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Top 10 Best North America Sailing Trips

Found 713 Sailing Trips activities in North America. Sort by Popularity. - Page 10
 

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

(4.8 of 58 reviews)

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More

Start From $61.48
 
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

  • North America
  • Superb58 reviews4.8

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....

    Start From $61.48
 
 

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

(4.8 of 105 reviews)

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More

Free Cancellation
Start From $63.00
 
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

  • North America
  • Superb105 reviews4.8

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....

    Free Cancellation
    Start From $63.00
 
 

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

(4.8 of 261 reviews)

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Sail toward Diamond Head on the famous Waikiki ... More

Free Cancellation
Start From $53.36
 
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

  • North America
  • Superb261 reviews4.8

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sai....

    Free Cancellation
    Start From $53.36
 
 

Mexico City: Xochimilco at sunrise + Breakfast and transportation

(5 of 125 reviews)

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for the environment. This is not the traditional Xochimilco of the trajineras;... More

Free Cancellation
Start From $159.30
 
Mexico City: Xochimilco at sunrise + Breakfast and transportation Likely to Sell Out

Mexico City: Xochimilco at sunrise + Breakfast and transportation

  • North America
  • Superb125 reviews5

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural....

    Free Cancellation
    Start From $159.30
 
 

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

(4.9 of 208 reviews)

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure yo... More

Free Cancellation
Start From $119.00
 
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways Likely to Sell Out

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

  • North America
  • Superb208 reviews4.9

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....

    Free Cancellation
    Start From $119.00
 
 

Scenic Day Sails in Newport Harbor and Narragansett Bay Aquidneck

(5 of 33 reviews)

Set sail aboard Aquidneck on a memorable journey through Newport Harbor and Narragansett Bay, where the winds are perfect for an afternoon adventure. Guests can relax and soak in the stunning views of iconic landmarks like the Pel... More

Free Cancellation
Start From $55.00
 
Scenic Day Sails in Newport Harbor and Narragansett Bay Aquidneck Likely to Sell Out

Scenic Day Sails in Newport Harbor and Narragansett Bay Aquidneck

  • North America
  • Superb33 reviews5

Set sail aboard Aquidneck on a memorable journey through Newport Harbor and Narragansett Bay, where ....

    Free Cancellation
    Start From $55.00
 
 

Isla Mujeres, Cancún Private Sunset Trip

(5 of 85 reviews)

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the sunset and experience the moment. We are here to bring you the the quality service you so rightly deserve. Our adored crew ensure... More

Free Cancellation
Private Tour
Start From $450.00
 
Isla Mujeres, Cancún Private Sunset Trip Likely to Sell Out

Isla Mujeres, Cancún Private Sunset Trip

  • North America
  • Superb85 reviews5

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the....

    Free Cancellation
    Private Tour
    Start From $450.00
 
 

Luxury Sunset Sail on Serendipity Catamaran in Charleston

(5 of 26 reviews)

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local wildlife as the sun dips below the horizon. This up... More

Free Cancellation
Private Tour
Start From $150.00
 
Luxury Sunset Sail on Serendipity Catamaran in Charleston Likely to Sell Out

Luxury Sunset Sail on Serendipity Catamaran in Charleston

  • North America
  • Superb26 reviews5

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seab....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

(4.8 of 42 reviews)

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear waters teeming with vibrant coral reefs a... More

Free Cancellation
Private Tour
Start From $126.82
 
Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea Likely to Sell Out

Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

  • North America
  • Superb42 reviews4.8

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine lan....

    Free Cancellation
    Private Tour
    Start From $126.82
 
 

Friday Night Firework Cruise in Waikiki

(4.8 of 35 reviews)

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More

Free Cancellation
Private Tour
Start From $69.99
 
Friday Night Firework Cruise in Waikiki Likely to Sell Out

Friday Night Firework Cruise in Waikiki

  • North America
  • Superb35 reviews4.8

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

(4.9 of 1,016 reviews)

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More

Free Cancellation
Private Tour
Start From $108.91
 
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses Likely to Sell Out

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

  • North America
  • Superb1,016 reviews4.9

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Exclusive Isla Mujeres and Cancun Private Yacht Tour

(5 of 42 reviews)

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set the stage for a day of exhilaration and relaxation. Cruise along the mesmerizing Cancun coastlines, dive into vibrant coral reefs du... More

Free Cancellation
Private Tour
Start From $720.00
 
Exclusive Isla Mujeres and Cancun Private Yacht Tour Likely to Sell Out

Exclusive Isla Mujeres and Cancun Private Yacht Tour

  • North America
  • Superb42 reviews5

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set th....

