Everything was pretty much perfect."

Trip dates & details
Save this trip to your favorites or other list

Health Safety +

More
Mackinac Island featuring Niagara Falls
Save this trip to your favorites or other list
5/5 Excellent
51 reviews
Group Tour
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Lake Michigan, Mackinac Island, Niagara Falls

Highlights

  • Travel through time and flash back to the Roaring 20’s and historical architecture
  • Your guide tells of a legacy of innovative automobiles, how it all began, and the man behind it all ~ Henry Ford. A man who built his legacy from the ground up in Dearborn, MI
  • Experience a bit of German architecture, shops and restaurants right in Michigan’s Little Bavaria. Willkommen to Frankenmuth, where you will see a simpler way of life, and where it’s Christmas all year long
  • What do horse and carriages, family owned businesses and a Revolutionary Fort all have in common? They can all be found in 3.8 square miles of history on Mackinac Island, the island that time has forgotten. Enjoy this place that is still steeped in the 18th and 19th century ways
  • Get up close and personal on the Canadian side of roaring Niagara Falls

Themes

50 plus, Culinary & Wine, Cultural, Education / Learning, Nature & Wildlife, Photography

What travelers are saying

"We loved this trip. Our guide was excellent. We really enjoyed all the included highlights. Our favorite was Biltmore Estate. It is a must!"

Trip dates & details
Save this trip to your favorites or other list
More
13 trips exactly matchall of the the filters you selected. We are displaying some similar trips.
My selections:
Sailing

North America Reviews & Ratings

4.6/5  Excellent
3,209  Reviews
See all North America tour reviews
Excellent
1,471
Great
457
Average
73
Disappointing
24
Terrible
13
I

Ida

Oct 2015

Written on

A great variety of experiences (learning about

A great variety of experiences (learning about culture, but also being in nature and doing some more physically challenging activities). Great tour leader and great ...

B

Begum

Oct 2015

Written on

I love our tour leader Edith and

I love our tour leader Edith and the support we got from her was excellent!

P

Paul

Sep 2015

Written on

I felt we covered a lot in

I felt we covered a lot in a short time and there was a flexible app...

g

geraint

Sep 2015

Written on

Great country, people, food and quality of

Great country, people, food and quality of the trip & leader

X

Xiao

Sep 2015

Written on

I thoroughly enjoyed my Intrepid tour and

I thoroughly enjoyed my Intrepid tour and all the optional activities on offer. It's great to travel with the comforts of having transport and accommodation already ...

Write a Review

North America Tour Selection Trips

  • To keep your tour manageable, think regionally: the Northwestern or Southwestern U.S., the Canadian Maritimes, Canadian Rockies, etc.
  • U.S. national parks are some of the finest in the world and a good place to keep tour prices down, especially if you like camping.
  • While most of its citizens live near the U.S. border, Canada is the world’s second largest country, with vast wilderness, mountain and coastal areas awaiting exploration.
  • Greenland, one of the least visited islands in the world, is part of North America, too – and has a fascinating Arctic culture and landscape.
  • Mexico is far more diverse than you might imagine: think Mayan culture vs. modern-day Mexico City, Oaxacan marketplaces vs. Cancun party scene.

Additional details

What Countries are in North America?

North America consists of Canada, Mexico, and the United States (including the Hawaiian Islands and the U.S. Virgin Islands).

What is the best time to visit North America?

The best time to visit North America will vary based on destination. 

Travelers booking a trip to Alaska or northern Canada may want to avoid the cold, dark winters as most guided tours only operate in the warmer months and transportation may be difficult to find. If you are hoping to see the Northern Lights, the “shoulder seasons” of late fall and early spring may be your best bet; the skies will be dark enough to see the beauty of the lights, but the climate won’t be as harsh. 

The best time to visit Mexico is the dry season between December and April. Temperatures are warm enough during this time to enjoy the beach and the sun while avoiding the rainy season of late summer to early fall. Keep in mind that prices peak around the holiday season. 

The southern and eastern regions of the United States can get extremely hot and humid in the summer and freezing in the winter-- avoid weather extremes by visiting in the fall or spring. The Pacific Northwest tends to be warmest and driest during the summer and fall, but don’t be surprised if you encounter rainy skies at any time of year. 

Skiers and snowboarders will naturally want to head to the mountains during winter or early spring when there is enough snow on the peaks. Hikers can avoid snow-covered or muddy trails during winter by visiting in the late summer or fall. 

Safety tips for traveling in North America

North America is generally considered a safe place to travel, although there is crime in the big cities and in some areas of Mexico. Of course, it is important to use common sense and be aware of your surroundings when traveling to any new place. 

Safety tips for traveling in North America:

  • Watch out for pickpockets. Keep your phone, wallet, and other valuables close and out of sight.
  • Don’t carry large sums of cash.
  • Use certified taxicab companies to avoid being ripped off.
  • Ask your tour guide or hotel staff about areas to avoid. 
  • When around wildlife, never get too close. Most national and state parks provide instructions online or at visitor centers on what to do if you encounter wildlife.
  • If you will be driving a car in an unfamiliar country, get familiar with the driving laws and customs of the country to avoid accidents and traffic stops.
  • When traveling alone, give a friend or family member a copy of your itinerary and don’t mention to any strangers that you are alone.

Always Find the Best

On Travelstride you can find 2859 trips to North America and more than 20,000 trips worldwide ranging from budget to luxury and private guided to group tours and everything in between. Only on Stride can you find and compare expert-planned trips from 1,000+ tour operators, cruise lines and local experts. Read traveler and professional reviews so you can confidently find your perfect trip.

Top Tour Companies on Travelstride:
All 1,600+ companies >
Sign in to reveal savings up to $700 per person!