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Top 10 Best North America Sailing Trips

Found 671 Sailing Trips activities in North America. Sort by Popularity. - Page 15
 

Private Key West Sandbar and Paddle by Boat

(4.9 of 31 reviews)

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More

Free Cancellation
Private Tour
Start From $600.00
 
Private Key West Sandbar and Paddle by Boat

Private Key West Sandbar and Paddle by Boat

  • North America
  • Superb31 reviews4.9

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Chacahua Afternoon Journey

(4.9 of 14 reviews)

As a team we try to create journeys that are worth investing your time and confidence. We try to do our best to get out of the same schedules that our fellow colleagues offer this tour is whole afternoon experience that show us al... More

Free Cancellation
Private Tour
Start From $68.06
 
Chacahua Afternoon Journey

Chacahua Afternoon Journey

  • North America
  • Superb14 reviews4.9

As a team we try to create journeys that are worth investing your time and confidence. We try to do ....

    Free Cancellation
    Private Tour
    Start From $68.06
 
 

Condor Sailing Public Dolphin and Sightseeing Cruise

(4.3 of 6 reviews)

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Free Cancellation
Private Tour
Start From $104.00
 
Condor Sailing Public Dolphin and Sightseeing Cruise

Condor Sailing Public Dolphin and Sightseeing Cruise

  • North America
  • Exellent6 reviews4.3

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....

    Free Cancellation
    Private Tour
    Start From $104.00
 
 

Luxury Sunset Dinner Cruise in Cabo

(4.3 of 6 reviews)

This sunset tour in Los Cabos is unique and different because it combines the breathtaking beauty of the Sea of Cortez with the opportunity to explore one of Mexico's most iconic landmarks, the Arch of Cabo San Lucas. Unlike other... More

Free Cancellation
Private Tour
Start From $145.00
 
Luxury Sunset Dinner Cruise in Cabo

Luxury Sunset Dinner Cruise in Cabo

  • North America
  • Exellent6 reviews4.3

This sunset tour in Los Cabos is unique and different because it combines the breathtaking beauty of....

    Free Cancellation
    Private Tour
    Start From $145.00
 
 

San Diego Bay Sailing Tour

(5 of 16 reviews)

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This group sail is li... More

Free Cancellation
Private Tour
Start From $95.00
 
San Diego Bay Sailing Tour Likely to Sell Out

San Diego Bay Sailing Tour

  • North America
  • Superb16 reviews5

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Sea to Sky Afternoon Sail

(5 of 199 reviews)

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain ranges. We will depart from the docks in Squamish (about 40 minut... More

Free Cancellation
Private Tour
Start From $132.45
 
Sea to Sky Afternoon Sail Likely to Sell Out

Sea to Sky Afternoon Sail

  • North America
  • Superb199 reviews5

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds w....

    Free Cancellation
    Private Tour
    Start From $132.45
 
 

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

(4.9 of 23 reviews)

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, lighthouses and more during this 1.5-hour experience!... More

Free Cancellation
Private Tour
Start From $57.24
 
Newport Sightseeing Day Sailing Experience on Schooner Adirondack Likely to Sell Out

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

  • North America
  • Superb23 reviews4.9

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....

    Free Cancellation
    Private Tour
    Start From $57.24
 
 

Shared Day Sail along Historic St Augustine Bayfront

(5 of 4 reviews)

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories on the sea. Our cruise is perfect for all water-lovers: families, couples, and friends. Some guests interact with the USCG licensed... More

Free Cancellation
Private Tour
Start From $129.00
 
Shared Day Sail along Historic St Augustine Bayfront Likely to Sell Out

Shared Day Sail along Historic St Augustine Bayfront

  • North America
  • Superb4 reviews5

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories o....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Boat & Yacht Tour Amazing Sandbar Adventure, Water Toys & Snorkel

(5 of 4 reviews)

Enjoy the day on the water with friends and family with Dolphin Water Sport. Our +650 reviews on Google with a score of 4.9 guarantee our quality. Come aboard our Boat and Yacht to enjoy an incredible Boat Trip in Miami. We'll cr... More

Free Cancellation
Private Tour
Start From $150.00
 
Boat & Yacht Tour Amazing Sandbar Adventure, Water Toys & Snorkel Likely to Sell Out

Boat & Yacht Tour Amazing Sandbar Adventure, Water Toys & Snorkel

  • North America
  • Superb4 reviews5

Enjoy the day on the water with friends and family with Dolphin Water Sport. Our +650 reviews on Goo....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu.

(4.4 of 7 reviews)

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. In Cancun you have an incredible opportunity to ... More

Free Cancellation
Private Tour
Start From $95.00
 
Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu. Likely to Sell Out

Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster....