    Free Cancellation
    Private Tour
    Start From $720.00
 
 

Daytime Sailing Along San Diego's Skyline

(5 of 160 reviews)

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More

Free Cancellation
Private Tour
Start From $99.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • North America
  • Superb160 reviews5

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

(4.9 of 87 reviews)

Discover the magic of the Laguna de los 7 Colores aboard our sailboat. Enjoy 5 hours of sailing, good music, unlimited drinks, delicious food, and moments to share. We created this experience for those who are looking for somethi... More

Special Offer
Free Cancellation
Private Tour
Start From $57.09
(Saving 20% ) $71.36
 
-20% Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch Likely to Sell Out

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

  • North America
  • Superb87 reviews4.9

Discover the magic of the Laguna de los 7 Colores aboard our sailboat. Enjoy 5 hours of sailing, goo....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $57.09
    (Saving 20% ) $71.36
 
 

Starfish, Stingrays and the Cozumel Turtle Sanctuary Snorkel Tour

(4.3 of 299 reviews)

People’s Choice- Best snorkeling tour! immerse in a world of Adventure and admire Spectacular marine life on this Cozumel Snorkeling trip. Enjoy 3 of the most popular Cozumel's marine attractions in the Mexican Caribbean. El C... More

Special Offer
Free Cancellation
Private Tour
Start From $65.00
(Saving inf% ) $0.00
 
-inf% Starfish, Stingrays and the Cozumel Turtle Sanctuary Snorkel Tour Likely to Sell Out

Starfish, Stingrays and the Cozumel Turtle Sanctuary Snorkel Tour

  • North America
  • Exellent299 reviews4.3

People’s Choice- Best snorkeling tour! immerse in a world of Adventure and admire Spectacular mar....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $65.00
    (Saving inf% ) $0.00
 
 

Tiki Pub Glow Party Cruise (Adults only)

(4.9 of 18 reviews)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic of the moonlit waters, paired with tunes and laughter. Join us for the most memora... More

Special Offer
Free Cancellation
Private Tour
Start From $89.95
(Saving inf% ) $0.00
 
-inf% Tiki Pub Glow Party Cruise (Adults only) Likely to Sell Out

Tiki Pub Glow Party Cruise (Adults only)

  • North America
  • Superb18 reviews4.9

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, si....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $89.95
    (Saving inf% ) $0.00
 
 

City Tour & Beach Club All Inclusive W Horse Ride & Water Sports

(3.4 of 5 reviews)

Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transported in a luxurious, air-conditioned vehicle, complete with complimentary beverages. Our tour includes visits to the stunning cathe... More

Special Offer
Free Cancellation
Private Tour
Start From $79.00
(Saving inf% ) $0.00
 
-inf% City Tour & Beach Club All Inclusive W Horse Ride & Water Sports Likely to Sell Out

City Tour & Beach Club All Inclusive W Horse Ride & Water Sports

  • North America
  • Good5 reviews3.4

Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transpor....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $79.00
    (Saving inf% ) $0.00
 
 

Polynesian Canoe Day Sail

(4.9 of 29 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Special Offer
Free Cancellation
Private Tour
Start From $170.00
(Saving 15% ) $200.00
 
-15% Polynesian Canoe Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • North America
  • Superb29 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $170.00
    (Saving 15% ) $200.00
 
 

San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

(5 of 85 reviews)

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More

Special Offer
Free Cancellation
Private Tour
Start From $125.00
(Saving inf% ) $0.00
 
-inf% San Diego Sailing Cruise Small Group 6 Guests Classic Yacht Likely to Sell Out

San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

  • North America
  • Superb85 reviews5

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $125.00
    (Saving inf% ) $0.00
 
 

Kona Tradewind Catamaran Day Sail

(4.8 of 51 reviews)

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More

Special Offer
Free Cancellation
Private Tour
Start From $89.00
(Saving inf% ) $0.00
 
-inf% Kona Tradewind Catamaran Day Sail Likely to Sell Out

Kona Tradewind Catamaran Day Sail

  • North America
  • Superb51 reviews4.8

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $89.00
    (Saving inf% ) $0.00
 
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