  • North America
  • Exellent7 reviews4.4

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out o....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

All inclusive fun! Music, boat tour, snorkel, open bar & lunch

(5 of 3 reviews)

This is the stuff bucket list memories are made of. Grab your loved ones and dance, eat, drink, swim, relax and laugh! Nothing could be better so get booked now! ... More

Free Cancellation
Private Tour
Start From $110.00
 
All inclusive fun! Music, boat tour, snorkel, open bar & lunch Likely to Sell Out

All inclusive fun! Music, boat tour, snorkel, open bar & lunch

  • North America
  • Superb3 reviews5

This is the stuff bucket list memories are made of. Grab your loved ones and dance, eat, drink, swim....

    Free Cancellation
    Private Tour
    Start From $110.00
 
 

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

(5 of 25 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated ... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique Likely to Sell Out

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

  • North America
  • Superb25 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Sailing Adventure on Okanagan Lake from Penticton & Naramata BC

(5 of 43 reviews)

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More

Free Cancellation
Private Tour
Start From $184.98
 
Sailing Adventure on Okanagan Lake from Penticton & Naramata BC Likely to Sell Out

Sailing Adventure on Okanagan Lake from Penticton & Naramata BC

  • North America
  • Superb43 reviews5

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....

    Free Cancellation
    Private Tour
    Start From $184.98
 
 

Boat ride to the Arch and Snorkel

(5 of 41 reviews)

Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a smooth ride through the Sea of ​​Cortez Our guide and captain who are biologists will share interesting and professional infor... More

Free Cancellation
Private Tour
Start From $72.25
 
Boat ride to the Arch and Snorkel Likely to Sell Out

Boat ride to the Arch and Snorkel

  • North America
  • Superb41 reviews5

Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a s....

    Free Cancellation
    Private Tour
    Start From $72.25
 
 

Guided Reef Snorkel + Sunset Sail - Small Groups with Honest Eco

(5 of 11 reviews)

Guided Reef Snorkel + Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows you t... More

Free Cancellation
Private Tour
Start From $117.17
 
Guided Reef Snorkel + Sunset Sail - Small Groups with Honest Eco Likely to Sell Out

Guided Reef Snorkel + Sunset Sail - Small Groups with Honest Eco

  • North America
  • Superb11 reviews5

Guided Reef Snorkel + Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What ....

    Free Cancellation
    Private Tour
    Start From $117.17
 
 

Jolly Roger Pirate Show and Dinner Cruise with Open Bar

(4.6 of 8 reviews)

Spend you vacations' funniest evening along with Jolly Roger's flamboyant priate crew. Cruise along the Cancun coast while singing, drinking, dancing and participating in a variety of hilarious games and contests. The little pirat... More

Free Cancellation
Private Tour
Start From $149.00
 
Jolly Roger Pirate Show and Dinner Cruise with Open Bar Likely to Sell Out

Jolly Roger Pirate Show and Dinner Cruise with Open Bar

  • North America
  • Superb8 reviews4.6

Spend you vacations' funniest evening along with Jolly Roger's flamboyant priate crew. Cruise along ....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Luxury Snorkel Adventure in Cabo

(4.8 of 36 reviews)

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at either one of this beach areas is where boat captain will make a stop for snorkeling at one ... More

Free Cancellation
Private Tour
Start From $149.00
 
Luxury Snorkel Adventure in Cabo Likely to Sell Out

Luxury Snorkel Adventure in Cabo

  • North America
  • Superb36 reviews4.8

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located ....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

(5 of 14 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More

Free Cancellation
Private Tour
Start From $89.00
 
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise Likely to Sell Out

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

  • North America
  • Superb14 reviews5

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Amazing Snorkeling Experience + Real Mexican Tacos

(4.3 of 11 reviews)

This is the classic snorkeling experience when you come to Cancun, it is a must tour in your Itinerary. When you do this experience you feel a connection with nature, it is like taking a little bit of Cancun with you back home. Se... More

Free Cancellation
Private Tour
Start From $39.00
 
Amazing Snorkeling Experience + Real Mexican Tacos Likely to Sell Out

Amazing Snorkeling Experience + Real Mexican Tacos

  • North America
  • Exellent11 reviews4.3

This is the classic snorkeling experience when you come to Cancun, it is a must tour in your Itinera....

    Free Cancellation
    Private Tour
    Start From $39.00
 
 

Private Sail on the Cape Fear River Aboard a Classic Yacht

(4.3 of 11 reviews)

Our private charters offer insider access to the Cape Fear River under the guidance of a local captain who has sailed these waters - and the wide Atlantic beyond - professionally for more than a decade. Our steward's comparable ex... More

Free Cancellation
Private Tour
Start From $515.00
 
Private Sail on the Cape Fear River Aboard a Classic Yacht Likely to Sell Out

Private Sail on the Cape Fear River Aboard a Classic Yacht

  • North America
  • Exellent11 reviews4.3

Our private charters offer insider access to the Cape Fear River under the guidance of a local capta....

    Free Cancellation
    Private Tour
    Start From $515.00
 
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